LIGHT-EMITTING MATERIAL WITH A POLYCYCLIC LIGAND
20220363700 · 2022-11-17
Inventors
- Zhihong Dai (Beijing, CN)
- Cuifang Zhang (Beijing, CN)
- Qi Zhang (Beijing, CN)
- Nannan Lu (Beijing, CN)
- Chi Yuen Raymond Kwong (Beijing, CN)
- Chuanjun Xia (Beijing, CN)
Cpc classification
Y02E10/549
GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
International classification
Abstract
Provided is a luminescent material having a polycyclic ligand. The luminescent material is a new metal complex having a polycyclic ligand and may be used as luminescent materials in electroluminescent devices. These new metal complexes achieve red light emission, have a very narrow full width at half maximum, and can achieve high saturation luminescence. In addition, these new metal complexes, when used as luminescent materials in electroluminescent devices, can achieve red light emission, have a very narrow full width at half maximum, achieve high saturation luminescence, reduce or maintain a low voltage, greatly improve device efficiency and lifetime, and provide better device performance. Further provided are an electroluminescent device and a compound composition.
Claims
1. A metal complex, comprising a metal M and a ligand L.sub.a coordinated with the metal M, wherein the metal M is selected from metals having a relative atomic mass greater than 40, and L.sub.a has a structure represented by Formula 1: ##STR00050## wherein, Z.sub.1 and Z.sub.2 are each independently selected from C or N, and Z.sub.1 and Z.sub.2 are different; W is, at each occurrence identically or differently, selected from B, N or P; ring A, ring C, and ring D are, at each occurrence identically or differently, selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms; ring B is selected from a heterocyclic ring having 2 to 30 carbon atoms or a heteroaromatic ring having 2 to 30 carbon atoms; R.sub.a, R.sub.b, R.sub.c, and R.sub.d represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution; R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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; adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring.
2. The metal complex of claim 1, wherein in the L.sub.a, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; and ring B is selected form a heteroaromatic ring having 2 to 18 carbon atoms; preferably, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, an aza-naphthalene ring, a furan ring, a thiophene ring, an isoxazole ring, an isothiazole ring, a pyrrole ring, a pyrazole ring, a benzofuran ring, a benzothiophene ring, an azabenzofuran ring or an azabenzothiophene ring; and ring B is selected from a pyrrole ring, an indole ring, an imidazole ring, a pyrazole ring, a triazole ring or an azaindole ring; more preferably, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from a benzene ring, a naphthalene ring, a pyridine ring or a pyrimidine ring; and ring B is selected from a pyrrole ring, an indole ring or an azaindole ring.
3. The metal complex of claim 1, wherein the L.sub.a is selected from a structure represented by any one of Formula 2 to Formula 19: ##STR00051## ##STR00052## ##STR00053## ##STR00054## wherein, Z.sub.1 and Z.sub.2 are each independently selected from C or N, and Z.sub.1 and Z.sub.2 are different; W is, at each occurrence identically or differently, selected from B, N or P; A.sub.1 to A.sub.5 are, at each occurrence identically or differently, selected from N or CR.sub.a; B.sub.1 to B.sub.4 are, at each occurrence identically or differently, selected from N or CR.sub.b; C.sub.1 to C.sub.4 are, at each occurrence identically or differently, selected from N or CR.sub.c; D.sub.1 to D.sub.4 are, at each occurrence identically or differently, selected from N or CR.sub.d; X.sub.1 is, at each occurrence identically or differently, selected from O, S, Se, NR.sub.c, CR.sub.cR.sub.c, SiR.sub.cR.sub.c or PR.sub.c; X.sub.2 is, at each occurrence identically or differently, selected from O, S, Se, NR.sub.d, CR.sub.dR.sub.d, SiR.sub.dR.sub.d or PR.sub.d; Z.sub.3 is, at each occurrence identically or differently, selected from O, S, Se, NR.sub.z, CR.sub.zR.sub.z, SiR.sub.zR.sub.z or PR.sub.z; R.sub.a, R.sub.b, R.sub.c, R.sub.d, and R.sub.z 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; adjacent substituents R.sub.a, R.sub.b, R.sub.c, R.sub.d, and R.sub.z can be optionally joined to form a ring; preferably, L.sub.a is selected from a structure represented by Formula 2, Formula 3, Formula 7, Formula 8, Formula 9 or Formula 12; more preferably, L.sub.a is selected from a structure represented by Formula 2, Formula 3 or Formula 12.
4. The metal complex of claim 3, wherein in Formula 1 to Formula 19, Z.sub.1 is N, and Z.sub.2 is C; or in Formula 1 to Formula 19, Z.sub.1 is C, and Z.sub.2 is N.
5. The metal complex of claim 3, wherein in Formula 1 to Formula 19, W is N.
6. The metal complex of claim 3, wherein in Formula 2 to Formula 18, Z.sub.1 is N, and at least one of D.sub.1 and D.sub.2 is N; or in Formula 2 to Formula 17 and Formula 19, Z.sub.2 is N, and at least one of C.sub.1 and C.sub.2 is N; preferably, in Formula 2 to Formula 18, Z.sub.1 is N, and one of D.sub.1 and D.sub.2 is N; or in Formula 2 to Formula 17 and Formula 19, Z.sub.2 is N, and one of C.sub.1 and C.sub.2 is N; more preferably, in Formula 2 to Formula 18, Z.sub.1 is N, and D.sub.2 is N; or in Formula 2 to Formula 17 and Formula 19, Z.sub.2 is N, and C.sub.1 is N.
7. The metal complex of claim 3, wherein in Formula 2 to Formula 19, A.sub.1 to A.sub.5 are each independently selected from CR.sub.a, and B.sub.1 to B.sub.4 are each independently selected from CR.sub.b; in Formula 2 to Formula 17 and Formula 19, C.sub.1 to C.sub.4 are each independently selected from CR.sub.c; in Formula 2 to Formula 18, D.sub.1 to D.sub.4 are each independently selected from CR.sub.d; and the R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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; adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring; preferably, the R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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 alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 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 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, a cyano group, and combinations thereof; more preferably, the R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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 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, a cyano group, and combinations thereof.
8. The metal complex of claim 3, wherein in Formula 2 to Formula 19, at least one of A.sub.1 to A.sub.n is, at each occurrence identically or differently, selected from CR.sub.a, and the A.sub.n corresponds to one having the largest serial number of A.sub.1 to A.sub.5 in any one of Formula 2 to Formula 19; and the R.sub.a is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, a cyano group, a hydroxyl group, a sulfanyl group, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring 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, and combinations thereof; adjacent substituents R.sub.a can be optionally joined to form a ring; preferably, in Formula 2 to Formula 14, Formula 18 and Formula 19, at least one of A.sub.1 to A.sub.3 is, at each occurrence identically or differently, selected from CR.sub.a; and in Formula 15 to Formula 17, A.sub.1 is selected from CR.sub.a; more preferably, the R.sub.a is, at each occurrence identically or differently, selected from the group consisting of: deuterium, fluorine, a cyano group, a hydroxyl group, a sulfanyl group, an amino group, a methoxy group, a phenoxy group, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, piperidyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantly, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermanyl, triethylgermanyl, phenyl, pyridyl, triazinyl, and combinations thereof.
9. The metal complex of claim 3, wherein in Formula 2 to Formula 17 and Formula 19, C.sub.2 is, at each occurrence identically or differently, selected from CR.sub.c, and the R.sub.c is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, a cyano group, 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, and combinations thereof; preferably, the R.sub.c is, at each occurrence identically or differently, selected from the group consisting of: deuterium, a cyano group, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermanyl, triethylgermanyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.
10. The metal complex of claim 3, wherein in Formula 2 to Formula 19, at least one of B.sub.1 to B.sub.n is selected from CR.sub.b, and the B.sub.n corresponds to one having the largest serial number of B.sub.1 to B.sub.4 in any one of Formula 2 to Formula 19; and/or in Formula 2 to Formula 18, at least one of D.sub.1 to D.sub.n is selected from CR.sub.d, and the D.sub.n corresponds to one having the largest serial number of D.sub.1 to D.sub.4 in any one of Formula 2 to Formula 18; and the R.sub.b and R.sub.d 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, 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, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof; preferably, in Formula 2 to Formula 12, Formula 16, Formula 18 and Formula 19, B.sub.2 and/or B.sub.3 are selected from CR.sub.b; in Formula 13 to Formula 15 and Formula 17, B.sub.1 and/or B.sub.2 are selected from CR.sub.b; and in Formula 2 to Formula 18, D.sub.1 and/or D.sub.2 are selected from CR.sub.d; more preferably, the R.sub.b and R.sub.d are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, a cyano group, a hydroxyl group, a sulfanyl group, an amino group, a methoxy group, a phenoxy group, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, piperidyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermanyl, triethylgermanyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.
11. The metal complex of claim 1, wherein L.sub.a is, at each occurrence identically or differently, selected from the group consisting of the following structures: ##STR00055## ##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## ##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## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## wherein TMS represents trimethylsilyl, and Ph represents phenyl; wherein, optionally, hydrogen in the structures L.sub.a1 to L.sub.a1342 can be partially or completely substituted with deuterium.
12. The metal complex of claim 1, having 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 Ir, Rh, Re, Os, Pt, Au or Cu; preferably, the metal M is selected from Ir, Pt or Os; more preferably, the metal M is 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; 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 is equal to an oxidation state of the metal M; when m is equal to 2 or 3, a plurality of L.sub.a can be identical or different; when n is equal to 2, two L.sub.b can be identical or different; and when q is equal to 2, two L.sub.c can be identical or different; L.sub.a, L.sub.b, and L.sub.c can be optionally joined to form a multi-dentate ligand; L.sub.b and L.sub.c are, at each occurrence identically or differently, selected from the group consisting of the following structures: ##STR00262## wherein, R.sub.i, R.sub.ii, and R.sub.iii represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution; X.sub.a 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; X.sub.b and X.sub.c are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NR.sub.N2; R.sub.i, R.sub.ii, R.sub.iii, R.sub.N1, R.sub.N2, 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; adjacent substituents R.sub.i, R.sub.ii, R.sub.iii, R.sub.N1, R.sub.N2, R.sub.C1, and R.sub.C2 can be optionally joined to form a ring.
13. The metal complex of claim 12, wherein L.sub.b is, at each occurrence identically or differently, selected from the following structure: ##STR00263## wherein R.sub.1 to R.sub.7 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; preferably, at least one or two of R.sub.1 to R.sub.3 are selected from 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 or combinations thereof, and/or at least one or two of R.sub.4 to R.sub.6 are selected from 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 or combinations thereof; more preferably, at least two of R.sub.1 to R.sub.3 are selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms or combinations thereof; and/or at least two of R.sub.4 to R.sub.6 are selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms or combinations thereof.
