ORGANIC ELECTROLUMINESCENT MATERIAL AND DEVICE THEREOF
20230240129 · 2023-07-27
Inventors
- Ming Sang (Beijing, CN)
- Zheng Wang (Beijing, CN)
- Hongbo Li (Beijing, CN)
- Chi Yuen Raymond Kwong (Beijing, CN)
- Chuanjun Xia (Beijing, CN)
Cpc classification
International classification
Abstract
Provided are an organic electroluminescent material and device. The organic electroluminescent material is a metal complex comprising a ligand L.sub.a having a structure of Formula 1. When applied to organic electroluminescent devices, these metal complexes can provide very good device performance, especially an extended device lifetime and improved device efficiency and have a huge application prospect in aspects of white and low blue light sources. Further provided are an organic electroluminescent device comprising the metal complex and a compound composition comprising the metal complex.
Claims
1. A metal complex, comprising a metal M and a ligand L.sub.a coordinated to the metal M, wherein L.sub.a has a structure represented by Formula 1: ##STR00031## wherein the metal M is selected from a metal with a relative atomic mass greater than 40; Z is selected from the group consisting of O, S, Se, NR′, CR′R′ and SiR′R′; when two R′ are present at the same time, the two R′ are the same or different; the substituent R.sub.y represents mono-substitution, multiple substitutions or non-substitution; X.sub.1 to X.sub.8 are, at each occurrence identically or differently, selected from C, CR.sub.x or N, and at least one of X.sub.1 to X.sub.4 is selected from C and joined to pyridine in Formula 1; the substituent R.sub.n has a structure represented by Formula 2: ##STR00032## wherein in Formula 2, the substituents R.sub.A and R.sub.B represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution; the ring A and the ring B are identically or differently selected from a carbocyclic ring having 3 to 30 ring atoms or a heterocyclic ring having 3 to 30 ring atoms; A.sub.1, A.sub.2, B.sub.1, B.sub.2 and E are, at each occurrence identically or differently, selected from C, N, B, P, CR′″, SiR′″ or GeR′″; L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof, the substituents R′, R″, R′″, R.sub.x, R.sub.y, R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof, “*” represents a position where Formula 2 is joined; and adjacent substituents R′, R.sub.x, R″, R′″, R.sub.A, R.sub.B, R.sub.y can be optionally joined to form a ring.
2. The metal complex according to claim 1, wherein the metal complex has a general formula of M(L.sub.a).sub.m(L.sub.b).sub.n(L.sub.c).sub.q; wherein the metal M is selected from a metal with a relative atomic mass greater than 40; preferably, M is, at each occurrence identically or differently, selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; more preferably, M is, at each occurrence identically or differently, selected from Pt or Ir; L.sub.a, L.sub.b and L.sub.c are a first ligand, a second ligand and a third ligand coordinated to the metal M, respectively, and L.sub.c is the same as or different from L.sub.a or L.sub.b; wherein L.sub.a, L.sub.b and L.sub.c can be optionally joined to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q equals to the oxidation state of the metal M; when m is greater than or equal to 2, multiple L.sub.a are the same or different; when n is equal to 2, two L.sub.b are the same or different; when q is equal to 2, two L.sub.c are the same or different; L.sub.b and L.sub.c are, at each occurrence identically or differently, selected from a structure represented by any one of the group consisting of: ##STR00033## wherein the substituents R.sub.a and R.sub.b represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution; X.sub.b is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR.sub.N1 and CR.sub.C1R.sub.C2; the substituents R.sub.a, R.sub.b, R.sub.c, R.sub.N1, R.sub.C1 and R.sub.C2 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof, and adjacent substituents R.sub.a, R.sub.b, R.sub.c, R.sub.N1, R.sub.C1 and R.sub.C2 can be optionally joined to form a ring.
3. The metal complex according to claim 1, wherein the metal complex has a general formula of Ir(L.sub.a).sub.m(L.sub.b).sub.3-m and is represented by Formula 3: ##STR00034## wherein m is selected from 1, 2 or 3; when m is selected from 1, two L.sub.b are the same or different; when m is selected from 2 or 3, multiple L.sub.a are the same or different; Z is selected from the group consisting of O, S, Se, NR′, CR′R′ and SiR′R′; when two R′ are present at the same time, the two R′ are the same or different; the substituent R.sub.y represents mono-substitution, multiple substitutions or non-substitution; X.sub.3 to X.sub.8 are, at each occurrence identically or differently, selected from CR.sub.x or N; the substituent R.sub.n has a structure represented by Formula 2: ##STR00035## wherein in Formula 2, the substituents R.sub.A and R.sub.B represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution; the ring A and the ring B are identically or differently selected from a carbocyclic ring having 3 to 30 ring atoms or a heterocyclic ring having 3 to 30 ring atoms; A.sub.1, A.sub.2, B.sub.1, B.sub.2 and E are, at each occurrence identically or differently, selected from C, N, B, P, CR′″, SiR′″ or GeR′″; L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof, the substituents R.sub.1 to R.sub.8, R′, R″, R′″, R.sub.x, R.sub.y, R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof, “*” represents a position where Formula 2 is joined; adjacent substituents R′, R.sub.x, R″, R′″, R.sub.A, R.sub.B, R.sub.y can be optionally joined to form a ring; and adjacent substituents R.sub.1 to R.sub.8 can be optionally joined to form a ring.
4. The metal complex according to claim 1, wherein Z is selected from O or S; preferably, Z is selected from O.
5. The metal complex according to claim 1, wherein X.sub.1 to X.sub.8 are, at each occurrence identically or differently, selected from CR.sub.x, and the substituent R.sub.x is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano and combinations thereof, preferably, the substituent R.sub.x is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, biphenyl, pyridyl, trimethylsilyl, trimethylgermanyl and combinations thereof.
6. The metal complex according to claim 1, wherein the substituent R.sub.n has a structure represented by Formula 4: ##STR00036## wherein A.sub.3 to A.sub.6 are, at each occurrence identically or differently, selected from CR.sub.A or N; B.sub.3 to B.sub.6 are, at each occurrence identically or differently, selected from CR.sub.B or N; L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclylene having 3 to 20 ring atoms, arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms or a combination thereof, the substituents R.sub.A, R.sub.B and R″ are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof, adjacent substituents R″, R.sub.A, R.sub.B can be optionally joined to form a ring; and “*” represents a position where Formula 4 is joined.
7. The metal complex according to claim 6, wherein A.sub.3 to A.sub.6 are, at each occurrence identically or differently, selected from CR.sub.A and/or B.sub.3 to B.sub.6 are, at each occurrence identically or differently, selected from CR.sub.B; and the substituents R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano and combinations thereof, preferably, the substituents R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano and combinations thereof, more preferably, the substituents R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl and combinations thereof.
8. The metal complex according to claim 1, wherein L is selected from a single bond, O, S, Se, NR″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, substituted or unsubstituted arylene having 6 to 10 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 10 carbon atoms or a combination thereof, preferably, L is selected from a single bond, O, S, NR″, substituted or unsubstituted alkylene having 1 to 10 carbon atoms or phenylene; more preferably, L is selected from a single bond.
9. The metal complex according to claim 3, wherein at least one of X.sub.3 to X.sub.8 is CR.sub.x, and the substituent R.sub.x is selected from cyano or fluorine; preferably, at least one of X.sub.5 to X.sub.8 is CR.sub.x, and the substituent R.sub.x is selected from cyano or fluorine; more preferably, X.sub.7 or X.sub.8 is CR.sub.x, and R.sub.x is selected from cyano; or X.sub.7 is CR.sub.x, and the substituent R.sub.x is selected from fluorine.
10. The metal complex according to claim 3, wherein at least two of X.sub.3 to X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is selected from cyano or fluorine, and another substituent R.sub.x is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, isocyano and combinations thereof, preferably, at least two of X.sub.5 to X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is selected from cyano or fluorine, and another substituent R.sub.x is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, isocyano and combinations thereof, more preferably, X.sub.7 and X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is cyano or fluorine, and another substituent R.sub.x is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, isocyano and combinations thereof.
11. The metal complex according to claim 1, wherein R.sub.n is, at each occurrence identically or differently, selected from the group consisting of: ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## wherein optionally, hydrogens in An.sub.1 to An.sub.52, An.sub.54 to An.sub.58 and An.sub.61 to An.sub.96 can be partially or fully deuterated.
12. The metal complex according to claim 1, wherein the substituent R.sub.y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 6 to 20 carbon atoms and combinations thereof, preferably, at least one substituent R.sub.y is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof.
13. The metal complex according to claim 3, wherein at least one or at least two of the substituents R.sub.1 to R.sub.8 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof, and the total number of carbon atoms in all of the substituents R.sub.1 to R.sub.4 and/or the substituents R.sub.5 to R.sub.8 is at least 4; and preferably, at least one or at least two of the substituents R.sub.1 to R.sub.4 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof, and the total number of carbon atoms in all of the substituents R.sub.1 to R.sub.4 is at least 4; and/or at least one or at least two of the substituents R.sub.5 to R.sub.8 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof, and the total number of carbon atoms in all of the substituents R.sub.5 to R.sub.8 is at least 4.
14. The metal complex according to claim 3, wherein at least one, at least two, at least three or all of the substituents R.sub.2, R.sub.3, R.sub.6 and R.sub.7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof, preferably, at least one, at least two, at least three or all of the substituents R.sub.2, R.sub.3, R.sub.6 and R.sub.7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms and combinations thereof, more preferably, at least one, at least two, at least three or all of the substituents R.sub.2, R.sub.3, R.sub.6 and R.sub.7 are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, neopentyl, t-pentyl and combinations thereof, optionally, hydrogens in the above groups can be partially or fully deuterated.
