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. Compound of the general formula (1) ##STR00432## where the following applies to the symbols and indices used: ETG is an organic electron-transporting group from the group of the electron-deficient heteroaromatic groups, where the ETG is preferably a heteroaryl group having 5 to 60 aromatic ring atoms, where very preferred heteroatoms are N-atoms and very particularly preferred ETGs are selected from the group of the triazines, pyrimidines, pyrazines, pyridines, quinazolines, benzimidazoles, quinolines, isoquinolines and naphthyridines and especially preferred ETGs are selected from the group of the triazines, pyrimidines, pyrazines and pyridines; the ETG may be substituted by one or more radicals R.sup.1, which may be identical or different on each occurrence; W is an electron-rich organic group which conducts holes, where W is preferably selected from the group of the arylamines, triarylamines, bridged amines, where preferred bridged amines here are dihydroacridines, dihydrophenazines, phenoxazines and phenothiazines, carbazoles, bridged carbazoles, biscarbazoles, benzocarbazoles, indenocarbazoles and indolocarbazoles; W may be substituted by one or more radicals R.sup.1, which may be identical or different on each occurrence; V is O or S, preferably O; Y is a divalent bridge; Y preferably represents an aromatic or heteroaromatic ring system having 5 to 60 ring atoms; the divalent bridge Y very preferably has 5 to 30 ring atoms, particularly preferably 5 to 18 ring atoms, very preferably 5 to 12 ring atoms, especially 5 to 10 aromatic ring atoms, more preferably the bridge has precisely 6 ring atoms and most preferably the bridge is a phenylene bridge; n is either 0 or 1, preferably 0, where n equals 0 means that the ETG and the ring B are linked directly to one another by a single bond; r is an integer from 0, 1, 2 or 3, preferably 0 or 1 and very preferably 0; s is an integer from 0, 1, 2 or 3, preferably 0 or 1 and very preferably 0; 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)(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 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; 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; R.sup.4, R.sup.5 are, 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)(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.

2. Compound according to claim 1 having the general formula (2) ##STR00433## where: X is N or CR.sup.1, where at least one of the five groups X in ring A represents an N atom, preferably two of the five groups X in ring A are equal to N and very preferably three of the five groups X in ring A are equal to N, and the ring A is very particularly preferably a triazine, especially preferably a 1,3,5-triazine.

3. Compound according to claim 1 or 2, characterised in that W is defined by the formula (W-1) ##STR00434## where: U is N or CR.sup.1, preferably CR.sup.1, where the dotted line denotes the bond from the group W to the ring C.

4. Compound according to one or more of claims 1 to 3, characterised in that the compound has the following formula: ##STR00435##

5. Compound according to one or more of claims 1 to 4, characterised in that the compound has the general formula (6): ##STR00436##

6. Compound according to one or more of claims 1 to 5, characterised in that the compound has the general formula (7): ##STR00437##

7. Compound according to one or more of claims 1 to 6, characterised in that the group W is a carbazole, indenocarbazole or indolocarbazole.

8. Compound according to one or more of claims 1 to 7, characterised in that the group W is a group of the formula (W-2) ##STR00438##

9. Compound according to one or more of claims 1 to 8, characterised in that the group W is a group of the formula (W-5) ##STR00439## where the above definitions apply to the indices and symbols used and where furthermore: Tp, Tq are, identically or differently, a divalent bridge; Tp and Tq are preferably selected from N(R.sup.2), B(R.sup.2), O, C(R.sup.2).sub.2, Si(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, S, S═O, SO.sub.2, P(R.sup.2) and P(═O)R.sup.2; N(R.sup.2), O, C(R.sup.2).sub.2 and S are very preferred here and N(R.sup.2) and C(R.sup.2).sub.2 are especially preferred; U′ is, identically or differently on each occurrence, CR.sup.2 or N, preferably CR.sup.2; p is 0 or 1; where p equals 0 means that the ring E and the ring D are linked by a single bond; q is 0 or 1; where q equals 0 means that the ring E and the ring D are linked by a single bond; and where p+q=1 or 2 and is preferably equal to 1; and where Tp and Tq are each bonded to adjacent groups U of the ring D in any possible orientation; and where furthermore each group U which is bonded to Tp or Tq represents a carbon atom.

10. Composition comprising at least one compound according to one or more of claims 1 to 9 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 and hole-blocking materials.

11. Composition according to claim 10, characterised in that the additional compound is a host material or matrix material.

12. Composition according to claims 10 to 11, characterised in that the additional compound has a band gap of 2.5 eV or more, preferably 3.0 eV or more, very preferably 3.5 eV or more.

13. Formulation comprising at least one compound according to one or more of claims 1 to 9 or at least one composition according to one or more of claims 10 to 12 and at least one solvent.