14. The metal complex of claim 13, wherein L.sub.b is, at each occurrence identically or differently, selected from the group consisting of the following structures: ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## wherein, L.sub.c is, at each occurrence identically or differently, selected from the group consisting of the following structures: ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370##
15. The metal complex of claim 14, wherein the metal complex is an Ir complex and has a structure represented by any one of Ir(L.sub.a)(L.sub.b)(L.sub.c), Ir(L.sub.a).sub.2(L.sub.b), Ir(L.sub.a).sub.2(L.sub.c) and Ir(L.sub.a)(L.sub.c).sub.2; when the metal complex has a structure of Ir(L.sub.a)(L.sub.b)(L.sub.c), L.sub.a is selected from any one of the group consisting of L.sub.a1 to L.sub.a1342, L.sub.b is selected from any one of the group consisting of L.sub.b1 to L.sub.b322, and L.sub.c is selected from any one of the group consisting of L.sub.c1 to L.sub.c231; when the metal complex has a structure of Ir(L.sub.a).sub.2(L.sub.b), L.sub.a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.a1 to L.sub.a1342, and L.sub.b is selected from any one of the group consisting of L.sub.b1 to L.sub.b322; when the metal complex has a structure of Ir(L.sub.a).sub.2(L.sub.c), L.sub.a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.a1 to L.sub.a1342, and L.sub.c is selected from any one of the group consisting of L.sub.c1 to L.sub.c231; and when the metal complex has a structure of Ir(L.sub.a)(L.sub.c).sub.2, L.sub.a is selected from any one of the group consisting of L.sub.a1 to L.sub.a1342, and L.sub.c is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.c1 to L.sub.c231; more preferably, the metal complex is selected from the group consisting of Compound 1 to Compound 530, and Compound 1 to Compound 530 have a general formula of Ir(L.sub.a).sub.2(L.sub.b), wherein two L.sub.a are identical and L.sub.a and L.sub.b are respectively selected from structures listed in the following table: TABLE-US-00004 Compound No. L.sub.a L.sub.b 1 L.sub.a27 L.sub.b31 2 L.sub.a27 L.sub.b57 3 L.sub.a28 L.sub.b31 4 L.sub.a28 L.sub.b57 5 L.sub.a29 L.sub.b31 6 L.sub.a29 L.sub.b57 7 L.sub.a30 L.sub.b31 8 L.sub.a30 L.sub.b57 9 L.sub.a33 L.sub.b31 10 L.sub.a33 L.sub.b57 11 L.sub.a35 L.sub.b31 12 L.sub.a35 L.sub.b57 13 L.sub.a37 L.sub.b31 14 L.sub.a37 L.sub.b57 15 L.sub.a41 L.sub.b31 16 L.sub.a41 L.sub.b57 17 L.sub.a43 L.sub.b31 18 L.sub.a43 L.sub.b57 19 L.sub.a27 L.sub.b66 20 L.sub.a27 L.sub.b88 21 L.sub.a28 L.sub.b66 22 L.sub.a28 L.sub.b88 23 L.sub.a29 L.sub.b66 24 L.sub.a29 L.sub.b88 25 L.sub.a30 L.sub.b66 26 L.sub.a30 L.sub.b88 27 L.sub.a33 L.sub.b66 28 L.sub.a33 L.sub.b88 29 L.sub.a35 L.sub.b66 30 L.sub.a35 L.sub.b88 31 L.sub.a37 L.sub.b66 32 L.sub.a37 L.sub.b88 33 L.sub.a41 L.sub.b66 34 L.sub.a41 L.sub.b88 35 L.sub.a43 L.sub.b66 36 L.sub.a43 L.sub.b88 37 L.sub.a27 L.sub.b90 38 L.sub.a27 L.sub.b122 39 L.sub.a28 L.sub.b90 40 L.sub.a28 L.sub.b122 41 L.sub.a29 L.sub.b90 42 L.sub.a29 L.sub.b122 43 L.sub.a30 L.sub.b90 44 L.sub.a30 L.sub.b122 45 L.sub.a33 L.sub.b90 46 L.sub.a33 L.sub.b122 47 L.sub.a35 L.sub.b90 48 L.sub.a35 L.sub.b122 49 L.sub.a37 L.sub.b90 50 L.sub.a37 L.sub.b122 51 L.sub.a41 L.sub.b90 52 L.sub.a41 L.sub.b122 53 L.sub.a43 L.sub.b90 54 L.sub.a43 L.sub.b122 55 L.sub.a27 L.sub.b126 56 L.sub.a27 L.sub.b139 57 L.sub.a28 L.sub.b126 58 L.sub.a28 L.sub.b139 59 L.sub.a29 L.sub.b126 60 L.sub.a29 L.sub.b139 61 L.sub.a30 L.sub.b126 62 L.sub.a30 L.sub.b139 63 L.sub.a33 L.sub.b126 64 L.sub.a33 L.sub.b139 65 L.sub.a35 L.sub.b126 66 L.sub.a35 L.sub.b139 67 L.sub.a37 L.sub.b126 68 L.sub.a37 L.sub.b139 69 L.sub.a41 L.sub.b126 70 L.sub.a41 L.sub.b139 71 L.sub.a43 L.sub.b126 72 L.sub.a43 L.sub.b139 73 L.sub.a27 L.sub.b245 74 L.sub.a35 L.sub.b245 75 L.sub.a28 L.sub.b245 76 L.sub.a37 L.sub.b245 77 L.sub.a29 L.sub.b245 78 L.sub.a41 L.sub.b245 79 L.sub.a30 L.sub.b245 80 L.sub.a43 L.sub.b245 81 L.sub.a33 L.sub.b245 82 L.sub.a44 L.sub.b245 83 L.sub.a51 L.sub.b31 84 L.sub.a51 L.sub.b57 85 L.sub.a56 L.sub.b31 86 L.sub.a56 L.sub.b57 87 L.sub.a58 L.sub.b31 88 L.sub.a58 L.sub.b57 89 L.sub.a74 L.sub.b31 90 L.sub.a74 L.sub.b57 91 L.sub.a79 L.sub.b31 92 L.sub.a79 L.sub.b57 93 L.sub.a81 L.sub.b31 94 L.sub.a81 L.sub.b57 95 L.sub.a97 L.sub.b31 96 L.sub.a97 L.sub.b57 97 L.sub.a102 L.sub.b31 98 L.sub.a102 L.sub.b57 99 L.sub.a104 L.sub.b31 100 L.sub.a104 L.sub.b57 101 L.sub.a120 L.sub.b31 102 L.sub.a120 L.sub.b57 103 L.sub.a125 L.sub.b31 104 L.sub.a125 L.sub.b57 105 L.sub.a212 L.sub.b31 106 L.sub.a212 L.sub.b57 107 L.sub.a214 L.sub.b31 108 L.sub.a214 L.sub.b57 109 L.sub.a217 L.sub.b31 110 L.sub.a217 L.sub.b57 111 L.sub.a219 L.sub.b31 112 L.sub.a219 L.sub.b57 113 L.sub.a226 L.sub.b31 114 L.sub.a226 L.sub.b57 115 L.sub.a304 L.sub.b31 116 L.sub.a304 L.sub.b57 117 L.sub.a306 L.sub.b31 118 L.sub.a306 L.sub.b57 119 L.sub.a309 L.sub.b31 120 L.sub.a309 L.sub.b57 121 L.sub.a311 L.sub.b31 122 L.sub.a311 L.sub.b57 123 L.sub.a321 L.sub.b31 124 L.sub.a321 L.sub.b57 125 L.sub.a323 L.sub.b31 126 L.sub.a323 L.sub.b57 127 L.sub.a332 L.sub.b31 128 L.sub.a332 L.sub.b57 129 L.sub.a351 L.sub.b31 130 L.sub.a351 L.sub.b57 131 L.sub.a356 L.sub.b31 132 L.sub.a356 L.sub.b57 133 L.sub.a375 L.sub.b31 134 L.sub.a375 L.sub.b57 135 L.sub.a422 L.sub.b31 136 L.sub.a422 L.sub.b57 137 L.sub.a427 L.sub.b31 138 L.sub.a427 L.sub.b57 139 L.sub.a450 L.sub.b31 140 L.sub.a450 L.sub.b57 141 L.sub.a473 L.sub.b31 142 L.sub.a473 L.sub.b57 143 L.sub.a496 L.sub.b31 144 L.sub.a496 L.sub.b57 145 L.sub.a606 L.sub.b31 146 L.sub.a606 L.sub.b57 147 L.sub.a611 L.sub.b31 148 L.sub.a611 L.sub.b57 149 L.sub.a634 L.sub.b31 150 L.sub.a634 L.sub.b57 151 L.sub.a899 L.sub.b31 152 L.sub.a899 L.sub.b57 153 L.sub.a923 L.sub.b31 154 L.sub.a923 L.sub.b57 155 L.sub.a51 L.sub.b66 156 L.sub.a51 L.sub.b88 157 L.sub.a56 L.sub.b66 158 L.sub.a56 L.sub.b88 159 L.sub.a58 L.sub.b66 160 L.sub.a58 L.sub.b88 161 L.sub.a74 L.sub.b66 162 L.sub.a74 L.sub.b88 163 L.sub.a79 L.sub.b66 164 L.sub.a79 L.sub.b88 165 L.sub.a81 L.sub.b66 166 L.sub.a81 L.sub.b88 167 L.sub.a97 L.sub.b66 168 L.sub.a97 L.sub.b88 169 L.sub.a102 L.sub.b66 170 L.sub.a102 L.sub.b88 171 L.sub.a104 L.sub.b66 172 L.sub.a104 L.sub.b88 173 L.sub.a120 L.sub.b66 174 L.sub.a120 L.sub.b88 175 L.sub.a125 L.sub.b66 176 L.sub.a125 L.sub.b88 177 L.sub.a212 L.sub.b66 178 L.sub.a212 L.sub.b88 179 L.sub.a214 L.sub.b66 180 L.sub.a214 L.sub.b88 181 L.sub.a217 L.sub.b66 182 L.sub.a217 L.sub.b88 183 L.sub.a219 L.sub.b66 184 L.sub.a219 L.sub.b88 185 L.sub.a226 L.sub.b66 186 L.sub.a226 L.sub.b88 187 L.sub.a304 L.sub.b66 188 L.sub.a304 L.sub.b88 189 L.sub.a306 L.sub.b66 190 L.sub.a306 L.sub.b88 191 L.sub.a309 L.sub.b66 192 L.sub.a309 L.sub.b88 193 L.sub.a311 L.sub.b66 194 L.sub.a311 L.sub.b88 195 L.sub.a321 L.sub.b66 196 L.sub.a321 L.sub.b88 197 L.sub.a323 L.sub.b66 198 L.sub.a323 L.sub.b88 199 L.sub.a332 L.sub.b66 200 L.sub.a332 L.sub.b88 201 L.sub.a351 L.sub.b66 202 L.sub.a351 L.sub.b88 203 L.sub.a356 L.sub.b66 204 L.sub.a356 L.sub.b88 205 L.sub.a375 L.sub.b66 206 L.sub.a375 L.sub.b88 207 L.sub.a422 L.sub.b66 208 L.sub.a422 L.sub.b88 209 L.sub.a427 L.sub.b66 210 L.sub.a427 L.sub.b88 211 L.sub.a450 L.sub.b66 212 L.sub.a450 L.sub.b88 213 L.sub.a473 L.sub.b66 214 L.sub.a473 L.sub.b88 215 L.sub.a496 L.sub.b66 216 L.sub.a496 L.sub.b88 217 L.sub.a606 L.sub.b66 218 L.sub.a606 L.sub.b88 219 L.sub.a611 L.sub.b66 220 L.sub.a611 L.sub.b88 221 L.sub.a634 L.sub.b66 222 L.sub.a634 L.sub.b88 223 L.sub.a899 L.sub.b66 224 L.sub.a899 L.sub.b88 225 L.sub.a923 L.sub.b66 226 L.sub.a923 L.sub.b88 227 L.sub.a51 L.sub.b90 228 L.sub.a51 L.sub.b122 229 L.sub.a56 L.sub.b90 230 L.sub.a56 L.sub.b122 231 L.sub.a58 L.sub.b90 232 L.sub.a58 L.sub.b122 233 L.sub.a74 L.sub.b90 234 