MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

Abstract

The invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.

Claims

1.-14. (canceled)

15. An electronic device comprising at least one compound of formula (1) ##STR00627## wherein Z is the same or different at each instance and is O or S; A is R or Z; R.sup.b is Ar or a free electron pair; where, when A=Z, the oxygen or sulfur atom represented by Z is bonded to the carbon atom via a double bond, and R.sup.b is Ar; in addition, R.sup.b is a free electron pair when A=R, and there is a double bond between the carbon atom to which A is bonded and the nitrogen atom to which R.sup.b is bonded; R.sup.a is the same or different and is R, or the two R.sup.a groups together with the nitrogen atom and the carbon atom to which they bind form a group of one of the formulae (2), (3) and (4) ##STR00628## where the dotted bond in each case indicates the linkage within formula (1); X is the same or different at each instance and is CR or N; or two adjacent X groups are a group of the formula (5) or (6) ##STR00629## where the dotted bonds indicate the linkage of this group in the formula (2), formula (3) or formula (4); Y is the same or different at each instance and is CR or N; W is the same or different at each instance and is NAr, O, S or C(R).sub.2; 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 radicals; R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′).sub.2, N(R.sup.1).sub.2, OAr′, SAr′, 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 R.sup.1 radicals, 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, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R.sup.1 radicals; at the same time, two R radicals together may also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic 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 is 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 each 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 and where one or more hydrogen atoms in the alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN, 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; at the same time, two or more R.sup.1 radicals together may form an aliphatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F.

16. The electronic device as claimed in claim 15, wherein the compound of the formula (1) contains at least one substituent Ar and/or in that it contains at least one substituent R which is an aromatic or heteroaromatic ring system.

17. The electronic device as claimed in claim 15, wherein the compound of the formula (1) is selected from the compounds of the formulae (7a) and (8a) ##STR00630## where the symbols used have the definitions given in claim 15.

18. The electronic device as claimed in claim 15, selected from the compounds of the formulae (7-1) to (7-9) and (8-1) to (8-11) ##STR00631## ##STR00632## ##STR00633## ##STR00634## where the symbols have the definitions given in claim 15.

19. The electronic device as claimed in claim 15, wherein the compound of the formula (1) is selected from the compounds of the formulae (7-1a) to (7-9a) and (8-1a) to (8-11a) ##STR00635## ##STR00636## ##STR00637## ##STR00638## where the symbols have the definitions given in claim 15.

20. The electronic device as claimed in claim 15, wherein, when A=R, this R radical 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 in that the R radical shown explicitly in formulae (8) and (8-1) to (8-11) which is bonded to the triazinone skeleton 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.

21. The electronic device as claimed in claim 15, wherein Ar is the same or different at each instance and represents an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more R radicals.

22. The electronic device as claimed in claim 15, wherein R is the same or different at each instance and is selected from the group consisting of H, D, F, N(Ar′).sub.2, CN, OR.sup.1, a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl or alkenyl group may each be substituted by one or more R.sup.1 radicals, but is preferably unsubstituted, and where one or more nonadjacent CH.sub.2 groups may be replaced by O, or an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals; at the same time, two R radicals together may also form an aliphatic, aromatic or heteroaromatic ring system.

23. The electronic device as claimed in claim 15, wherein Ar and R, if R is an aromatic or heteroaromatic ring system, are the same or different at each instance and are selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of these groups, each of which may be substituted by one or more R radicals.

24. The electronic device as claimed in claim 15, selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, dye-sensitized organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes and organic plasmon-emitting devices.

25. The electronic device as claimed in claim 15 which is an organic electroluminescent device, wherein the compound of formula (1) is used in an emitting layer as matrix material for phosphorescent emitters or for emitters that exhibit TADF and/or in an electron transport layer and/or in a hole blocker layer.