14. Use of at least one compound according to one or more of claims 1 to 9 or at least one composition according to one or more of claims 10 to 12 in an electronic device, preferably in an organic electroluminescent device, very preferably in an organic light-emitting diode (OLED) or organic light-emitting electrochemical cell (OLEC, LEEC, LEC), very particularly preferably in an OLED, preferably in an emission layer (EML), electron-transport layer (ETL) and in a hole-blocking layer (HBL), very preferably in an EML and ETL and very particularly preferably in an EML.

15. Electronic device comprising at least one compound according to one or more of claims 1 to 9 or at least one composition according to one or more of claims 10 to 12, preferably in an emission layer (EML), electron-transport layer (ETL) and in a hole-blocking layer (HBL), very preferably in an EML and ETL and very particularly preferably in an EML.

16. Electronic device according to claim 15, characterised in that it is selected from organic integrated circuits (OCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors, preferably an organic electroluminescent device.

17. Electronic device according to claim 15 or 16, characterised in that it 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.

18. Process for the production of an electronic device according to one or more of claims 15 to 17, characterised in that at least one organic layer is applied by gas-phase deposition or from solution.

19. Electronic device according to claim 17, for use in medicine for phototherapy, preferably for phototherapy of the skin.

Description

EXAMPLES

[0191] 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 2-dibenzofuran-4-yl-4,6-diphenyl-1,3,5-triazine

[0192] ##STR00246##

[0193] 28.9 g (136 mmol) of dibenzofuran-4-boronic acid, 33 g (124.1 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 78.9 ml (158 mmol) of Na.sub.2CO.sub.3 (2 M solution) are suspended in 120 ml of toluene, 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 45 g (112 mmol), corresponding to 91% of theory.

[0194] The following compounds can be obtained analogously:

TABLE-US-00002 Starting material Starting material 1 2 Product Yield [00247] [00248] [00249] 82% [00250] [00251] [00252] 79% [00253] [00254] [00255] 70% [00256] [00257] [00258] 78% [00259] [00260] [00261] 82% [00262] [00263] [00264] 80% [00265] [00266] [00267] 84%

Example 2

Synthesis of 2-(8-bromodibenzofuran-4-yl)-4,6-diphenyl-1,3,5-triazine

[0195] ##STR00268##

[0196] 16 g (41 mmol) of 2-dibenzofuran-4-yl-4,6-diphenyl-1,3,5-triazine are initially introduced in 100 ml of dry dimethylformamide (DMF) with 8 mg of N-bromosuccinimide (NBS) (45 mmol, 1.1 mol %). The reaction mixture is heated at 120° C. for 24 h, and the solvent is then removed in vacuo. The residue is purified by column chromatography on silica gel with heptane/DCM (2/1) as eluent. The yield is 14.6 g (30 mmol), corresponding to 75% of theory.

[0197] The following compounds can be obtained analogously:

TABLE-US-00003 Starting material 1 Product Yield [00269] [00270] 73% [00271] [00272] 58% [00273] [00274] 61% [00275] [00276] 62% [00277] [00278] 63% [00279] [00280] 74% [00281] [00282] 59%

Example 3

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

[0198] ##STR00283##

[0199] A degassed solution of 70 g (147 mmol) of 2-(8-bromodibenzofuran-4-yl)-4,6-diphenyl-1,3,5-triazine and 35.7 g (147 mmol) of 3-phenyl-9H-carbazole in 600 ml of toluene is saturated with N.sub.2 for 1 h. Then, firstly 2.09 ml (8.6 mmol) of P(tBu).sub.3, then 1.38 g (6.1 mmol) of palladium(II) acetate are added gto the solution, and 17.7 g (185 mmol) of NaOtBu in the solid state are subsequently added to the solution. The reaction mixture is heated under reflux for 1 h. After cooling to room temperature, 500 ml of water are carefully added. The aqueous phase is washed with 3×50 ml of toluene, dried over MgSO.sub.4, and the solvent is removed in vacuo. The crude product is then purified by chromatography over silica gel with heptane/ethyl acetate (20/1). The residue is recrystallised from toluene and finally sublimed in a high vacuum (p=5×10.sup.−6 mbar).

[0200] The yield is 77.7 g (121 mmol), corresponding to 83% of theory.

