MATERIALS FOR ELECTRONIC DEVICES

Abstract

The application relates to compounds having functional substituents in a specific spatial arrangement, to devices comprising same, and to the preparation and use thereof.

Claims

1.-25. (canceled)

26. Compound of the general formula (1) ##STR00497## where the following applies to the symbols and indices used: A and A are, identically or differently from one another, an aromatic or heteroaromatic ring having 5 or 6 ring atoms, which may be substituted by one or more radicals R.sup.1, which may be independent of one another; ETG is an organic electron-transporting group (ETG) from the group of electron-deficient heteroaromatic groups, where the group ETG may be substituted by one or more radicals R.sup.1, which are independent of one another; Z is a single bond or a divalent group; if Z is a single bond, the group ETG is then bonded directly to the carbon atom of ring A; V is O; W is a single bond; m is either 0 or 1; n is either 0 or 1, where m=n; Ar.sup.3 is an aromatic or heteroaromatic ring or ring system having 5 to 30 ring atoms, where the ring or ring system may in each case be substituted by one or more radicals R.sup.2, which may be substituted by one or more radicals R.sup.3, where two or more radicals R.sup.2 may form a ring closure with one another; R.sup.1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(?O)R.sup.2, P(?O).sub.2R.sup.2).sub.2, S(?O)R.sup.2, S(?O).sub.2R.sup.2, OSO.sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R.sup.2, where one or more non-adjacent CH.sub.2 groups may be replaced by R.sup.2C?CR.sup.2, C?C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C?O, C?S, C?Se, C?NR.sup.2, P(?O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.2, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a combination of two or more of these groups or a crosslinkable group Q; two or more adjacent radicals R.sup.1 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred for two or more adjacent radicals R.sup.1 not to form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R.sup.2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R.sup.3).sub.2, CN, NO.sub.2, Si(R.sup.3).sub.3, B(OR.sup.3).sub.2, C(?O)R.sup.3, P(?O.sub.2R.sup.3).sub.2, S(?O)R.sup.3, S(?O).sub.2R.sup.3, OSO.sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R.sup.3, where one or more non-adjacent CH.sub.2 groups may be replaced by R.sup.3C?CR.sup.3, C?C, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C?O, C?S, C?Se, C?NR.sup.3, P(?O)(R.sup.3), SO, SO.sub.2, NR.sup.3, O, S or CONR.sup.3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, or a combination of two or more of these groups; two or more adjacent radicals R.sup.2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R.sup.3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; two or more substituents R.sup.3 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; p is an integer from 1 to 7; R.sup.4 is, identically or differently on each occurrence, N(R.sup.2).sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(?O)R.sup.2, P(?O)(R.sup.2).sub.2, S(?O)R.sup.2, S(?O).sub.2R.sup.2, OSO.sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R.sup.2, where one or more non-adjacent CH.sub.2 groups may be replaced by R.sup.2C?CR.sup.2, C?C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C?O, C?S, C?Se, C?NR.sup.2, P(?O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.2, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a combination of two or more of these groups; two or more adjacent radicals R.sup.4 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

27. Compound according to claim 26, characterised in that m=n=1.

28. Compound according to claim 26, characterised in that it has the formula (2) ##STR00498## where the above definitions apply to the indices and symbols used, and where: X is, identically or differently on each occurrence, N or CR.sup.1; Q is, identically or differently on each occurrence, X?X, S, O or NR.sup.1.

29. Compound according to claim 26, characterised in that it has the formula (3) ##STR00499##

30. Compound according to claim 26, characterised in that it has the formula (3a) ##STR00500## where s and t can be integers from 0 to 3 and where s+t is equal to an integer from 0 to 6.

31. Compound according to claim 26, characterised in that it has the formula (3b) ##STR00501## where p is an integer from 1 to 4.

32. Compound according to claim 26, characterised in that it has the formula (3c) ##STR00502##

33. Compound according to claim 26, characterised in that the ETG is an electron-deficient heteroaromatic group and is selected from the following groups: ##STR00503## where the dashed bond marks the bonding position, R.sup.1 is as defined above, and Q represents on each occurrence, identically or differently, CR.sup.1 or N, and Q is NR.sup.1, O or S; where at least one Q is equal to N and/or at least one Q is equal to NR.sup.1.

34. Compound according to claim 26, characterised in that Z is a single bond or a divalent aromatic or heteroaromatic ring or ring system having 5 to 60 ring atoms.

35. Process for the preparation of the compound according to claim 26 with the aid of Suzuki coupling.

36. Process for the preparation of the compound according to claim 26 with the aid of Buchwald or Ullmann coupling.

37. Composition comprising at least one compound according to claim 26 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials, hole-blocking materials, n-dopants and p-dopants.

38. Composition according to claim 38, characterised in that the additional compound is a phosphorescent emitter.

39. Composition according to claim 38, characterised in that the additional compound is a host material or matrix material.