26. The electronic device as claimed in claim 15 which is an organic electroluminescent device, wherein the compound of the formula (1) is used as matrix material for a phosphorescent emitter in combination with a further matrix material, and in that the further matrix material is selected from the group consisting of aromatic ketones, aromatic phosphine oxides, aromatic sulfoxides, aromatic sulfones, triarylamines, carbazole derivatives, biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles, boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, dibenzofuran-carbazole derivatives, dibenzofuran-amine derivatives or carbazoleamines.

27. A compound of formula (1′) ##STR00639## where the symbols used have the definitions given in claim 15, wherein the compound contains a heteroaryl group in at least one of the substituents Ar or R.

28. A compound as claimed in claim 27, wherein the heteroaryl group is selected from the group consisting of dibenzofuran, dibenzothiophene and carbazole.

Description

EXAMPLES

[0117] The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. For the compounds known from the literature, the corresponding CAS numbers are also reported in each case.

Synthesis Examples

a) 1-(4-Bromophenyl)-4,6-diphenyl-1,3,5-triazin-2-one

[0118] ##STR00359##

[0119] To a solution of 48.8 g (150 mmol) of 1,4,6-triphenyl-1,3,5-triazin-2-one in chloroform (900 ml) is added N-bromosuccinimide (26.6 g, 150 mmol) in portions at 0° C. with exclusion of light, and the mixture is stirred at this temperature for 2 h. The reaction is ended by addition of sodium sulfite solution and the mixture is stirred at room temperature for a further 30 min. After phase separation, the organic phase is washed with water and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is dissolved in toluene and filtered through silica gel. Subsequently, the crude product is recrystallized from toluene/heptane. Yield: 45 g (112 mmol), 75% of theory, colorless solid.

[0120] The following compounds can be obtained analogously:

TABLE-US-00002 Reactant 1 Product 1 Product 2 Yield 1a [00360] [00361] 50% 2a [00362] [00363] [00364] 40%/ 50% 3a [00365] [00366] [00367] 40%/ 50% 4a [00368] [00369] [00370] 50%/ 30% 5a [00371] [00372] 40% 6a [00373] [00374] 55%

b) 1-[4-(9,9-Dimethylfluoren-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazin-2-one

[0121] ##STR00375##

[0122] 62.8 g (155 mmol) of 1-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazin-2-one, 41 g (172 mmol) of 9,9-dimethyl-9H-fluorene-2-boronic acid and 36 g (340 mmol) of sodium carbonate are suspended in 1000 ml of ethylene glycol dimethyl ether and 280 ml of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, filtered through silica gel and then concentrated to dryness. The product is purified via column chromatography on silica gel with toluene/heptane (1:2) and finally sublimed under high vacuum (p=5×10.sup.−7 mbar) (99.9% purity). The yield is 57 g (112 mmol), corresponding to 72% of theory.

[0123] The following compounds are prepared in an analogous manner:

TABLE-US-00003 Reactant 1 Reactant 2 Product Yield 1b [00376] [00377] [00378] 77% 2b [00379] [00380] [00381] 82% 3b [00382] [00383] [00384] 77% 4b [00385] [00386] [00387] 81% 5b [00388] [00389] [00390] 74% 6b [00391] [00392] [00393] 76% 7b [00394] [00395] [00396] 81% 8b [00397] [00398] [00399] 88% 9b [00400] [00401] [00402] 80% 10b [00403] [00404] [00405] 89% 11b [00406] [00407] [00408] 63% 12b [00409] [00410] [00411] 66% 13b [00412] [00413] [00414] 85% 14b [00415] [00416] [00417] 86% 15b [00418] [00419] [00420] 82% 16b [00421] [00422] [00423] 90% 17b [00424] [00425] [00426] 78% 18b [00427] [00428] [00429] 78% 19b [00430] [00431] [00432] 67% 20b [00433] [00434] [00435] 71% 21b [00436] [00437] [00438] 63% 22b [00439] [00440] [00441] 64% 23b [00442] [00443] [00444] 61% 24b [00445] [00446] [00447] 73% 25b [00448] [00449] [00450] 62% 26b [00451] [00452] [00453] 65% 27b [00454] [00455] [00456] 66% 28b [00457] [00458] [00459] 65% 29b [00460] [00461] [00462] 72% 30b [00463] [00464] [00465] 78% 31b [00466] [00467] [00468] 68% 32b [00469] [00470] [00471] 59% 33b [00472] [00473] [00474] 67% 34b [00475] [00476] [00477] 78%

c) 7,9-Bis(4-dibenzofuran-4-ylphenyl)-3-phenylpyrido[1,2-a][1,3,5]triazine-2,4-dione

