ORGANIC ELECTROLUMINESCENCE DEVICES

Abstract

The invention relates to organic electroluminescence devices containing indone carbazole derivatives.

Claims

1.-14. (canceled)

15. An organic electroluminescent device comprising anode, cathode and at least one emitting layer containing at least one phosphorescent compound, characterized in that the emitting layer contains at least one compound of formula (1) ##STR00819## where the symbols and indices used are as follows: X two adjacent X are a group of the following formula (2), and the two other X are CR, ##STR00820##  where the two dotted bonds represent the linkage of this group; HetAr is an electron-deficient heteroaryl group which has 6 to 14 aromatic ring atoms and may be substituted by one or more R radicals, with the proviso that the heteroaryl group contains at least two nitrogen atoms; R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.1).sub.2, N(Ar′).sub.2, CN, NO.sub.2, OR.sup.1, SR.sup.1, COOR.sup.1, C(═O)N(R.sup.1).sub.2, Si(R.sup.1).sub.3, B(OR.sup.1).sub.2, C(═O)R.sup.1, P(═O)(R.sup.1).sub.2, S(═O)R.sup.1, S(═O).sub.2R.sup.1, OSO.sub.2R.sup.1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more 12.sup.1 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.1).sub.2, C═O, NR.sup.1, O, S or CONR.sup.1, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals; R′ is the same or different at each instance and is a straight-chain alkyl group having 1 to carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the straight-chain, branched or cyclic alkyl group may in each case be substituted by one or more R.sup.1 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by O, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals; it is also possible here for two R′ radicals together to form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; R.sup.1 if the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, OR.sup.2, SR.sup.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 group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.2).sub.2, C═O, NR.sup.2, O, S or CONR.sup.2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals; it is possible here for two or more R.sup.1 radicals together to form a ring system; R.sup.2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which it is also possible for one or more hydrogen atoms to be replaced by F; m is 0, 1 or 2; and n is the same or different at each instance and is 0, 1, 2, 3 or 4.

16. The organic electroluminescent device as claimed in claim 15, characterized in that the compound of the formula (1) is selected from the compounds of the formulae (3), (4) and (5) ##STR00821## where the symbols and indices have the definitions given in claim 15.

17. The organic electroluminescent device as claimed in claim 15, characterized in that the compound of the formula (1) is selected from the compounds of the formulae (3a-1), (3a-2), (4a-1), (4a-2), (5a-1) and (5a-2) ##STR00822## ##STR00823## where HetAr, R and R′ have the definitions given in claim 15.

18. The organic electroluminescent device as claimed in claim 15, characterized in that the compound of the formula (1) is selected from the compounds of the formulae (3b), (4b) and (5b) ##STR00824## where HetAr, R and R′ have the definitions given in claim 15.

19. The organic electroluminescent device as claimed in claim 15, characterized in that HetAr has 6 to 10 aromatic ring atoms that may be substituted by one or more R radicals, and in that HetAr has two or three nitrogen atoms and no further heteroatoms in the base skeleton.

20. The organic electroluminescent device as claimed in claim 15, characterized in that HetAr is selected from the structures of the formulae (HetAr-1) to (HetAr-8) ##STR00825## where the dotted bond represents the bond to the nitrogen atom, R has the definitions given in claim 15 and Y is as follows: Y is the same or different at each instance and is CR or N, with the proviso that at least two symbols Y and not more than three symbols Y are N.

21. The organic electroluminescent device as claimed in claim 15, characterized in that HetAr is selected from the structures of the formulae (HetAr-1a) to (HetAr-1d), (HetAr-2a), (HetAr-3a), (HetAr-4a), (HetAr-5a), (HetAr-6a), (HetAr-7a) and (HetAr-8a), ##STR00826## ##STR00827## where Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, and the further symbols have the definitions given in claim 15.