40. Composition according to claim 38, characterised in that the additional compound has a band gap of 2.5 eV or more.

41. Formulation comprising at least one compound according to claim 26 and at least one solvent.

42. Electronic device comprising at least one compound according to claim 26.

43. Electronic device according to claim 42, characterised in that the electronic device is selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors.

44. Electronic device according to claim 42, characterised in that the electronic device is an organic electroluminescent device which is also selected from the group consisting of organic light-emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs), preferably OLECs and OLEDs, very preferably OLEDs.

45. Process for the production of an electronic device according to claim 42, characterised in that at least one organic layer is applied by gas-phase deposition or from solution.

46. Electronic device according to claim 44, for use in medicine for phototherapy, preferably for use for phototherapy of the skin, very preferably for use for the treatment or prevention of psoriasis, atopic dermatitis, jaundice, jaundice of the newborn, vitiligo, inflammation, pain and for use for wound healing.

47. Use of the device according to claim 44 in cosmetics, preferably for the treatment or prevention of skin ageing, skin wrinkles, crow's feet, acne, blackheads and cellulite.

48. Use of the device according to claim 44 in displays or for lighting.

49. Compound of the general formula (1) ##STR00504## where the following applies to the symbols and indices used: A and A are, identically or differently from one another, an aromatic or heteroaromatic ring having 5 or 6 ring atoms, which may be substituted by one or more radicals R.sup.1, which may be independent of one another; ETG is an organic electron-transporting group (ETG) from the group of electron-deficient heteroaromatic groups, where the ETG is preferably a heteroaryl group having 5 to 60 aromatic ring atoms, where nitrogen atoms represent very preferred heteroatoms and very particularly preferred ETGs are selected from the group triazines, pyrimidines, pyrazines, pyrazoles, pyridazines, quinoles, isoquinolines, thiazoles, benzothiazoles, oxazoles, benzoxazoles, imidazoles, benzimidazoles and pyridines and where the group ETG may be substituted by one or more radicals R.sup.1, which are independent of one another; Z is a single bond or a divalent group; if Z is a single bond, the group ETG is then bonded directly to the carbon atom of ring A; V is O; W is a single bond; m is either 0 or 1; n is either 0 or 1, where m=n; Ar.sup.3 is an aromatic or heteroaromatic ring or ring system having 5 to 30 ring atoms, where the ring or ring system may in each case be substituted by one or more radicals R.sup.2, which may be substituted by one or more radicals R.sup.3, where two or more radicals R.sup.2 may form a ring closure with one another; R.sup.1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(?O)R.sup.2, P(?O).sub.2R.sup.2).sub.2, S(?O)R.sup.2, S(?O).sub.2R.sup.2, OSO.sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R.sup.2, where one or more non-adjacent CH.sub.2 groups may be replaced by R.sup.2C?CR.sup.2, C?C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C?O, C?S, C?Se, C?NR.sup.2, P(?O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.2, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a combination of two or more of these groups or a crosslinkable group Q; two or more adjacent radicals R.sup.1 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred for two or more adjacent radicals R.sup.1 not to form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R.sup.2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R.sup.3).sub.2, CN, NO.sub.2, Si(R.sup.3).sub.3, B(OR.sup.3).sub.2, C(?O)R.sup.3, P(?O)(R.sup.3).sub.2, S(?O)R.sup.3, S(?O).sub.2R.sup.3, OSO.sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R.sup.3, where one or more non-adjacent CH.sub.2 groups may be replaced by R.sup.3C?CR.sup.3, C?C, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C?O, C?S, C?Se, C?NR.sup.3, P(?O)(R.sup.3), SO, SO.sub.2, NR.sup.3, O, S or CONR.sup.3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, or a combination of two or more of these groups; two or more adjacent radicals R.sup.2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R.sup.3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; two or more substituents R.sup.3 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; p is an integer from 1 to 7, preferably from 1 to 4, very preferably from 1 to 3, particularly preferably 1 or 2, very particularly preferably precisely 2 and especially preferably precisely 1; R.sup.4 is, identically or differently on each occurrence, N(R.sup.2).sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(?O)R.sup.2, P(?O)(R.sup.2).sub.2, S(?O)R.sup.2, S(?O).sub.2R.sup.2, OSO.sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R.sup.2, where one or more non-adjacent CH.sub.2 groups may be replaced by R.sup.2C?CR.sup.2, C?C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C?O, C?S, C?Se, C?NR.sup.2, P(?O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.2, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or a combination of two or more of these groups.

Description

EXAMPLES

[0186] The following syntheses are carried out, unless indicated otherwise, under a protective-gas atmosphere in dried solvents. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The numbers in square brackets for chemical compounds which are known from the literature relate to the CAS numbers.