L.sub.a74 L.sub.b122 235 L.sub.a79 L.sub.b90 236 L.sub.a79 L.sub.b122 237 L.sub.a81 L.sub.b90 238 L.sub.a81 L.sub.b122 239 L.sub.a97 L.sub.b90 240 L.sub.a97 L.sub.b122 241 L.sub.a102 L.sub.b90 242 L.sub.a102 L.sub.b122 243 L.sub.a104 L.sub.b90 244 L.sub.a104 L.sub.b122 245 L.sub.a120 L.sub.b90 246 L.sub.a120 L.sub.b122 247 L.sub.a125 L.sub.b90 248 L.sub.a125 L.sub.b122 249 L.sub.a212 L.sub.b90 250 L.sub.a212 L.sub.b122 251 L.sub.a214 L.sub.b90 252 L.sub.a214 L.sub.b122 253 L.sub.a217 L.sub.b90 254 L.sub.a217 L.sub.b122 255 L.sub.a219 L.sub.b90 256 L.sub.a219 L.sub.b122 257 L.sub.a226 L.sub.b90 258 L.sub.a226 L.sub.b122 259 L.sub.a304 L.sub.b90 260 L.sub.a304 L.sub.b122 261 L.sub.a306 L.sub.b90 262 L.sub.a306 L.sub.b122 263 L.sub.a309 L.sub.b90 264 L.sub.a309 L.sub.b122 265 L.sub.a311 L.sub.b90 266 L.sub.a311 L.sub.b122 267 L.sub.a321 L.sub.b90 268 L.sub.a321 L.sub.b122 269 L.sub.a323 L.sub.b90 270 L.sub.a323 L.sub.b122 271 L.sub.a332 L.sub.b90 272 L.sub.a332 L.sub.b122 273 L.sub.a351 L.sub.b90 274 L.sub.a351 L.sub.b122 275 L.sub.a356 L.sub.b90 276 L.sub.a356 L.sub.b122 277 L.sub.a375 L.sub.b90 278 L.sub.a375 L.sub.b122 279 L.sub.a422 L.sub.b90 280 L.sub.a422 L.sub.b122 281 L.sub.a427 L.sub.b90 282 L.sub.a427 L.sub.b122 283 L.sub.a450 L.sub.b90 284 L.sub.a450 L.sub.b122 285 L.sub.a473 L.sub.b90 286 L.sub.a473 L.sub.b122 287 L.sub.a496 L.sub.b90 288 L.sub.a496 L.sub.b122 289 L.sub.a606 L.sub.b90 290 L.sub.a606 L.sub.b122 291 L.sub.a611 L.sub.b90 292 L.sub.a611 L.sub.b122 293 L.sub.a634 L.sub.b90 294 L.sub.a634 L.sub.b122 295 L.sub.a899 L.sub.b90 296 L.sub.a899 L.sub.b122 297 L.sub.a923 L.sub.b90 298 L.sub.a923 L.sub.b122 299 L.sub.a51 L.sub.b126 300 L.sub.a51 L.sub.b139 301 L.sub.a56 L.sub.b126 302 L.sub.a56 L.sub.b139 303 L.sub.a58 L.sub.b126 304 L.sub.a58 L.sub.b139 305 L.sub.a74 L.sub.b126 306 L.sub.a74 L.sub.b139 307 L.sub.a79 L.sub.b126 308 L.sub.a79 L.sub.b139 309 L.sub.a81 L.sub.b126 310 L.sub.a81 L.sub.b139 311 L.sub.a97 L.sub.b126 312 L.sub.a97 L.sub.b139 313 L.sub.a102 L.sub.b126 314 L.sub.a102 L.sub.b139 315 L.sub.a104 L.sub.b126 316 L.sub.a104 L.sub.b139 317 L.sub.a120 L.sub.b126 318 L.sub.a120 L.sub.b139 319 L.sub.a125 L.sub.b126 320 L.sub.a125 L.sub.b139 321 L.sub.a212 L.sub.b126 322 L.sub.a212 L.sub.b139 323 L.sub.a214 L.sub.b126 324 L.sub.a214 L.sub.b139 325 L.sub.a217 L.sub.b126 326 L.sub.a217 L.sub.b139 327 L.sub.a219 L.sub.b126 328 L.sub.a219 L.sub.b139 329 L.sub.a226 L.sub.b126 330 L.sub.a226 L.sub.b139 331 L.sub.a304 L.sub.b126 332 L.sub.a304 L.sub.b139 333 L.sub.a306 L.sub.b126 334 L.sub.a306 L.sub.b139 335 L.sub.a309 L.sub.b126 336 L.sub.a309 L.sub.b139 337 L.sub.a311 L.sub.b126 338 L.sub.a311 L.sub.b139 339 L.sub.a321 L.sub.b126 340 L.sub.a321 L.sub.b139 341 L.sub.a323 L.sub.b126 342 L.sub.a323 L.sub.b139 343 L.sub.a332 L.sub.b126 344 L.sub.a332 L.sub.b139 345 L.sub.a351 L.sub.b126 346 L.sub.a351 L.sub.b139 347 L.sub.a356 L.sub.b126 348 L.sub.a356 L.sub.b139 349 L.sub.a375 L.sub.b126 350 L.sub.a375 L.sub.b139 351 L.sub.a422 L.sub.b126 352 L.sub.a422 L.sub.b139 353 L.sub.a427 L.sub.b126 354 L.sub.a427 L.sub.b139 355 L.sub.a450 L.sub.b126 356 L.sub.a450 L.sub.b139 357 L.sub.a473 L.sub.b126 358 L.sub.a473 L.sub.b139 359 L.sub.a496 L.sub.b126 360 L.sub.a496 L.sub.b139 361 L.sub.a606 L.sub.b126 362 L.sub.a606 L.sub.b139 363 L.sub.a611 L.sub.b126 364 L.sub.a611 L.sub.b139 365 L.sub.a634 L.sub.b126 366 L.sub.a634 L.sub.b139 367 L.sub.a899 L.sub.b126 368 L.sub.a899 L.sub.b139 369 L.sub.a923 L.sub.b126 370 L.sub.a923 L.sub.b139 371 L.sub.a51 L.sub.b245 372 L.sub.a309 L.sub.b245 373 L.sub.a56 L.sub.b245 374 L.sub.a311 L.sub.b245 375 L.sub.a58 L.sub.b245 376 L.sub.a321 L.sub.b245 377 L.sub.a74 L.sub.b245 378 L.sub.a323 L.sub.b245 379 L.sub.a79 L.sub.b245 380 L.sub.a332 L.sub.b245 381 L.sub.a81 L.sub.b245 382 L.sub.a351 L.sub.b245 383 L.sub.a97 L.sub.b245 384 L.sub.a356 L.sub.b245 385 L.sub.a102 L.sub.b245 386 L.sub.a375 L.sub.b245 387 L.sub.a104 L.sub.b245 388 L.sub.a422 L.sub.b245 389 L.sub.a120 L.sub.b245 390 L.sub.a427 L.sub.b245 391 L.sub.a125 L.sub.b245 392 L.sub.a450 L.sub.b245 393 L.sub.a212 L.sub.b245 394 L.sub.a473 L.sub.b245 395 L.sub.a214 L.sub.b245 396 L.sub.a496 L.sub.b245 397 L.sub.a217 L.sub.b245 398 L.sub.a606 L.sub.b245 399 L.sub.a219 L.sub.b245 400 L.sub.a611 L.sub.b245 401 L.sub.a226 L.sub.b245 402 L.sub.a634 L.sub.b245 403 L.sub.a304 L.sub.b245 404 L.sub.a899 L.sub.b245 405 L.sub.a306 L.sub.b245 406 L.sub.a923 L.sub.b245 407 L.sub.a993 L.sub.b31 408 L.sub.a993 L.sub.b90 409 L.sub.a997 L.sub.b31 410 L.sub.a997 L.sub.b90 411 L.sub.a1008 L.sub.b31 412 L.sub.a1008 L.sub.b90 413 L.sub.a995 L.sub.b31 414 L.sub.a995 L.sub.b90 415 L.sub.a1300 L.sub.b31 416 L.sub.a1300 L.sub.b88 417 L.sub.a1308 L.sub.b31 418 L.sub.a1308 L.sub.b88 419 L.sub.a1314 L.sub.b31 420 L.sub.a1314 L.sub.b88 421 L.sub.a1315 L.sub.b31 422 L.sub.a1315 L.sub.b88 423 L.sub.a1316 L.sub.b31 424 L.sub.a1316 L.sub.b88 425 L.sub.a1317 L.sub.b31 426 L.sub.a1317 L.sub.b88 427 L.sub.a1321 L.sub.b31 428 L.sub.a1321 L.sub.b88 429 L.sub.a1323 L.sub.b31 430 L.sub.a1323 L.sub.b88 431 L.sub.a1324 L.sub.b31 432 L.sub.a1324 L.sub.b88 433 L.sub.a1326 L.sub.b31 434 L.sub.a1326 L.sub.b88 435 L.sub.a1330 L.sub.b31 436 L.sub.a1330 L.sub.b88 437 L.sub.a1331 L.sub.b31 438 L.sub.a1331 L.sub.b88 439 L.sub.a1334 L.sub.b31 440 L.sub.a1334 L.sub.b88 441 L.sub.a1335 L.sub.b31 442 L.sub.a1335 L.sub.b88 443 L.sub.a1338 L.sub.b31 444 L.sub.a1338 L.sub.b88 445 L.sub.a1339 L.sub.b31 446 L.sub.a1339 L.sub.b88 447 L.sub.a1340 L.sub.b31 448 L.sub.a1340 L.sub.b88 449 L.sub.a993 L.sub.b122 450 L.sub.a993 L.sub.b126 451 L.sub.a997 L.sub.b122 452 L.sub.a997 L.sub.b126 453 L.sub.a1008 L.sub.b122 454 L.sub.a1008 L.sub.b126 455 L.sub.a995 L.sub.b122 456 L.sub.a995 L.sub.b126 457 L.sub.a1300 L.sub.b122 458 L.sub.a1300 L.sub.b126 459 L.sub.a1308 L.sub.b122 460 L.sub.a1308 L.sub.b126 461 L.sub.a1314 L.sub.b122 462 L.sub.a1314 L.sub.b126 463 L.sub.a1315 L.sub.b122 464 L.sub.a1315 L.sub.b126 465 L.sub.a1316 L.sub.b122 466 L.sub.a1316 L.sub.b126 467 L.sub.a1317 L.sub.b122 468 L.sub.a1317 L.sub.b126 469 L.sub.a1321 L.sub.b122 470 L.sub.a1321 L.sub.b126 471 L.sub.a1323 L.sub.b122 472 L.sub.a1323 L.sub.b126 473 L.sub.a1324 L.sub.b122 474 L.sub.a1324 L.sub.b126 475 L.sub.a1326 L.sub.b122 476 L.sub.a1326 L.sub.b126 477 L.sub.a1330 L.sub.b122 478 L.sub.a1330 L.sub.b126 479 L.sub.a1331 L.sub.b122 480 L.sub.a1331 L.sub.b126 481 L.sub.a1334 L.sub.b122 482 L.sub.a1334 L.sub.b126 483 L.sub.a1335 L.sub.b122 484 L.sub.a1335 L.sub.b126 485 L.sub.a1338 L.sub.b122 486 L.sub.a1338 L.sub.b126 487 L.sub.a1339 L.sub.b122 488 L.sub.a1339 L.sub.b126 489 L.sub.a1340 L.sub.b122 490 L.sub.a1340 L.sub.b126 491 L.sub.a997 L.sub.b139 492 L.sub.a997 L.sub.b135 493 L.sub.a1008 L.sub.b139 494 L.sub.a1008 L.sub.b135 495 L.sub.a995 L.sub.b139 496 L.sub.a995 L.sub.b135 497 L.sub.a1300 L.sub.b139 498 L.sub.a1300 L.sub.b135 499 L.sub.a1308 L.sub.b139 500 L.sub.a1308 L.sub.b135 501 L.sub.a1314 L.sub.b139 502 L.sub.a1314 L.sub.b135 503 L.sub.a1315 L.sub.b139 504 L.sub.a1315 L.sub.b135 505 L.sub.a1316 L.sub.b139 506 L.sub.a1316 L.sub.b135 507 L.sub.a1317 L.sub.b139 508 L.sub.a1317 L.sub.b135 509 L.sub.a1321 L.sub.b139 510 L.sub.a1321 L.sub.b135 511 L.sub.a1323 L.sub.b139 512 L.sub.a1323 L.sub.b135 513 L.sub.a1324 L.sub.b139 514 L.sub.a1324 L.sub.b135 515 L.sub.a1326 L.sub.b139 516 L.sub.a1326 L.sub.b135 517 L.sub.a1330 L.sub.b139 518 L.sub.a1330 L.sub.b135 519 L.sub.a1331 L.sub.b139 520 L.sub.a1331 L.sub.b135 521 L.sub.a1334 L.sub.b139 522 L.sub.a1334 L.sub.b135 523 L.sub.a1335 L.sub.b139 524 L.sub.a1335 L.sub.b135 525 L.sub.a1338 L.sub.b139 526 L.sub.a1338 L.sub.b135 527 L.sub.a1339 L.sub.b139 528 L.sub.a1339 L.sub.b135 529 L.sub.a1340 L.sub.b139 530 L.sub.a1340 L.sub.b135