22. The organic electroluminescent device as claimed in claim 21, characterized in that Ar is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene joined via the 1, 2, 3 or 4 position, spirobifluorene joined via the 1, 2, 3 or 4 position, naphthalene, indole, benzofuran, benzothiophene, carbazole joined via the 1, 2, 3 or 4 position, dibenzofuran joined via the 1, 2, 3 or 4 position, dibenzothiophene joined via the 1, 2, 3 or 4 position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which may be substituted by one or more R.sup.1 radicals, or a combination of two or three of these groups.

23. The organic electroluminescent device as claimed in claim 21, characterized in that Ar is selected from phenyl, ortho-, meta- or para-biphenyl, terphenyl, quaterphenyl, fluorene joined via the 1, 2, 3 or 4 position, spirobifluorene joined via the 1, 2, 3 or 4 position, naphthalene, indole, benzofuran, benzothiophene, carbazole joined via the 1, 2, 3 or 4 position, dibenzofuran joined via the 1, 2, 3 or 4 position, dibenzothiophene joined via the 1, 2, 3 or 4 position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which may be substituted by one or more R.sup.1 radicals, or a combination of two or three of these groups.

24. The organic electroluminescent device as claimed in claim 15, characterized in that: R is the same or different at each instance and is selected from the group consisting of H, D, an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or a N(Ar′).sub.2 group; R′ is the same or different at each instance and is selected from the group consisting of a straight-chain alkyl group having 1 to 6 carbon atoms or a cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group may be substituted in each case by one or more R.sup.1 radicals, or an aromatic or heteroaromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals; it is also possible here for two R′ radicals together to form a ring system, giving rise to a spiro system; R.sup.1 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group may be substituted in each case by one or more R.sup.2 radicals, or an aromatic or heteroaromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals; and R.sup.2 is the same or different at each instance and is H, an alkyl group having 1 to 4 carbon atoms or an aryl group which has 6 to 10 carbon atoms and may be substituted by an alkyl group having 1 to 4 carbon atoms.

25. The organic electroluminescent device as claimed in claim 15, characterized in that the phosphorescent compound used is a red-, orange- or yellow-phosphorescing compound.

26. The organic electroluminescent device as claimed in claim 15, characterized in that the emitting layer consists of exactly one compound of the formula (1) and one or more phosphorescent compounds.

27. The organic electroluminescent device as claimed in claim 15, characterized in that the emitting layer, apart from the compound of the formula (1) and the phosphorescent compound, contains at least one further matrix material selected from the group consisting of carbazole derivatives, biscarbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, bridged carbazole derivatives or triarylamines.

28. A formulation comprising at least one compound of formula (1) as claimed in claim 15, at least one phosphorescent compound and at least one solvent.

29. A process for production of an organic electroluminescent device which comprises utilizing the formulation as claimed in claim 27.

Description

EXAMPLES

[0090] The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The solvents and reagents can be purchased from ALDRICH or ABCR. The numbers given for the reactants that are not commercially available are the corresponding CAS numbers.

a) (2-Chlorophenyl)(11,11-dimethyl-11H-benzoraffluoren-9-yl)amine

[0091] ##STR00681##

[0092] 47 g (145 mmol) of 9-bromo-11,11-dimethyl-11H-benzo[a]fluorene, 16.8 g (159 mmol) of 2-chloroaniline, 41.9 g (436.2 mmol) of sodium tert-butoxide and 1.06 (1.45 mmol) of Pd(dppf)Cl.sub.2 are dissolved in 500 ml of toluene and stirred under reflux for 5 h. The reaction mixture is cooled down to room temperature, extended with toluene and filtered through Celite. The filtrate is concentrated under reduced pressure and the residue is crystallized from toluene/heptane. The product is isolated as a colourless solid. Yield: 33 g (89 mmol), 70% of theory.