15. The metal complex according to claim 11, wherein L.sub.a is, at each occurrence identically or differently, selected from the group consisting of L.sub.a1 to L.sub.a821, wherein L.sub.a1 to L.sub.a821 have the following specific structures: L.sub.a1 to L.sub.a773 have the following general formula: ##STR00050## wherein R.sub.n, R.sub.Y1 to R.sub.Y3, R.sub.X4 to R.sub.X8 and Z are selected from atoms or groups in the following table: TABLE-US-00005 Ligand L.sub.a No. R.sub.n R.sub.Y1 R.sub.Y2 R.sub.Y3 R.sub.X4 R.sub.X5 R.sub.X6 R.sub.X7 R.sub.X8 Z L.sub.a1 A.sub.n1 H H H H H H H H O L.sub.a2 A.sub.n2 H H H H H H H H O L.sub.a3 A.sub.n3 H H H H H H H H O L.sub.a4 A.sub.n4 H H H H H H H H O L.sub.a5 A.sub.n5 H H H H H H H H O L.sub.a6 A.sub.n6 H H H H H H H H O L.sub.a7 A.sub.n7 H H H H H H H H O L.sub.a8 A.sub.n8 H H H H H H H H O L.sub.a9 A.sub.n9 H H H H H H H H O L.sub.a10 A.sub.n10 H H H H H H H H O L.sub.a11 A.sub.n11 H H H H H H H H O L.sub.a12 A.sub.n12 H H H H H H H H O L.sub.a13 A.sub.n13 H H H H H H H H O L.sub.a14 A.sub.n14 H H H H H H H H O L.sub.a15 A.sub.n15 H H H H H H H H O L.sub.a16 A.sub.n16 H H H H H H H H O L.sub.a17 A.sub.n17 H H H H H H H H O L.sub.a18 A.sub.n18 H H H H H H H H O L.sub.a19 A.sub.n19 H H H H H H H H O L.sub.a20 A.sub.n20 H H H H H H H H O L.sub.a21 A.sub.n21 H H H H H H H H O L.sub.a22 A.sub.n22 H H H H H H H H O L.sub.a23 A.sub.n23 H H H H H H H H O L.sub.a24 A.sub.n24 H H H H H H H H O L.sub.a25 A.sub.n25 H H H H H H H H O L.sub.a26 A.sub.n26 H H H H H H H H O L.sub.a27 A.sub.n27 H H H H H H H H O L.sub.a28 A.sub.n28 H H H H H H H H O L.sub.a29 A.sub.n29 H H H H H H H H O L.sub.a30 A.sub.n30 H H H H H H H H O L.sub.a31 A.sub.n31 H H H H H H H H O L.sub.a32 A.sub.n32 H H H H H H H H O L.sub.a33 A.sub.n33 H H H H H H H H O L.sub.a34 A.sub.n34 H H H H H H H H O L.sub.a35 A.sub.n35 H H H H H H H H O L.sub.a36 A.sub.n36 H H H H H H H H O L.sub.a37 A.sub.n37 H H H H H H H H O L.sub.a38 A.sub.n38 H H H H H H H H O L.sub.a39 A.sub.n39 H H H H H H H H O L.sub.a40 A.sub.n40 H H H H H H H H O L.sub.a41 A.sub.n41 H H H H H H H H O L.sub.a42 A.sub.n42 H H H H H H H H O L.sub.a43 A.sub.n43 H H H H H H H H O L.sub.a44 A.sub.n44 H H H H H H H H O L.sub.a45 A.sub.n45 H H H H H H H H O L.sub.a46 A.sub.n46 H H H H H H H H O L.sub.a47 A.sub.n47 H H H H H H H H O L.sub.a48 A.sub.n48 H H H H H H H H O L.sub.a49 A.sub.n49 H H H H H H H H O L.sub.a50 A.sub.n50 H H H H H H H H O L.sub.a51 A.sub.n51 H H H H H H H H O L.sub.a52 A.sub.n52 H H H H H H H H O L.sub.a53 A.sub.n53 H H H H H H H H O L.sub.a54 A.sub.n54 H H H H H H H H O L.sub.a55 A.sub.n55 H H H H H H H H O L.sub.a56 A.sub.n56 H H H H H H H H O L.sub.a57 A.sub.n57 H H H H H H H H O L.sub.a58 A.sub.n58 H H H H H H H H O L.sub.a59 A.sub.n59 H H H H H H H H O L.sub.a60 A.sub.n60 H H H H H H H H O L.sub.a61 A.sub.n61 H H H H H H H H O L.sub.a62 A.sub.n62 H H H H H H H H O L.sub.a63 A.sub.n63 H H H H H H H H O L.sub.a64 A.sub.n64 H H H H H H H H O L.sub.a65 A.sub.n65 H H H H H H H H O L.sub.a66 A.sub.n66 H H H H H H H H O L.sub.a67 A.sub.n67 H H H H H H H H O L.sub.a68 A.sub.n68 H H H H H H H H O L.sub.a69 A.sub.n69 H H H H H H H H O L.sub.a70 A.sub.n70 H H H H H H H H O L.sub.a71 A.sub.n71 H H H H H H H H O L.sub.a72 A.sub.n72 H H H H H H H H O L.sub.a73 A.sub.n73 H H H H H H H H O L.sub.a74 A.sub.n74 H H H H H H H H O L.sub.a75 A.sub.n75 H H H H H H H H O L.sub.a76 A.sub.n76 H H H H H H H H O L.sub.a77 A.sub.n77 H H H H H H H H O L.sub.a78 A.sub.n78 H H H H H H H H O L.sub.a79 A.sub.n79 H H H H H H H H O L.sub.a80 A.sub.n80 H H H H H H H H O L.sub.a81 A.sub.n81 H H H H H H H H O L.sub.a82 A.sub.n82 H H H H H H H H O L.sub.a83 A.sub.n83 H H H H H H H H O L.sub.a84 A.sub.n84 H H H H H H H H O L.sub.a85 A.sub.n85 H H H H H H H H O L.sub.a86 A.sub.n86 H H H H H H H H O L.sub.a87 A.sub.n87 H H H H H H H H O L.sub.a88 A.sub.n88 H H H H H H H H O L.sub.a89 A.sub.n89 H H H H H H H H O L.sub.a90 A.sub.n90 H H H H H H H H O L.sub.a91 A.sub.n91 H H H H H H H H O L.sub.a92 A.sub.n92 H H H H H H H H O L.sub.a93 A.sub.n93 H H H H H H H H O L.sub.a94 A.sub.n94 H H H H H H H H O L.sub.a95 A.sub.n95 H H H H H H H H O L.sub.a96 A.sub.n96 H H H H H H H H O L.sub.a97 A.sub.n1 H CD.sub.3 H H H H H H O L.sub.a98 A.sub.n10 H CD.sub.3 H H H H H H O L.sub.a99 A.sub.n13 H CD.sub.3 H H H H H H O L.sub.a100 A.sub.n31 H CD.sub.3 H H H H H H O L.sub.a101 A.sub.n34 H CD.sub.3 H H H H H H O L.sub.a102 A.sub.n53 H CD.sub.3 H H H H H H O L.sub.a103 A.sub.n57 H CD.sub.3 H H H H H H O L.sub.a104 A.sub.n58 H CD.sub.3 H H H H H H O L.sub.a105 A.sub.n59 H CD.sub.3 H H H H H H O L.sub.a106 A.sub.n60 H CD.sub.3 H H H H H H O L.sub.a107 A.sub.n84 H CD.sub.3 H H H H H H O L.sub.a108 A.sub.n91 H CD.sub.3 H H H H H H O L.sub.a109 A.sub.n93 H CD.sub.3 H H H H H H O L.sub.a110 A.sub.n94 H CD.sub.3 H H H H H H O L.sub.a111 A.sub.n96 H CD.sub.3 H H H H H H O L.sub.a112 A.sub.n1 H R.sub.s1 H H H H H H O L.sub.a113 A.sub.n10 H R.sub.s1 H H H H H H O L.sub.a114 A.sub.n13 H R.sub.s1 H H H H H H O L.sub.a115 A.sub.n31 H R.sub.s1 H H H H H H O L.sub.a116 A.sub.n34 H R.sub.s1 H H H H H H O L.sub.a117 A.sub.n53 H R.sub.s1 H H H H H H O L.sub.a118 A.sub.n57 H R.sub.s1 H H H H H H O L.sub.a119 A.sub.n58 H R.sub.s1 H H H H H H O L.sub.a120 A.sub.n59 H R.sub.s1 H H H H H H O L.sub.a121 A.sub.n60 H R.sub.s1 H H H H H H O L.sub.a122 A.sub.n84 H R.sub.s1 H H H H H H O L.sub.a123 A.sub.n91 H R.sub.s1 H H H H H H O L.sub.a124 A.sub.n93 H R.sub.s1 H H H H H H O L.sub.a125 A.sub.n94 H R.sub.s1 H H H H H H O L.sub.a126 A.sub.n96 H R.sub.s1 H H H H H H O L.sub.a127 A.sub.n1 H R.sub.s2 H H H H H H O L.sub.a128 A.sub.n10 H R.sub.s2 H H H H H H O L.sub.a129 A.sub.n13 H R.sub.s2 H H H H H H O L.sub.a130 A.sub.n31 H R.sub.s2 H H H H H H O L.sub.a131 A.sub.n34 H R.sub.s2 H H H H H H O L.sub.a132 A.sub.n53 H R.sub.s2 H H H H H H O L.sub.a133 A.sub.n57 H R.sub.s2 H H H H H H O L.sub.a134 A.sub.n58 H R.sub.s2 H H H H H H O L.sub.a135 A.sub.n59 H R.sub.s2 H H H H H H O L.sub.a136 A.sub.n60 H R.sub.s2 H H H H H H O L.sub.a137 A.sub.n84 H R.sub.s2 H H H H H H O L.sub.a138 A.sub.n91 H R.sub.s2 H H H H H H O L.sub.a139 A.sub.n93 H R.sub.s2 H H H H H H O L.sub.a140 A.sub.n94 H R.sub.s2 H H H H H H O L.sub.a141 A.sub.n96 H R.sub.s2 H H H H H H O L.sub.a142 A.sub.n1 H R.sub.s3 H H H H H H O L.sub.a143 A.sub.n10 H R.sub.s3 H H H H H H O L.sub.a144 A.sub.n13 H R.sub.s3 H H H H H H O L.sub.a145 A.sub.n31 H R.sub.s3 H H H H H H O L.sub.a146 A.sub.n34 H R.sub.s3 H H H H H H O L.sub.a147 A.sub.n53 H R.sub.s3 H H H H H H O L.sub.a148 A.sub.n57 H R.sub.s3 H H H H H H O L.sub.a149 A.sub.n58 H R.sub.s3 H H H H H H O L.sub.a150 A.sub.n59 H R.sub.s3 H H H H H H O L.sub.a151 A.sub.n60 H R.sub.s3 H H H H H H O L.sub.a152 A.sub.n84 H R.sub.s3 H H H H H H O L.sub.a153 A.sub.n91 H R.sub.s3 H H H H H H O L.sub.a154 A.sub.n93 H R.sub.s3 H H H H H H O L.sub.a155 A.sub.n94 H R.sub.s3 H H H H H H O L.sub.a156 A.sub.n96 H R.sub.s3 H H H H H H O L.sub.a157 A.sub.n1 H R.sub.s4 H H H H H H O L.sub.a158 A.sub.n10 H R.sub.s4 H H H H H H O L.sub.a159 A.sub.n13 H R.sub.s4 H H H H H H O L.sub.a160 A.sub.n31 H R.sub.s4 H H H H H H O L.sub.a161 A.sub.n34 H R.sub.s4 H H H H H H O L.sub.a162 A.sub.n53 H R.sub.s4 H H H H H H O L.sub.a163 A.sub.n57 H R.sub.s4 H H H H H H O L.sub.a164 A.sub.n58 H R.sub.s4 H H H H H H O L.sub.a165 A.sub.n59 H R.sub.s4 H H H H H H O L.sub.a166 A.sub.n60 H R.sub.s4 H H H H H H O L.sub.a167 A.sub.n84 H R.sub.s4 H H H H H H O L.sub.a168 A.sub.n91 H R.sub.s4 H H H H H H O L.sub.a169 A.sub.n93 H R.sub.s4 H H H H H H O L.sub.a170 A.sub.n94 H R.sub.s4 H H H H H H O L.sub.a171 A.sub.n96 H R.sub.s4 H H H H H H O L.sub.a172 A.sub.n1 H R.sub.s5 H H H H H H O L.sub.a173 A.sub.n10 H R.sub.s5 H H H H H H O L.sub.a174 A.sub.n13 H R.sub.s5 H H H H H H O L.sub.a175 A.sub.n31 H R.sub.s5 H H H H H H O L.sub.a176 A.sub.n34 H R.sub.s5 H H H H H H O L.sub.a177 A.sub.n53 H R.sub.s5 H H H H H H O L.sub.a178 A.sub.n57 H R.sub.s5 H H H H H H O L.sub.a179 A.sub.n58 H R.sub.s5 H H H H H H O L.sub.a180 A.sub.n59 H R.sub.s5 H H H H H H O L.sub.a181 A.sub.n60 H R.sub.s5 H H H H H H O L.sub.a182 A.sub.n84 H R.sub.s5 H H H H H H O L.sub.a183 A.sub.n91 H R.sub.s5 H H H H H H O L.sub.a184 A.sub.n93 H R.sub.s5 H H H H H H O L.sub.a185 A.sub.n94 H R.sub.s5 H H H H H H O L.sub.a186 A.sub.n96 H R.sub.s5 H H H H H H O L.sub.a187 A.sub.n1 H R.sub.s6 H H H H H H O L.sub.a188 A.sub.n10 H R.sub.s6 H H H H H H O L.sub.a189 A.sub.n13 H R.sub.s6 H H H H H H O L.sub.a190 A.sub.n31 H R.sub.s6 H H H H H H O L.sub.a191 A.sub.n34 H R.sub.s6 H H H H H H O L.sub.a192 A.sub.n53 H R.sub.s6 H H H H H H O L.sub.a193 A.sub.n57 H R.sub.s6 H H H H H H O L.sub.a194 A.sub.n58 H R.sub.s6 H H H H H H O L.sub.a195 A.sub.n59 H R.sub.s6 H H H H H H O L.sub.a196 A.sub.n60 H R.sub.s6 H H H H H H O L.sub.a197 A.sub.n84 H R.sub.s6 H H H H H H O L.sub.a198 A.sub.n91 H R.sub.s6 H H H H H H O L.sub.a199 A.sub.n93 H R.sub.s6 H H H H H H O L.sub.a200 A.sub.n94 H R.sub.s6 H H H H H H O L.sub.a201 A.sub.n96 H R.sub.s6 H H H H H H O L.sub.a202 A.sub.n1 H H H H H H H CN O L.sub.a203 A.sub.n2 H H H H H H H CN O L.sub.a204 A.sub.n3 H H H H H H H CN O L.sub.a205 A.sub.n4 H H H H H H H CN O L.sub.a206 A.sub.n5 H H H H H H H CN O L.sub.a207 A.sub.n6 H H H H H H H CN O L.sub.a208 A.sub.n7 H H H H H H H CN O L.sub.a209 A.sub.n8 H H H H H H H CN O L.sub.a210 A.sub.n9 H H H H H H H CN O L.sub.a211 A.sub.n10 H H H H H H H CN O L.sub.a212 A.sub.n11 H H H H H H H CN O L.sub.a213 A.sub.n12 H H H H H H H CN O L.sub.a214 A.sub.n13 H H H H H H H CN O L.sub.a215 A.sub.n14 H H H H H H H CN O L.sub.a216 A.sub.n15 H H H H H H H CN O L.sub.a217 A.sub.n16 H H H H H H H CN O L.sub.a218 A.sub.n17 H H H H H H H CN O L.sub.a219 A.sub.n18 H H H H H H H CN O L.sub.a220 A.sub.n19 H H H H H H H CN O L.sub.a221 A.sub.n20 H H H H H H H CN O L.sub.a222 A.sub.n21 H H H H H H H CN O L.sub.a223 A.sub.n22 H H H H H H H CN O L.sub.a224 A.sub.n23 H H H H H H H CN O L.sub.a225 A.sub.n24 H H H H H H H CN O L.sub.a226 A.sub.n25 H H H H H H H CN O L.sub.a227 A.sub.n26 H H H H H H H CN O L.sub.a228 A.sub.n27 H H H H H H H CN O L.sub.a229 A.sub.n28 H H H H H H H CN O L.sub.a230 A.sub.n29 H H H H H H H CN O L.sub.a231 A.sub.n30 H H H H H H H CN O L.sub.a232 A.sub.n31 H H H H H H H CN O L.sub.a233 A.sub.n32 H H H H H H H CN O L.sub.a234 A.sub.n33 H H H H H H H CN O L.sub.a235 A.sub.n34 H H H H H H H CN O L.sub.a236 A.sub.n35 H H H H H H H CN O L.sub.a237 A.sub.n36 H H H H H H H CN O L.sub.a238 A.sub.n37 H H H H H H H CN O L.sub.a239 A.sub.n38 H H H H H H H CN O L.sub.a240 A.sub.n39 H H H H H H H CN O L.sub.a241 A.sub.n40 H H H H H H H CN O L.sub.a242 A.sub.n41 H H H H H H H CN O L.sub.a243 A.sub.n42 H H H H H H H CN O L.sub.a244 A.sub.n43 H H H H H H H CN O L.sub.a245 A.sub.n44 H H H H H H H CN O L.sub.a246 A.sub.n45 H H H H H H H CN O L.sub.a247 A.sub.n46 H H H H H H H CN O L.sub.a248 A.sub.n47 H H H H H H H CN O L.sub.a249 A.sub.n48 H H H H H H H CN O L.sub.a250 A.sub.n49 H H H H H H H CN O L.sub.a251 A.sub.n50 H H H H H H H CN O L.sub.a252 A.sub.n51 H H H H H H H CN O L.sub.a253 A.sub.n52 H H H H H H H CN O L.sub.a254 A.sub.n53 H H H H H H H CN O L.sub.a255 A.sub.n54 H H H H H H H CN O L.sub.a256 A.sub.n55 H H H H H H H CN O L.sub.a257 A.sub.n56 H H H H H H H CN O L.sub.a258 A.sub.n57 H H H H H H H CN O L.sub.a259 A.sub.n58 H H H H H H H CN O L.sub.a260 A.sub.n59 H H H H H H H CN O L.sub.a261 A.sub.n60 H H H H H H H CN O L.sub.a262 A.sub.n61 H H H H H H H CN O L.sub.a263 A.sub.n62 H H H H H H H CN O L.sub.a264 A.sub.n63 H H H H H H H CN O L.sub.a265 A.sub.n64 H H H H H H H CN O L.sub.a266 A.sub.n65 H H H H H H H CN O L.sub.a267 A.sub.n66 H H H H H H H CN O L.sub.a268 A.sub.n67 H H H H H H H CN O L.sub.a269 A.sub.n68 H H H H H H H CN O L.sub.a270 A.sub.n69 H H H H H H H CN O L.sub.a271 A.sub.n70 H H H H H H H CN O L.sub.a272 A.sub.n71 H H H H H H H CN O L.sub.a273 A.sub.n72 H H H H H H H CN O L.sub.a274 A.sub.n73 H H H H H H H CN O L.sub.a275 A.sub.n74 H H H H H H H CN O L.sub.a276 A.sub.n75 H H H H H H H CN O L.sub.a277 A.sub.n76 H H H H H H H CN O L.sub.a278 A.sub.n77 H H H H H H H CN O L.sub.a279 A.sub.n78 H H H H H H H CN O L.sub.a280 A.sub.n79 H H H H H H H CN O L.sub.a281 A.sub.n80 H H H H H H H CN O L.sub.a282 A.sub.n81 H H H H H H H CN O L.sub.a283 A.sub.n82 H H H H H H H CN O L.sub.a284 A.sub.n83 H H H H H H H CN O L.sub.a285 A.sub.n84 H H H H H H H CN O L.sub.a286 A.sub.n85 H H H H H H H CN O L.sub.a287 A.sub.n86 H H H H H H H