16. An electroluminescent device, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex of claim 1.
17. The electroluminescent device of claim 16, wherein the organic layer is an emissive layer, and the metal complex is a luminescent material.
18. The electroluminescent device of claim 17, wherein the electroluminescent device emits red light or white light.
19. The electroluminescent device of claim 18, wherein the emissive layer further comprises at least one host material; preferably, the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
20. A compound composition, comprising the metal complex of claim 1.
Description
BRIEF DESCRIPTION OF DRAWINGS
[0022]
[0023]
DETAILED DESCRIPTION
[0024] OLEDs can be fabricated on various types of substrates such as glass, plastic, and metal foil.
[0025] 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 F.sub.4-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.
[0026] 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.
[0027] 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.
[0028] An OLED can be encapsulated by a barrier layer.
[0029] 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.
[0030] The materials and structures described herein may be used in other organic electronic devices listed above.
[0031] 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.
[0032] 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.
[0033] 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.
[0034] 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).
[0035] 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.
[0036] 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 (AEs-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
[0037] Halogen or halide—as used herein includes fluorine, chlorine, bromine, and iodine.
[0038] 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, a 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.
[0039] 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.
[0040] 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-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropylsilylethyl. Additionally, the heteroalkyl group may be optionally substituted.
[0041] 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.
[0042] 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.
[0043] 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.
[0044] 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.
[0045] 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.
[0046] 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.
[0047] 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.
[0048] 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.
[0049] 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.
[0050] 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.
[0051] Alkylgermanyl—as used herein contemplates a 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.
[0052] 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.
[0053] 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.
[0054] 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, amino, acyl, carbonyl, a carboxylic acid group, an ester group, sulfinyl, sulfonyl, and phosphino may be substituted with one or more groups 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 group having 6 to 20 carbon atoms, unsubstituted alkylgermanyl group 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.
[0055] 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.
[0056] 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 may 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.
[0057] In the compounds mentioned in the present disclosure, multiple substitutions refer to a range that includes di-substitutions, up to the maximum available substitutions. When substitution in the compounds mentioned in the present disclosure represents multiple substitutions (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 have the same structure or different structures.
[0058] 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.
[0059] 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:
##STR00004##
[0060] 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:
##STR00005##
[0061] The expression that adjacent substituents can be optionally joined to form a ring is also intended to mean that two substituents bonded to further distant carbon atoms are joined to each other via a chemical bond to form a ring, which can be exemplified by the following formula:
##STR00006##
[0062] 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:
##STR00007##
[0063] According to an embodiment of the present disclosure, a metal complex is disclosed, the metal complex comprises a metal M and a ligand L.sub.a coordinated to the metal M, wherein the metal M is selected from metals having a relative atomic mass greater than 40, and the ligand L.sub.a has a structure represented by Formula 1:
##STR00008##
[0064] wherein,
[0065] Z.sub.1 and Z.sub.2 are each independently selected from C or N, and Z.sub.1 and Z.sub.2 are different;
[0066] W is, at each occurrence identically or differently, selected from B, N or P;
[0067] ring A, ring C, and ring D are, at each occurrence identically or differently, selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
[0068] ring B is selected from a heterocyclic ring having 2 to 30 carbon atoms or a heteroaromatic ring having 2 to 30 carbon atoms;
[0069] R.sub.a, R.sub.b, R.sub.c, and R.sub.d represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
[0070] R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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;
[0071] adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring.
[0072] In the present disclosure, the expression that adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring is intended to mean that any one or more of groups of adjacent substituents, such as adjacent substituents R.sub.a, adjacent substituents R.sub.b, adjacent substituents R.sub.c, adjacent substituents R.sub.d, adjacent substituents R.sub.a and R.sub.b, adjacent substituents R.sub.a and R.sub.d, and adjacent substituents R.sub.b and R.sub.c, can be joined to form a ring. Obviously, it is possible that none of these groups of adjacent substituents are joined to form a ring.
[0073] According to an embodiment of the present disclosure, wherein, in the L.sub.a, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; and ring B is selected form a heteroaromatic ring having 2 to 18 carbon atoms.
[0074] According to an embodiment of the present disclosure, wherein, in the L.sub.a, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from an aromatic ring having 6 to 10 carbon atoms or a heteroaromatic ring having 5 to 10 ring atoms; and ring B is selected form a heteroaromatic ring having 5 to 10 ring atoms.
[0075] According to an embodiment of the present disclosure, wherein, in the L.sub.a, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, an aza-naphthalene ring, a furan ring, a thiophene ring, an isoxazole ring, an isothiazole ring, a pyrrole ring, a pyrazole ring, a benzofuran ring, a benzothiophene ring, an azabenzofuran ring or an azabenzothiophene ring; and ring B is selected from a pyrrole ring, an indole ring, an imidazole ring, a pyrazole ring, a triazole ring or an azaindole ring.
[0076] According to an embodiment of the present disclosure, wherein, in the L.sub.a, ring A, ring C, and ring D are, at each occurrence identically or differently, selected from a benzene ring, a naphthalene ring, a pyridine ring or a pyrimidine ring; and ring B is selected from a pyrrole ring, an indole ring or an azaindole ring.
[0077] According to an embodiment of the present disclosure, wherein, the L.sub.a is selected from a structure represented by any one of Formula 2 to Formula 19:
##STR00009## ##STR00010## ##STR00011## ##STR00012##
[0078] wherein,
[0079] Z.sub.1 and Z.sub.2 are each independently selected from C or N, and Z.sub.1 and Z.sub.2 are different;
[0080] W is, at each occurrence identically or differently, selected from B, N or P;
[0081] A.sub.1 to A.sub.5 are, at each occurrence identically or differently, selected from N or CR.sub.a;
[0082] B.sub.1 to B.sub.4 are, at each occurrence identically or differently, selected from N or CR.sub.b;
[0083] C.sub.1 to C.sub.4 are, at each occurrence identically or differently, selected from N or CR.sub.c;
[0084] D.sub.1 to D.sub.4 are, at each occurrence identically or differently, selected from N or CR.sub.d;
[0085] X.sub.1 is, at each occurrence identically or differently, selected from O, S, Se, NR.sub.c, CR.sub.cR.sub.c, SiR.sub.cR.sub.c or PR.sub.c;
[0086] X.sub.2 is, at each occurrence identically or differently, selected from O, S, Se, NR.sub.d, CR.sub.dR.sub.d, SiR.sub.dR.sub.d or PR.sub.d;
[0087] Z.sub.3 is, at each occurrence identically or differently, selected from O, S, Se, NR.sub.z, CR.sub.zR.sub.z, SiR.sub.zR.sub.z or PR.sub.z;
[0088] R.sub.a, R.sub.b, R.sub.c, R.sub.d, and R.sub.z 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;
[0089] adjacent substituents R.sub.a, R.sub.b, R.sub.c, R.sub.d, and R.sub.z can be optionally joined to form a ring.
[0090] In this embodiment, the expression that adjacent substituents R.sub.a, R.sub.b, R.sub.c, R.sub.d, and R.sub.z can be optionally joined to form a ring is intended to mean that any one or more of groups of adjacent substituents, such as adjacent substituents R.sub.a, adjacent substituents R.sub.b, adjacent substituents R.sub.c, adjacent substituents R.sub.d, adjacent substituents R.sub.a and R.sub.b, adjacent substituents R.sub.a and R.sub.d, and adjacent substituents R.sub.b and R.sub.c, adjacent substituents R.sub.a and R.sub.z, adjacent substituents R.sub.d and R.sub.z, and adjacent substituents R.sub.z, can be joined to form a ring. Obviously, it is possible that none of these groups of adjacent substituents are joined to form a ring.
[0091] According to an embodiment of the present disclosure, wherein, L.sub.a is selected from a structure represented by Formula 2, Formula 3, Formula 7, Formula 8, Formula 9 or Formula 12.
[0092] According to an embodiment of the present disclosure, wherein, L.sub.a is selected from a structure represented by Formula 2, Formula 3, Formula 9 or Formula 12.
[0093] According to an embodiment of the present disclosure, wherein, L.sub.a is selected from a structure represented by Formula 2, Formula 3 or Formula 12.
[0094] According to an embodiment of the present disclosure, wherein, in Formula 1 to Formula 19, Z.sub.1 is N, and Z.sub.2 is C.
[0095] According to an embodiment of the present disclosure, wherein, in Formula 1 to Formula 19, Z.sub.1 is C, and Z.sub.2 is N.
[0096] According to an embodiment of the present disclosure, wherein, in Formula 1 to Formula 19, W is N.
[0097] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 18, Z.sub.1 is N, and at least one of D.sub.1 and D.sub.2 is N; or in Formula 2 to Formula 17 and Formula 19, Z.sub.2 is N, and at least one of C.sub.1 and C.sub.2 is N.