Example 1

Synthesis of 3-dibenzofuran-4-yi-6,9-diphenyl-9H-carbazole

[0187] ##STR00203##

[0188] 28.9 g (136 mmol) of dibenzofuran-4-boronic acid, 40 g (124.1 mmol) of 3-bromo-9-phenyl-9H-carbazole and 78.9 ml (158 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of toulene, 120 ml of ethanol and 100 ml of water. 2.6 g (2.2 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 49.7 g (121 mmol), corresponding to 97% of theory.

[0189] The following compounds can be obtained analogously:

TABLE-US-00002 Starting material 1 Starting material 2 Product Yield [00204] [00205] [00206] 69% [00207] [00208] [00209] 92% [00210] [00211] [00212] 68% [00213] [00214] [00215] 77% [00216] [00217] [00218] 63% [00219] [00220] [00221] 75% [00222] [00223] [00224] 71% [00225] [00226] [00227] 75% [00228] [00229] [00230] 83%

Example 2

Synthesis of 1-dibenzofuran-4-yl-2-phenyl-1H-benzimidazole

[0190] ##STR00231##

[0191] 8.0 g (42.2 mmol) of copper(I) iodide and 11.7 ml (97.5 mmol) of trans-cyclohexanediamine are added to a vigorously stirred suspension of 42 g (234 mmol) of 2-phenyl-1H-benzimidazole, 57.7 g (234 mmol) of 4-bromodibenzofuran and 416.4 g (1961 mmol) of potassium phosphate in 1170 ml of dioxane, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol. Yield: 52 g (144 mmol), 85% of theory.

[0192] The following compounds can be obtained analogously:

TABLE-US-00003 Starting material 1 Starting material 2 Product Yield [00232] [00233] [00234] 88% [00235] [00236] [00237] 82%

Example 3

Synthesis of 3,9-diphenyl-6-(6-trimethylsilanyldibenzofuran-4-yl)-9H-carbazole

[0193] ##STR00238##

[0194] 127 ml (225.4 mmol) of n-buthyllithium (2.5 M in hexane) are added dropwise to a solution, cooled to 20? C., of 58.7 g (121 mmol) of 3-dibenzofuran-4-yl-6,9-diphenyl-9H-carbazole and 28 g (242 mmol) of TMEDA in 1000 ml of THF. The reaction mixture is stirred at room temperature for 3 h, then cooled to 0? C., and 26 g (242 mmol) of chlorotrimetylsilane are added dropwise over the course of 30 min., and the mixture is stirred at room temperature for 8 h. The solvent is subsequently removed in vacuo, and the residue is purified by chromatography on silica gel with chloroform as eluent. Yield: 41 g (72 mmol), 61% of theory.

[0195] The following compounds can be obtained analogously:

TABLE-US-00004 Starting material 1 Product Yield [00239] [00240] 63% [00241] [00242] 59% [00243] [00244] 57% [00245] [00246] 52% [00247] [00248] 60% [00249] [00250] 54% [00251] [00252] 59% [00253] [00254] 76% [00255] [00256] 78% [00257] [00258] 69%

Example 4

Synthesis of 6-(3,9-diphenyl-9H-carbazol-3-yl)-4-dibenzofuranyl-boronic acid

[0196] ##STR00259##

[0197] 21 g (86 mmol) of bromine tribromide are added dropwise under protective gas to a solution of 40 g (72 mmol) of 3,9-diphenyl-6-(6-trimethylsilanyl-dibenzofuran-4-yl)-9H-carbazole in 500 ml of dichloromethane, and the mixture is stirred at room temperature for 10 h. A little water is then slowly added to the mixture, and the residue which precipitates out is filtered off and washed with heptane. The yield is 32 g (61 mmol), corresponding to 85% of theory.

[0198] The following compounds can be obtained analogously.

TABLE-US-00005 Starting material 1 Product Yield [00260] [00261] 80% [00262] [00263] 83% [00264] [00265] 81% [00266] [00267] 79% [00268] [00269] 69% [00270] [00271] 78% [00272] [00273] 77% [00274] [00275] 82% [00276] [00277] 85% [00278] [00279] 80%

Example 5

Synthesis of 6-(3,9-diphenyl-9H-carbazol-3-yl)-4-dibenzofuranyl-boronic acid

[0199] ##STR00280##

[0200] 9 g (32 mmol) of 4,6-dibenzofurandiylbisboronic acid, 12.5 g (31.6 mmol) of 3-bromo-9-phenyl-9H-carbazole, 31 ml (63 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of toulene, 120 ml of ethanol. 0.73 g (0.63 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 11.2 g (21 mmol), corresponding to 67% of theory.

[0201] The following compounds can be obtained analogously:

TABLE-US-00006 Starting material 1 Starting material 2 [00281] [00282] [00283] [00284] [00285] [00286] [00287] [00288] Product Yield [00289] 85% [00290] 69% [00291] 74% [00292] 76%

Example 6

Synthesis of 10-(6-bromodibenzofuran-4-yl)-7-phenyl-7H-12-thia-7-azaindeno[1,2-a]fluorene

[0202] ##STR00293##

[0203] 12.5 g (32 mmol) of 5-phenyl-5H[1]benzothieno[3,2-c]carbazol-3-yl) boronic acid, 8.9 g (31.6 mmol) of 4,6-dibromodibenzofuran, 31 ml (63 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of toulene and 120 ml of ethanol. 0.73 g (0.63 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 13.3 g (22 mmol), corresponding to 73% of theory.