[0093] The following compounds can be prepared in an analogous manner:

TABLE-US-00004 Reactant 1 Reactant 2 Product Yield 1a [00682] [00683] [00684] 79% [1804905-31-4] 2a [00685] [00686] [00687] 77% [1800333-59-8] 3a [00688] [00689] [00690] 78% [1263204-40-5] 1d [00691] [00692] [00693] 79% [119839-39-2] 4a [00694] [00695] [00696] 74% 1f [00697] [00698] [00699] 81% [1198396-29-0] 5a [00700] [00701] [00702] 78% [1198396-35-8] 6a [00703]   [1674335-13-7] [00704] [00705] 77%

b) Cyclization

[0094] ##STR00706##

[0095] 48 g (129 mmol) of (2-chlorophenyl)(11,11-dimethyl-11H-benzo[a]fluoren-9-yl)amine, 53 g (389 mmol) of potassium carbonate, 4.5 g (12 mmol) of tricyclohexylphosphine tetrafluoroborate, 1.38 g (6 mmol) of palladium(II) acetate and 3.3 g (32 mmol) of pivalic acid are suspended in 500 ml of dimethylacetamide and stirred under reflux for 6 h. After cooling, 300 ml of water and 400 ml of dichloromethane are added to the reaction mixture. The mixture is stirred for 30 min, the organic phase is separated off and filtered through a short Celite bed, and then the solvent is removed under reduced pressure. The crude product is subjected to hot extraction with toluene and recrystallized from toluene. The product is isolated as a beige solid. Yield: 34 g (102 mmol), 78% of theory.

[0096] The following compounds can be prepared in an analogous manner:

TABLE-US-00005 Reactant Product Yield 1b [00707] [00708] 79% 2b [00709] [00710] 77% 3b [00711] [00712] 78% 4b [00713] [00714] 75% 5b [00715] [00716] 78% 6b [00717] [00718] 73% 7b [00719] [00720] 71% 8b [00721] [00722] 76%

c) 11,11-Dimethyl-3-(2-nitrophenyl)-11H-benzo[b]fluorene

[0097] ##STR00723##

[0098] To a well-stirred, degassed suspension of 59 g (183.8 mmol) of 2-nitrobenzeneboronic acid, 54 g (184 mmol) of 3-bromo-11,11-dimethyl-11H-benzo[b]fluorene and 66.5 g (212.7 mmol) of potassium carbonate in a mixture of 250 ml of water and 250 ml of THF are added 1.7 g (1.49 mmol) of Pd(PPh.sub.3).sub.4, and the mixture is heated under reflux for 17 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and once with 200 ml of saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to dryness by rotary evaporation. The grey residue is recrystallized from hexane. The precipitated crystals are filtered off with suction, washed with a little MeOH and dried under reduced pressure. Yield: 53 g (146 mmol), 80% of theory.

[0099] The following compounds can be prepared in an analogous manner:

TABLE-US-00006 Reactant 1 Reactant 2 Product Yield 1c [00724] [00725] [00726] 74% [1927921-26-3] 2c [00727]   [1674335-13-7] [00728] [00729] 77%

d) Carbazole Synthesis

[0100] ##STR00730##

[0101] A mixture of 87 g (240 mmol) of 11,11-dimethyl-3-(2-nitrophenyI)-11H-benzo[b]fluorene and 290.3 ml (1669 mmol) of triethyl phosphite is heated under reflux for 12 h. Subsequently, the rest of the triethyl phosphite is distilled off (72-76° C./9 mmHg). Water/MeOH (1:1) is added to the residue, and the solids are filtered off and recrystallized. Yield: 58 g (176 mmol), 74% of theory.

[0102] The following compounds can be prepared in an analogous manner:

TABLE-US-00007 Reactant Product Yield 1d [00731] [00732] 79% 2d [00733] [00734] 76%

e) Nucleophilic Substitution

[0103] ##STR00735##

[0104] 4.2 g (106 mmol) of NaH (60% in mineral oil) are dissolved in 300 ml of dimethylformamide under a protective atmosphere. 35 g (106 mmol) of 7,9-dihydro-7,7-dimethylbenz[6,7]indeno[2,1-b]carbazole are dissolved in 250 ml of DMF and added dropwise to the reaction mixture. After 1 h at room temperature, a solution of 2-chloro-4,6-diphenyl-[1,3,5]triazine (34.5 g, 0.122 mol) in 200 ml of THF is added dropwise. The reaction mixture is stirred at room temperature for 12 h and then poured onto ice. After warming to room temperature, the solids that precipitate out are filtered and washed with ethanol and heptane. The residue is subjected to hot extraction with toluene, recrystallized from toluene/n-heptane and finally sublimed under high vacuum. The purity is 99.9%. Yield 39 g (69 mmol), 66% of theory.