[0124] ##STR00478##

[0125] 25.8 g (40 mmol) of 6-phenyl-1H-quinazoline-2,4-dione, 61.2 g (85 mmol) of 4-iodobenzene, 44.7 g (320 mmol) of potassium carbonate, 3 g (16 mmol) of copper(I) iodide and 3.6 g (16 mmol) of 1,3-di(pyridin-2-yl)propane-1,3-dione are stirred in 100 ml of DMF at 150° C. for 30 h. The solution is diluted with water and extracted twice with ethyl acetate. The combined organic phases are dried over Na.sub.2SO.sub.4 and concentrated by rotary evaporation. The residue is purified by chromatography (EtOAc/hexane: 2/3). The residue is recrystallized from toluene and finally sublimed under high vacuum (p=5×10.sup.−5 mbar). The purity is 99.9%. The yield is 20.8 g (28.8 mmol); 72% of theory.

[0126] The following compounds are prepared in an analogous manner:

TABLE-US-00004 Reactant 1 Reactant 2 Product Yield 1c [00479] [00480] [00481] 68% 2c [00482] [00483] [00484] 64% 3c [00485] [00486] [00487] 71% 4c [00488] [00489] [00490] 83% 5c [00491] [00492] [00493] 75% 6c [00494] [00495] [00496] 67% 7c [00497] [00498] [00499] 66% 8c [00500] [00501] [00502] 63% 9c [00503] [00504] [00505] 71% 10c [00506] [00507] [00508] 59% 11c [00509] [00510] [00511] 75%

e) 2-Phenyl-7-[3-(9-phenylcarbazol-3-yl)carbazol-9-yl]pyrido[1,2-a][1,3,5]triazin-4-one

[0127] ##STR00512##

[0128] 20.4 g (50 mmol) of 9-phenyl-3,3′-bi-9H-carbazole and 17.1 g (50 mmol) of 7-bromo-2-phenylpyrido[1,2-a][1,3,5]triazin-4-one are dissolved in 400 ml of toluene under an argon atmosphere. 1.0 g (5 mmol) of tri-tert-butylphosphine is added and the mixture is stirred under an argon atmosphere. 0.6 g (2 mmol) of Pd(OAc).sub.2 is added and the mixture is stirred under an argon atmosphere, and then 9.5 g (99 mmol) of sodium tert-butoxide are added. The reaction mixture is stirred under reflux for 24 h. After cooling, the organic phase is separated, washed three times with 200 ml of water, dried over MgSO.sub.4 and filtered, and the solvent is removed under reduced pressure. The residue is purified by column chromatography using silica gel (eluent: DCM/heptane (1:3)). The residue is subjected to hot extraction with toluene and recrystallized from toluene/n-heptane and finally sublimed under high vacuum. The yield is 28.4 g (42 mmol), corresponding to 85% of theory.

[0129] The following compounds can be prepared analogously:

TABLE-US-00005 Reactant 1 Reactant 2 Product Yield 1e [00513] [00514] [00515] 73% 2e [00516] [00517] [00518] 70% 3e [00519] [00520] [00521] 68% 4e [00522] [00523] [00524] 73% 5e [00525] [00526] [00527] 84% 6e [00528] [00529] [00530] 82% 7e [00531] [00532] [00533] 67% 8e [00534] [00535] [00536] 62% 9e [00537] [00538] [00539] 60% 10e [00540] [00541] [00542] 83% 11e [00543] [00544] [00545] 88% 12e [00546] [00547] [00548] 78% 13e [00549] [00550] [00551] 90% 14e [00552] [00553] [00554] 71% 15e [00555] [00556] [00557] 92% 16e [00558] [00559] [00560] 89% 17e [00561] [00562] [00563] 77% 18e [00564] [00565] [00566] 73% 19e [00567] [00568] [00569] 65% 20e [00570] [00571] [00572] 67%