[0098] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 18, Z.sub.1 is N, and one of D.sub.1 and D.sub.2 is N; or in Formula 2 to Formula 17 and Formula 19, Z.sub.2 is N, and one of C.sub.1 and C.sub.2 is N.
[0099] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 18, Z.sub.1 is N, and D.sub.2 is N; or in Formula 2 to Formula 17 and Formula 19, Z.sub.2 is N, and C.sub.1 is N.
[0100] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 19, A.sub.1 to A.sub.5 are each independently selected from CR.sub.a, and B.sub.1 to B.sub.4 are each independently selected from CR.sub.b; in Formula 2 to Formula 17 and Formula 19, C.sub.1 to C.sub.4 are each independently selected from CR.sub.c; in Formula 2 to Formula 18, D.sub.1 to D.sub.4 are each independently selected from CR.sub.d; and the R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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] adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring.
[0102] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 19, A.sub.1 to A.sub.5 are each independently selected from CR.sub.a, and B.sub.1 to B.sub.4 are each independently selected from CR.sub.b; in Formula 2 to Formula 17 and Formula 19, C.sub.1 to C.sub.4 are each independently selected from CR.sub.c; in Formula 2 to Formula 18, D.sub.1 to D.sub.4 are each independently selected from CR.sub.d; and the R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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 alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 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 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, a cyano group, and combinations thereof;
[0103] adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring.
[0104] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 19, A.sub.1 to A.sub.5 are each independently selected from CR.sub.a, and B.sub.1 to B.sub.4 are each independently selected from CR.sub.b; in Formula 2 to Formula 17 and Formula 19, C.sub.1 to C.sub.4 are each independently selected from CR.sub.c; in Formula 2 to Formula 18, D.sub.1 to D.sub.4 are each independently selected from CR.sub.d; and the R.sub.a, R.sub.b, R.sub.c, and R.sub.d 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 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, a cyano group, and combinations thereof;
[0105] adjacent substituents R.sub.a, R.sub.b, R.sub.c, and R.sub.d can be optionally joined to form a ring.
[0106] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 19, at least one of A.sub.1 to A.sub.n is, at each occurrence identically or differently, selected from CR.sub.a, and the A.sub.n corresponds to one having the largest serial number of A.sub.1 to A.sub.5 in any one of Formula 2 to Formula 19; and the R.sub.a is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, a cyano group, a hydroxyl group, a sulfanyl group, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring 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, and combinations thereof;
[0107] adjacent substituents R.sub.a can be optionally joined to form a ring.
[0108] In the present disclosure, the expression that adjacent substituents R.sub.a can be optionally joined to form a ring is intended to mean that any adjacent substituents R.sub.a can be joined to form a ring. Obviously, it is possible that none of adjacent substituents R.sub.a are joined to form a ring.
[0109] In this embodiment, in Formula 2 to Formula 19, at least one of A.sub.1 to A.sub.n is, at each occurrence identically or differently, selected from CR.sub.a, and the A.sub.n corresponds to one having the largest serial number of A.sub.1 to A.sub.5 in any one of Formula 2 to Formula 19. For example, for Formula 2, the A.sub.n corresponds to A.sub.3 whose serial number is the largest in A.sub.1 to A.sub.5 in Formula 2, that is, in Formula 2, at least one of A.sub.1 to A.sub.3 is, at each occurrence identically or differently, selected from CR.sub.a. For another example, for Formula 4, the A.sub.n corresponds to A.sub.5 whose serial number is the largest in A.sub.1 to A.sub.5 in Formula 4, that is, in Formula 4, at least one of A.sub.1 to A.sub.5 is, at each occurrence identically or differently, selected from CR.sub.a. For another example, for Formula 15, the A.sub.n corresponds to A.sub.1 whose serial number is the largest in A.sub.1 to A.sub.5 in Formula 15, that is, in Formula 15, A.sub.1 is, at each occurrence identically or differently, selected from CR.sub.a.
[0110] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 14, Formula 18 and Formula 19, at least one of A.sub.1 to A.sub.3 is, at each occurrence identically or differently, selected from CR.sub.a; and in Formula 15 to Formula 17, A.sub.1 is selected from CR.sub.a.
[0111] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 14, Formula 18 and Formula 19, at least one of A.sub.1 to A.sub.3 is, at each occurrence identically or differently, selected from CR.sub.a; in Formula 15 to Formula 17, A.sub.1 is selected from CR.sub.a; and the R.sub.a is, at each occurrence identically or differently, selected from the group consisting of: deuterium, fluorine, a cyano group, a hydroxyl group, a sulfanyl group, an amino group, a methoxy group, a phenoxy group, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, piperidyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantly, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermanyl, triethylgermanyl, phenyl, pyridyl, triazinyl, and combinations thereof.
[0112] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 17 and Formula 19, C.sub.2 is, at each occurrence identically or differently, selected from CR.sub.c, and the R.sub.c is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, a cyano group, 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, and combinations thereof.
[0113] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 17 and Formula 19, C.sub.2 is, at each occurrence identically or differently, selected from CR.sub.c, and the R.sub.c is, at each occurrence identically or differently, selected from the group consisting of: deuterium, a cyano group, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermanyl, triethylgermanyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.
[0114] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 19, at least one of B.sub.1 to B.sub.n is selected from CR.sub.b, and the B.sub.n corresponds to one having the largest serial number of B.sub.1 to B.sub.4 in any one of Formula 2 to Formula 19; and/or in Formula 2 to Formula 18, at least one of D.sub.1 to D.sub.n is selected from CR.sub.d, and the D.sub.n corresponds to one having the largest serial number of D.sub.1 to D.sub.4 in any one of Formula 2 to Formula 18; and the R.sub.b and R.sub.d 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, 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, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
[0115] In this embodiment, in Formula 2 to Formula 19, at least one of B.sub.1 to B.sub.1 is, at each occurrence identically or differently, selected from CR.sub.b, and the B.sub.n corresponds to one having the largest serial number of B.sub.1 to B.sub.4 in any one of Formula 2 to Formula 19. For example, for Formula 2, the B.sub.1 corresponds to B.sub.4 whose serial number is the largest in B.sub.1 to B.sub.4 in Formula 2, that is, in Formula 2, at least one of B.sub.1 to B.sub.4 is, at each occurrence identically or differently, selected from CR.sub.b. For another example, for Formula 13, the B.sub.1 corresponds to B.sub.2 whose serial number is the largest in B.sub.1 to B.sub.4 in Formula 13, that is, in Formula 13, at least one of B.sub.1 to B.sub.2 is, at each occurrence identically or differently, selected from CR.sub.b.
[0116] In this embodiment, in Formula 2 to Formula 18, at least one of D.sub.1 to D.sub.n is, at each occurrence identically or differently, selected from CR.sub.d, and the D.sub.n corresponds to one having the largest serial number of D.sub.1 to D.sub.4 in any one of Formula 2 to Formula 18. For example, for Formula 2, the D.sub.n corresponds to D.sub.2 whose serial number is the largest in D.sub.1 to D.sub.4 in Formula 2, that is, in Formula 2, at least one of D.sub.1 to D.sub.2 is, at each occurrence identically or differently, selected from CR.sub.d. For another example, for Formula 12, the D.sub.n corresponds to D.sub.4 whose serial number is the largest in D.sub.1 to D.sub.4 in Formula 12, that is, in Formula 12, at least one of D.sub.1 to D.sub.4 is, at each occurrence identically or differently, selected from CR.sub.d.
[0117] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 12, Formula 16, Formula 18 and Formula 19, B.sub.2 and/or B.sub.3 are selected from CR.sub.b; in Formula 13 to Formula 15 and Formula 17, B.sub.1 and/or B.sub.2 are selected from CR.sub.b; and in Formula 2 to Formula 18, D.sub.1 and/or D.sub.2 are selected from CR.sub.d.
[0118] According to an embodiment of the present disclosure, wherein, in Formula 2 to Formula 12, Formula 16, Formula 18 and Formula 19, B.sub.2 and/or B.sub.3 are selected from CR.sub.b; in Formula 13 to Formula 15 and Formula 17, B.sub.1 and/or B.sub.2 are selected from CR.sub.b; in Formula 2 to Formula 18, D.sub.1 and/or D.sub.2 are selected from CR.sub.d; and the R.sub.b and R.sub.d are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, a cyano group, a hydroxyl group, a sulfanyl group, an amino group, a methoxy group, a phenoxy group, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, piperidyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermanyl, triethylgermanyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.
[0119] According to an embodiment of the present disclosure, wherein, in Formula 5 to Formula 8, Formula 10, Formula 11 and Formula 15 to Formula 17, Z.sub.3 is, at each occurrence identically or differently, selected from O, S or Se; in Formula 18, X.sub.1 is, at each occurrence identically or differently, selected from O, S or Se; and in Formula 19, X.sub.2 is, at each occurrence identically or differently, selected from O, S or Se.
[0120] According to an embodiment of the present disclosure, wherein, in Formula 5 to Formula 8, Formula 10, Formula 11 and Formula 15 to Formula 17, Z.sub.3 is, at each occurrence identically or differently, selected from O or S; in Formula 18, X.sub.1 is, at each occurrence identically or differently, selected from O or S; and in Formula 19, X.sub.2 is, at each occurrence identically or differently, selected from O or S.
[0121] According to an embodiment of the present disclosure, wherein, L.sub.a is, at each occurrence identically or differently, selected from the group consisting of L.sub.a1 to L.sub.a1297, wherein for the specific structures of L.sub.a1 to L.sub.a1297, reference is made to claim 11.
[0122] According to an embodiment of the present disclosure, wherein, L.sub.a is, at each occurrence identically or differently, selected from the group consisting of L.sub.a1 to L.sub.a1342, wherein for the specific structures of L.sub.a1 to L.sub.a1342, reference is made to claim 11.
[0123] According to an embodiment of the present disclosure, wherein, hydrogen in the structures of L.sub.a1 to L.sub.a1297 can be partially or completely substituted with deuterium.
[0124] According to an embodiment of the present disclosure, wherein, hydrogen in the structures of L.sub.a1 to L.sub.a1342 can be partially or completely substituted with deuterium.
[0125] According to an embodiment of the present disclosure, 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;
[0126] wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; 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; 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 is equal to an oxidation state of the metal M; when m is equal to 2 or 3, a plurality of L.sub.a can be identical or different; when n is equal to 2, two L.sub.b can be identical or different; and when q is equal to 2, two L.sub.c can be identical or different;
[0127] L.sub.a, L.sub.b, and L.sub.c can be optionally joined to form a multi-dentate ligand;
[0128] L.sub.b and L.sub.c are, at each occurrence identically or differently, selected from the group consisting of the following structures:
##STR00013##
[0129] wherein,
[0130] R.sub.i, R.sub.ii, and R.sub.iii represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
[0131] X.sub.a 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;
[0132] X.sub.b and X.sub.c are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NR.sub.N2;
[0133] R.sub.i, R.sub.ii, R.sub.iii, R.sub.N1, R.sub.N2, 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;
[0134] adjacent substituents R.sub.i, R.sub.ii, R.sub.iii, R.sub.N1, R.sub.N2, R.sub.C1, and R.sub.C2 can be optionally joined to form a ring.