CN O L.sub.a288 A.sub.n87 H H H H H H H CN O L.sub.a289 A.sub.n88 H H H H H H H CN O L.sub.a290 A.sub.n89 H H H H H H H CN O L.sub.a291 A.sub.n90 H H H H H H H CN O L.sub.a292 A.sub.n91 H H H H H H H CN O L.sub.a293 A.sub.n92 H H H H H H H CN O L.sub.a294 A.sub.n93 H H H H H H H CN O L.sub.a295 A.sub.n94 H H H H H H H CN O L.sub.a296 A.sub.n95 H H H H H H H CN O L.sub.a297 A.sub.n96 H H H H H H H CN O L.sub.a298 A.sub.n1 H CD.sub.3 H H H H H CN O L.sub.a299 A.sub.n10 H CD.sub.3 H H H H H CN O L.sub.a300 A.sub.n13 H CD.sub.3 H H H H H CN O L.sub.a301 A.sub.n31 H CD.sub.3 H H H H H CN O L.sub.a302 A.sub.n34 H CD.sub.3 H H H H H CN O L.sub.a303 A.sub.n53 H CD.sub.3 H H H H H CN O L.sub.a304 A.sub.n57 H CD.sub.3 H H H H H CN O L.sub.a305 A.sub.n58 H CD.sub.3 H H H H H CN O L.sub.a306 A.sub.n59 H CD.sub.3 H H H H H CN O L.sub.a307 A.sub.n60 H CD.sub.3 H H H H H CN O L.sub.a308 A.sub.n84 H CD.sub.3 H H H H H CN O L.sub.s309 A.sub.n91 H CD.sub.3 H H H H H CN O L.sub.a310 A.sub.n93 H CD.sub.3 H H H H H CN O L.sub.a311 A.sub.n94 H CD.sub.3 H H H H H CN O L.sub.a312 A.sub.n96 H CD.sub.3 H H H H H CN O L.sub.a313 A.sub.n1 H R.sub.s1 H H H H H CN O L.sub.a314 A.sub.n10 H R.sub.s1 H H H H H CN O L.sub.a315 A.sub.n13 H R.sub.s1 H H H H H CN O L.sub.a316 A.sub.n31 H R.sub.s1 H H H H H CN O L.sub.a317 A.sub.n34 H R.sub.s1 H H H H H CN O L.sub.a318 A.sub.n53 H R.sub.s1 H H H H H CN O L.sub.a319 A.sub.n57 H R.sub.s1 H H H H H CN O L.sub.a320 A.sub.n58 H R.sub.s1 H H H H H CN O L.sub.a321 A.sub.n59 H R.sub.s1 H H H H H CN O L.sub.a322 A.sub.n60 H R.sub.s1 H H H H H CN O L.sub.a323 A.sub.n84 H R.sub.s1 H H H H H CN O L.sub.a324 A.sub.n91 H R.sub.s1 H H H H H CN O L.sub.a325 A.sub.n93 H R.sub.s1 H H H H H CN O L.sub.a326 A.sub.n94 H R.sub.s1 H H H H H CN O L.sub.a327 A.sub.n96 H R.sub.s1 H H H H H CN O L.sub.a328 A.sub.n1 H R.sub.s2 H H H H H CN O L.sub.a329 A.sub.n10 H R.sub.s2 H H H H H CN O L.sub.a330 A.sub.n13 H R.sub.s2 H H H H H CN O L.sub.a331 A.sub.n31 H R.sub.s2 H H H H H CN O L.sub.a332 A.sub.n34 H R.sub.s2 H H H H H CN O L.sub.a333 A.sub.n53 H R.sub.s2 H H H H H CN O L.sub.a334 A.sub.n57 H R.sub.s2 H H H H H CN O L.sub.a335 A.sub.n58 H R.sub.s2 H H H H H CN O L.sub.a336 A.sub.n59 H R.sub.s2 H H H H H CN O L.sub.a337 A.sub.n60 H R.sub.s2 H H H H H CN O L.sub.a338 A.sub.n84 H R.sub.s2 H H H H H CN O L.sub.a339 A.sub.n91 H R.sub.s2 H H H H H CN O L.sub.a340 A.sub.n93 H R.sub.s2 H H H H H CN O L.sub.a341 A.sub.n94 H R.sub.s2 H H H H H CN O L.sub.a342 A.sub.n96 H R.sub.s2 H H H H H CN O L.sub.a343 A.sub.n1 H R.sub.s3 H H H H H CN O L.sub.a344 A.sub.n10 H R.sub.s3 H H H H H CN O L.sub.a345 A.sub.n13 H R.sub.s3 H H H H H CN O L.sub.a346 A.sub.n31 H R.sub.s3 H H H H H CN O L.sub.a347 A.sub.n34 H R.sub.s3 H H H H H CN O L.sub.a348 A.sub.n53 H R.sub.s3 H H H H H CN O L.sub.a349 A.sub.n57 H R.sub.s3 H H H H H CN O L.sub.a350 A.sub.n58 H R.sub.s3 H H H H H CN O L.sub.a351 A.sub.n59 H R.sub.s3 H H H H H CN O L.sub.a352 A.sub.n60 H R.sub.s3 H H H H H CN O L.sub.a353 A.sub.n84 H R.sub.s3 H H H H H CN O L.sub.a354 A.sub.n91 H R.sub.s3 H H H H H CN O L.sub.a355 A.sub.n93 H R.sub.s3 H H H H H CN O L.sub.a356 A.sub.n94 H R.sub.s3 H H H H H CN O L.sub.a357 A.sub.n96 H R.sub.s3 H H H H H CN O L.sub.a358 A.sub.n1 H R.sub.s4 H H H H H CN O L.sub.a359 A.sub.n10 H R.sub.s4 H H H H H CN O L.sub.a360 A.sub.n13 H R.sub.s4 H H H H H CN O L.sub.a361 A.sub.n31 H R.sub.s4 H H H H H CN O L.sub.a362 A.sub.n33 H R.sub.s4 H H H H H CN O L.sub.a363 A.sub.n34 H R.sub.s4 H H H H H CN O L.sub.a364 A.sub.n53 H R.sub.s4 H H H H H CN O L.sub.a365 A.sub.n57 H R.sub.s4 H H H H H CN O L.sub.a366 A.sub.n58 H R.sub.s4 H H H H H CN O L.sub.a367 A.sub.n59 H R.sub.s4 H H H H H CN O L.sub.a368 A.sub.n60 H R.sub.s4 H H H H H CN O L.sub.a369 A.sub.n84 H R.sub.s4 H H H H H CN O L.sub.a370 A.sub.n91 H R.sub.s4 H H H H H CN O L.sub.a371 A.sub.n93 H R.sub.s4 H H H H H CN O L.sub.a372 A.sub.n94 H R.sub.s4 H H H H H CN O L.sub.a373 A.sub.n96 H R.sub.s4 H H H H H CN O L.sub.a374 A.sub.n1 H H H H H H CN H O L.sub.a375 A.sub.n2 H H H H H H CN H O L.sub.a376 A.sub.n3 H H H H H H CN H O L.sub.a377 A.sub.n4 H H H H H H CN H O L.sub.a378 A.sub.n5 H H H H H H CN H O L.sub.a379 A.sub.n6 H H H H H H CN H O L.sub.a380 A.sub.n7 H H H H H H CN H O L.sub.a381 A.sub.n8 H H H H H H CN H O L.sub.a382 A.sub.n9 H H H H H H CN H O L.sub.a383 A.sub.n10 H H H H H H CN H O L.sub.a384 A.sub.n11 H H H H H H CN H O L.sub.a385 A.sub.n12 H H H H H H CN H O L.sub.a386 A.sub.n13 H H H H H H CN H O L.sub.a387 A.sub.n14 H H H H H H CN H O L.sub.a388 A.sub.n15 H H H H H H CN H O L.sub.a389 A.sub.n16 H H H H H H CN H O L.sub.a390 A.sub.n17 H H H H H H CN H O L.sub.a391 A.sub.n18 H H H H H H CN H O L.sub.a392 A.sub.n19 H H H H H H CN H O L.sub.a393 A.sub.n20 H H H H H H CN H O L.sub.a394 A.sub.n21 H H H H H H CN H O L.sub.a395 A.sub.n22 H H H H H H CN H O L.sub.a396 A.sub.n23 H H H H H H CN H O L.sub.a397 A.sub.n24 H H H H H H CN H O L.sub.a398 A.sub.n25 H H H H H H CN H O L.sub.a399 A.sub.n26 H H H H H H CN H O L.sub.a400 A.sub.n27 H H H H H H CN H O L.sub.a401 A.sub.n28 H H H H H H CN H O L.sub.a402 A.sub.n29 H H H H H H CN H O L.sub.a403 A.sub.n30 H H H H H H CN H O L.sub.a404 A.sub.n31 H H H H H H CN H O L.sub.a405 A.sub.n32 H H H H H H CN H O L.sub.a406 A.sub.n33 H H H H H H CN H O L.sub.a407 A.sub.n34 H H H H H H CN H O L.sub.a408 A.sub.n35 H H H H H H CN H O L.sub.a409 A.sub.n36 H H H H H H CN H O L.sub.a410 A.sub.n37 H H H H H H CN H O L.sub.a411 A.sub.n38 H H H H H H CN H O L.sub.a412 A.sub.n39 H H H H H H CN H O L.sub.a413 A.sub.n40 H H H H H H CN H O L.sub.a414 A.sub.n41 H H H H H H CN H O L.sub.a415 A.sub.n42 H H H H H H CN H O L.sub.a416 A.sub.n43 H H H H H H CN H O L.sub.a417 A.sub.n44 H H H H H H CN H O L.sub.a418 A.sub.n45 H H H H H H CN H O L.sub.a419 A.sub.n46 H H H H H H CN H O L.sub.a420 A.sub.n47 H H H H H H CN H O L.sub.a421 A.sub.n48 H H H H H H CN H O L.sub.a422 A.sub.n49 H H H H H H CN H O L.sub.a423 A.sub.n50 H H H H H H CN H O L.sub.a424 A.sub.n51 H H H H H H CN H O L.sub.a425 A.sub.n52 H H H H H H CN H O L.sub.a426 A.sub.n53 H H H H H H CN H O L.sub.a427 A.sub.n54 H H H H H H CN H O L.sub.a428 A.sub.n55 H H H H H H CN H O L.sub.a429 A.sub.n56 H H H H H H CN H O L.sub.a430 A.sub.n57 H H H H H H CN H O L.sub.a431 A.sub.n58 H H H H H H CN H O L.sub.a432 A.sub.n59 H H H H H H CN H O L.sub.a433 A.sub.n60 H H H H H H CN H O L.sub.a434 A.sub.n61 H H H H H H CN H O L.sub.a435 A.sub.n62 H H H H H H CN H O L.sub.a436 A.sub.n63 H H H H H H CN H O L.sub.a437 A.sub.n64 H H H H H H CN H O L.sub.a438 A.sub.n65 H H H H H H CN H O L.sub.a439 A.sub.n66 H H H H H H CN H O L.sub.a440 A.sub.n67 H H H H H H CN H O L.sub.a441 A.sub.n68 H H H H H H CN H O L.sub.a442 A.sub.n69 H H H H H H CN H O L.sub.a443 A.sub.n70 H H H H H H CN H O L.sub.a444 A.sub.n71 H H H H H H CN H O L.sub.a445 A.sub.n72 H H H H H H CN H O L.sub.a446 A.sub.n73 H H H H H H CN H O L.sub.a447 A.sub.n74 H H H H H H CN H O L.sub.a448 A.sub.n75 H H H H H H CN H O L.sub.a449 A.sub.n76 H H H H H H CN H O L.sub.a450 A.sub.n77 H H H H H H CN H O L.sub.a451 A.sub.n78 H H H H H H CN H O L.sub.a452 A.sub.n79 H H H H H H CN H O L.sub.a453 A.sub.n80 H H H H H H CN H O L.sub.a454 A.sub.n81 H H H H H H CN H O L.sub.a455 A.sub.n82 H H H H H H CN H O L.sub.a456 A.sub.n83 H H H H H H CN H O L.sub.a457 A.sub.n84 H H H H H H CN H O L.sub.a458 A.sub.n85 H H H H H H CN H O L.sub.a459 A.sub.n86 H H H H H H CN H O L.sub.a460 A.sub.n87 H H H H H H CN H O L.sub.a461 A.sub.n88 H H H H H H CN H O L.sub.a462 A.sub.n89 H H H H H H CN H O L.sub.a463 A.sub.n90 H H H H H H CN H O L.sub.a464 A.sub.n91 H H H H H H CN H O L.sub.a465 A.sub.n92 H H H H H H CN H O L.sub.a466 A.sub.n93 H H H H H H CN H O L.sub.a467 A.sub.n94 H H H H H H CN H O L.sub.a468 A.sub.n95 H H H H H H CN H O L.sub.a469 A.sub.n96 H H H H H H CN H O L.sub.a470 A.sub.n1 H CD.sub.3 H H H H CN H O L.sub.a471 A.sub.n10 H CD.sub.3 H H H H CN H O L.sub.a472 A.sub.n13 H CD.sub.3 H H H H CN H O L.sub.a473 A.sub.n31 H CD.sub.3 H H H H CN H O L.sub.a474 A.sub.n34 H CD.sub.3 H H H H CN H O L.sub.a475 A.sub.n53 H CD.sub.3 H H H H CN H O L.sub.a476 A.sub.n57 H CD.sub.3 H H H H CN H O L.sub.a477 A.sub.n58 H CD.sub.3 H H H H CN H O L.sub.a478 A.sub.n59 H CD.sub.3 H H H H CN H O L.sub.a479 A.sub.n60 H CD.sub.3 H H H H CN H O L.sub.a480 A.sub.n84 H CD.sub.3 H H H H CN H O L.sub.a481 A.sub.n91 H CD.sub.3 H H H H CN H O L.sub.a482 A.sub.n93 H CD.sub.3 H H H H CN H O L.sub.a483 A.sub.n94 H CD.sub.3 H H H H CN H O L.sub.a484 A.sub.n96 H CD.sub.3 H H H H CN H O L.sub.a485 A.sub.n1 H R.sub.s2 H H H H CN H O L.sub.a486 A.sub.n10 H R.sub.s2 H H H H CN H O L.sub.a487 A.sub.n13 H R.sub.s2 H H H H CN H O L.sub.a488 A.sub.n31 H R.sub.s2 H H H H CN H O L.sub.a489 A.sub.n34 H R.sub.s2 H H H H CN H O L.sub.a490 A.sub.n53 H R.sub.s2 H H H H CN H O L.sub.a491 A.sub.n57 H R.sub.s2 H H H H CN H O L.sub.a492 A.sub.n58 H R.sub.s2 H H H H CN H O L.sub.a493 A.sub.n59 H R.sub.s2 H H H H CN H O L.sub.a494 A.sub.n60 H R.sub.s2 H H H H CN H O L.sub.a495 A.sub.n84 H R.sub.s2 H H H H CN H O L.sub.a496 A.sub.n91 H R.sub.s2 H H H H CN H O L.sub.a497 A.sub.n93 H R.sub.s2 H H H H CN H O L.sub.a498 A.sub.n94 H R.sub.s2 H H H H CN H O L.sub.a499 A.sub.n96 H R.sub.s2 H H H H CN H O L.sub.a500 A.sub.n1 H R.sub.s3 H H H H CN H O L.sub.a501 A.sub.n10 H R.sub.s3 H H H H CN H O L.sub.a502 A.sub.n13 H R.sub.s3 H H H H CN H O L.sub.a503 A.sub.n31 H R.sub.s3 H H H H CN H O L.sub.a504 A.sub.n34 H R.sub.s3 H H H H CN H O L.sub.a505 A.sub.n53 H R.sub.s3 H H H H CN H O L.sub.a506 A.sub.n57 H R.sub.s3 H H H H CN H O L.sub.a507 A.sub.n58 H R.sub.s3 H H H H CN H O L.sub.a508 A.sub.n59 H R.sub.s3 H H H H CN H O L.sub.a509 A.sub.n60 H R.sub.s3 H H H H CN H O L.sub.a510 A.sub.n84 H R.sub.s3 H H H H CN H O L.sub.a511 A.sub.n91 H R.sub.s3 H H H H CN H O L.sub.a512 A.sub.n93 H R.sub.s3 H H H H CN H O L.sub.a513 A.sub.n94 H R.sub.s3 H H H H CN H O L.sub.a514 A.sub.n96 H R.sub.s3 H H H H CN H O L.sub.a515 A.sub.n1 H R.sub.s4 H H H H CN H O L.sub.a516 A.sub.n10 H R.sub.s4 H H H H CN H O L.sub.a517 A.sub.n13 H R.sub.s4 H H H H CN H O L.sub.a518 A.sub.n31 H R.sub.s4 H H H H CN H O L.sub.a519 A.sub.n34 H R.sub.s4 H H H H CN H O L.sub.a520 A.sub.n53 H R.sub.s4 H H H H CN H O L.sub.a521 A.sub.n57 H R.sub.s4 H H H H CN H O L.sub.a522 A.sub.n58 H R.sub.s4 H H H H CN H O L.sub.a523 A.sub.n59 H R.sub.s4 H H H H CN H O L.sub.a524 A.sub.n60 H R.sub.s4 H H H H CN H O L.sub.a525 A.sub.n84 H R.sub.s4 H H H H CN H O L.sub.a526 A.sub.n91 H R.sub.s4 H H H H CN H O L.sub.a527 A.sub.n93 H R.sub.s4 H H H H CN H O L.sub.a528 A.sub.n94 H R.sub.s4 H H H H CN H O L.sub.a529 A.sub.n96 H R.sub.s4 H H H H CN H O L.sub.a530 A.sub.n1 H H H H H H CN D O L.sub.a531 A.sub.n1 H H H H H H CN R.sub.s7 O L.sub.a532 A.sub.n1 H H H H H H CN R.sub.s8 O L.sub.a533 A.sub.n1 H H H H H H CN R.sub.s9 O L.sub.a534 A.sub.n1 H H H H H H CN R.sub.s10 O L.sub.a535 A.sub.n1 H H H H H H CN R.sub.s11 O L.sub.a536 A.sub.n1 H H H H H H CN R.sub.s12 O L.sub.a537 A.sub.n1 H H H H H H CN R.sub.s13 O L.sub.a538 A.sub.n1 H H H H H H CN R.sub.s14 O L.sub.a539 A.sub.n1 H H H H H H CN R.sub.s15 O L.sub.a540 A.sub.n1 H H H H H H CN R.sub.s16 O L.sub.a541 A.sub.n1 H H H H H H CN R.sub.s17 O L.sub.a542 A.sub.n34 H H H H H H CN D O L.sub.a543 A.sub.n34 H H H H H H CN R.sub.s7 O L.sub.a544 A.sub.n34 H H H H H H CN R.sub.s8 O L.sub.a545 A.sub.n34 H H H H H H CN R.sub.s9 O L.sub.a546 A.sub.n34 H H H H H H CN R.sub.s10 O L.sub.a547 A.sub.n34 H H H H H H CN R.sub.s11 O L.sub.a548 A.sub.n34 H H H H H H CN R.sub.s12 O L.sub.a549 A.sub.n34 H H H H H H CN R.sub.s13 O L.sub.a550 A.sub.n34 H H H H H H CN R.sub.s14 O L.sub.a551 A.sub.n34 H H H H H H CN R.sub.s15 O L.sub.a552 A.sub.n34 H H H H H H CN R.sub.s16 O L.sub.a553 A.sub.n34 H H H H H H CN R.sub.s17 O L.sub.a554 A.sub.n1 H H H H H CN H H O L.sub.a555 A.sub.n10 H H H H H CN H H O L.sub.a556 A.sub.n13 H H H H H CN H H O L.sub.a557 A.sub.n31 H H H H H CN H H O L.sub.a558 A.sub.n34 H H H H H CN H H O L.sub.a559 A.sub.n53 