f) Benzofuro[3,2-c]carbazol-5-yl-[1,3,5]triazino[2,1-b][1,3]benzoxazol-4-one

[0130] ##STR00573##

[0131] To 20 g (50 mmol) of 3-bromo-4-(2-bromophenyl)dibenzofuran are added 500 ml of toluene, 2.3 g (2.5 mmol) of tris(dibenzylideneacetone)dipalladium(0), 10 ml of 1 M t-Bu.sub.3P in toluene and 11.5 g (120 mmol) of sodium tert-butoxide. Subsequently, 8.8 g (40 mmol) of 2-amino-[1,3,5]triazino[2,1-b][1,3]benzoxazol-4-one is added. The mixture is heated to 110° C. for 20 h, then cooled to room temperature, and 400 ml of water is added. The mixture is extracted with ethyl acetate, then the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from toluene and from dichloromethane/iso-propanol and finally sublimed under high vacuum. The purity is 99.9%. The yield is 10.6 g (24.5 mmol), corresponding to 49% of theory.

[0132] The following compounds can be prepared analogously:

TABLE-US-00006 Reactant 1 Reactant 2 Product Yield 1f [00574] [00575] [00576] 45% 2f [00577] [00578] [00579] 51% 3f [00580] [00581] [00582] 43% 4f [00583] [00584] [00585] 41% 5f [00586] [00587] [00588] 46% 6f [00589] [00590] [00591] 39%

[0133] Production of the OLEDs

[0134] Examples E1 to E27 which follow (see table 1) present the use of the materials of the invention in OLEDs.

[0135] Pretreatment for examples E1 to E27: Glass plates 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 plates form the substrates to which the OLEDs are applied.

[0136] 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 aluminum 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.

[0137] All materials are applied by thermal vapor 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. What is meant here by details given in such a form as EG1:IC2:TEG1 (49%:44%:7%) is that the material EG1 is present in the layer in a proportion by volume of 49%, IC2 in a proportion by volume of 44%, and TEG1 in a proportion by volume of 7%. Analogously, the electron transport layer may also consist of a mixture of two materials.

[0138] The OLEDs are characterized in a standard manner. For this purpose, electroluminescence spectra, current efficiency (CE, measured in cd/A) and external quantum efficiency (EQE, measured in %) are determined as a function of luminance, calculated from current-voltage-luminance characteristics assuming Lambertian emission characteristics. Electroluminescence spectra are determined at a luminance of 1000 cd/m.sup.2, and these are used to calculate the CIE 1931 x and y color coordinates. The results thus obtained can be found in table 3.

[0139] Compounds EG1 to EG11 and EG17 to EG25 are used in examples E1 to E20 as matrix material in the emission layer of phosphorescent green OLEDs. Compounds EG12 to EG16 are used in examples E21 to E25 as matrix material in the emission layer of phosphorescent red OLEDs. Compounds EG5 to EG7 are used in examples E26 to E27 as electron transporter in the ETM layer of phosphorescent green OLEDs.