[0135] In this embodiment, the expression that adjacent substituents R.sub.i, R.sub.ii, R.sub.iii, R.sub.N1, R.sub.N2, 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 in the structures of L.sub.b and L.sub.c, such as adjacent substituents R.sub.i, adjacent substituents R.sub.ii, adjacent substituents R.sub.iii, adjacent substituents R.sub.i and R.sub.ii, adjacent substituents R.sub.ii and R.sub.iii, adjacent substituents R.sub.i and R.sub.iii, adjacent substituents R.sub.i and R.sub.N1, adjacent substituents R.sub.i and R.sub.C1, adjacent substituents R.sub.i and R.sub.C2, adjacent substituents R.sub.ii and R.sub.N1, adjacent substituents R.sub.iii and R.sub.N1, adjacent substituents R.sub.ii and R.sub.C1, adjacent substituents R.sub.ii and R.sub.C2, adjacent substituents R.sub.iii and R.sub.C1, adjacent substituents R.sub.iii and R.sub.C2, adjacent substituents R.sub.i and R.sub.N2, adjacent substituents R.sub.ii and R.sub.N2, and adjacent substituents R.sub.C1 and R.sub.C2, may be joined to form a ring. Obviously, it is possible that none of these substituents are joined to form a ring.
[0136] In this embodiment, L.sub.a, L.sub.b, and L.sub.c can be optionally joined to form a multi-dentate ligand, for example, any two or three of L.sub.a, L.sub.b, and L.sub.c can be joined to form a tetradentate ligand or a hexadentate ligand. Obviously, it is possible that none of L.sub.a, L.sub.b, and L.sub.c are joined so that no multi-dentate ligand is formed.
[0137] According to an embodiment of the present disclosure, wherein, the metal M is selected from Ir, Pt or Os.
[0138] According to an embodiment of the present disclosure, wherein, the metal M is Ir.
[0139] According to an embodiment of the present disclosure, wherein, L.sub.b is, at each occurrence identically or differently, selected from the following structure:
##STR00014##
[0140] wherein R.sub.1 to R.sub.7 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.
[0141] According to an embodiment of the present disclosure, wherein, L.sub.b is, at each occurrence identically or differently, selected from the following structure:
##STR00015##
[0142] wherein at least one or two of R.sub.1 to R.sub.3 are selected from 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 or combinations thereof; and/or at least one or two of R.sub.4 to R.sub.6 are selected from 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 or combinations thereof.
[0143] According to an embodiment of the present disclosure, wherein, L.sub.b is, at each occurrence identically or differently, selected from the following structure:
##STR00016##
[0144] wherein at least two of R.sub.1 to R.sub.3 are selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms or combinations thereof; and/or at least two of R.sub.4 to R.sub.6 are selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms or combinations thereof.
[0145] According to an embodiment of the present disclosure, wherein, L.sub.b is, at each occurrence identically or differently, selected from the group consisting of L.sub.b1 to L.sub.b322, wherein for the specific structures of L.sub.b1 to L.sub.b322, reference is made to claim 14.
[0146] According to an embodiment of the present disclosure, wherein, L.sub.c is, at each occurrence identically or differently, selected from the group consisting of L.sub.c1 to L.sub.c231, wherein for the specific structures of L.sub.c1 to L.sub.c231, reference is made to claim 14.
[0147] According to an embodiment of the present disclosure, wherein, the metal complex is an Ir complex and has a structure represented by any one of Ir(L.sub.a)(L.sub.b)(L.sub.c), Ir(L.sub.a).sub.2(L.sub.b), Ir(L.sub.a).sub.2(L.sub.c) and Ir(L.sub.a)(L.sub.c).sub.2; when the metal complex has a structure of Ir(L.sub.a)(L.sub.b)(L.sub.c), L.sub.a is selected from any one of the group consisting of L.sub.a1 to L.sub.a1297, L.sub.b is selected from any one of the group consisting of L.sub.b1 to L.sub.b322, and L.sub.c is selected from any one of the group consisting of L.sub.c1 to L.sub.c231; when the metal complex has a structure of Ir(L.sub.a).sub.2(L.sub.b), L.sub.a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.a1 to L.sub.a1297, and L.sub.b is selected from any one of the group consisting of L.sub.b1 to L.sub.b322; when the metal complex has a structure of Ir(L.sub.a).sub.2(L.sub.c), L.sub.a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.a1 to L.sub.a1297, and L.sub.c is selected from any one of the group consisting of L.sub.c1 to L.sub.c231; and when the metal complex has a structure of Ir(L.sub.a)(L.sub.c).sub.2, L.sub.a is selected from any one of the group consisting of L.sub.a1 to L.sub.a1297, and L.sub.c is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.c1 to L.sub.c231.
[0148] According to an embodiment of the present disclosure, wherein, the metal complex is an Ir complex and has a structure represented by any one of Ir(L.sub.a)(L.sub.b)(L.sub.c), Ir(L.sub.a).sub.2(L.sub.b), Ir(L.sub.a).sub.2(L.sub.c) and Ir(L.sub.a)(L.sub.c).sub.2; when the metal complex has a structure of Ir(L.sub.a)(L.sub.b)(L.sub.c), L.sub.a is selected from any one of the group consisting of L.sub.a1 to L.sub.a1342, L.sub.b is selected from any one of the group consisting of L.sub.b1 to L.sub.b322, and L.sub.c is selected from any one of the group consisting of L.sub.c1 to L.sub.c231; when the metal complex has a structure of Ir(L.sub.a).sub.2(L.sub.b), L.sub.a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.a1 to L.sub.a1342, and L.sub.b is selected from any one of the group consisting of L.sub.b1 to L.sub.b322; when the metal complex has a structure of Ir(L.sub.a).sub.2(L.sub.c), L.sub.a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.a1 to L.sub.a1342, and L.sub.c is selected from any one of the group consisting of L.sub.c1 to L.sub.c231; and when the metal complex has a structure of Ir(L.sub.a)(L.sub.c).sub.2, L.sub.a is selected from any one of the group consisting of L.sub.a1 to L.sub.a1342, and L.sub.c is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L.sub.c1 to L.sub.c231.
[0149] According to an embodiment of the present disclosure, wherein, the metal complex is selected from the group consisting of Compound 1 to Compound 406, wherein for the specific structures of Compound 1 to Compound 406, reference is made to claim 15.
[0150] According to an embodiment of the present disclosure, wherein, the metal complex is selected from the group consisting of Compound 1 to Compound 530, wherein for the specific structures of Compound 1 to Compound 530, reference is made to claim 15.
[0151] According to an embodiment of the present disclosure, an electroluminescent device is further disclosed, the electroluminescent device comprises:
[0152] an anode,
[0153] a cathode, and
[0154] an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex, and the specific structure of the metal complex is shown in any of the embodiments described above.
[0155] According to an embodiment of the present disclosure, in the device, the organic layer is an emissive layer, and the compound is a luminescent material.
[0156] According to an embodiment of the present disclosure, the electroluminescent device emits red light.
[0157] According to an embodiment of the present disclosure, the electroluminescent device emits white light.
[0158] According to an embodiment of the present disclosure, in the device, the organic layer further comprises at least one host material.
[0159] According to an embodiment of the present disclosure, in the device, the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0160] According to an embodiment of the present disclosure, in the device, the host material may be a conventional host material in the existing art, for example, may typically comprises the following host materials without limitation:
##STR00017## ##STR00018## ##STR00019##
[0161] According to another embodiment of the present disclosure, a compound composition is further disclosed. The compound composition comprises a metal complex whose specific structure is as shown in any of the embodiments described above.
[0162] Combination with Other Materials
[0163] 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.
[0164] 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, compound disclosed herein may be used in combination with a wide variety of emissive dopants, 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.
MATERIAL SYNTHESIS EXAMPLE
[0165] The method for preparing a compound of the present disclosure is not limited herein. Typically, the following compounds are taken as examples without limitations, and synthesis routes and preparation methods thereof are described below.
Synthesis Example 1: Synthesis of Compound 63
[0166] Step 1: Synthesis of Intermediate 3
##STR00020##
[0167] 1,6,7-trichloroisoquinoline (Intermediate 1, 4.3 g, 14.2 mmol), Intermediate 2 (3.3 g, 14.2 mmol), Pd(PPh.sub.3).sub.4 (809 mg, 0.7 mmol) and Na.sub.2CO.sub.3 (2.3 g, 21.3 mmol) were mixed in dioxane/H.sub.2O (56 mL/14 mL), purged with nitrogen, and reacted overnight at 80° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature, diluted with ethyl acetate and extracted, and the organic phase was concentrated and purified by column chromatography to give Intermediate 3 (3.4 g).
[0168] Step 2: Synthesis of Intermediate 4
##STR00021##
[0169] Intermediate 3 (3.4 g, 9 mmol), CuBr (129 mg, 0.9 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (TMDH, 1.33 g, 7.2 mmol) and Cs.sub.2CO.sub.3 (7.33 g, 22.5 mmol) were mixed in DMF (90 mL), purged with nitrogen, and reacted at 135° C. for 5 hours. The reaction solution was cooled to room temperature, and water was added to the reaction solution. The product was precipitated and filtered. The filter cake was washed with an appropriate amount of water and PE, dried, then refluxed in EtOH for 3 hours and filtered to give Intermediate 4 (2.6 g).
[0170] Step 3: Synthesis of Intermediate 5
##STR00022##
[0171] Intermediate 4 (2.6 g, 7.63 mmol), Pd.sub.2(dba).sub.3 (137.4 mg, 0.15 mmol), tBuDavePhos (307.3 mg, 0.9 mmol, 6 mol %) and LiOAc (2.52 g, 38.2 mmol) were mixed in DMF (24 mL) and purged with nitrogen, TMS-TMS (2.22 g, 15.2 mmol) and H.sub.2O (275 mg, 15.3 mmol) were added, and the mixture reacted overnight at 100° C. The reaction solution was cooled, added with water, and extracted by EA. The organic phase was collected, and the residue was concentrated and purified by column chromatography to give Intermediate 5 (2.4 g).
[0172] Step 4: Synthesis of Iridium dimer 6
##STR00023##
[0173] Intermediate 5 (1.8 g, 4.75 mmol) and IrCl.sub.3.3H.sub.2O (465 mg, 1.32 mmol) were mixed in ethoxyethanol (27 mL) and water (9 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 6 which can be directly used in the next step without further purification.
[0174] Step 5: Synthesis of Compound 63
##STR00024##
[0175] Iridium dimer 6 prepared in step 4, 3,7-diethyl-3,7-dimethyl-4,6-nonanedione (476 mg, 1.98 mmol), K.sub.2CO.sub.3 (912 mg, 6.6 mmol) and ethoxyethanol (36 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM and placed into a 250 mL flask. EtOH (about 10 mL) was added to the flask, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH to give the crude product. The crude product was purified by column chromatography to give Compound 63 (300 mg). The product was confirmed as the target product with a molecular weight of 1186.5.
Synthesis Example 2: Synthesis of Compound 38
[0176] Step 1: Synthesis of Iridium dimer 8
##STR00025##
[0177] Intermediate 7 (400 mg, 1.1 mmol) and IrCl.sub.3.3H.sub.2O (113 mg, 0.32 mmol) were mixed in ethoxyethanol (6 mL) and water (2 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 8 which can be directly used in the next step without further purification.