H H H H H CN H H O L.sub.a560 A.sub.n57 H H H H H CN H H O L.sub.a561 A.sub.n58 H H H H H CN H H O L.sub.a562 A.sub.n59 H H H H H CN H H O L.sub.a563 A.sub.n60 H H H H H CN H H O L.sub.a564 A.sub.n84 H H H H H CN H H O L.sub.a565 A.sub.n91 H H H H H CN H H O L.sub.a566 A.sub.n93 H H H H H CN H H O L.sub.a567 A.sub.n94 H H H H H CN H H O L.sub.a568 A.sub.n1 H H H H CN H H H O L.sub.a569 A.sub.n10 H H H H CN H H H O L.sub.a570 A.sub.n13 H H H H CN H H H O L.sub.a571 A.sub.n31 H H H H CN H H H O L.sub.a572 A.sub.n34 H H H H CN H H H O L.sub.a573 A.sub.n53 H H H H CN H H H O L.sub.a574 A.sub.n57 H H H H CN H H H O L.sub.a575 A.sub.n58 H H H H CN H H H O L.sub.a576 A.sub.n59 H H H H CN H H H O L.sub.a577 A.sub.n60 H H H H CN H H H O L.sub.a578 A.sub.n84 H H H H CN H H H O L.sub.a579 A.sub.n91 H H H H CN H H H O L.sub.a580 A.sub.n93 H H H H CN H H H O L.sub.a581 A.sub.n94 H H H H CN H H H O L.sub.a582 A.sub.n1 H H H H H H F H O L.sub.a583 A.sub.n2 H H H H H H F H O L.sub.a584 A.sub.n3 H H H H H H F H O L.sub.a585 A.sub.n4 H H H H H H F H O L.sub.a586 A.sub.n5 H H H H H H F H O L.sub.a587 A.sub.n6 H H H H H H F H O L.sub.a588 A.sub.n7 H H H H H H F H O L.sub.a589 A.sub.n8 H H H H H H F H O L.sub.a590 A.sub.n9 H H H H H H F H O L.sub.a591 A.sub.n10 H H H H H H F H O L.sub.a592 A.sub.n11 H H H H H H F H O L.sub.a593 A.sub.n12 H H H H H H F H O L.sub.a594 A.sub.n13 H H H H H H F H O L.sub.a595 A.sub.n14 H H H H H H F H O L.sub.a596 A.sub.n15 H H H H H H F H O L.sub.a597 A.sub.n16 H H H H H H F H O L.sub.a598 A.sub.n17 H H H H H H F H O L.sub.a599 A.sub.n18 H H H H H H F H O L.sub.a600 A.sub.n19 H H H H H H F H O L.sub.a601 A.sub.n20 H H H H H H F H O L.sub.a602 A.sub.n21 H H H H H H F H O L.sub.a603 A.sub.n22 H H H H H H F H O L.sub.a604 A.sub.n23 H H H H H H F H O L.sub.a605 A.sub.n24 H H H H H H F H O L.sub.a606 A.sub.n25 H H H H H H F H O L.sub.a607 A.sub.n26 H H H H H H F H O L.sub.a608 A.sub.n27 H H H H H H F H O L.sub.a609 A.sub.n28 H H H H H H F H O L.sub.a610 A.sub.n29 H H H H H H F H O L.sub.a611 A.sub.n30 H H H H H H F H O L.sub.a612 A.sub.n31 H H H H H H F H O L.sub.a613 A.sub.n32 H H H H H H F H O L.sub.a614 A.sub.n33 H H H H H H F H O L.sub.a615 A.sub.n34 H H H H H H F H O L.sub.a616 A.sub.n35 H H H H H H F H O L.sub.a617 A.sub.n36 H H H H H H F H O L.sub.a618 A.sub.n37 H H H H H H F H O L.sub.a619 A.sub.n38 H H H H H H F H O L.sub.a620 A.sub.n39 H H H H H H F H O L.sub.a621 A.sub.n40 H H H H H H F H O L.sub.a622 A.sub.n41 H H H H H H F H O L.sub.a623 A.sub.n42 H H H H H H F H O L.sub.a624 A.sub.n43 H H H H H H F H O L.sub.a625 A.sub.n44 H H H H H H F H O L.sub.a626 A.sub.n45 H H H H H H F H O L.sub.a627 A.sub.n46 H H H H H H F H O L.sub.a628 A.sub.n47 H H H H H H F H O L.sub.a629 A.sub.n48 H H H H H H F H O L.sub.a630 A.sub.n49 H H H H H H F H O L.sub.a631 A.sub.n50 H H H H H H F H O L.sub.a632 A.sub.n51 H H H H H H F H O L.sub.a633 A.sub.n52 H H H H H H F H O L.sub.a634 A.sub.n53 H H H H H H F H O L.sub.a635 A.sub.n54 H H H H H H F H O L.sub.a636 A.sub.n55 H H H H H H F H O L.sub.a637 A.sub.n56 H H H H H H F H O L.sub.a638 A.sub.n57 H H H H H H F H O L.sub.a639 A.sub.n58 H H H H H H F H O L.sub.a640 A.sub.n59 H H H H H H F H O L.sub.a641 A.sub.n60 H H H H H H F H O L.sub.a642 A.sub.n61 H H H H H H F H O L.sub.a643 A.sub.n62 H H H H H H F H O L.sub.a644 A.sub.n63 H H H H H H F H O L.sub.a645 A.sub.n64 H H H H H H F H O L.sub.a646 A.sub.n65 H H H H H H F H O L.sub.a647 A.sub.n66 H H H H H H F H O L.sub.a648 A.sub.n67 H H H H H H F H O L.sub.a649 A.sub.n68 H H H H H H F H O L.sub.a650 A.sub.n69 H H H H H H F H O L.sub.a651 A.sub.n70 H H H H H H F H O L.sub.a652 A.sub.n71 H H H H H H F H O L.sub.a653 A.sub.n72 H H H H H H F H O L.sub.a654 A.sub.n73 H H H H H H F H O L.sub.a655 A.sub.n74 H H H H H H F H O L.sub.a656 A.sub.n75 H H H H H H F H O L.sub.a657 A.sub.n76 H H H H H H F H O L.sub.a658 A.sub.n77 H H H H H H F H O L.sub.a659 A.sub.n78 H H H H H H F H O L.sub.a660 A.sub.n79 H H H H H H F H O L.sub.a661 A.sub.n80 H H H H H H F H O L.sub.a662 A.sub.n81 H H H H H H F H O L.sub.a663 A.sub.n82 H H H H H H F H O L.sub.a664 A.sub.n83 H H H H H H F H O L.sub.a665 A.sub.n84 H H H H H H F H O L.sub.a666 A.sub.n85 H H H H H H F H O L.sub.a667 A.sub.n86 H H H H H H F H O L.sub.a668 A.sub.n87 H H H H H H F H O L.sub.a669 A.sub.n88 H H H H H H F H O L.sub.a670 A.sub.n89 H H H H H H F H O L.sub.a671 A.sub.n90 H H H H H H F H O L.sub.a672 A.sub.n91 H H H H H H F H O L.sub.a673 A.sub.n92 H H H H H H F H O L.sub.a674 A.sub.n93 H H H H H H F H O L.sub.a675 A.sub.n94 H H H H H H F H O L.sub.a676 A.sub.n95 H H H H H H F H O L.sub.a677 A.sub.n96 H H H H H H F H O L.sub.a678 A.sub.n1 H H H H H H F D O L.sub.a679 A.sub.n1 H H H H H H F R.sub.s7 O L.sub.a680 A.sub.n1 H H H H H H F R.sub.s8 O L.sub.a681 A.sub.n1 H H H H H H F R.sub.s9 O L.sub.a682 A.sub.n1 H H H H H H F R.sub.s10 O L.sub.a683 A.sub.n1 H H H H H H F R.sub.s11 O L.sub.a834 A.sub.n1 H H H H H H F R.sub.s12 O L.sub.a685 A.sub.n1 H H H H H H F R.sub.s13 O L.sub.a686 A.sub.n1 H H H H H H F R.sub.s14 O L.sub.a687 A.sub.n1 H H H H H H F R.sub.s15 O L.sub.a688 A.sub.n1 H H H H H H F R.sub.s16 O L.sub.a689 A.sub.n1 H H H H H H F R.sub.s17 O L.sub.a690 A.sub.n34 H H H H H H F D O L.sub.a691 A.sub.n34 H H H H H H F R.sub.s7 O L.sub.a692 A.sub.n34 H H H H H H F R.sub.s8 O L.sub.a693 A.sub.n34 H H H H H H F R.sub.s9 O L.sub.a694 A.sub.n34 H H H H H H F R.sub.s10 O L.sub.a695 A.sub.n34 H H H H H H F R.sub.s11 O L.sub.a696 A.sub.n34 H H H H H H F R.sub.s12 O L.sub.a697 A.sub.n34 H H H H H H F R.sub.s13 O L.sub.a698 A.sub.n34 H H H H H H F R.sub.s14 O L.sub.a699 A.sub.n34 H H H H H H F R.sub.s15 O L.sub.a700 A.sub.n34 H H H H H H F R.sub.s16 O L.sub.a701 A.sub.n34 H H H H H H F R.sub.s17 O L.sub.a702 A.sub.n1 H H H H H H H H S L.sub.a703 A.sub.n10 H H H H H H H H S L.sub.a704 A.sub.n13 H H H H H H H H S L.sub.a705 A.sub.n31 H H H H H H H H S L.sub.a706 A.sub.n34 H H H H H H H H S L.sub.a707 A.sub.n53 H H H H H H H H S L.sub.a708 A.sub.n57 H H H H H H H H S L.sub.a709 A.sub.n58 H H H H H H H H S L.sub.a710 A.sub.n59 H H H H H H H H S L.sub.a711 A.sub.n60 H H H H H H H H S L.sub.a712 A.sub.n84 H H H H H H H H S L.sub.a713 A.sub.n91 H H H H H H H H S L.sub.a714 A.sub.n93 H H H H H H H H S L.sub.a715 A.sub.n94 H H H H H H H H S L.sub.a716 A.sub.n96 H H H H H H H H S L.sub.a717 A.sub.n1 H H H H H H H CN S L.sub.a718 A.sub.n10 H H H H H H H CN S L.sub.a719 A.sub.n13 H H H H H H H CN S L.sub.a720 A.sub.n31 H H H H H H H CN S L.sub.a721 A.sub.n34 H H H H H H H CN S L.sub.a722 A.sub.n53 H H H H H H H CN S L.sub.a723 A.sub.n57 H H H H H H H CN S L.sub.a724 A.sub.n58 H H H H H H H CN S L.sub.a725 A.sub.n59 H H H H H H H CN S L.sub.a726 A.sub.n60 H H H H H H H CN S L.sub.a727 A.sub.n84 H H H H H H H CN S L.sub.a728 A.sub.n91 H H H H H H H CN S L.sub.a729 A.sub.n93 H H H H H H H CN S L.sub.a730 A.sub.n94 H H H H H H H CN S L.sub.a731 A.sub.n96 H H H H H H H CN S L.sub.a732 A.sub.n1 H H H H H H CN H S L.sub.a733 A.sub.n10 H H H H H H CN H S L.sub.a734 A.sub.n13 H H H H H H CN H S L.sub.a735 A.sub.n31 H H H H H H CN H S L.sub.a736 A.sub.n34 H H H H H H CN H S L.sub.a737 A.sub.n53 H H H H H H CN H S L.sub.a738 A.sub.n57 H H H H H H CN H S L.sub.a739 A.sub.n58 H H H H H H CN H S L.sub.a740 A.sub.n59 H H H H H H CN H S L.sub.a741 A.sub.n60 H H H H H H CN H S L.sub.a742 A.sub.n84 H H H H H H CN H S L.sub.a743 A.sub.n91 H H H H H H CN H S L.sub.a744 A.sub.n93 H H H H H H CN H S L.sub.a745 A.sub.n94 H H H H H H CN H S L.sub.a746 A.sub.n96 H H H H H H CN H S L.sub.a747 A.sub.n1 H H H H H H F H S L.sub.a748 A.sub.n10 H H H H H H F H S L.sub.a749 A.sub.n13 H H H H H H F H S L.sub.a750 A.sub.n31 H H H H H H F H S L.sub.a751 A.sub.n34 H H H H H H F H S L.sub.a752 A.sub.n53 H H H H H H F H S L.sub.a753 A.sub.n57 H H H H H H F H S L.sub.a754 A.sub.n58 H H H H H H F H S L.sub.a755 A.sub.n59 H H H H H H F H S L.sub.a756 A.sub.n60 H H H H H H F H S L.sub.a757 A.sub.n84 H H H H H H F H S L.sub.a758 A.sub.n91 H H H H H H F H S L.sub.a759 A.sub.n93 H H H H H H F H S L.sub.a760 A.sub.n94 H H H H H H F H S L.sub.a761 A.sub.n96 H H H H H H F H S L.sub.a762 A.sub.n1 H H H H H H H H Se L.sub.a763 A.sub.n1 H H H H H H H CN Se L.sub.a764 A.sub.n1 H H H H H H CN H Se L.sub.a765 A.sub.n1 H H H H H H F H Se L.sub.a766 A.sub.n1 H H H H H H H H Si(CH.sub.3).sub.2 L.sub.a767 A.sub.n1 H H H H H H H CN Si(CH.sub.3).sub.2 L.sub.a768 A.sub.n1 H H H H H H CN H Si(CH.sub.3).sub.2 L.sub.a769 A.sub.n1 H H H H H H F H Si(CH.sub.3).sub.2 L.sub.a770 A.sub.n1 H H H H H H H H NPh L.sub.a771 A.sub.n1 H H H H H H H CN NPh L.sub.a772 A.sub.n1 H H H H H H CN H NPh L.sub.a773 A.sub.n1 H H H H H H F H NPh L.sub.a774 to L.sub.a789 have the following general formula: ##STR00051## wherein R.sub.n, R.sub.Y1 to R.sub.Y3, R.sub.X4 to R.sub.X8 and Z are selected from atoms or groups in the following table: TABLE-US-00006 Ligand L.sub.a No. R.sub.n R.sub.Y1 R.sub.Y2 R.sub.Y3 R.sub.X4 R.sub.X5 R.sub.X6 R.sub.X7 R.sub.X8 Z L.sub.a774 A.sub.n1 H H H H H H H H O L.sub.a775 A.sub.n1 H H H H H H H CN O L.sub.a776 A.sub.n1 H H H H H H CN H O L.sub.a777 A.sub.n1 H H H H H H F H O L.sub.a778 A.sub.n31 H H H H H H H H O L.sub.a779 A.sub.n31 H H H H H H H CN O L.sub.a780 A.sub.n31 H H H H H H CN H O L.sub.a781 A.sub.n31 H H H H H H F H O L.sub.a782 A.sub.n34 H H H H H H H H O L.sub.a783 A.sub.n34 H H H H H H H CN O L.sub.a784 A.sub.n34 H H H H H H CN H O L.sub.a785 A.sub.n34 H H H H H H F H O L.sub.a786 A.sub.n53 H H H H H H H H O L.sub.a787 A.sub.n53 H H H H H H H CN O L.sub.a788 A.sub.n53 H H H H H H CN H O L.sub.a789 A.sub.n53 H H H H H H F H O L.sub.a790 to L.sub.a805 have the following general formula: ##STR00052## wherein R.sub.n, R.sub.Y1 to R.sub.Y3, R.sub.X4 to R.sub.X5 and Z are selected from atoms or groups in the following table: TABLE-US-00007 Ligand L.sub.a No. R.sub.n R.sub.Y1 R.sub.Y2 R.sub.Y3 R.sub.X4 R.sub.X5 R.sub.X6 R.sub.X7 R.sub.X8 Z L.sub.a790 A.sub.n1 H H H H H H H H O L.sub.a791 A.sub.n1 H H H H H H H CN O L.sub.a792 A.sub.n1 H H H H H H CN H O L.sub.a793 A.sub.n1 H H H H H H F H O L.sub.a794 A.sub.n31 H H H H H H H H O L.sub.a795 A.sub.n31 H H H H H H H CN O L.sub.a796 A.sub.n31 H H H H H H CN H O L.sub.a797 A.sub.n31 H H H H H H F H O L.sub.a798 A.sub.n34 H H H H H H H H O L.sub.a799 A.sub.n34 H H H H H H H CN O L.sub.a800 A.sub.n34 H H H H H H CN H O L.sub.a801 A.sub.n34 H H H H H H F H O L.sub.a802 A.sub.n53 H H H H H H H H O L.sub.a803 A.sub.n53 H H H H H H H CN O L.sub.a804 A.sub.n53 H H H H H H CN H O L.sub.a805 A.sub.n53 H H H H H H F H O L.sub.a806 to L.sub.a821 have the following general formula: ##STR00053## wherein R.sub.n, R.sub.Y1 to R.sub.Y3, R.sub.X4 to R.sub.X7 and Z are selected from atoms or groups in the following table: TABLE-US-00008 Ligand L.sub.a No. R.sub.n R.sub.Y1 R.sub.Y2 R.sub.Y3 R.sub.X4 R.sub.X5 R.sub.X6 R.sub.X7 Z L.sub.a806 A.sub.n1 H H H H H H H O L.sub.a807 A.sub.n31 H H H H H H H O L.sub.a808 A.sub.n34 H H H H H H H O L.sub.a809 A.sub.n53 H H H H H H H O L.sub.a810 A.sub.n1 H H H H H H CN O L.sub.a811 A.sub.n31 H H H H H H CN O L.sub.a812 A.sub.n34 H H H H H H CN O L.sub.a813 A.sub.n53 H H H H H H CN O L.sub.a814 A.sub.n1 H H H H H H F O L.sub.a815 A.sub.n31 H H H H H H F O L.sub.a816 A.sub.n34 H H H H H H F O L.sub.a817 A.sub.n53 H H H H H H F O L.sub.a818 A.sub.n1 H H H H H H A.sub.n1 O L.sub.a819 A.sub.n31 H H H H H H A.sub.n1 O L.sub.a820 A.sub.n34 H H H H H H A.sub.n1 O L.sub.a821 A.sub.n53 H H H H H H A.sub.n1 O wherein ##STR00054## ##STR00055## wherein “*” represents a position where R.sub.s1 to R.sub.s17 are each joined; optionally, hydrogens in L.sub.a1 to L.sub.a821 can be partially or fully deuterated.
16. The metal complex according to claim 15, wherein L.sub.b is, at each occurrence identically or differently, selected from the group consisting of: ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## wherein optionally, hydrogen atoms in L.sub.b1 to L.sub.b334 can be partially or fully deuterated.