TABLE-US-00007 TABLE 1 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness E1 HATCN SpMA1 SpMA2 EG1:IC2:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (49%:44%:7%) 40 nm  5 nm 30 nm 1 nm E2 HATCN SpMA1 SpMA2 EG2:IC2:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (49%:44%:7%) 40 nm  5 nm 30 nm 1 nm E3 HATCN SpMA1 SpMA2 EG3:IC2:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (49%:44%:7%) 40 nm  5 nm 30 nm 1 nm E4 HATCN SpMA1 SpMA2 EG4:IC2:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (49%:44%:7%) 40 nm  5 nm 30 nm 1 nm E5 HATCN SpMA1 SpMA2 EG5:IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (45%:45%:10%) 30 nm 10 nm 30 nm 1 nm E6 HATCN SpMA1 SpMA2 EG6: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 30 nm 10 nm 30 nm 1 nm E7 HATCN SpMA1 SpMA2 EG7: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 30 nm 10 nm 30 nm 1 nm E8 HATCN SpMA1 SpMA2 EG8: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E9 HATCN SpMA1 SpMA2 EG9: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E10 HATCN SpMA1 SpMA2 EG10: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E11 HATCN SpMA1 SpMA2 EG11: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E12 HATCN SpMA1 SpMA2 EG17: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E13 HATCN SpMA1 SpMA2 EG18: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E14 HATCN SpMA1 SpMA2 EG19: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E15 HATCN SpMA1 SpMA2 EG20: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E16 HATCN SpMA1 SpMA2 EG21: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E17 HATCN SpMA1 SpMA2 EG22: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E18 HATCN SpMA1 SpMA2 EG23: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E19 HATCN SpMA1 SpMA2 EG24: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E20 HATCN SpMA1 SpMA2 EG25: IC3:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm 30 nm 1 nm E21 HATCN SpMA1 SpMA2 EG12:TER5 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm 30 nm 1 nm E22 HATCN SpMA1 SpMA2 EG13:TER5 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm 30 nm 1 nm E23 HATCN SpMA1 SpMA2 EG14:TER5 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm 30 nm 1 nm E24 HATCN SpMA1 SpMA2 EG15:TER5 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm 30 nm 1 nm E25 HATCN SpMA1 SpMA2 EG16:TER5 ST2 ST2:LiQ (50%:50%) LiQ 5 nm 125 nm 10 nm (97%:3%) 35 nm 10 nm 30 nm 1 nm E26 HATCN SpMA1 SpMA2 IC1:TEG1 — EG5 LiQ 5 nm  70 nm 15 nm (90%:10%) 25 nm 45 nm 3 nm E27 HATCN SpMA1 SpMA2 IC1:TEG1 — EG7 LiQ 5 nm  70 nm 15 nm (90%:10%) 25 nm 45 nm 3 nm

TABLE-US-00008 TABLE 2 Structural formulae of the materials for the OLEDs [00592] [00593] [00594] [00595] [00596] [00597] [00598] [00599] [00600] [00601] [00602] [00603] [00604] [00605] [00606] [00607] [00608] [00609] [00610] [00611] [00612] [00613] [00614] [00615] [00616] [00617] [00618] [00619] [00620] [00621] [00622] [00623] [00624] [00625] [00626]

TABLE-US-00009 TABLE 3 Data of the OLEDs U1000 CE1000 EQE 1000 CIE x/y at Ex. (V) (cd/A) (%) 1000 cd/m.sup.2 E1 3.5 68 19 0.35/0.61 E2 3.4 67 17 0.33/0.62 E3 3.4 69 18 0.35/0.61 E4 3.3 71 16 0.35/0.62 E5 3.2 70 18.4 0.33/0.63 E6 3.1 67 18.0 0.33/0.62 E7 3.2 69 18.8 0.32/0.64 E8 3.1 74 20.1 0.32/0.63 E9 3.1 73 20.8 0.33/0.62 E10 3.1 73 19.8 0.33/0.63 E11 3.1 72 20.7 0.33/0.63 E12 3.2 73 20.8 0.33/0.63 E13 3.1 68 19.8 0.33/0.63 E14 3.1 73 20.8 0.33/0.62 E15 3.3 67 19.3 0.33/0.63 E16 3.1 72 20.2 0.33/0.63 E17 3.2 70 21.1 0.33/0.62 E18 3.1 73 19.8 0.33/0.62 E19 3.2 71 20.2 0.33/0.63 E20 3.1 73 21.7 0.33/0.62 E21 3.8 22 20 0.66/0.34 E22 3.9 21 22 0.65/0.33 E23 3.8 22 21 0.66/0.34 E24 3.7 24 22 0.67/0.34 E25 3.5 23 21 0.66/0.34 E26 3.4 64 18 0.33/0.63 E27 3.3 64 18.5 0.33/0.62