[0204] The following compounds can be obtained analogously.

TABLE-US-00007 Starting material 1 Starting material 2 [00294] [00295] [00296] [00297] [00298] [00299] [00300] [00301] [00302] [00303] [00304] [00305] [00306] [00307] [00308] [00309] [00310] [00311] [00312] [00313] [00314] [00315] Product Yield [00316] 51% [00317] 65% [00318] 69% [00319] 67% [00320] 62% [00321] 62% [00322] 61% [00323] 64% [00324] 66% [00325] 56% [00326] 72%

[0205] The following compounds can also be obtained analogously by a second addition reaction with the corresponding boro acids: The residue is recrystallised from toluene and finally sublimed in a high vacuum (p=5?10 mbar).

TABLE-US-00008 Starting material 1 Starting material 2 [00327] [00328] [00329] [00330] [00331] [00332] [00333] [00334] [00335] [00336] [00337] [00338] [00339] [00340] [00341] [00342] [00343] [00344] [00345] [00346] [00347] [00348] [00349] [00350] [00351] [00352] [00353] [00354] [00355] [00356] [00357] [00358] [00359] [00360] [00361] [00362] [00363] [00364] [00365] [00366] [00367] [00368] Product Yield [00369] 81% [00370] 79% [00371] 66% [00372] 78% [00373] 77% [00374] 79% [00375] 83% [00376] 83% [00377] 74% [00378] 78% [00379] 79% [00380] 77% [00381] 65% [00382] 69% [00383] 69% [00384] 71% [00385] 79% [00386] 76% [00387] 83% [00388] 80% [00389] 81%

Example 7

Synthesis of 3-[6-(4,6-diphenyl-1,3,5-triazin-2-yl)dibenzofuran-4-yl]-6,9-diphenyl-9H-carbazole

[0206] ##STR00390##

[0207] 37 g (70 mmol) of 6-(3,9-diphenyl-9H-carbazol-3-yl)-4-dibenzofuranyl-boronic acid, 18.8 g (70 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 78.9 ml (158 mmol) of Na.sub.2CO.sub.3(2 M solution) are suspended in 120 ml of ethanol and 100 ml of water. 1.3 g (1.1 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After the mixture has been cooled, dichloromethane is added, and the organic phase is separated off and filtered through silica gel. The yield is 41 g (58 mmol), corresponding to 83% of theory. The residue is recrystallised from toluene and finally sublimed in a high vacuum (p=5?10.sup.?5 mbar). The purity is 99.9%.

[0208] The following compounds can be obtained analogously.

TABLE-US-00009 Starting material 1 Starting material 2 [00391] [00392] [00393] [00394] [00395] [00396] Product Yield [00397] 59% [00398] 67% [00399] 68%

Example 8

Synthesis of 8-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,6,9-triphenyl-9H,9H-[1,2]bicarbazolyl

[0209] ##STR00400##

[0210] 50.4 g (70.58 mmol) of 8-(4,6-diphenyl-1,3,5-triazin-2-yl)-6,9-diphenyl-9H,9H-[1,2]bicarbazolyl and 16.4 g (105.87 mmol) of bromobenzene are dissolved in toluene, and the mixture is degassed by introduction of a protective gas. 7 ml (7 mmol, 1 M solution in toluene) of tri-tert-butylphos-phine, 633.8 mg (2.82 mmol) of Pd(OAc).sub.2 and 10.2 g (105.87 mmol) of NaOtBu are subsequently added. The solids are degassed in advance, and the reaction mixture is subsequently degassed and then stirred under reflux for 3 h. The warm reaction solution is filtered through aluminium oxide B (activity grade 1), washed with water, dried and evaporated. The yield is 44 g (55 mmol), corresponding to 79% of theory. The residue is recrystallised from toluene and finally sublimed in a high vacuum (p=5?10.sup.?5 mbar). The purity is 99.9%.

[0211] The following compounds can be obtained analogously.