17. The metal complex according to claim 2, wherein L.sub.c is, at each occurrence identically or differently, selected from the group consisting of: ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177##
18. The metal complex according to claim 16, wherein the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 435, wherein Metal Complex 1 to Metal Complex 435 have the structure of IrL.sub.a(L.sub.b).sub.2, wherein the two L.sub.b are the same and L.sub.a and L.sub.b correspond to structures shown in the following table, respectively: TABLE-US-00009 Metal Metal Metal Complex L.sub.a L.sub.b Complex L.sub.a L.sub.b Complex L.sub.a L.sub.b 1 L.sub.a1 L.sub.b1 2 L.sub.a31 L.sub.b1 3 L.sub.a34 L.sub.b1 4 L.sub.a53 L.sub.b1 5 L.sub.a91 L.sub.b1 6 L.sub.a93 L.sub.b1 7 L.sub.a94 L.sub.b1 8 L.sub.a96 L.sub.b1 9 L.sub.a97 L.sub.b1 10 L.sub.a202 L.sub.b1 11 L.sub.a232 L.sub.b1 12 L.sub.a235 L.sub.b1 13 L.sub.a254 L.sub.b1 14 L.sub.a298 L.sub.b1 15 L.sub.a374 L.sub.b1 16 L.sub.a404 L.sub.b1 17 L.sub.a407 L.sub.b1 18 L.sub.a426 L.sub.b1 19 L.sub.a464 L.sub.b1 20 L.sub.a466 L.sub.b1 21 L.sub.a467 L.sub.b1 22 L.sub.a469 L.sub.b1 23 L.sub.a470 L.sub.b1 24 L.sub.a473 L.sub.b1 25 L.sub.a474 L.sub.b1 26 L.sub.a475 L.sub.b1 27 L.sub.a481 L.sub.b1 28 L.sub.a482 L.sub.b1 29 L.sub.a483 L.sub.b1 30 L.sub.a484 L.sub.b1 31 L.sub.a582 L.sub.b1 32 L.sub.a612 L.sub.b1 33 L.sub.a615 L.sub.b1 34 L.sub.a634 L.sub.b1 35 L.sub.a732 L.sub.b1 36 L.sub.a810 L.sub.b1 37 L.sub.a1 L.sub.b3 38 L.sub.a31 L.sub.b3 39 L.sub.a34 L.sub.b3 40 L.sub.a53 L.sub.b3 41 L.sub.a91 L.sub.b3 42 L.sub.a93 L.sub.b3 43 L.sub.a94 L.sub.b3 44 L.sub.a96 L.sub.b3 45 L.sub.a97 L.sub.b3 46 L.sub.a202 L.sub.b3 47 L.sub.a232 L.sub.b3 48 L.sub.a235 L.sub.b3 49 L.sub.a254 L.sub.b3 50 L.sub.a298 L.sub.b3 51 L.sub.a374 L.sub.b3 52 L.sub.a404 L.sub.b3 53 L.sub.a407 L.sub.b3 54 L.sub.a426 L.sub.b3 55 L.sub.a464 L.sub.b3 56 L.sub.a466 L.sub.b3 57 L.sub.a467 L.sub.b3 58 L.sub.a469 L.sub.b3 59 L.sub.a470 L.sub.b3 60 L.sub.a473 L.sub.b3 61 L.sub.a474 L.sub.b3 62 L.sub.a475 L.sub.b3 63 L.sub.a481 L.sub.b3 64 L.sub.a482 L.sub.b3 65 L.sub.a483 L.sub.b3 66 L.sub.a484 L.sub.b3 67 L.sub.a582 L.sub.b3 68 L.sub.a612 L.sub.b3 69 L.sub.a615 L.sub.b3 70 L.sub.a634 L.sub.b3 71 L.sub.a732 L.sub.b3 72 L.sub.a810 L.sub.b3 73 L.sub.a1 L.sub.b8 74 L.sub.a31 L.sub.b8 75 L.sub.a34 L.sub.b3 76 L.sub.a53 L.sub.b8 77 L.sub.a91 L.sub.b8 78 L.sub.a93 L.sub.b8 79 L.sub.a94 L.sub.b8 80 L.sub.a96 L.sub.b8 81 L.sub.a97 L.sub.b8 82 L.sub.a202 L.sub.b8 83 L.sub.a232 L.sub.b8 84 L.sub.a235 L.sub.b8 85 L.sub.a254 L.sub.b8 86 L.sub.a298 L.sub.b8 87 L.sub.a374 L.sub.b8 88 L.sub.a404 L.sub.b8 89 L.sub.a407 L.sub.b8 90 L.sub.a426 L.sub.b8 91 L.sub.a464 L.sub.b8 92 L.sub.a466 L.sub.b8 93 L.sub.a467 L.sub.b8 94 L.sub.a469 L.sub.b8 95 L.sub.a470 L.sub.b8 96 L.sub.a473 L.sub.b8 97 L.sub.a474 L.sub.b8 98 L.sub.a475 L.sub.b8 99 L.sub.a481 L.sub.b8 100 L.sub.a482 L.sub.b8 101 L.sub.a483 L.sub.b8 102 L.sub.a484 L.sub.b8 103 L.sub.a582 L.sub.b8 104 L.sub.a612 L.sub.b8 105 L.sub.a615 L.sub.b8 106 L.sub.a634 L.sub.b8 107 L.sub.a732 L.sub.b8 108 L.sub.a810 L.sub.b8 109 L.sub.a1 L.sub.b73 110 L.sub.a31 L.sub.b73 111 L.sub.a34 L.sub.b73 112 L.sub.a53 L.sub.b73 113 L.sub.a91 L.sub.b73 114 L.sub.a93 L.sub.b73 115 L.sub.a94 L.sub.b73 116 L.sub.a96 L.sub.b73 117 L.sub.a97 L.sub.b73 118 L.sub.a202 L.sub.b73 119 L.sub.a232 L.sub.b73 120 L.sub.a235 L.sub.b73 121 L.sub.a254 L.sub.b73 122 L.sub.a298 L.sub.b73 123 L.sub.a374 L.sub.b73 124 L.sub.a404 L.sub.b73 125 L.sub.a407 L.sub.b73 126 L.sub.a426 L.sub.b73 127 L.sub.a464 L.sub.b73 128 L.sub.a466 L.sub.b73 129 L.sub.a467 L.sub.b73 130 L.sub.a469 L.sub.b73 131 L.sub.a470 L.sub.b73 132 L.sub.a473 L.sub.b73 133 L.sub.a474 L.sub.b73 134 L.sub.a475 L.sub.b73 135 L.sub.a481 L.sub.b73 136 L.sub.a482 L.sub.b73 137 L.sub.a483 L.sub.b73 138 L.sub.a484 L.sub.b73 139 L.sub.a582 L.sub.b73 140 L.sub.a612 L.sub.b73 141 L.sub.a615 L.sub.b73 142 L.sub.a634 L.sub.b73 143 L.sub.a732 L.sub.b73 144 L.sub.a810 L.sub.b73 145 L.sub.a1 L.sub.b81 146 L.sub.a31 L.sub.b81 147 L.sub.a34 L.sub.b81 148 L.sub.a53 L.sub.b81 149 L.sub.a91 L.sub.b81 150 L.sub.a93 L.sub.b81 151 L.sub.a94 L.sub.b81 152 L.sub.a96 L.sub.b81 153 L.sub.a97 L.sub.b81 154 L.sub.a202 L.sub.b81 155 L.sub.a232 L.sub.b81 156 L.sub.a235 L.sub.b81 157 L.sub.a254 L.sub.b81 158 L.sub.a298 L.sub.b81 159 L.sub.a374 L.sub.b81 160 L.sub.a404 L.sub.b81 161 L.sub.a407 L.sub.b81 162 L.sub.a426 L.sub.b81 163 L.sub.a464 L.sub.b81 164 L.sub.a466 L.sub.b81 165 L.sub.a467 L.sub.b81 166 L.sub.a469 L.sub.b81 167 L.sub.a470 L.sub.b81 168 L.sub.a473 L.sub.b81 169 L.sub.a474 L.sub.b81 170 L.sub.a475 L.sub.b81 171 L.sub.a481 L.sub.b81 172 L.sub.a482 L.sub.b81 173 L.sub.a483 L.sub.b81 174 L.sub.a484 L.sub.b81 175 L.sub.a582 L.sub.b81 176 L.sub.a612 L.sub.b81 177 L.sub.a615 L.sub.b81 178 L.sub.a634 L.sub.b81 179 L.sub.a732 L.sub.b81 180 L.sub.a810 L.sub.b81 181 L.sub.a1 L.sub.b84 182 L.sub.a31 L.sub.b84 183 L.sub.a34 L.sub.b84 184 L.sub.a53 L.sub.b84 185 L.sub.a91 L.sub.b84 186 L.sub.a93 L.sub.b84 187 L.sub.a94 L.sub.b84 188 L.sub.a96 L.sub.b84 189 L.sub.a97 L.sub.b84 190 L.sub.a202 L.sub.b84 191 L.sub.a232 L.sub.b84 192 L.sub.a235 L.sub.b84 193 L.sub.a254 L.sub.b84 194 L.sub.a298 L.sub.b84 195 L.sub.a374 L.sub.b84 196 L.sub.a404 L.sub.b84 197 L.sub.a407 L.sub.b84 198 L.sub.a426 L.sub.b84 199 L.sub.a464 L.sub.b84 200 L.sub.a466 L.sub.b84 201 L.sub.a467 L.sub.b84 202 L.sub.a469 L.sub.b84 203 L.sub.a470 L.sub.b84 204 L.sub.a473 L.sub.b84 205 L.sub.a474 L.sub.b84 206 L.sub.a475 L.sub.b84 207 L.sub.a481 L.sub.b84 208 L.sub.a482 L.sub.b84 209 L.sub.a483 L.sub.b84 210 L.sub.a484 L.sub.b84 211 L.sub.a582 L.sub.b84 212 L.sub.a612 L.sub.b84 213 L.sub.a481 L.sub.b84 214 L.sub.a634 L.sub.b84 215 L.sub.a732 L.sub.b84 216 L.sub.a484 L.sub.b84 217 L.sub.a1 L.sub.b88 218 L.sub.a31 L.sub.b88 219 L.sub.a34 L.sub.b88 220 L.sub.a53 L.sub.b88 221 L.sub.a91 L.sub.b88 222 L.sub.a93 L.sub.b88 223 L.sub.a94 L.sub.b88 224 L.sub.a96 L.sub.b88 225 L.sub.a97 L.sub.b88 226 L.sub.a202 L.sub.b88 227 L.sub.a232 L.sub.b88 228 L.sub.a235 L.sub.b88 229 L.sub.a254 L.sub.b88 230 L.sub.a298 L.sub.b88 231 L.sub.a374 L.sub.b88 232 L.sub.a404 L.sub.b88 233 L.sub.a407 L.sub.b88 234 L.sub.a426 L.sub.b88 235 L.sub.a464 L.sub.b88 236 L.sub.a466 L.sub.b88 237 L.sub.a467 L.sub.b88 238 L.sub.a469 L.sub.b88 239 L.sub.a470 L.sub.b88 240 L.sub.a473 L.sub.b88 241 L.sub.a474 L.sub.b88 242 L.sub.a475 L.sub.b88 243 L.sub.a481 L.sub.b88 244 L.sub.a482 L.sub.b88 245 L.sub.a483 L.sub.b88 246 L.sub.a484 L.sub.b88 247 L.sub.a582 L.sub.b88 248 L.sub.a612 L.sub.b88 249 L.sub.a615 L.sub.b88 250 L.sub.a634 L.sub.b88 251 L.sub.a732 L.sub.b88 252 L.sub.a810 L.sub.b88 253 L.sub.a1 L.sub.b112 254 L.sub.a31 L.sub.b112 255 L.sub.a34 L.sub.b112 256 L.sub.a53 L.sub.b112 257 L.sub.a91 L.sub.b112 258 L.sub.a93 L.sub.b112 259 L.sub.a94 L.sub.b112 260 L.sub.a96 L.sub.b112 261 L.sub.a97 L.sub.b112 262 L.sub.a202 L.sub.b112 263 L.sub.a232 L.sub.b112 264 L.sub.a235 L.sub.b112 265 L.sub.a254 L.sub.b112 266 L.sub.a298 L.sub.b112 267 L.sub.a374 L.sub.b112 268 L.sub.a404 L.sub.b112 269 L.sub.a407 L.sub.b112 270 L.sub.a426 L.sub.b112 271 L.sub.a464 L.sub.b112 272 L.sub.a466 L.sub.b112 273 L.sub.a467 L.sub.b112 274 L.sub.a469 L.sub.b112 275 L.sub.a470 L.sub.b112 276 L.sub.a473 L.sub.b112 277 L.sub.a474 L.sub.b112 278 L.sub.a475 L.sub.b112 279 L.sub.a481 L.sub.b112 280 L.sub.a482 L.sub.b112 281 L.sub.a483 L.sub.b112 282 L.sub.a484 L.sub.b112 283 L.sub.a582 L.sub.b112 284 L.sub.a612 L.sub.b112 285 L.sub.a615 L.sub.b112 286 L.sub.a634 L.sub.b112 287 L.sub.a732 L.sub.b112 288 L.sub.a810 L.sub.b112 289 L.sub.a1 L.sub.b164 290 L.sub.a31 L.sub.b164 291 L.sub.a34 L.sub.b164 292 L.sub.a53 L.sub.b164 293 L.sub.a91 L.sub.b164 294 L.sub.a93 L.sub.b164 295 L.sub.a94 L.sub.b164 296 L.sub.a96 L.sub.b164 297 L.sub.a97 L.sub.b164 298 L.sub.a202 L.sub.b164 299 L.sub.a232 L.sub.b164 300 L.sub.a235 L.sub.b164 301 L.sub.a254 L.sub.b164 302 L.sub.a298 L.sub.b164 303 L.sub.a374 L.sub.b164 304 L.sub.a404 L.sub.b164 305 L.sub.a407 L.sub.b164 306 L.sub.a426 L.sub.b164 307 L.sub.a464 L.sub.b164 308 L.sub.a466 L.sub.b164 309 L.sub.a467 L.sub.b164 310 L.sub.a469 L.sub.b164 311 L.sub.a470 L.sub.b164 312 L.sub.a473 L.sub.b164 313 L.sub.a474 L.sub.b164 314 L.sub.a475 L.sub.b164 315 L.sub.a481 L.sub.b164 316 L.sub.a482 L.sub.b164 317 L.sub.a483 L.sub.b164 318 L.sub.a484 L.sub.b164 319 L.sub.a582 L.sub.b164 320 L.sub.a612 L.sub.b164 321 L.sub.a615 L.sub.b164 322 L.sub.a634 L.sub.b164 323 L.sub.a732 L.sub.b164 324 L.sub.a810 L.sub.b164 325 L.sub.a1 L.sub.b209 326 L.sub.a31 L.sub.b209 327 L.sub.a34 L.sub.b209 328 L.sub.a53 L.sub.b209 329 L.sub.a91 L.sub.b209 330 L.sub.a93 L.sub.b209 331 L.sub.a94 L.sub.b209 332 L.sub.a96 L.sub.b209 333 L.sub.a97 L.sub.b209 334 L.sub.a202 L.sub.b209 335 L.sub.a232 L.sub.b209 336 L.sub.a235 L.sub.b209 337 L.sub.a254 L.sub.b209 338 L.sub.a298 L.sub.b209 339 L.sub.a374 L.sub.b209 340 L.sub.a404 L.sub.b209 341 L.sub.a407 L.sub.b209 342 L.sub.a426 L.sub.b209 343 L.sub.a464 L.sub.b209 344 L.sub.a466 L.sub.b209 345 L.sub.a467 L.sub.b209 346 L.sub.a469 L.sub.b209 347 L.sub.a470 L.sub.b209 348 L.sub.a473 L.sub.b209 349 L.sub.a474 L.sub.b209 350 L.sub.a475 L.sub.b209 351 L.sub.a481 L.sub.b209 352 L.sub.a482 L.sub.b209 353 L.sub.a483 L.sub.b209 354 L.sub.a484 L.sub.b209 355 L.sub.a582 L.sub.b209 356 L.sub.a612 L.sub.b209 357 L.sub.a615 L.sub.b209 358 L.sub.a634 L.sub.b209 359 L.sub.a732 L.sub.b209 360 L.sub.a810 L.sub.b209 362 L.sub.a1 L.sub.b329 362 L.sub.a31 L.sub.b329 363 L.sub.a34 L.sub.b329 364 L.sub.a53 L.sub.b329 365 L.sub.a91 L.sub.b329 366 L.sub.a93 L.sub.b329 367 L.sub.a94 L.sub.b329 368 L.sub.a96 L.sub.b329 369 L.sub.a97 L.sub.b329 370 L.sub.a202 L.sub.b329 371 L.sub.a232 L.sub.b329 372 L.sub.a235 L.sub.b329 373 L.sub.a254 L.sub.b329 374 L.sub.a298 L.sub.b329 375 L.sub.a374 L.sub.b329 376 L.sub.a404 L.sub.b329 377 L.sub.a407 L.sub.b329 378 L.sub.a426 L.sub.b329 379 L.sub.a464 L.sub.b329 380 L.sub.a466 L.sub.b329 381 L.sub.a467 L.sub.b329 382 L.sub.a469 L.sub.b329 383 L.sub.a470 L.sub.b329 384 L.sub.a473 L.sub.b329 385 L.sub.a474 L.sub.b329 386 L.sub.a475 L.sub.b329 387 L.sub.a481 L.sub.b329 388 L.sub.a482 L.sub.b329 389 L.sub.a483 L.sub.b329 390 L.sub.a484 L.sub.b329 391 L.sub.a582 L.sub.b329 392 L.sub.a612 L.sub.b329 393 L.sub.a615 L.sub.b329 394 L.sub.a634 L.sub.b329 395 L.sub.a732 L.sub.b329 396 L.sub.a810 L.sub.b329 397 L.sub.a1 L.sub.b333 398 L.sub.a31 L.sub.b333 399 L.sub.a34 L.sub.b333 400 L.sub.a53 L.sub.b333 401 L.sub.a91 L.sub.b333 402 L.sub.a93 L.sub.b333 403 L.sub.a94 L.sub.b333 404 L.sub.a96 L.sub.b333 405 L.sub.a97 L.sub.b333 406 L.sub.a202 L.sub.b333 407 L.sub.a232 L.sub.b333 408 L.sub.a235 L.sub.b333 409 L.sub.a254 L.sub.b333 410 L.sub.a298 L.sub.b333 411 L.sub.a374 L.sub.b333 412 L.sub.a404 L.sub.b333 413 L.sub.a407 L.sub.b333 414 L.sub.a426 L.sub.b333 415 L.sub.a464 L.sub.b333 416 L.sub.a466 L.sub.b333 417 L.sub.a467 L.sub.b333 418 L.sub.a469 L.sub.b333 419 L.sub.a470 L.sub.b333 420 L.sub.a473 L.sub.b333 421 L.sub.a474 L.sub.b333 422 L.sub.a475 L.sub.b333 423 L.sub.a481 L.sub.b333 424 L.sub.a482 L.sub.b333 425 L.sub.a483 L.sub.b333 426 L.sub.a484 L.sub.b333 427 L.sub.a582 L.sub.b333 428 L.sub.a612 L.sub.b333 429 L.sub.a615 L.sub.b333 430 L.sub.a634 L.sub.b333 431 L.sub.a732 L.sub.b333 432 L.sub.a810 L.sub.b333 433 L.sub.a422 L.sub.b81 434 L.sub.a422 L.sub.b332 435 L.sub.a422 L.sub.b333
19. An organic electroluminescent device, comprising: an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises the metal complex according to claim 1.