[0105] The following compounds can be prepared in an analogous manner:

TABLE-US-00008 Reactant 1 Reactant 2 Product Yield 1e [00736]   [213765-59-7] [00737]   [3842-55-5] [00738] 60% 2e [00739]   [2102515-67-1] [00740]   1384480-21-0 [00741] 61% 3e [00742]   [2102515-67-1] [00743]   92853-85-5 [00744] 57% 4e [00745]   [213765-59-7] [00746]   1260393-65-4 [00747] 60% 5e [00748]   [213675-59-7] [00749]   2915-16-4 [00750] 63% 6e [00751]   [2102515-67-1] [00752]   [1616499-38-7] [00753] 72% 7e [00754]   [213765-59-7] [00755]   [1403252-58-3] [00756] 74% 8e [00757]   [213765-59-7] [00758]   [1373265-66-7] [00759] 62% 9e [00760]   [2102515-67-1] [00761]   [1373317-91-9] [00762] 67% 10e [00763]   [213765-59-7] [00764]   [14003252-55-0] [00765] 61% 11e [00766]   [2102515-67-1] [00767]   [30169-34-7] [00768] 63% 12e [00769]   [2102515-67-1] [00770]   [29874-83-7] [00771] 67% 13e [00772]   [2102515-67-1] [00773]   [6484-25-9] [00774] 62% 14e [00775]   [213765-59-7] [00776]   [7065-92-1] [00777] 66% 15e [00778]   [213765-59-7] [00779]   [29874-83-7] [00780] 63% 16e [00781] [00782]   [1292317-90-8] [00783] 60% 17e [00784]   [213765-59-7] [00785]   [900463-54-9] [00786] 61% 18e [00787] [00788]   [3842-55-5] [00789] 71% 19e [00790]   [213765-59-7] [00791]   [7065-92-1] [00792] 74%

f) Bromination

[0106] ##STR00793##

[0107] 129 g (230 mmol) of compound 1e are initially charged in 1000 ml of THF. Subsequently, a solution of 41.7 g (234.6 mmol) of NBS in 500 ml of THF is added dropwise in the dark at −15° C., the mixture is allowed to come to RT and stirring is continued at this temperature for 4 h. Subsequently, 150 ml of water are added to the mixture and extraction is effected with CH.sub.2Cl.sub.2. The organic phase is dried over MgSO.sub.4 and the solvents are removed under reduced pressure. The product is subjected to extractive stirring with hot hexane and filtered off with suction. Yield: 78.3 g (121 mmol), 53% of theory; purity by .sup.1H NMR about 97%.

[0108] The following compounds can be prepared in an analogous manner:

TABLE-US-00009 Reactant Product Yield 1f [00794] [00795] 56% 2f [00796] [00797] 61%

g) Suzuki Reaction

[0109] ##STR00798##

[0110] 25.8 g (42.12 mmol) of the compound 1f, 13.4 g (47 mmol) of 9-phenylcarbazole-3-boronic acid and 29.2 g of Rb.sub.2CO.sub.3 are suspended in 250 ml of p-xylene. To this suspension are added 0.95 g (4.2 mmol) of Pd(OAc).sub.2 and 12.6 ml of a 1M tri-tert-butylphosphine solution in toluene. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 200 ml each time of water and then concentrated to dryness. The residue is subjected to hot extraction with toluene, recrystallized from toluene and finally sublimed under high vacuum. The purity is 99.9%. Yield: 24 g (31 mmol); 70% of theory.

[0111] The following compounds can be prepared in an analogous manner:

TABLE-US-00010 Reactant 1 Reactant 2 Product Yield 1g [00799] [00800]   [1493715-37-9] [00801] 60% 2g [00802] [00803]   [1133057-97-2] [00804] 61%

Production of the OLEDs

[0112] Examples I1 to I9 which follow (see table 1) present the use of the material of the invention in OLEDs.