TABLE-US-00010 Starting material 1 Starting material 2 [00401] [00402] [00403] [00404] [00405] [00406] [00407] [00408] [00409] [00410] Product Yield [00411] 79% [00412] 80% [00413] 80% [00414] 70% [00415] 69%

Example 10 (Comparison)

Synthesis of 3-(4-[6-(4,6-diphenyl-1,3,5-triazin-2-yl)dibenzofuran-4-yl]-phenyl)-9-phenyl-9H-carbazole

a) Synthesis of 2-(6-bromodibenzofuran-4-yl)-4,6-diphenyl-1,3,5-triazine

[0212] ##STR00416##

[0213] 80 g (245 mmol) of 4,6-dibromodibenzofuran are dissolved in 500 ml of dried THF in a flask which has been dried by heating. The reaction mixture is cooled to ?78? C. 57 ml of a 1.9 M solution of n-phenyllithium in dibutyl ether (115 mmol) are slowly added dropwise at this temperature. The batch is stirred at ?73? C. for a further 1 hour. 65 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (245 mmol) are subsequently dissolved in 150 ml of THF and added dropwise at ?70? C. When the addition is complete, the reaction mixture is slowly warmed to room temperature, stirred at room temperature overnight, quenched with water and subsequently evaporated in a rotary evaporator, during which a white solid precipitates out. The batch is then cooled to room temperature, and the solid which has precipitated out is filtered off with suction and rinsed with methanol. The yield is 40 g (84 mmol), corresponding to 34% of theory.

b) Synthesis of 3-{4-[6-(4,6-diphenyl-1,3,5-triazin-2-yl)dibenzofuran-4-yl]phenyl}-9-phenyl-9H-carbazole

[0214] ##STR00417##

[0215] 33.4 g (70 mmol) of 2-(6-bromodibenzofuran-4-yl)-4,6-diphenyl-1,3,5-triazine, 25.4 g (70 mmol) of 4-(9-phenyl-9H-carbazol-3-yl)phenylboromic acid, 78.9 ml (158 mmol) of Na.sub.2CO.sub.3(2 M solution) are suspended in 120 ml of ethanol and 100 ml of water. 1.3 g (1.1 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After the mixture has been cooled, dichloromethane is added, and the organic phase is separated off, filtered through silica gel and recrystallised from toluene. The yield is 40 g (56 mmol), corresponding to 80% of theory.

[0216] The following compound can be prepared analogously.

TABLE-US-00011 Starting material 1 Starting material 2 [00418] [00419] Product Yield [00420] 86%

Example 11 (Comparison)

Synthesis of 3-(7-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]dibenzo-furan-4-yl)-9-phenyl-9H-carbazole

a) Preparation of 2-(4-dibenzofuran-3-ylphenyl)-4,6-diphenyl-1,3,5-triazine

[0217] ##STR00421##

24 g (70 mmol) of 4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) boronic acid, 17.3 g (70 mmol) of 3-bromodibenzofuran, 78.9 ml (158 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of ethanol and 100 ml of water. 1.3 g (1.1 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After the mixture has been cooled, dichloromethane is added, and the organic phase is separated off, filtered through silica gel and recrystallised from toluene. The yield is 28 g (58 mmol), corresponding to 86% of theory.

[0218] The following compound can be prepared analogously.

TABLE-US-00012 Starting material 1 Starting material 2 Product Yield [00422] [00423] [00424] 87%

b) Synthesis of 2,4-diphenyl-6-[4-(6-trimethylsilanyldibenzofuran-3-yl)-phenyl]-1,3,5 triazine

[0219] ##STR00425##

[0220] 127 ml (225.4 mmol) of n-buthyllithium (2.5 M in hexane) are added dropwise to a solution, cooled to 20? C., of 57.4 g (121 mmol) of 2-(4-dibenzo-furan-3-ylphenyl)-4,6-diphenyl-1,3,5 triazine and 28 g (242 mmol) of TMEDA in 1000 ml of THF. The reaction mixture is stirred at room temperature for 3 h, then cooled to 0? C., and 26 g (242 mmol) of chlorotrimetylsilane are added dropwise over the course of 30 min. The mixture is stirred at room temperature for 8 h. The solvent is subsequently removed in vacuo, and the residue is purified by chromatography on silica gel with chloroform as eluent. Yield: 41 g (74 mmol), 63% of theory.

[0221] The following compound can be prepared analogously.

TABLE-US-00013 Starting material 1 Product Yield [00426] [00427] 87%

c) Synthesis of 3-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]dibenzo-furan-6-boronic acid

[0222] ##STR00428##

[0223] 21 g (86 mmol) of bromine tribromide are added dropwise under protective gas to a solution of 39 g of 2,4-diphenyl-6-[4-(6-trimethylsilanyldibenzo-furan-3-yl)phenyl]-1,3,5-triazine in 500 ml of dichloromethane, and the mixture is stirred at room temperature for 10 h. A little water is then slowly added to the mixture, and the residue which precipitates out is filtered off and washed with heptane. The yield is 32 g (62 mmol), corresponding to 87% of theory.

[0224] The following compound can be prepared analogously.

TABLE-US-00014 Starting material 1 Product Yield [00429] [00430] 90%

d) Synthesis of 3-(7-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-dibenzofuran-4-yl)-6,9-diphenyl-9H-carbazoles

[0225] ##STR00431##

[0226] 36 g (70 mmol) of 3-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)]phenyl]dibenzo-furan-6-boronic acid 27 g (70 mmol) of 3-bromo-6,9-diphenyl-9H-carbazole and 78.9 ml (158 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of ethanol and 100 ml of water. 1.3 g (1.1 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After the mixture has been cooled, dichloromethane is added, and the organic phase is separated off, filtered through silica gel and recrystallised from toluene. The residue is recrystallised from toluene and finally sublimed in a high vacuum (p=5?10.sup.?5 mbar). The yield is 36 g (53 mmol), corresponding to 80% of theory.