[0178] Step 2: Synthesis of Compound 38
##STR00026##
[0179] Iridium dimer 8 prepared in step 1, 3,7-diethyl-3-methylnonane-4,6-dione (289 mg, 1.28 mmol), K.sub.2CO.sub.3 (442 mg, 3.2 mmol) and ethoxyethanol (6 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM and placed into a 250 mL flask. EtOH (about 10 mL) was added to the flask, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH to give the crude product. The crude product was purified by column chromatography to give Compound 38 (100 mg). The product was confirmed as the target product with a molecular weight of 1140.5.
Synthesis Example 3: Synthesis of Compound 260
[0180] Step 1: Synthesis of Iridium Dimer 10
##STR00027##
[0181] Intermediate 9 (156 mg, 0.35 mmol) and IrCl.sub.3.3H.sub.2O (41 mg, 0.11 mmol) were mixed in ethoxyethanol (3 mL) and water (1 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 10 which can be directly used in the next step without further purification.
[0182] Step 2: Synthesis of Compound 260
##STR00028##
[0183] Iridium dimer 10 prepared in step 1, 3,7-diethyl-3-methylnonane-4,6-dione (37.4 mg, 0.17 mmol), K.sub.2CO.sub.3 (76 mg, 0.55 mmol) and ethoxyethanol (5 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM and placed into a 250 mL flask. EtOH (about 10 mL) was added to the flask, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH to give the crude product. The crude product was purified by column chromatography to give Compound 260 (40 mg). The product was confirmed as the target product with a molecular weight of 1308.7.
Synthesis Example 4: Synthesis of Compound 192
[0184] Step 1: Synthesis of Iridium Dimer 12
##STR00029##
[0185] Intermediate 11 (1.4 g, 3.12 mmol) and IrCl.sub.3.3H.sub.2O (400 mg, 1.13 mmol) were mixed in ethoxyethanol (27 mL) and water (9 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 12 which can be directly used in the next step without further purification.
[0186] Step 2: Synthesis of Compound 192
##STR00030##
[0187] Iridium dimer 12 prepared in step 1, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (452 mg, 1.7 mmol), K.sub.2CO.sub.3 (781 mg, 5.65 mmol) and ethoxyethanol (25 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at room temperature. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM and placed into a 250 mL flask. EtOH (about 10 mL) was added to the flask, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH to give the crude product. The crude product was purified by column chromatography to give Compound 192 (167 mg). The product was confirmed as the target product with a molecular weight of 1352.6.
Synthesis Example 5: Synthesis of Compound 278
[0188] Step 1: Synthesis of Iridium Dimer 14
##STR00031##
[0189] Intermediate 13 (100 mg, 0.26 mmol) and IrCl.sub.3.3H.sub.2O (35 mg, 0.1 mmol) were mixed in ethoxyethanol (3 mL) and water (1 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 14 which can be directly used in the next step without further purification.
[0190] Step 2: Synthesis of Compound 278
##STR00032##
[0191] Iridium dimer 14 prepared in step 1, 3,7-diethyl-3-methylnonane-4,6-dione (50 mg, 0.22 mmol), K.sub.2CO.sub.3 (70 mg, 0.5 mmol), ethoxyethanol (2 mL) and DMF (2 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 50° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM and placed into a 50 mL flask. EtOH (about 2 mL) was added to the flask, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH to give the crude product. The crude product was purified by column chromatography to give Compound 278 (3 mg). The product was confirmed as the target product with a molecular weight of 1170.5.
Synthesis Example 6: Synthesis of Compound 256
[0192] Step 1: Synthesis of Intermediate 16
##STR00033##
[0193] Intermediate 15 (2.33 g, 5.67 mmol), Pd.sub.2(dba).sub.3 (201 mg, 0.22 mmol), tBuDavePhos (450 mg, 1.32 mmol) and LiOAc (1.88 g, 28.4 mmol) were mixed in DMF (19 mL) and purged with nitrogen, hexamethyldigermane (2.4 g, 10.2 mmol) and H.sub.2O (205 mg, 11.4 mmol) were added, and the mixture reacted overnight at 135° C. The reaction solution was cooled, and water was added to the reaction solution. The precipitated product was filtered and dissolved with EA. The crude product was concentrated and purified by column chromatography to give Intermediate 16 (1.4 g).
[0194] Step 2: Synthesis of Iridium Dimer 17
##STR00034##
[0195] Intermediate 16 (1.4 g, 2.8 mmol) and IrCl.sub.3.3H.sub.2O (395 mg, 1.12 mmol) were mixed in ethoxyethanol (27 mL) and water (9 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 17 which can be directly used in the next step without further purification.
[0196] Step 3: Synthesis of Compound 256
##STR00035##
[0197] Iridium dimer 17 prepared in step 2, 3,7-diethyl-3-methylnonane-4,6-dione (380 mg, 1.68 mmol), K.sub.2CO.sub.3 (774 mg, 5.6 mmol) and ethoxyethanol (25 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was dissolved with DCM. EtOH (about 10 mL) was added to the solution, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH. The crude product was subjected to column chromatography to give Compound 256 (150 mg). The product was confirmed as the target product with a molecular weight of 1404.5.
Synthesis Example 7: Synthesis of Compound 321
[0198] Step 1: Synthesis of Iridium Dimer 19
##STR00036##
[0199] Intermediate 18 (210 mg, 0.47 mmol) and IrCl.sub.3.3H.sub.2O (56 mg, 0.16 mmol) were mixed in ethoxyethanol (3.9 mL) and water (1.3 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 19 which can be directly used in the next step without further purification.
[0200] Step 2: Synthesis of Compound 321
##STR00037##
[0201] Iridium dimer 19 prepared in step 1, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (56 mg, 0.23 mmol), K.sub.2CO.sub.3 (110 mg, 0.8 mmol) and ethoxyethanol (5 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was dissolved with DCM. EtOH (about 2 mL) was added to the solution, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH. The crude product was subjected to column chromatography to give Compound 321 (50 mg). The product was confirmed as the target product with a molecular weight of 1322.7.
Synthesis Example 8: Synthesis of Compound 28
[0202] Step 1: Synthesis of Compound 28
##STR00038##
[0203] Iridium dimer 6 (0.67 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (535 mg, 2 mmol), K.sub.2CO.sub.3 (926 mg, 6.7 mmol) and ethoxyethanol (36 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM until the crude product was dissolved. EtOH (about 5 mL) was added to the solution, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH to give the crude product. The crude product was purified by column chromatography to give Compound 28 (240 mg). The product was confirmed as the target product with a molecular weight of 1212.4.
Synthesis Example 9: Synthesis of Compound 416
[0204] Step 1: Synthesis of Intermediate 21
##STR00039##
[0205] Intermediate 20 (8.38 g, 20.8 mmol), Pd(OAc).sub.2 (234 mg, 1.04 mmol), tBu.sub.3P.BF.sub.4 (603 mg, 2.08 mmol), K.sub.2CO.sub.3 (5.75 g, 41.58 mmol) and DMAc were added to a reaction flask, purged with nitrogen, and reacted overnight at 135° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature, diluted with water, and extracted three times with EA, and the organic phase was combined, dried, concentrated and separated by column chromatography to give Intermediate 21 (2.67 g).
[0206] Step 2: Synthesis of Intermediate 22
##STR00040##
[0207] Intermediate 21 (2.18 g, 6.8 mmol), bis(pinacolato)diboron (3.45 g, 13.6 mmol), Pd(OAc).sub.2 (76 mg, 0.36 mmol), Cy.sub.3P.BF.sub.4 (250 mg, 0.27 mmol), KOAc (2.0 g, 20.4 mmol) and 1,4-dioxane (13 mL) were added to a reaction flask, purged with nitrogen, and reacted overnight at 105° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature, water was added to the reaction system, and the aqueous phase was extracted with EA, and the organic phase was combined, dried, subjected to rotary evaporation to remove the solvent and purified by column chromatography to give Intermediate 22 (1.68 g).
[0208] Step 3: Synthesis of Intermediate 23
##STR00041##
[0209] Intermediate 1 (780 mg, 3.31 mmol), Intermediate 22 (1.37 g, 3.31 mmol), Pd(PPh.sub.3).sub.4 (192 mg, 0.16 mmol) and Na.sub.2CO.sub.3 (0.53 g, 4.97 mmol) were mixed in 1,4-dioxane/H.sub.2O (28 mL/7 mL), purged with nitrogen, and reacted overnight at 80° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature, diluted with EA and extracted by adding water, and the organic phase was collected, concentrated and subjected to column chromatography to give Intermediate 23 (0.72 g).
[0210] Step 4: Synthesis of Intermediate 24
##STR00042##
[0211] Intermediate 23 (0.95 g, 1.97 mmol) and Cs.sub.2CO.sub.3 (1.6 g, 4.91 mmol) were mixed in DMF (20 mL), purged with nitrogen, and reacted at 135° C. for 1 hour. After the reaction was completed, the reaction solution was cooled to room temperature, and water was added to the reaction solution. The product was precipitated and filtered. The filter cake was washed with an appropriate amount of water and petroleum ether and dried to give Intermediate 24 (0.86 g).
[0212] Step 5: Synthesis of Intermediate 25
##STR00043##
[0213] Intermediate 24 (0.94 g, 2.1 mmol), neopentylboronic acid (0.49 g, 4.2 mmol), Pd.sub.2(dba).sub.3 (48 mg, 0.05 mmol), SPhos (86 mg, 0.21 mmol) and K.sub.3PO.sub.4 (1.68 mg, 6.3 mmol) were mixed in toluene (25 mL), purged with nitrogen, and reacted overnight at 110° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature, concentrated and purified by column chromatography to give Intermediate 25 (0.7 g).
[0214] Step 6: Synthesis of Iridium Dimer 26
##STR00044##
[0215] The mixture of Intermediate 25 (1.0 g, 2.07 mmol), iridium trichloride trihydrate (240 mg, 0.68 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was placed in a high-pressure reaction kettle and reacted at 160° C. for 24 hours. After the reaction was cooled to room temperature, the mixture was filtered to give iridium dimer 26 as red solids which can be directly used in the next step without further purification.
[0216] Step 7: Synthesis of Compound 416
##STR00045##
[0217] The iridium dimer 26 prepared step 6, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.26 g, 1.0 mmol) and potassium carbonate (0.47 g, 3.4 mmol) were mixed in ethoxyethanol (15 mL), purged with nitrogen, and reacted at 40° C. for 24 hours. The reaction solution was filtered through Celite, and the filter cake was washed with ethanol. The crude product was dissolved in DCM, ethanol (about 5 mL) was added to the solution, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH. The crude product was purified by column chromatography to give Compound 416 (80 mg). The product was confirmed as the target product with a molecular weight of 1420.6.
Synthesis Example 10: Synthesis of Compound 470
[0218] Step 1: Synthesis of Iridium Dimer 28
##STR00046##
[0219] Intermediate 27 (110 mg, 0.25 mmol) and IrCl.sub.3.3H.sub.2O (35 mg, 0.1 mmol) were mixed in ethoxyethanol (6 mL) and water (2 mL), purged with nitrogen, and refluxed at 130° C. for 24 hours. After the reaction was cooled to room temperature, the reaction solution was concentrated to remove the solvent to give iridium dimer 28 which can be directly used in the next step without further purification.