20. The organic electroluminescent device according to claim 19, wherein the organic layer comprising the metal complex is a light-emitting layer.
21. The organic electroluminescent device according to claim 20, wherein the light-emitting layer further comprises a first host compound; preferably, the light-emitting layer further comprises a second host compound; more preferably, at least one of the host compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, aza-dibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene and combinations thereof.
22. The organic electroluminescent device according to claim 21, wherein the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer; preferably, the weight of the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.
23. A compound composition, comprising the metal complex according to claim 1.
Description
BRIEF DESCRIPTION OF DRAWINGS
[0030]
[0031]
DETAILED DESCRIPTION
[0032] OLEDs can be fabricated on various types of substrates such as glass, plastic, and metal foil.
[0033] More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference herein in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference herein in its entirety. Examples of host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference herein in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference herein in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference herein in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers are described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference herein in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference herein in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference herein in its entirety.
[0034] The layered structure described above is provided by way of non-limiting examples. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely. It may also include other layers not specifically described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimum performance. Any functional layer may include several sublayers. For example, the emissive layer may have two layers of different emitting materials to achieve desired emission spectrum.
[0035] In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may include a single layer or multiple layers.
[0036] An OLED can be encapsulated by a barrier layer.
[0037] Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablets, phablets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles displays, and vehicle tail lights.
[0038] The materials and structures described herein may be used in other organic electronic devices listed above.
[0039] As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from the substrate. There may be other layers between the first and second layers, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
[0040] As used herein, “solution processible” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
[0041] A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
[0042] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistics limit through delayed fluorescence. As used herein, there are two types of delayed fluorescence, i.e. P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated from triplet-triplet annihilation (TTA).
[0043] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the transition between the triplet states and the singlet excited states. Compounds that are capable of generating E-type delayed fluorescence are required to have very small singlet-triplet gaps to convert between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A distinctive feature of TADF is that the delayed component increases as temperature rises. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay from the triplet state, the fraction of back populated singlet excited states can potentially reach 75%. The total singlet fraction can be 100%, far exceeding 25% of the spin statistics limit for electrically generated excitons.
[0044] E-type delayed fluorescence characteristics can be found in an exciplex system or in a single compound. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE.sub.S-T). Organic, non-metal containing, donor-acceptor luminescent materials may be able to achieve this. The emission in these materials is generally characterized as a donor-acceptor charge-transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds generally results in small ΔE.sub.S-T. These states may involve CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety such as amino- or carbazole-derivatives and an electron acceptor moiety such as N-containing six-membered aromatic rings.
Definition of Terms of Substituents
[0045] Halogen or halide—as used herein includes fluorine, chlorine, bromine, and iodine.
[0046] Alkyl—as used herein includes both straight and branched chain alkyl groups. Alkyl may be alkyl having 1 to 20 carbon atoms, preferably alkyl having 1 to 12 carbon atoms, and more preferably alkyl having 1 to 6 carbon atoms. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a neopentyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl group. Of the above, preferred are a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, a neopentyl group, and an n-hexyl group. Additionally, the alkyl group may be optionally substituted.
[0047] Cycloalkyl—as used herein includes cyclic alkyl groups. The cycloalkyl groups may be those having 3 to 20 ring carbon atoms, preferably those having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcylcohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, preferred are cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcylcohexyl. Additionally, the cycloalkyl group may be optionally substituted.
[0048] Heteroalkyl—as used herein, includes a group formed by replacing one or more carbons in an alkyl chain with a hetero-atom(s) selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom, and a boron atom. Heteroalkyl may be those having 1 to 20 carbon atoms, preferably those having 1 to 10 carbon atoms, and more preferably those having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butylmethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl group may be optionally substituted.
[0049] Alkenyl—as used herein includes straight chain, branched chain, and cyclic alkene groups. Alkenyl may be those having 2 to 20 carbon atoms, preferably those having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, 1-propenyl group, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butandienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl group may be optionally substituted.
[0050] Alkynyl—as used herein includes straight chain alkynyl groups. Alkynyl may be those having 2 to 20 carbon atoms, preferably those having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Of the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl. Additionally, the alkynyl group may be optionally substituted.
[0051] Aryl or an aromatic group—as used herein includes non-condensed and condensed systems. Aryl may be those having 6 to 30 carbon atoms, preferably those having 6 to 20 carbon atoms, and more preferably those having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenylyl, 4″-t-butyl-p-terphenyl-4-yl, o-cumenyl, m-cumenyl, p-cumenyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, and m-quarterphenyl. Additionally, the aryl group may be optionally substituted.
[0052] Heterocyclic groups or heterocycle—as used herein include non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, where at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, each of which includes at least one hetero-atom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. Additionally, the heterocyclic group may be optionally substituted.
[0053] Heteroaryl—as used herein, includes non-condensed and condensed hetero-aromatic groups having 1 to 5 hetero-atoms, where at least one hetero-atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. A hetero-aromatic group is also referred to as heteroaryl. Heteroaryl may be those having 3 to 30 carbon atoms, preferably those having 3 to 20 carbon atoms, and more preferably those having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.
[0054] Alkoxy—as used herein, is represented by —O-alkyl, —O-cycloalkyl, —O-heteroalkyl, or —O-heterocyclic group. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as those described above. Alkoxy groups may be those having 1 to 20 carbon atoms, preferably those having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy group may be optionally substituted.
[0055] Aryloxy—as used herein, is represented by —O-aryl or —O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. Aryloxy groups may be those having 6 to 30 carbon atoms, preferably those having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy. Additionally, the aryloxy group may be optionally substituted.
[0056] Arylalkyl—as used herein, contemplates alkyl substituted with an aryl group. Arylalkyl may be those having 7 to 30 carbon atoms, preferably those having 7 to 20 carbon atoms, and more preferably those having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, alpha-naphthylmethyl, 1-alpha-naphthylethyl, 2-alpha-naphthylethyl, 1-alpha-naphthylisopropyl, 2-alpha-naphthylisopropyl, beta-naphthylmethyl, 1-beta-naphthylethyl, 2-beta-naphthylethyl, 1-beta-naphthylisopropyl, 2-beta-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Of the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl. Additionally, the arylalkyl group may be optionally substituted.
[0057] Alkylsilyl—as used herein, contemplates a silyl group substituted with an alkyl group. Alkylsilyl groups may be those having 3 to 20 carbon atoms, preferably those having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl t-butylsilyl, and methyldi-t-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.
[0058] Arylsilyl—as used herein, contemplates a silyl group substituted with an aryl group. Arylsilyl groups may be those having 6 to 30 carbon atoms, preferably those having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl t-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.
[0059] Alkylgermanyl—as used herein contemplates germanyl substituted with an alkyl group. The alkylgermanyl may be those having 3 to 20 carbon atoms, preferably those having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-t-butylgermanyl, triisobutylgermanyl, dimethyl-t-butylgermanyl, and methyldi-t-butylgermanyl. Additionally, the alkylgermanyl may be optionally substituted.
[0060] Arylgermanyl—as used herein contemplates a germanyl substituted with at least one aryl group or heteroaryl group. Arylgermanyl may be those having 6 to 30 carbon atoms, preferably those having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, and diphenyl-t-butylgermanyl. Additionally, the arylgermanyl may be optionally substituted.
[0061] The term “aza” in azadibenzofuran, azadibenzothiophene, etc. means that one or more of C—H groups in the respective aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene encompasses dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs with two or more nitrogens in the ring system. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.
[0062] In the present disclosure, unless otherwise defined, when any term of the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic group, substituted arylalkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, a substituted carboxylic acid group, a substituted ester group, substituted sulfinyl, substituted sulfonyl, and substituted phosphino is used, it means that any group of alkyl, cycloalkyl, heteroalkyl, heterocyclic group, arylalkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, a carboxylic acid group, an ester group, sulfinyl, sulfonyl, and phosphino may be substituted with one or more moieties selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, unsubstituted arylalkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl group having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0063] It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or an attached fragment are considered to be equivalent.
[0064] In the compounds mentioned in the present disclosure, hydrogen atoms may be partially or fully replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. The replacement by other stable isotopes in the compounds may be preferred due to its enhancements of device efficiency and stability.
[0065] In the compounds mentioned in the present disclosure, multiple substitution refers to a range that includes a di-substitution, up to the maximum available substitution. When substitution in the compounds mentioned in the present disclosure represents multiple substitution (including di-, tri-, and tetra-substitutions, etc.), that means the substituent may exist at a plurality of available substitution positions on its linking structure, the substituents present at a plurality of available substitution positions may be the same structure or different structures.
[0066] In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be joined to form a ring unless otherwise explicitly defined, for example, adjacent substituents can be optionally joined to form a ring. In the compounds mentioned in the present disclosure, the expression that adjacent substituents can be optionally joined to form a ring includes a case where adjacent substituents may be joined to form a ring and a case where adjacent substituents are not joined to form a ring. When adjacent substituents can be optionally joined to form a ring, the ring formed may be monocyclic or polycyclic (including spirocyclic, endocyclic, fusedcyclic, and etc.), as well as alicyclic, heteroalicyclic, aromatic, or heteroaromatic. In such expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms which are directly bonded to each other, or substituents bonded to carbon atoms which are more distant from each other. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms which are directly bonded to each other.
[0067] The expression that adjacent substituents can be optionally joined to form a ring is also intended to mean that two substituents bonded to the same carbon atom are joined to each other via a chemical bond to form a ring, which can be exemplified by the following formula:
##STR00006##
[0068] The expression that adjacent substituents can be optionally joined to form a ring is also intended to mean that two substituents bonded to carbon atoms which are directly bonded to each other are joined to each other via a chemical bond to form a ring, which can be exemplified by the following formula:
##STR00007##
[0069] The expression that adjacent substituents can be optionally joined to form a ring is also intended to mean that two substituents bonded to a further distant carbon atom are joined to each other via a chemical bond to form a ring, which can be exemplified by the following formula:
##STR00008##
[0070] Furthermore, the expression that adjacent substituents can be optionally joined to form a ring is also intended to mean that, in the case where one of the two substituents bonded to carbon atoms which are directly bonded to each other represents hydrogen, the second substituent is bonded at a position at which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
##STR00009##
[0071] According to an embodiment of the present disclosure, disclosed is a metal complex comprising a metal M and a ligand L.sub.a coordinated to the metal M, wherein L.sub.a has a structure represented by Formula 1:
##STR00010##
[0072] wherein
[0073] the metal M is selected from a metal with a relative atomic mass greater than 40;
[0074] Z is selected from the group consisting of O, S, Se, NR′, CR′R′ and SiR′R′; when two R′ are present at the same time, the two R′ are the same or different;
[0075] the substituent R.sub.y represents mono-substitution, multiple substitutions or non-substitution;
[0076] X.sub.1 to X.sub.8 are, at each occurrence identically or differently, selected from C, CR.sub.x or N; and two of X.sub.1 to X.sub.4 are selected from C, one C is joined to pyridine in Formula 1, and the other C is coordinated to the metal to form a metal-carbon bond;
[0077] the substituent R.sub.a has a structure represented by Formula 2:
##STR00011##
[0078] wherein in Formula 2,
[0079] the substituents R.sub.A and R.sub.B represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
[0080] the ring A and the ring B are identically or differently selected from a carbocyclic ring having 3 to 30 ring atoms or a heterocyclic ring having 3 to 30 ring atoms;
[0081] A.sub.1, A.sub.2, B.sub.1, B.sub.2 and E are, at each occurrence identically or differently, selected from C, N, B, P, CR′″, SiR′″ or GeR′″;
[0082] L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof;
[0083] the substituents R′, R″, R′″, R.sub.x, R.sub.y, R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof,
[0084] “*” represents a position where Formula 2 is joined; and
[0085] adjacent substituents R′, R.sub.x, R″, R′″, R.sub.A, R.sub.B, R.sub.y can be optionally joined to form a ring.
[0086] In the present disclosure, the expression that “L is selected from a single bond” is intended to mean that Formula 2 has the following structure:
##STR00012##
wherein A.sub.1, A.sub.2, B.sub.1, B.sub.2, E, the ring A, the ring B, R.sub.A and R.sub.B are defined as described herein.
[0087] In the present disclosure, the expression that “adjacent substituents R′, R.sub.x, R″, R′″, R.sub.A, R.sub.B, R.sub.y can be optionally joined to form a ring” is intended to mean that any one or more of groups of adjacent substituents, such as two substituents R′, two substituents R.sub.x, two substituents R.sub.A, two substituents R.sub.B, two substituents R.sub.y, substituents R′ and R.sub.x, substituents R′ and R.sub.y, substituents R.sub.A and R.sub.B, substituents R.sub.A and R″, substituents R″ and R.sub.B, substituents R.sub.A and R.sub.y and substituents R.sub.y and R.sub.B, can be joined to form a ring. Obviously, it is also possible that none of these substituents are joined to form a ring.
[0088] According to an embodiment of the present disclosure, the ligand L.sub.a is, at each occurrence identically or differently, selected from any one of the group consisting of the following structures:
##STR00013##
[0089] wherein
[0090] Z is selected from the group consisting of O, S, Se, NR′, CR′R′ and SiR′R′; when two R′ are present at the same time, the two R′ are the same or different;
[0091] the substituent R.sub.y represents mono-substitution, multiple substitutions or non-substitution; in Formula 1a and Formula 1c, X.sub.3 to X.sub.5 are, at each occurrence identically or differently, selected from CR.sub.x or N;
[0092] in Formula 1b, X.sub.1 and X.sub.4 to X.sub.5 are, at each occurrence identically or differently, selected from CR.sub.x or N;
[0093] in Formula 1d and Formula 1e, X.sub.1, X.sub.2, and X.sub.5 to X.sub.5 are, at each occurrence identically or differently, selected from CR.sub.x or N;
[0094] the substituent R.sub.n has a structure represented by Formula 2:
##STR00014##
[0095] wherein in Formula 2,
[0096] the substituents R.sub.A and R.sub.B represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
[0097] the ring A and the ring B are identically or differently selected from a carbocyclic ring having 3 to 30 ring atoms or a heterocyclic ring having 3 to 30 ring atoms;
[0098] A.sub.1, A.sub.2, B.sub.1, B.sub.2 and E are, at each occurrence identically or differently, selected from C, N, B, P, CR′″, SiR′″ or GeR′″;
[0099] L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof,
[0100] the substituents R′, R″, R′″, R.sub.x, R.sub.y, R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof,
[0101] “*” represents a position where Formula 2 is joined; and
[0102] adjacent substituents R′, R.sub.x, R″, R′″, R.sub.A, R.sub.B, R.sub.y can be optionally joined to form a ring.