[0227] The following compound can be prepared analogously,

TABLE-US-00015 Starting material 1 Starting material 2 [00432] [00433] Product Yield [00434] 86%

Example 12

Synthesis of 3-dibenzofuran-4-yl-9-phenyl-9H-carbazole

[0228] ##STR00435##

[0229] 28.9 g (136 mmol) of dibenzofuran-4-boronic acid, 40 g (124.1 mmol) of 3-bromo-9-phenyl-9H-carbazoles and 78.9 ml (158 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of toulene, 120 ml of ethanol and 100 ml of water. 2.6 g (2.2 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 49.7 g (121 mmol), corresponding to 97% of theory.

[0230] The following compound can be obtained analogously:

TABLE-US-00016 Starting material 1 Starting material 2 Product Yield [00436] [00437] [00438] 69%

Example 13

Synthesis of 9-phenyl-3-(6-trimethylsilanyldibenzofuran-4-yl)-9H-carbazole

[0231] ##STR00439##

[0232] 127 ml (225.4 mmol) of n-buthyllithium (2.5 M in hexane) are added dropwise to a solution, cooled to 20? C., of 49 g (121 mmol) of 3-dibenzofuran-4-yl-9-phenyl-9H-carbazole and 28 g (242 mmol) of TMEDA in 1000 ml of THF. The reaction mixture is stirred at room temperature for 3 h, then cooled to 0? C., and 26 g (242 mmol) of chlorotrimetylsilane are added dropwise over the course of 30 min., and the mixture is stirred at room temperature for 8 h. The solvent is subsequently removed in vacuo, and the residue is purified by chromatography on silica gel with chloroform as eluent. Yield: 34 g (72 mmol), 60% of theory.

[0233] The following compounds can be obtained analogously.

TABLE-US-00017 Starting material 1 Product Yield [00440] [00441] 65% [00442] [00443] 64%

Example 14

Synthesis of B-[6-(phenyl-9H-carbazol-3-yl)-4-benzofuranyl]boronic acid

[0234] ##STR00444##

[0235] 21 g (86 mmol) of bromine tribromide are added dropwise under protective gas to a solution of 34 g (72 mmol) of B-[6-(phenyl-9H-carbazol-3-yl)-4-dibenzofuranyl]boronic acid in 500 ml of dichloromethane, and the mixture is stirred at room temperature for 10 h. A little water is then slowly added to the mixture, and the residue which precipitates out is filtered off and washed with heptane. The yield is 28 g (62 mmol), corresponding to 86% of theory.

[0236] The following compounds can be obtained analogously.

TABLE-US-00018 Starting material 1 Product Yield [00445] [00446] 69% [00447] [00448] 78%

Example 15

Synthesis of 10-(6-bromodibenzofuran-4-yl)-7-phenyl-7H-12-thia-7-azaindeno[1,2-a]fluorene

[0237] ##STR00449##

[0238] 12.5 g (32 mmol) of 5-phenyl-5H[1]benzothieno[3,2-c]carbazol-3-ylboronic acid, 8.9 g (31.6 mmol) of 4,6-dibromodibenzofuran, 31 ml (63 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of toluene, 120 ml of ethanol. 0.73 g (0.63 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 13.3 g (22 mmol), corresponding to 73% of theory.

[0239] The following compounds can be obtained analogously

TABLE-US-00019 Starting material 1 Starting material 2 Product Yield [00450] [00451] [00452] 87% [00453] [00454] [00455] 89%

Example 16

[0240] Production and Characterisation of the OLEDs

[0241] The data of various OLEDs are presented in the following examples V1-V7 and E1-E23 (see Tables 1 and 2).

[0242] Pretreatment for Examples V1-E23: Glass plates which have been coated with structured ITO (indium tin oxide) in a thickness of 50 nm are coated with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), purchased as CLEVIOS? P VP Al 4083 from Heraeus Precious Metals GmbH, Germany, applied by spin coating from aqueous solution) for improved processing. These coated glass plates form the substrates to which the OLEDs are applied.

[0243] The OLEDs have in principle the following layer structure: substrate/hole-transport layer (HTL)/interlayer (IL)/electron-blocking layer (EBL)/emission layer (EML)/optional hole-blocking layer (HBL)/electron-transport layer (ETL)/optional electron-injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer with a thickness of 100 nm. The precise structure of the OLEDs is shown in Table 1. The materials required for the production of the OLEDs are shown in Table 3.