[0220] Step 2: Synthesis of Compound 470
##STR00047##
[0221] Iridium dimer 28 prepared in step 1, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (36 mg, 0.15 mmol), K.sub.2CO.sub.3 (69 mg, 0.5 mmol) and ethoxyethanol (5 mL) were mixed in a 100 mL single-necked flask, purged with nitrogen, and reacted overnight at 45° C. After TLC detected that the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was filtered through Celite, the filter cake was washed with an appropriate amount of EtOH, and the crude product was dissolved with DCM. EtOH (about 2 mL) was added to the solution, and DCM was removed through rotary evaporation at room temperature. Then solids were precipitated, filtered and washed with an appropriate amount of EtOH. The crude product was subjected to column chromatography to give Compound 470 (30 mg). The product was confirmed as the target product with a molecular weight of 1282.6.
[0222] The persons skilled in the art will appreciate that the above preparation methods are merely examples. The persons skilled in the art can obtain other compound structures of the present disclosure through the modifications of the preparation methods.
DEVICE EXAMPLE
Device Example 1
[0223] First, a glass substrate having an indium tin oxide (ITO) anode with a thickness of 120 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. Next, 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 at a vacuum degree of about 10.sup.−8 torr. Compound HI was used as a hole injection layer (HIL) with a thickness of 100 Å. Compound HT was used as a hole transporting layer (HTL) with a thickness of 400 Å. Compound EB was used as an electron blocking layer (EBL) with a thickness of 50 Å. Compound 63 of the present disclosure was doped in a host compound RH to be used as an emissive layer (EML, at a weight ratio of 2:98) with a thickness of 400 Å. Compound HB was used as a hole blocking layer (HBL) with a thickness of 50 Å. On the HBL, a compound ET and 8-hydroxyquinolinolato-lithium (Liq) were co-deposited as an electron transport layer (ETL) with a thickness of 350 Å. Finally, Liq with a thickness of 1 nm was deposited as an electron injection layer, and Al with a thickness of 120 nm was deposited as a cathode. The device was transferred back to the glovebox and encapsulated with a glass lid and a moisture absorbent to complete the device.
Device Comparative Example 1
[0224] The preparation method in Device Comparative Example 1 was the same as that in Device Example 1, except that Compound 63 of the present disclosure was replaced with Compound RD-A in the emissive layer (EML).
Device Comparative Example 2
[0225] The preparation method in Device Comparative Example 2 was the same as that in Device Example 1, except that Compound 63 of the present disclosure was replaced with Compound RD-B in the emissive layer (EML).
Device Example 2
[0226] The preparation method in Device Example 2 was the same as that in Device Example 1, except that Compound 63 of the present disclosure was replaced with Compound 28 in the emissive layer (EML).
Device Example 3
[0227] The preparation method in Device Example 3 was the same as that in Device Example 1, except that Compound HT was doped with Compound HT2 (at a weight ratio of 97:3) to replace Compound HI in the hole injection layer (HIL) and Compound 63 of the present disclosure was replaced with Compound 256 in the emissive layer (EML).
Device Example 4
[0228] The preparation method in Device Example 4 was the same as that in Device Example 3, except that Compound 256 of the present disclosure was replaced with Compound 416 in the emissive layer (EML).
[0229] The structures and thicknesses of some layers of the devices are shown in the following table. The layer using more than one material was obtained by doping different compounds at their weight ratios as recorded.
TABLE-US-00001 TABLE 1 Part structures of devices in Device Examples and Device Comparative Examples Device No. HIL HTL EBL EML HBL ETL Example 1 Compound HI Compound HT Compound EB Compound Compound HB Compound (100 Å) (400 Å) (50 Å) RH:Compound (50 Å) ET:Liq 63 (98:2) (40:60) (400 Å) (350 Å) Comparative Compound HI Compound HT Compound EB Compound Compound HB Compound Example 1 (100 Å) (400 Å) (50 Å) RH:Compound (50 Å) ET:Liq RD-A (98:2) (40:60) (400 Å) (350 Å) Comparative Compound HI Compound HT Compound EB Compound Compound HB Compound Example 2 (100 Å) (400 Å) (50 Å) RH:Compound (50 Å) ET:Liq RD-B (98:2) (40:60) (400 Å) (350 Å) Example 2 Compound HI Compound HT Compound EB Compound Compound HB Compound (100 Å) (400 Å) (50 Å) RH:Compound (50 Å) ET:Liq 28 (98:2) (40:60) (400 Å) (350 Å) Example 3 Compound Compound HT Compound EB Compound Compound HB Compound HT:Compound (400 Å) (50 Å) RH:Compound (50 Å) ET:Liq HT2 (97:3) 256 (98:2) (40:60) (100 Å) (400 Å) (350 Å) Example 4 Compound Compound HT Compound EB Compound Compound HB Compound HT:Compound (400 Å) (50 Å) RH:Compound (50 Å) ET:Liq HT2 (97:3) 416 (98:2) (40:60) (100 Å) (400 Å) (350 Å)
[0230] The structures of the materials used in the devices are shown as follows:
##STR00048## ##STR00049##
[0231] The IVL characteristics of the devices were measured. Table 2 shows the data of maximum emission wavelength (?.sub.max), full width at half maximum (FWHM), driving voltage (V) and external quantum efficiency (EQE) measured at a current density of 15 mA/cm.sup.2 and lifetime (LT97) data measured at a current density of 80 mA/cm.sup.2.
TABLE-US-00002 TABLE 2 Device data λ.sub.max FWHM Voltage EQE LT97 Device No. (nm) (nm) (V) (%) (h) Example 1 623 21.4 3.64 24.8 67.00 Comparative 568 31.5 3.64 5.64 3.30 Example 1 Comparative 578 17.7 3.84 6.73 1.85 Example 2 Example 2 622 20.2 3.58 22.2 54 Example 3 619 21.3 3.65 25.3 43 Example 4 669 33.2 3.66 18.22 362
[0232] As can be clearly seen from the data in Table 2, the Examples of the present disclosure had extremely significant performance advantages over the Comparative Examples. Specifically, although the full width at half maximum of Examples 1, 2 and 3 was slightly wider than that of Comparative Example 2, it is to be noted that the full width at half maximum of Comparative Example 2 was extremely narrow, and thus the full width at half maximum of Examples 1, 2 and 3 was also extremely narrow. In addition, the full width at half maximum of Examples 1 to 3 was further surprisingly narrowed by up to 10 nm on the basis of the very high level of the full width at half maximum of Comparative Example 1, which is very rare, indicating that the compound disclosed in the present disclosure can achieve luminescence of very high saturation. Furthermore, the driving voltages of Examples 1 to 3 were maintained at a low voltage level equivalent to that in Comparative Example 1 and reduced by about 5% (3.64 V vs 3.84 V, 3.58 V vs 3.84 V and 3.65 V vs 3.84 V) compared with the driving voltage of Comparative Example 2. More importantly, other device performances of Examples 1 to 3, such as efficiency and lifetime, had achieved overall improvement compared with Comparative Examples 1 and 2. The external quantum efficiency of Example 1 was nearly 3.7 times that of Comparative Example 2 (24.8% vs 6.73%) and 4.4 times that of Comparative Example 1 (24.8% vs 5.64%), the external quantum efficiency of Example 2 was nearly 3.3 times that of Comparative Example 2 (22.2% vs 6.73%) and more than 3.9 times that of Comparative Example 1 (22.2% vs 5.64%), and the external quantum efficiency of Example 3 was nearly 3.8 times that of Comparative Example 2 (25.3% vs 6.73%) and 4.5 times that of Comparative Example 1 (25.3% vs 5.64%), indicating that the device efficiency had been greatly improved. The advantages of Examples 1 to 3 in terms of lifetime were even greater. The lifetime of Example 1 was more than 36 times that of Comparative Example 2 (67.00 hours vs 1.85 hours) and 20 times that of Comparative Example 1 (67.00 hours vs 3.30 hours), the lifetime of Example 2 was more than 29 times that of Comparative Example 2 (54 hours vs. 1.85 hours) and more than 16 times that of Comparative Example 1 (54 hours vs. 3.30 hours), and the lifetime pf Example 3 was more than 23 times that of Comparative Example 2 (43 hours vs. 1.85 hours) and 13 times that of Comparative Example 1 (43 hours vs. 3.30 hours). In addition, the colors of Examples 1, 2 and 3 were more deep red (623 nm, 622 nm and 619 nm), which can better meet the requirements of red luminescence. What's more, in Example 4 in the case where the emitting color was a very deep red (669 nm), the full width at half maximum was still at a level close to that of Comparative Example 1, and the driving voltage was also maintained at a low voltage level equivalent to that of Comparative Example 1. Moreover, the device efficiency of Example 4 was more than 3 times that of Comparative Example 1 (18.22% vs 5.64%) and 2.7 times that of Comparative Example 2 (18.22% vs 6.73%), and it is very rare to have such a high device efficiency even when the emission wavelength was greatly redshifted by more than 90 nm. It is particularly worth mentioning that Example 4 had great advantages in terms of lifetime, astonishingly reaching 362 hours, which was more than 109 times that of Comparative Example 1 and more than 195 times that of Comparative Example 2. The deep red light with such a wavelength in Example 4 has important applications in some special fields such as medicine and agricultural production, and its long device lifetime is very beneficial to its application prospect. Through the above comparison, it can be clearly seen that the metal complexes disclosed by the present disclosure have excellent performance and excellent application prospect.
[0233] Spectra Data
[0234] The photoluminescence (PL) spectra data of the compounds of the present disclosure and comparative compounds was measured using a fluorescence spectrophotometer F98 produced by SHANGHAI LENGGUANG TECHNOLOGY CO., LTD. Example samples and comparative example samples were prepared into solutions each with a concentration of 3×10.sup.−5 mol/L by using HPLC-grade dichloromethane and then excited at room temperature (298 K) using light with a wavelength of 500 nm, and their emission spectra were measured. Measurement results are shown in Table 3.
TABLE-US-00003 TABLE 3 PL data Compound No. λ.sub.max (nm) FWHM (nm) Compound 63 620 20.8 Compound 38 606 21.5 Compound 192 620 20.5 Compound 260 608 20.4 Compound 278 597 34.2 Compound 256 616 20.93 Compound 28 618 20.5 Compound 321 608 22.1 Compound 416 665 31.7 Compound 470 597 20.6 Compound RD-A 564 26.7 Compound RD-B 575 18.0
[0235] As can be seen from the data in Table 3, the compounds of the present disclosure had a redder color than comparison compounds, and their maximum emission wavelengths of PL were generally greatly redshifted, indicating that the compounds of the present disclosure can better meet the requirements of red luminescence in various wavelength ranges from light red to deep red. Meanwhile, the compounds of the present disclosure had very narrow full width at half maximum, indicating that the compounds of the present disclosure can achieve very saturated red light emission in electroluminescent devices.
[0236] In conclusion, the compounds disclosed in the present disclosure can achieve red light emission, have a very narrow full width at half maximum, and can achieve high saturation luminescence. In addition, these new metal complexes, when used as luminescent materials in electroluminescent devices, can enable the device to emit red light, have a very narrow full width at half maximum, achieve high saturation luminescence, reduce or maintain a low voltage, greatly improve device efficiency and lifetime, and provide better device performance, proving that the metal complexes disclosed in the present disclosure have excellent performance and excellent application prospect.
[0237] 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 comprise variations from 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.