[0103] According to an embodiment of the present disclosure, the metal complex has a general formula of M(L.sub.a).sub.m(L.sub.b).sub.n(L.sub.c).sub.q;
[0104] wherein
[0105] the metal M is selected from a metal with a relative atomic mass greater than 40; preferably, M is, at each occurrence identically or differently, selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; more preferably, M is, at each occurrence identically or differently, selected from Pt or Ir;
[0106] L.sub.a, L.sub.b and L.sub.c are a first ligand, a second ligand and a third ligand coordinated to the metal M, respectively, and L.sub.c is the same as or different from L.sub.a or L.sub.b; wherein L.sub.a, L.sub.b and L.sub.c can be optionally joined to form a multidentate ligand; for example, any two of the ligands L.sub.a, L.sub.b and L.sub.c are joined to form a tetradentate ligand, the ligands L.sub.a, L.sub.b and L.sub.c are joined to form a hexadentate ligand, or none of the ligands L.sub.a, L.sub.b and L.sub.c are joined to form a multidentate ligand;
[0107] m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q equals to the oxidation state of the metal M; when m is greater than or equal to 2, multiple L.sub.a are the same or different; when n is equal to 2, two L.sub.b are the same or different; when q is equal to 2, two L.sub.c are the same or different;
[0108] L.sub.b and L.sub.c are, at each occurrence identically or differently, selected from a structure represented by any one of the group consisting of:
##STR00015##
[0109] wherein
[0110] the substituents R.sub.a and R.sub.b represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
[0111] X.sub.b is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR.sub.N1 and CR.sub.C1R.sub.C2;
[0112] the substituents R.sub.a, R.sub.b, R.sub.c, R.sub.N1, R.sub.C1 and R.sub.C2 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof, and
[0113] adjacent substituents R.sub.a, R.sub.b, R.sub.c, R.sub.N1, R.sub.C1 and R.sub.C2 can be optionally joined to form a ring.
[0114] In the present disclosure, the expression that “adjacent substituents R.sub.a, R.sub.b, R.sub.c, R.sub.N1, R.sub.C1 and R.sub.C2 can be optionally joined to form a ring” is intended to mean that any one or more of groups of adjacent substituents, such as two substituents R.sub.a, two substituents R.sub.b, substituents R.sub.a and R.sub.b, substituents R.sub.a and R.sub.c, substituents R.sub.b and R.sub.c, substituents R.sub.a and R.sub.N1, substituents R.sub.b and R.sub.N1, substituents R.sub.a and R.sub.C1, substituents R.sub.a and R.sub.C2, substituents R.sub.b and R.sub.C1, substituents R.sub.b and R.sub.C2 and substituents R.sub.C1 and R.sub.C2, can be joined to form a ring. Obviously, it is also possible that none of these substituents are joined to form a ring.
[0115] According to an embodiment of the present disclosure, the metal complex has a general formula of Ir(L.sub.a).sub.m(L.sub.b).sub.3-m and is represented by Formula 3:
##STR00016##
[0116] wherein
[0117] m is selected from 1, 2 or 3; when m is selected from 1, two L.sub.b are the same or different; when m is selected from 2 or 3, multiple L.sub.a are the same or different;
[0118] Z is selected from the group consisting of O, S, Se, NR′, CR′R′ and SiR′R′; when two R′ are present at the same time, the two R′ are the same or different;
[0119] the substituent R.sub.y represents mono-substitution, multiple substitutions or non-substitution;
[0120] X.sub.3 to X.sub.5 are, at each occurrence identically or differently, selected from CR.sub.x or N;
[0121] the substituent R.sub.n has a structure represented by Formula 2:
##STR00017##
[0122] wherein in Formula 2,
[0123] the substituents R.sub.A and R.sub.B represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
[0124] the ring A and the ring B are identically or differently selected from a carbocyclic ring having 3 to 30 ring atoms or a heterocyclic ring having 3 to 30 ring atoms;
[0125] A.sub.1, A.sub.2, B.sub.1, B.sub.2 and E are, at each occurrence identically or differently, selected from C, N, B, P, CR′″, SiR′″ or GeR′″;
[0126] L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof,
[0127] the substituents R.sub.1 to R.sub.8, R′, R″, R′″, R.sub.x, R.sub.y, R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof,
[0128] “*” represents a position where Formula 2 is joined;
[0129] adjacent substituents R′, R.sub.x, R″, R′″, R.sub.A, R.sub.B, R.sub.y can be optionally joined to form a ring; and
[0130] adjacent substituents R.sub.1 to R.sub.8 can be optionally joined to form a ring.
[0131] In this embodiment, the expression that “adjacent substituents R.sub.1 to R.sub.8 can be optionally joined to form a ring” is intended to mean that any one or more of groups of any two adjacent substituents of R.sub.1 to R.sub.8 can be joined to form a ring. Obviously, it is also possible that none of these substituents are joined to form a ring.
[0132] According to an embodiment of the present disclosure, Z is selected from 0 or S.
[0133] According to an embodiment of the present disclosure, Z is selected from 0.
[0134] According to an embodiment of the present disclosure, X.sub.1 to X.sub.5 are, at each occurrence identically or differently, selected from CR.sub.x.
[0135] According to an embodiment of the present disclosure, X.sub.3 to X.sub.5 are, at each occurrence identically or differently, selected from CR.sub.x.
[0136] According to an embodiment of the present disclosure, at least one of X.sub.1 to X.sub.5 is selected from N. For example, one of X.sub.1 to X.sub.5 is selected from N, or two of X.sub.1 to X.sub.5 are selected from N.
[0137] According to an embodiment of the present disclosure, at least one of X.sub.3 to X.sub.5 is selected from N. For example, one of X.sub.3 to X.sub.5 is selected from N, or two of X.sub.3 to X.sub.5 are selected from N.
[0138] According to an embodiment of the present disclosure, the substituent R.sub.x is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano and combinations thereof.
[0139] According to an embodiment of the present disclosure, the substituent R.sub.x is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano and combinations thereof.
[0140] According to an embodiment of the present disclosure, the substituent R.sub.x is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, biphenyl, pyridyl, trimethylsilyl, trimethylgermanyl and combinations thereof, optionally, hydrogens in the above groups can be partially or fully deuterated.
[0141] According to an embodiment of the present disclosure, the substituent R.sub.n has a structure represented by Formula 4:
##STR00018##
[0142] wherein
[0143] A.sub.3 to A.sub.6 are, at each occurrence identically or differently, selected from CR.sub.A or N;
[0144] B.sub.3 to B.sub.6 are, at each occurrence identically or differently, selected from CR.sub.B or N;
[0145] L is selected from a single bond, O, S, SO.sub.2, Se, NR″, CR″R″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclylene having 3 to 20 ring atoms, arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms or a combination thereof,
[0146] the substituents R.sub.A, R.sub.B and R″ are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof,
[0147] adjacent substituents R″, R.sub.A, R.sub.B can be optionally joined to form a ring; and
[0148] “*” represents a position where Formula 4 is joined.
[0149] In the present disclosure, the expression that “adjacent substituents R″, R.sub.A, R.sub.B can be optionally joined to form a ring” is intended to mean that any one or more of groups of adjacent substituents, such as two substituents R″, two substituents R.sub.A, two substituents R.sub.B, substituents R″ and R.sub.A and substituents R″ and R.sub.B, can be joined to form a ring. Obviously, it is also possible that none of these substituents are joined to form a ring.
[0150] According to an embodiment of the present disclosure, the ring A and the ring B are identically or differently selected from a carbocyclic ring having 6 ring atoms or a heterocyclic ring having 5 to 6 ring atoms.
[0151] According to an embodiment of the present disclosure, the ring A and the ring B are identically or differently selected from a benzene ring or a heteroaromatic ring having 5 to 6 ring atoms.
[0152] According to an embodiment of the present disclosure, A.sub.3 to A.sub.6 are, at each occurrence identically or differently, selected from CR.sub.A, and the substituent R.sub.A is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano and combinations thereof.
[0153] According to an embodiment of the present disclosure, B.sub.3 to B.sub.6 are, at each occurrence identically or differently, selected from CR.sub.B, and the substituent R.sub.B is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, cyano and combinations thereof.
[0154] According to an embodiment of the present disclosure, the substituents R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano and combinations thereof.
[0155] According to an embodiment of the present disclosure, the substituents R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano and combinations thereof.
[0156] According to an embodiment of the present disclosure, the substituents R.sub.A and R.sub.B are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl and combinations thereof, optionally, hydrogens in the above groups can be partially or fully deuterated.
[0157] According to an embodiment of the present disclosure, L is selected from a single bond, O, S, Se, NR″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, R″C═CR″, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, substituted or unsubstituted heteroalkylene having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 10 ring atoms, substituted or unsubstituted arylene having 6 to 10 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 10 carbon atoms or a combination thereof.
[0158] According to an embodiment of the present disclosure, L is selected from a single bond, O, S, Se, NR″, SiR″R″, GeR″R″, BR″, PR″, P(O)R″, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, substituted or unsubstituted arylene having 6 to 10 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 10 carbon atoms or a combination thereof.
[0159] According to an embodiment of the present disclosure, L is selected from a single bond, O, S, NR″, substituted or unsubstituted alkylene having 1 to 10 carbon atoms or substituted or unsubstituted phenylene.
[0160] According to an embodiment of the present disclosure, L is selected from a single bond, O, S, NR″ or phenylene.
[0161] According to an embodiment of the present disclosure, the substituents R′, R″ and R′″ are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano and combinations thereof.
[0162] According to an embodiment of the present disclosure, the substituents R′, R″ and R′″ are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 6 carbon atoms, cyano and combinations thereof.
[0163] According to an embodiment of the present disclosure, the substituent R′, R″ and R′″ are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl and combinations thereof, optionally, hydrogens in the above groups can be partially or fully deuterated.
[0164] According to an embodiment of the present disclosure, at least one of X.sub.3 to X.sub.5 is CR.sub.x, and the substituent R.sub.x is selected from cyano or fluorine.
[0165] According to an embodiment of the present disclosure, at least one of X.sub.5 to X.sub.5 is CR.sub.x, and the substituent R.sub.x is selected from cyano or fluorine.
[0166] According to an embodiment of the present disclosure, X.sub.7 or X.sub.5 is CR.sub.x, and R.sub.x is selected from cyano.
[0167] According to an embodiment of the present disclosure, X.sub.7 is CR.sub.x, and R.sub.x is selected from fluorine.
[0168] According to an embodiment of the present disclosure, at least two of X.sub.3 to X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is selected from cyano or fluorine, and another substituent R.sub.x is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, isocyano and combinations thereof.
[0169] According to an embodiment of the present disclosure, at least two of X.sub.5 to X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is selected from cyano or fluorine, and another substituent R.sub.x is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, isocyano and combinations thereof.
[0170] According to an embodiment of the present disclosure, X.sub.7 and X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is cyano or fluorine, and the other substituent R.sub.x is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, isocyano and combinations thereof.
[0171] According to an embodiment of the present disclosure, X.sub.7 and X.sub.5 are selected from CR.sub.x, wherein one substituent R.sub.x is cyano or fluorine, and the other substituent R.sub.x is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, cyano, isocyano and combinations thereof.
[0172] According to an embodiment of the present disclosure, R.sub.n is, at each occurrence identically or differently, selected from the group consisting of An.sub.1 to An.sub.96, wherein the specific structures of An.sub.1 to An.sub.96 are referred to claim 11.
[0173] According to an embodiment of the present disclosure, hydrogens in An.sub.1 to An.sub.52, An.sub.54 to An.sub.58 and An.sub.61 to An.sub.96 can be partially or fully deuterated.
[0174] According to an embodiment of the present disclosure, the substituent R.sub.y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 6 to 20 carbon atoms and combinations thereof.
[0175] According to an embodiment of the present disclosure, the substituent R.sub.y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 12 carbon atoms and combinations thereof.
[0176] According to an embodiment of the present disclosure, at least one substituent R.sub.y is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof.
[0177] According to an embodiment of the present disclosure, at least one substituent R.sub.y is selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl and combinations thereof, optionally, hydrogens in the above groups can be partially or fully deuterated.
[0178] According to an embodiment of the present disclosure, at least one or at least two of the substituents R.sub.1 to R.sub.8 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof, and the total number of carbon atoms in all of R.sub.1 to R.sub.4 and/or R.sub.5 to R.sub.8 is at least 4.
[0179] According to an embodiment of the present disclosure, at least one or at least two of the substituents R.sub.1 to R.sub.4 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof, and the total number of carbon atoms in all of the substituents R.sub.1 to R.sub.4 is at least 4.
[0180] According to an embodiment of the present disclosure, at least one or at least two of the substituents R.sub.5 to R.sub.8 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof, and the total number of carbon atoms in all of the substituents R.sub.5 to R.sub.8 is at least 4.
[0181] According to an embodiment of the present disclosure, at least one, at least two, at least three or all of the substituents R.sub.2, R.sub.3, R.sub.6 and R.sub.7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof.
[0182] According to an embodiment of the present disclosure, at least one, at least two, at least three or all of the substituents R.sub.2, R.sub.3, R.sub.6 and R.sub.7 are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms and combinations thereof.
[0183] According to an embodiment of the present disclosure, at least one, at least two, at least three or all of the substituents R.sub.2, R.sub.3, R.sub.6 and R.sub.7 are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, neopentyl, t-pentyl and combinations thereof, optionally, hydrogens in the above groups can be partially or fully deuterated.
[0184] According to an embodiment of the present disclosure, the ligand L.sub.a is, at each occurrence identically or differently, selected from the group consisting of L.sub.a1 to L.sub.a821, wherein the specific structures of L.sub.a1 to L.sub.a821 are referred to claim 15.
[0185] According to an embodiment of the present disclosure, hydrogens in ligands L.sub.a1 to L.sub.a821 can be partially or fully deuterated.
[0186] According to an embodiment of the present disclosure, the ligand L.sub.b is, at each occurrence identically or differently, selected from the group consisting of L.sub.b1 to L.sub.b334, wherein the specific structures of L.sub.b1 to L.sub.b334 are referred to claim 16.
[0187] According to an embodiment of the present disclosure, hydrogens in ligands L.sub.b1 to L.sub.b334 can be partially or fully deuterated.
[0188] According to an embodiment of the present disclosure, the ligand L.sub.c is, at each occurrence identically or differently, selected from the group consisting of L.sub.c1 to L.sub.c360, wherein the specific structures of L.sub.c1 to L.sub.c360 are referred to claim 17.
[0189] According to an embodiment of the present disclosure, the metal complex has a general formula of Ir(L.sub.a).sub.3, Ir(L.sub.a)(L.sub.b).sub.2, Ir(L.sub.a).sub.2(L.sub.b), Ir(L.sub.a)(L.sub.c).sub.2, Ir(L.sub.a).sub.2(L.sub.c) or Ir(L.sub.a)(L.sub.b)(L.sub.c), wherein L.sub.a is, at each occurrence identically or differently, selected from the group consisting of L.sub.a1 to L.sub.a821, L.sub.b is, at each occurrence identically or differently, selected from the group consisting of L.sub.b1 to L.sub.b334, and the ligand L.sub.c is, at each occurrence identically or differently, selected from the group consisting of L.sub.c1 to L.sub.c360.
[0190] According to an embodiment of the present disclosure, the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 432, wherein the specific structures of Metal Complex 1 to Metal Complex 432 are referred to claim 18.
[0191] According to an embodiment of the present disclosure, hydrogens in Metal Complex 1 to Metal Complex 432 can be partially or fully deuterated.
[0192] According to an embodiment of the present disclosure, the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 435, wherein the specific structures of Metal Complex 1 to Metal Complex 435 are referred to claim 18.
[0193] According to an embodiment of the present disclosure, hydrogens in Metal Complex 1 to Metal Complex 435 can be partially or fully deuterated.
[0194] According to an embodiment of the present disclosure, disclosed is an organic electroluminescent device comprising an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises the metal complex in any one of the preceding embodiments.
[0195] According to an embodiment of the present disclosure, the organic layer comprising the metal complex is a light-emitting layer.
[0196] According to an embodiment of the present disclosure, the organic electroluminescent device emits green light.
[0197] According to an embodiment of the present disclosure, the organic electroluminescent device emits yellow light.
[0198] According to an embodiment of the present disclosure, the light-emitting layer further comprises a first host compound.
[0199] According to an embodiment of the present disclosure, the light-emitting layer further comprises a second host compound.
[0200] According to an embodiment of the present disclosure, at least one of the host compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, aza-dibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene and combinations thereof.
[0201] According to an embodiment of the present disclosure, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
[0202] According to an embodiment of the present disclosure, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.
[0203] According to an embodiment of the present disclosure, disclosed is a compound composition comprising the metal complex in any one of the preceding embodiments.
[0204] Combination with Other Materials
[0205] The materials described in the present disclosure for a particular layer in an organic light-emitting device can be used in combination with various other materials present in the device. The combinations of these materials are described in more detail in U.S. Pat. App. No. 20160359122 at paragraphs 0132-0161, which is incorporated by reference herein in its entirety. The materials described or referred to the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
[0206] The materials described herein as useful for a particular layer in an organic light-emitting device may be used in combination with a variety of other materials present in the device. For example, dopants disclosed herein may be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Pat. App. No. 20150349273, which is incorporated by reference herein in its entirety. The materials described or referred to the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
[0207] In the embodiments of material synthesis, all reactions were performed under nitrogen protection unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. Synthetic products were structurally confirmed and tested for properties using one or more conventional equipment in the art (including, but not limited to, nuclear magnetic resonance instrument produced by BRUKER, liquid chromatograph produced by SHIMADZU, liquid chromatograph-mass spectrometry produced by SHIMADZU, gas chromatograph-mass spectrometry produced by SHIMADZU, differential Scanning calorimeters produced by SHIMADZU, fluorescence spectrophotometer produced by SHANGHAI LENGGUANG TECH., electrochemical workstation produced by WUHAN CORRTEST, and sublimation apparatus produced by ANHUI BEQ, etc.) by methods well known to the persons skilled in the art. In the embodiments of the device, the characteristics of the device were also tested using conventional equipment in the art (including, but not limited to, evaporator produced by ANGSTROM ENGINEERING, optical testing system produced by SUZHOU FATAR, life testing system produced by SUZHOU FATAR, and ellipsometer produced by BEIJING ELLITOP, etc.) by methods well known to the persons skilled in the art. As the persons skilled in the art are aware of the above-mentioned equipment use, test methods and other related contents, the inherent data of the sample can be obtained with certainty and without influence, so the above related contents are not further described in this patent.