[0244] All materials are applied by thermal vapour deposition in a vacuum cham-ber. The emission layer here always consists of at least one matrix material (host material) and an emitting dopant (emitter), which are admixed with the matrix material or matrix materials in a certain proportion by volume by co-evaporation. An expression such as IC1:IC3:TEG1 (55%:35%:10%) here means that material IC1 is present in the layer in a proportion by volume of 55%, IC3 is present in the layer in a proportion of 35% and TEG1 is present in the layer in a proportion of 10%. Analogously, the electron-transport layer may also consist of a mixture of two materials.

[0245] The OLEDs are characterised by standard methods. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminous density, calculated from current/voltage/luminous density characteristic lines (IUL characteristic lines) assuming Lambert emission characteristics, and the lifetime are determined. The electroluminescence spectra are determined at a luminous density of 1000 cd/m.sup.2, and the CIE 1931 x and y colour coordi-nates are calculated therefrom. The term U1000 in Table 2 denotes the voltage required for a luminous density of 1000 cd/m.sup.2. CE1000 and PE1000 denote the current and power efficiency respectively which are achieved at 1000 cd/m.sup.2. Finally, EQE1000 denotes the external quantum efficiency at an operating luminous density of 1000 cd/m.sup.2. The lifetime LT is defined as the time after which the luminous density drops to a certain proportion L1 from the initial luminous density on operation at constant current. An expression of L0;j0=4000 cd/m.sup.2 and L1=70% in Table 2 means that the lifetime indicated in column LT corresponds to the time after which the initial luminous density drops from 4000 cd/m.sup.2 to 2800 cd/m.sup.2. Analogously, L0;j0=20 mA/cm.sup.2, L1=80%, means that the luminous density drops to 80% of its initial value after time LT on operation at 20 mA/cm.sup.2.

[0246] The data of the various OLEDs are summarised in Table 2. Examples V1-V7 are comparative examples in accordance with the prior art, Examples E1-E23 show data of OLEDs according to the invention.

[0247] Some of the examples are explained in greater detail below in order to illustrate the advantages of the OLEDs according to the invention.

[0248] Use of Mixtures According to the Invention in the Emission Layer of Phosphorescent OLEDs

[0249] The materials according to the invention give rise to significant improvements over the prior art in all parameters, especially with respect to lifetime and external quantum efficiency, on use as matrix materials in phosphorescent OLEDs.

[0250] The use of compounds FF1 and FF2 according to the invention in combination with the green-emitting dopant TEG1 enables an increase in the lifetime by about 3040% compared with the prior art StdT1 and StdT2 to be observed (Examples V1, E1 and V2, E2). Furthermore, compound FF3 according to the invention enables an external quantum efficiency which is increased by about 25% compared with the prior art StdT3 (Examples V3, E3).

TABLE-US-00020 TABLE 1 Structure of the OLEDS HTL IL EBL EML HBL ETL EIL Ex. Thickness Thickness Thickness Thickness Thickness Thickness Thickness V1 SpA1 HATCN SpMA1 StdT1:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm V2 SpA1 HATCN SpMA1 StdT2:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm V3 SpA1 HATCN SpMA1 StdT3:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm V4 SpA1 HATCN SpMA1 StdT4:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm V5 SpA1 HATCN SpMA1 StdT5:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm V6 SpA1 HATCN SpMA1 StdT6:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm V7 SpA1 HATCN SpMA1 StdT7:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E1 SpA1 HATCN SpMA1 FF1:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E2 SpA1 HATCN SpMA1 FF2:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E3 SpA1 HATCN SpMA1 FF3:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E4 SpA1 HATCN SpMA1 FF4:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 40 nm 30 nm E5 HATCN SpMA1 SpMA2 FF2:L1:TEY1 ST1 LiQ 5 nm 70 nm 15 nm (45%:45%:10%) 25 nm 45 nm 3 nm E6 SpA1 HATCN SpMA1 FF5:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E7 SpA1 HATCN SpMA1 FF2:TEG1 FF6:ST1 (50%:50%) LiQ 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm 3 nm E8 SpA1 HATCN SpMA1 FF7:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E9 SpA1 HATCN SpMA1 FF8:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E10 SpA1 HATCN SpMA1 FF9:TER3 ST1:LiQ (50%:50%) 90 nm 5 nm 130 nm (92%:8%) 30 nm 40 nm E11 SpA1 HATCN SpMA1 FF10:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E12 SpA1 HATCN SpMA1 FF11:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E13 SpA1 HATCN SpMA1 FF12:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E14 SpA1 HATCN SpMA1 FF13:TEG1 IC1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (45%:45%:10%) 30 nm 10 nm 30 nm E15 SpA1 HATCN SpMA1 FF14:IC3:TEG1 IC1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (45%:45%:10%) 30 nm 10 nm 30 nm E16 SpA1 HATCN SpMA1 FF15:IC3:TEG1 IC1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 10 nm 30 nm E17 SpA1 HATCN SpMA1 IC1:TEG1 FF16:ST1 (50%:50%) LiF 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm 1 nm E18 SpA1 HATCN SpMA1 IC1:TEG1 FF17 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 10 nm 30 nm E19 SpA1 HATCN SpMA1 IC1:TEG1 FF18:ST1 (50%:50%) LiQ 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm 3 nm E20 SpA1 HATCN SpMA1 FF19:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E21 SpA1 HATCN SpMA1 FF20:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E22 SpA1 HATCN SpMA1 FF21:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm E23 SpA1 HATCN SpMA1 FF22:TEG1 ST1:LiQ (50%:50%) 70 nm 5 nm 90 nm (90%:10%) 30 nm 40 nm