[0201] The following compounds can be obtained analogously:

TABLE-US-00004 Starting material 1 Starting material 2 Product Yield [00284] [00285] [00286] 92% [00287] [00288] [00289] 87% [00290] [00291] [00292] 87% [00293] [00294] [00295] 83% [00296] [00297] [00298] 57% [00299] [00300] [00301] 62% [00302] [00303] [00304] 72% [00305] [00306] [00307] 70% [00308] [00309] [00310] 72% [00311] [00312] [00313] 65% [00314] [00315] [00316] 68% [00317] [00318] [00319] 61% [00320] [00321] [00322] 72% [00323] [00324] [00325] 80% [00326] [00327] [00328] 95% [00329] [00330] [00331] 90%

Example 4

Synthesis of 2-dibenzofuran-4-yl-4-phenylquinazoline

[0202] ##STR00332##

[0203] 23 g (110.0 mmol) of dibenzofuran-4-boronic acid, 29.5 g (110.0 mmol) of 2-chloro-4-phenylquinazoline and 26 g (210.0 mmol) of sodium carbonate are suspended in 500 ml of ethylene glycol diamine ether and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension. 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 and from dichloromethane/heptane. The yield is 31 g (85 mmol), corresponding to 79% of theory.

[0204] The following compounds can be obtained analogously:

TABLE-US-00005 Starting material 1 Starting material 2 Product Yield [00333] [00334] [00335] 73% [00336] [00337] [00338] 69% [00339] [00340] [00341] 67% [00342] [00343] [00344] 63% [00345] [00346] [00347] 65% [00348] [00349] [00350] 66% [00351] [00352] [00353] 60%

Example 5

Synthesis of 2-(8-bromodibenzofuran-4-yl)-4-phenylquinazoline

[0205] ##STR00354##

[0206] 70.6 g (190.0 mmol) of 2-dibenzofuran-4-yl-4-phenylquinazoline are suspended in 2000 ml of acetic acid (100%) and 2000 ml of sulfuric acid (95-98%). 34 g (190 mmol) of NBS are added in portions to this suspension, and the mixture is stirred in the dark for 2 hours. Water/ice is then added, and the solid is separated off and rinsed with ethanol. The residue is recrystallised from toluene. The yield is 59 g (130 mmol), corresponding to 69% of theory.

[0207] In the case of thiophene derivatives, nitrobenzene is employed instead of sulfuric acid and elemental bromine is employed instead of NBS.

[0208] The following compounds can be obtained analogously:

TABLE-US-00006 Starting material Product Yield [00355] [00356] 61% [00357] [00358] 55% [00359] [00360] 31% [00361] [00362] 33% [00363] [00364] 30% [00365] [00366] 36% [00367] [00368] 58%

Example 6

Synthesis of 3-phenyl-9-[6-(4-phenylquinazolin-2-yl)dibenzofuran-2-yl]-9H-carbazole

[0209] ##STR00369##

[0210] A degassed solution of 70 g (147 mmol) of 2-(8-bromodibenzofuran-4-yl)-4-phenylquinazoline and 35.7 g (147 mmol) of 3-phenyl-9H-carbazole in 600 ml of toluene is saturated with N.sub.2 for 1 h. Then, firstly 2.09 ml (8.6 mmol) of P(tBu).sub.3, then 1.38 g (6.1 mmol) of palladium(II) acetate are added to the solution, and 17.7 g (185 mmol) of NaOtBu in the solid state are subsequently added. The reaction mixture is heated under reflux for 1 h. After cooling to room temperature, 500 ml of water are carefully added. The aqueous phase is washed 3 times with 50 ml of toluene, dried over MgSO.sub.4, and the solvent is removed in vacuo. The crude product is then purified by chromatography over silica gel with heptane/ethyl acetate (20/1). The residue is recrystallised from toluene and finally sublimed in a high vacuum (p=5×10.sup.−6 mbar).

[0211] The yield is 76 g (119 mmol), corresponding to 81% of theory.

[0212] The following compounds can be obtained analogously:

TABLE-US-00007 Starting material 1 Starting material 2 Product Yield [00370] [00371] [00372] 73% [00373] [00374] [00375] 71% [00376] [00377] [00378] 69% [00379] [00380] [00381] 71% [00382] [00383] [00384] 70% [00385] [00386] [00387] 66% [00388] [00389] [00390] 69% [00391] [00392] [00393] 78% [00394] [00395] [00396] 74% [00397] [00398] [00399] 75% [00400] [00401] [00402] 80% [00403] [00404] [00405] 72%

Example 16

[0213] Production and Characterisation of the OLEDs

[0214] The data of various OLEDs are presented in the following examples V1 to E12 (see Tables 1 and 2).

[0215] Pretreatment for Examples V1-E12: 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 AI 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.

[0216] The OLEDs have in principle the following layer structure: substrate/hole-transport layer (HTL)/optional 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.

[0217] All materials are applied by thermal vapour deposition in a vacuum chamber. 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 101 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.

[0218] 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 per cent) as a function of the luminous density, calculated from current/voltage/luminous density characteristic lines (IUL characteristic lines) assuming Lambert emission characteristics, 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 coordinates 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% means that the lifetime indicated 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.