Material Synthesis Example
[0208] The method for preparing a compound in the present disclosure is not limited herein. Typically, the following compounds are used as examples without limitation, and synthesis routes and preparation methods thereof are described below.
Synthesis Example 1: Synthesis of Metal Complex 159
[0209] Step 1:
##STR00019##
[0210] In a dry 250 mL round-bottom flask, 6-chloro-dibenzofuran-3-carbonitrile (3.4 g, 13.9 mmol), B.sub.2pin.sub.2 (4.1 g, 16.0 mmol), Pd(OAc).sub.2 (0.09 g, 0.4 mmol), Xphos (0.4 g, 0.8 mmol), KOAc (2.0 g, 21.0 mmol) and dioxane (90 mL) were added in sequence and heated to reflux for 12 h under N.sub.2 protection.
[0211] The above-obtained reaction solution was cooled and added with 2-bromo-4-fluoro-pyridine (2.9 g, 16.7 mmol), Pd(dppf)Cl.sub.2 (0.5 g, 0.7 mmol), K.sub.2CO.sub.3 (2.9 g, 16.7 mmol) and water (30 mL). The reaction solution was heated to reflux for 12 h under N.sub.2 protection. The reaction solution was cooled, extracted with DCM, and subjected to column chromatography to obtain Intermediate 1 (3.3 g, 82.5%).
[0212] Step 2:
##STR00020##
[0213] In a dry 250 mL round-bottom flask, Intermediate 1 (2.0 g, 6.9 mmol), carbazole (1.7 g, 10.4 mmol), potassium t-butoxide (1.4 g, 12.6 mmol) and DMF (50 mL) were added in sequence and heated to react for 12 h at 100° C. under N.sub.2 protection. The reaction was cooled, added with water and extracted with dichloromethane, the organic layer was washed twice with saturated sodium chloride, and the organic phases were collected, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified through column chromatography to obtain Intermediate 2 as a white solid (2.3 g, with a yield of 76.6%).
[0214] Step 3:
##STR00021##
[0215] In a dry 250 mL round-bottom flask, Intermediate 2 (1.6 g, 3.6 mmol), Intermediate 3 (2.0 g, 2.4 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence and heated to react for 144 h at 95° C. under N.sub.2 protection. The reaction was cooled and filtered through Celite. The reaction was washed twice with methanol and washed twice with n-hexane. Yellow solids on the Celite were dissolved with dichloromethane. The organic phases were collected, concentrated under reduced pressure, and purified through column chromatography to obtain Metal Complex 159 as a yellow solid (0.84 g, with a yield of 33.5%). The product structure was confirmed as the target product with a molecular weight of 1047.3.
Synthesis Example 2: Synthesis of Metal Complex 169
[0216] Step 1:
##STR00022##
[0217] In a dry 250 mL round-bottom flask, Intermediate 4 (1.0 g, 3.3 mmol), 3,6-di-t-butylcarbazole (1.1 g, 3.9 mmol), potassium t-butoxide (0.5 g, 4.9 mmol) and DMF (50 mL) were added in sequence and heated to react for 12 h at 100° C. under N.sub.2 protection. The reaction was cooled, added with water and extracted with dichloromethane, the organic layer was washed twice with saturated sodium chloride, and the organic phases were collected, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified through column chromatography to obtain Intermediate 5 as a white solid (1.1 g, with a yield of 61.1%).
[0218] Step 2:
##STR00023##
[0219] In a dry 250 mL round-bottom flask, Intermediate 5 (1.1 g, 1.9 mmol), Intermediate 3 (1.3 g, 1.6 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence and heated to react for 144 h at 95° C. under N.sub.2 protection. The reaction was cooled and filtered through Celite. The reaction was washed twice with methanol and washed twice with n-hexane. Yellow solids on the Celite were dissolved with dichloromethane. The organic phases were collected, concentrated under reduced pressure, and purified through column chromatography to obtain yellow Metal Complex 169 (0.45 g, with a yield of 23.9%). The product structure was confirmed as the target product with a molecular weight of 1176.5.
Synthesis Example 3: Synthesis of Metal Complex 411
[0220] Step 1:
##STR00024##
[0221] In a dry 250 mL round-bottom flask, Intermediate 2 (2.7 g, 6.2 mmol), Intermediate 6 (5.3 g, 5.7 mmol), 2-ethoxyethanol (50 mL) and DMF (50 mL) were added in sequence and heated to react for 144 h at 100° C. under N.sub.2 protection. The reaction was cooled and filtered through Celite. The reaction was washed twice with methanol and washed twice with n-hexane. Yellow solids on the Celite were dissolved with dichloromethane. The organic phases were collected, concentrated under reduced pressure, and purified through column chromatography to obtain Metal Complex 411 as a yellow solid (2.4 g, with a yield of 36.4%). The product structure was confirmed as the target product with a molecular weight of 1159.5.
Synthesis Example 4: Synthesis of Metal Complex 427
[0222] Step 1:
##STR00025##
[0223] In a dry 250 mL round-bottom flask, Intermediate 7 (2.1 g, 4.9 mmol), Intermediate 6 (3.8 g, 4.1 mmol), 2-ethoxyethanol (50 mL) and DMF (50 mL) were added in sequence and heated to react for 144 h at 100° C. under N.sub.2 protection. The reaction was cooled and filtered through Celite. The reaction was washed twice with methanol and washed twice with n-hexane. Yellow solids on the Celite were dissolved with dichloromethane. The organic phases were collected, concentrated under reduced pressure, and purified through column chromatography to obtain Metal Complex 427 as a yellow solid (2.8 g, with a yield of 59.0%). The product structure was confirmed as the target product with a molecular weight of 1152.5.
Synthesis Example 5: Synthesis of Metal Complex 433
[0224] Step 1:
##STR00026##
[0225] In a dry 250 mL round-bottom flask, Intermediate 8 (1.6 g, 3.6 mmol), Intermediate 3 (2.0 g, 2.4 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence and heated to react for 144 h at 95° C. under N.sub.2 protection. The reaction was cooled and filtered through Celite. The reaction was washed twice with methanol and washed twice with n-hexane. Yellow solids on the Celite were dissolved with dichloromethane. The organic phases were collected, concentrated under reduced pressure, and purified through column chromatography to obtain Metal Complex 433 as a yellow solid (0.84 g, with a yield of 33.5%). The product structure was confirmed as the target product with a molecular weight of 1048.3.
[0226] Those skilled in the art will appreciate that the above preparation methods are merely exemplary. Those skilled in the art can obtain other compound structures of the present disclosure through the modifications of the preparation methods.
Device Example 1
[0227] Firstly, a glass substrate having an indium tin oxide (ITO) anode with a thickness of 80 nm was cleaned and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was dried in a glovebox to remove moisture. Then, the substrate was mounted on a substrate holder and placed in a vacuum chamber. Organic layers specified below were sequentially deposited through vacuum thermal evaporation on the ITO anode at a rate of 0.2 to 2 Angstroms per second and a vacuum degree of about 10-8 torr. Compound HI was used as a hole injection layer (HIL). Compound HT was used as a hole transporting layer (HTL). Compound H1 was used as an electron blocking layer (EBL). Metal Complex 159 of the present disclosure, as a dopant, was co-deposited with Compound H1 and Compound H2 for use as an emissive layer (EML). On the EML, Compound H3 was used as a hole blocking layer (HBL). Compound ET and 8-hydroxyquinolinolato-lithium (Liq) were co-deposited for use as an electron transporting layer (ETL). Finally, 8-hydroxyquinolinolato-lithium (Liq) was deposited as an electron injection layer with a thickness of 1 nm and Al was deposited as a cathode with a thickness of 120 nm. The device was transferred back to the glovebox and encapsulated with a glass lid to complete the device.
Device Example 2
[0228] The implementation mode in Device Example 2 was the same as that in Device Example 1, except that in the emissive layer (EML), Metal Complex 159 of the present disclosure was replaced with Metal Complex 411, and the weight ratio of Compound H1, Compound H2 and Metal Complex 411 was 56:38:6.
Device Comparative Example 1
[0229] The implementation mode in Device Comparative Example 1 was the same as that in Device Example 1, except that in the emissive layer (EML), Metal Complex 159 of the present disclosure was replaced with Compound GD1.
Device Comparative Example 2
[0230] The implementation mode in Device Comparative Example 2 was the same as that in Device Example 1, except that in the emissive layer (EML), Metal Complex 159 of the present disclosure was replaced with Compound GD2.
Device Comparative Example 3
[0231] The implementation mode in Device Comparative Example 3 was the same as that in Device Example 1, except that in the emissive layer (EML), Metal Complex 159 of the present disclosure was replaced with Compound GD3.
[0232] Detailed structures and thicknesses of layers of the devices are shown in the following table. A layer using more than one material is obtained by doping different compounds at their weight ratio as recorded.
TABLE-US-00001 TABLE 1 Partial device structures of Device Examples 1 and 2 and Comparative Examples 1 to 3 Device ID HL HTL EBL EML HBL ETL Example 1 Compound Compound Compound Compound Compound Compound HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Metal Complex (40:60) 159 (47:47:6) (350 Å) (400 Å) Example 2 Compound Compound Compound Compound Compound Compound HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Metal Complex (40:60) 411 (56:38:6) (350 Å) (400 Å) Comparative Compound Compound Compound Compound Compound Compound Example 1 HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Compound GD1 (40:60) (47:47:6) (350 Å) (400 Å) Comparative Compound Compound Compound Compound Compound Compound Example 2 HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Compound GD2 (40:60) (47:47:6) (350 Å) (400 Å) Comparative Compound Compound Compound Compound Compound Compound Example 3 HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Compound GD3 (40:60) (47:47:6) (350 Å) (400 Å)
[0233] The materials used in the devices have the following structures:
##STR00027## ##STR00028## ##STR00029##
[0234] The current-voltage-luminance (IVL) characteristics of the devices were measured. Under 1000 cd/m.sup.2, the CIE data, maximum emission wavelength (λ.sub.max), full width at half maximum (FWHM), driving voltage (V), current efficiency (CE) and external quantum efficiency (EQE) of the devices were measured. Lifetime (LT97) data was tested at a constant current of 80 mA/cm.sup.2. The data was recorded and shown in Table 2.
TABLE-US-00002 TABLE 2 Device data of Device Examples 1 and 2 and Comparative Examples 1 to 3 λ.sub.max FWHM Voltage CE EQE LT 97 Device ID CIE (x, y) (nm) (nm) (V) (cd/A) (%) (h) Example 1 (0.406, 0.584) 544 58.7 2.55 103 27.39 62.5 Example 2 (0.428, 0.564) 547 62.7 2.69 98 26.60 67.2 Comparative (0.429, 0.564) 546 53.7 2.56 90 24.57 59.0 Example 1 Comparative (0.351, 0.627) 531 50.7 2.60 95 24.52 52.3 Example 2 Comparative (0.444, 0.549) 550 70.6 2.57 88 25.29 51.3 Example 3
[0235] Discussion
[0236] Table 2 shows the device performance of the metal complexes of the present disclosure and the comparative compounds. Metal Complex 159 of the present disclosure differs from Comparative Compound GD1 only in that the carbazole substituent is located at different substitution positions of pyridine in the ligand L.sub.a. Compared with Comparative Example 1, Example 1 has substantially the same driving voltage, the CE increased by 14.4%, the EQE increased by 11.4%, and the lifetime increased by 5.9%, indicating that the metal complex of the present application comprising a ligand L.sub.a with the substituent R.sub.n at the particular position can improve the device efficiency (CE and EQE) and the lifetime and significantly improve the overall performance of the device.
[0237] Metal Complex 159 of the present disclosure differs from Comparative Compound GD2 only in that a carbazole substitution exists at position 4 of pyridine in the ligand L.sub.a. Compared with Comparative Example 2, Example 1 has the slightly reduced driving voltage, the CE increased by 8.4%, the EQE increased by 11.7%, and the lifetime increased by 19.5%, indicating that the metal complex of the present application comprising the ligand L.sub.a with the substituent R.sub.n at the particular position can improve the device efficiency (CE and EQE) and the lifetime and significantly improve the overall performance of the device.
[0238] Metal Complex 159 of the present disclosure differs from Comparative Compound GD3 only in that a carbazole substituent, rather than phenyl, exists at position 4 of pyridine in the ligand L.sub.a. Compared with Comparative Example 3, Example 1 has substantially the same driving voltage, the CE increased by 17.0%, the EQE increased by 8.3%, and the lifetime increased by 21.8%, indicating that the metal complex of the present application comprising the ligand L.sub.a with the substituent R.sub.n at the particular position can improve the device efficiency (CE and EQE) and the lifetime and significantly improve the overall performance of the device.
[0239] In addition, the maximum emission wavelength of the device in Example 1 is in the region close to yellow light, and the device in Example 1 has achieved the device performance including a long lifetime and high efficiency, which has a huge application prospect in the aspects of white and low blue light sources.
[0240] In Example 2, Metal Complex 411 of the present disclosure is used as a light-emitting material in the emissive layer. The voltage, CE and EQE of Example 2 maintain excellent levels comparable to those of Example 1, and the lifetime of Example 2 is further improved. Meanwhile, the EQE and lifetime of Example 2 are significantly improved compared with those of Comparative Examples 1 to 3. Therefore, Example 2 has excellent light emission performance and an excellent device lifetime.
[0241] All the above results indicate that the metal complex of the present disclosure comprising the ligand L.sub.a with the substituent R.sub.n at the particular position, when applied to an organic electroluminescent device, can improve the device efficiency (CE and EQE) and the lifetime and achieve the beneficial effect of significantly improving the overall performance of the device.
Device Example 3
[0242] The implementation mode in Device Example 3 was the same as that in Device Example 2, except that in the emissive layer (EML), Metal Complex 411 of the present disclosure was replaced with Metal Complex 427.
Device Example 4
[0243] The implementation mode in Device Example 4 was the same as that in Device Example 2, except that in the emissive layer (EML), Metal Complex 411 of the present disclosure was replaced with Metal Complex 433.
[0244] Detailed structures and thicknesses of layers of the devices are shown in Table 3. A layer using more than one material is obtained by doping different compounds at their weight ratio as recorded.
TABLE-US-00003 TABLE 3 Device structures of Device Examples 3 and 4 Device ID HL HTL EBL EML HBL ETL Example 3 Compound Compound Compound Compound Compound Compound HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Metal Complex (40:60) 427 (56:38:6) (350 Å) (400 Å) Example 4 Compound Compound Compound Compound Compound Compound HI (100 Å) HT (350 Å) H1 (50 Å) H1:Compound H3 (50 Å) ET:Liq H2:Metal Complex (40:60) 433 (56:38:6) (350 Å) (400 Å)
[0245] The new materials used in the devices have the following structures:
##STR00030##
[0246] The IVL characteristics of the devices were measured. Under 1000 cd/m.sup.2, the CIE data, maximum emission wavelength (λ.sub.max), full width at half maximum (FWHM), driving voltage (V), current efficiency (CE) and external quantum efficiency (EQE) of the devices were measured. The data was recorded and shown in Table 4.
TABLE-US-00004 TABLE 4 Device data of Device Examples 3 and 4 λ.sub.max FWHM Voltage CE EQE Device ID CIE (x, y) (nm) (nm) (V) (cd/A) (%) Example 3 (0.433, 0.559) 550 66.6 2.83 96 26.40 Example 4 (0.373, 0.671) 536 54.5 2.60 107 27.72
[0247] Discussion:
[0248] Table 4 further shows the device performance of the metal complexes of the present disclosure. In Example 3 and Example 4, Metal Complex 427 and Metal Complex 433 of the present disclosure comprising the ligand L.sub.a with the substituent R.sub.n at the particular position are used as the light-emitting material in the emissive layer, respectively. The voltages, CE and EQE of Example 3 and Example 4 remain comparable to those of Example 1. Meanwhile, the EQE of Example 3 and the EQE of Example 4 are significantly improved compared with those of Comparative Examples 1 to 3.
[0249] All the above results indicate that the metal complexes of the present disclosure comprising ligands L.sub.a with different substituents R.sub.n at a particular position and different ligands L.sub.b, when applied to organic electroluminescent devices, can improve the device efficiency (CE and EQE) and/or the lifetime and achieve the beneficial effect of significantly improving the overall performance of the devices.
[0250] It is to be understood that various embodiments described herein are merely examples and not intended to limit the scope of the present disclosure. Therefore, it is apparent to the persons skilled in the art that the present disclosure as claimed may include variations of specific embodiments and preferred embodiments described herein. Many of materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present disclosure. It is to be understood that various theories as to why the present disclosure works are not intended to be limitative.