[0113] Pretreatment for Examples I1-I9:

[0114] Glass plaques coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plaques form the substrates to which the OLEDs are applied.

[0115] The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm. The exact structure of the OLEDs can be found in table 1. The materials required for production of the OLEDs are shown in table 2. The data of the OLEDs are listed in table 3.

[0116] All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer always consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as EG1:IC2:TER5 (55%:35%:10%) mean here that the material EG1 is present in the layer in a proportion by volume of 55%, 102 in a proportion by volume of 35% and TER5 in a proportion by volume of 10%. Analogously, the electron transport layer may also consist of a mixture of two materials.

[0117] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the current efficiency (CE, measured in cd/A) and the external quantum efficiency (EQE, measured in %) are determined as a function of luminance, calculated from current-voltage-luminance characteristics assuming Lambertian emission characteristics, as is the lifetime. The electroluminescence spectra are determined at a luminance of 1000 cd/m.sup.2, and the CIE 1931 x and y colour coordinates are calculated therefrom. The parameter U1000 in table 3 denotes the voltage which is required for a luminance of 1000 cd/m.sup.2. CE1000 and EQE1000 are current efficiency and the external quantum efficiency that are attained at 1000 cd/m.sup.2. The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion L1 in the course of operation with constant current density j.sub.0. A figure of L1=95% in table 3 means that the lifetime reported in the LT column corresponds to the time after which the luminance falls to 95% of its starting value.

[0118] Use of the Compounds of the Formula (1) as Matrix Material in OLEDs

[0119] A mixture of two host materials (matrix materials) is typically used in the emission layer of OLEDs in order to achieve an optimal charge balance and hence very good performance data of the OLEDs. With regard to simplified production of OLEDs, a reduction in the different materials used is desirable. Thus, the use of just one host material rather than a mixture of two host materials in the emission layer is advantageous.

[0120] With the use of the inventive compounds EG1 to EG7 in examples I1 to I9 as matrix material in the emission layer of phosphorescent red OLEDs, it can be shown that use as single material gives performance data of the OLEDs that are at least equally good or improved compared to a mixture with a second host material IC2 (I2 and I4). This constitutes a clear advantage from a production point of view.

TABLE-US-00011 TABLE 1 Construction of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness I1 HATCN SpMA1 SpMA3 EG1:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I2 HATCN SpMA1 SpMA3 EG1:IC2:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (72%:25%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I3 HATCN SpMA1 SpMA3 EG2:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I4 HATCN SpMA1 SpMA3 EG2:IC2:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (32%:65%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I5 HATCN SpMA1 SpMA3 EG3:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I6 HATCN SpMA1 SpMA3 EG4:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I7 HATCN SpMA1 SpMA3 EG5:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I8 HATCN SpMA1 SpMA3 EG6:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm I9 HATCN SpMA1 SpMA3 EG7:TER ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm (50%:50%) 30 nm 1 nm

TABLE-US-00012 TABLE 2 Structural formulae of the materials for the OLEDs [00805] HATCN [00806] SpMA1 [00807] SpMA3 [00808] TER [00809] IC2 [00810] LiQ [00811] ST2 [00812] EG1 [00813] EG2 [00814] EG3 [00815] EG4 [00816] EG5 [00817] EG6 [00818] EG7

TABLE-US-00013 TABLE 3 Data of the OLEDs EQE U1000 CE1000 1000 CIE x/y at j.sub.0 L1 LT Ex. (V) (cd/A) (%) 1000 cd/m.sup.2 (mA/cm.sup.2) (%) (h) I2 3.9 23 21 0.67/0.33 20 95 1310 I2 3.8 23 20 0.66/0.34 20 95 1160 I3 3.4 23 21 0.67/0.33 20 95 110 I4 3.8 24 21 0.67/0.33 20 95 70 I5 3.8 22 20 0.66/0.34 I6 3.5 23 22 0.66/0.34 I7 3.7 22 20 0.67/0.33 I8 3.9 23 21 0.66/0.34 I9 3.9 22 20 0.67/0.34