[0219] The data of the various OLEDs are summarised in Table 2. Examples V1-V5 are comparative examples in accordance with the prior art, Examples E1 to E12 show data of OLEDs according to the invention.

[0220] Some of the examples are explained in greater detail below in order to illustrate the advantages of the OLEDs according to the invention.

[0221] Use of Mixtures According to the Invention in the Emission Layer of Phosphorescent OLEDs

[0222] The materials according to the invention give rise to significant improvements in the power efficiency compared with the prior art on use as matrix materials in phosphorescent OLEDs. The use of compounds EG1 and EG2 according to the invention in combination with the green-emitting dopant TEG1 enables an increase in the power efficiency by up to 20% compared with the prior art to be observed (comparison of Example E1 with V1 and comparison of E2 with V2, V3, V4 and V5). Furthermore, the compounds according to the invention result in a significant improvement in the lifetime of the components. Thus, the lifetime of component E2 comprising matrix EG2 according to the invention is improved from 125 h to 210 h compared with the prior art V4 comprising SdT4 (L0;j0=20 mA/cm.sup.2, L1=80%).

TABLE-US-00008 TABLE 1 Structure of the OLEDs HTL/IL (HATCN; 5 nm)/EBL/EML/HBL/ETL/EIL HTL EBL EML HBL ETL EIL Ex. Thickness Thickness Thickness Thickness Thickness Thickness V1 SpA1 SpMA1  SdT1:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm V2 SpA1 SpMA1  SdT2:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm V3 SpA1 SpMA1  SdT3:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm V4 SpA1 SpMA1  SdT4:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm V5 SpA1 SpMA1  SdT5:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E1 SpA1 SpMA1  .sup. EG1:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E2 SpA1 SpMA1  .sup. EG2:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E3 SpA1 SpMA1  .sup. EG3:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E4 SpA1 SpMA1  .sup. EG4:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E5 SpA1 SpMA1  .sup. EG5:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E6 SpA1 SpMA1  .sup. EG6:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (95%:5%)  10 nm (50%:50%) 30 nm 30 nm E7 SpA1 SpMA1  IC1:TEG1 EG7 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E8 SpA1 SpMA1  .sup. EG8:TEG1 ST2 ST2:LiQ — 70 nm 90 nm (90%:10%) 10 nm (50%:50%) 30 nm 30 nm E9 SpA1 SpMA1 EG9:IC3:TEG1 IC1 ST2:LiQ — 70 nm 90 nm (60%:35%:5%) 10 nm (50%:50%) 30 nm 30 nm E10 SpA1 SpMA1 .sup. E10:TER1 — ST2:LiQ — 90 nm 130 nm  (92%:8%)  (50%:50%) 40 nm 40 nm E11 SpA1 SpMA1 .sup. E11:TER1 — ST2:LiQ — 90 nm 130 nm  (92%:8%)  (50%:50%) 40 nm 40 nm E12 SpA1 SpMA1  IC1:TEG1 — EG12:ST2 .sup.  LiQ 70 nm 90 nm (90%:10%) (50%:50%) 3 nm 30 nm 40 nm

TABLE-US-00009 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 V1 3.5 48 43 12.8% 0.32/0.64 V2 3.6 51 44 13.7% 0.33/0.63 V3 4.1 50 38 13.3% 0.33/0.63 V4 3.4 52 49 14.1% 0.33/0.62 V5 4.4 48 34 12.9% 0.33/0.62 E1 3.3 53 51 14.2% 0.33/0.63 E2 3.2 54 53 13.9% 0.32/0.65 E3 3.4 53 49 14.5% 0.32/0.63 E4 3.6 58 51 15.4% 0.32/0.64 E5 3.4 46 43 13.1% 0.33/0.62 E6 3.5 51 46 13.8% 0.32/0.63 E7 3.3 61 58 16.7% 0.33/0.63 E8 3.6 51 45 14.0% 0.33/0.63 E9 3.4 56 49 15.7% 0.33/0.62 E10 4.1 13 10 12.3% 0.67/0.33 E11 4.3 12  9 12.4% 0.66/0.34 E12 3.4 62 57 16.9% 0.33/0.63

TABLE-US-00010 TABLE 3 Structural formulae of the materials for the OLEDs [00406] HATCN [00407] SpA1 [00408] SpMA1 [00409] LiQ [00410] IC1 [00411] ST2 [00412] IC3 [00413] TEG1 [00414] TER1 [00415] SdT1 [00416] SdT2 [00417] SdT3 [00418] 4SdT [00419] SdT5 [00420] EG1 [00421] EG2 [00422] EG3 [00423] EG4 [00424] EG5 [00425] EG6 [00426] EG7 [00427] EG8 [00428] EG9 [00429] EG10 [00430] EG11 [00431] EG12