TABLE-US-00021 TABLE 2 Data of the OLEDs U1000 CE1000 PE1000 EQE CIE x/y at Ex. (V) (cd/A) (lm/W) 1000 1000 cd/m.sup.2 L.sub.0; j.sub.0 L1 % LT (h) V1 3.6 50 44 14.4% 0.33/0.62 20 mA/cm.sup.2 80 120 V2 3.3 60 57 17.0% 0.34/0.62 20 mA/cm.sup.2 80 110 V3 4.1 41 31 11.9% 0.32/0.63 20 mA/cm.sup.2 80 110 V4 3.3 57 54 15.5% 0.32/0.63 20 mA/cm.sup.2 80 100 V5 3.7 59 50 15.6% 0.33/0.62 20 mA/cm.sup.2 80 110 V6 3.8 61 50 16.3% 0.33/0.62 20 mA/cm.sup.2 80 120 V7 3.7 65 55 17.3% 0.33/0.63 20 mA/cm.sup.2 80 160 E1 3.5 52 46 14.6% 0.33/0.62 20 mA/cm.sup.2 80 160 E2 3.3 63 59 17.2% 0.33/0.63 20 mA/cm.sup.2 80 155 E3 3.5 51 45 14.8% 0.34/0.62 20 mA/cm.sup.2 80 100 E4 3.1 65 66 17.4% 0.33/0.63 20 mA/cm.sup.2 80 150 E5 2.7 86 100 24.5% 0.42/0.57 50 mA/cm.sup.2 90 95 E6 3.4 65 60 17.1% 0.33/0.62 20 mA/cm.sup.2 80 150 E7 3.3 56 53 16.2% 0.33/0.62 20 mA/cm.sup.2 80 145 E8 3.5 62 56 16.9% 0.38/0.59 20 mA/cm.sup.2 80 130 E9 3.4 60 55 16.8% 0.38/0.59 20 mA/cm.sup.2 80 145 E10 4.5 11 8 12.0% 0.67/0.33 4000 cd/m.sup.2 80 310 E11 3.6 50 44 14.4% 0.33/0.62 20 mA/cm.sup.2 80 130 E12 3.4 63 58 17.0% 0.32/0.63 20 mA/cm.sup.2 80 160 E13 3.5 62 56 17.3% 0.32/0.63 20 mA/cm.sup.2 80 150 E14 3.6 57 50 15.3% 0.33/0.62 20 mA/cm.sup.2 80 105 E15 3.4 57 53 16.0% 0.34/0.63 20 mA/cm.sup.2 80 410 E16 3.5 58 52 16.1% 0.34/0.63 20 mA/cm.sup.2 80 290 E17 3.2 67 66 18.1% 0.33/0.62 20 mA/cm.sup.2 80 160 E18 3.3 66 62 17.8% 0.33/0.62 20 mA/cm.sup.2 80 170 E19 3.1 69 70 18.4% 0.33/0.62 20 mA/cm.sup.2 80 165 E20 3.5 62 56 17.1% 0.34/0.62 20 mA/cm.sup.2 80 135 E21 3.5 57 51 15.6% 0.33/0.63 20 mA/cm.sup.2 80 85 E22 3.4 51 47 14.8% 0.34/0.62 20 mA/cm.sup.2 80 80 E23 3.6 53 46 15.0% 0.33/0.62 20 mA/cm.sup.2 80 95

TABLE-US-00022 TABLE 3 Structural formulae of the materials for the OLEDs [00456] HATCN [00457] SpA1 [00458] SpMA1 [00459] LiQ [00460] SpMA2 [00461] TEY1 [00462] L1 [00463] ST1 [00464] IC1 [00465] IC3 [00466] StdT1 [00467] StdT2 [00468] StdT3 [00469] StdT4 [00470] StdT5 [00471] StdT6 [00472] StdT7 [00473] TER3 [00474] TEG1 [00475] FF1 [00476] FF2 [00477] FF3 [00478] FF4 [00479] FF5 [00480] FF6 [00481] FF7 [00482] FF8 [00483] FF9 [00484] FF10 [00485] FF11 [00486] FF12 [00487] FF13 [00488] FF14 [00489] FF15 [00490] FF16 [00491] FF17 [00492] FF18 [00493] FF19 [00494] FF20 [00495] FF21 [00496] FF22