Carbazole derivatives

Abstract

The present invention relates to carbazole derivatives, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.

Claims

1. A compound comprising at least one structure of the formula (I) ##STR00451## where the symbols used are as follows: X is the same or different at each instance and is N or CR.sup.1, or C if the indolo group is bonded to X; W.sup.1 is O, S, C(R.sup.1).sub.2, P(O)Ar or Si(R.sup.1).sub.2; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(O)Ar.sup.1, C(O)R.sup.2, P(O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2CCR.sup.2, CC, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, CO, CS, CSe, CNR.sup.2, C(O)O, C(O)NR.sup.2, NR.sup.2, P(O)(R.sup.2), O, S, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.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, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, 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 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; Ar.sup.1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; at the same time, two Ar.sup.1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom may also be joined together via a bridge by a single bond or a bridge selected from the group consisting of B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, CO, CNR.sup.2, CC(R.sup.2).sub.2, O, S, SO, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(O)R.sup.3, CR.sup.3C(R.sup.3).sub.2, C(O)OR.sup.3, C(O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(O)R.sup.3, S(O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.3CCR.sup.3, CC, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, CO, CS, CNR.sup.3, C(O)O, C(O)NR.sup.3, NR.sup.3, P(O)(R.sup.3), O, S, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.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.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

2. The compound according to claim 1, comprising at least one structure of the formula (IIa), (IIb), (IIc), (IId), (IIe) or MO ##STR00452## where the symbols Ar, W.sup.1 and X used have the definition given in claim 1.

3. The compound according to claim 1, comprising at least one structure of the formula (IIIa), (IIIb), (IIIc), (IIId), (IIIe) or (IIIf) ##STR00453## where the symbols R.sup.1, Ar, W.sup.1 and X have the definition given in claim 1 and m is 0, 1, 2, 3 or 4.

4. The compound according to claim 1, comprising at least one structure of the formula (IVa), (IVb), (IVc), (IVd), (IVe) or (IVf) ##STR00454## where the symbols R.sup.1, Ar, W.sup.1 and X have the definition given in claim 1 and o is 0, 1 or 2.

5. The compound according to claim 1, comprising at least one structure of the formula (Va), (Vb), (Vc), (Vd), (Ve) or (Vf) ##STR00455## where the symbols R.sup.1, Ar, W.sup.1 and X used have the definition given in claim 1 and I is 0, 1, 2, 3, 4, 5 or 6.

6. The compound according to claim 1, comprising at least one structure of the formula (VIa), (VIb), (VIc), (VId), (VIe) or (VIf) ##STR00456## where the symbols R.sup.1, Ar, W.sup.1 and X have the definition given in claim 1, l is 0, 1, 2, 3, 4, 5 or 6, m is 0, 1, 2, 3 or 4 and o is 0, 1 or 2.

7. The compound according to claim 1, wherein the Ar group comprises or constitutes a hole transport group.

8. The compound according to claim 1, wherein the Ar group comprises or constitutes an electron transport group.

9. The compound according to claim 8, wherein the Ar group is a group that can be represented by the formula (QL)
Q-L.sup.1-Formula (QL) in which L.sup.1 represents a bond or 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 Q is an electron transport group, where R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.1).sub.2, N(R.sup.2).sub.2, C(O)Ar.sup.1, C(O)R.sup.2, P(O)(Ar.sup.1).sub.2, P(Ar.sup.1).sub.2, B(Ar.sup.1).sub.2, B(OR.sup.2).sub.2, Si(Ar.sup.1).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2CCR.sup.2, CC, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, CO, CS, CSe, CNR.sup.2, C(O)O, C(O)NR.sup.2, NR.sup.2, P(O)(R.sup.2), O, S, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.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, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; Ar.sup.1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; at the same time, two AO radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom may also be joined together via a bridge by a single bond or a bridge selected from the group consisting of B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, CO, CNR.sup.2, CC(R.sup.2).sub.2, O, S, SO, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(O)R.sup.2; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR.sup.3).sub.2, NO.sub.2, C(O)R.sup.3, CR.sup.3C(R.sup.3).sub.2, C(O)OR.sup.3, C(O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, P(R.sup.3).sub.2, B(R.sup.3).sub.2, N(R.sup.3).sub.2, NO.sub.2, P(O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(O)R.sup.3, S(O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sup.2 groups may be replaced by R.sup.3CCR.sup.3, CC, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, CO, CS, CNR.sup.3, C(O)O, C(O)NR.sup.3, NR.sup.3, P(O)(R.sup.3), O, S, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.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.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

10. An oligomer, polymer or dendrimer containing one or more compounds according to claim 1, wherein, rather than a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

11. A composition comprising the oligomer, polymer or dendrimer according to claim 10 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

12. A composition comprising at least one compound according to claim 1 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

13. A formulation comprising the composition according to claim 12 and at least one solvent.

14. A formulation comprising at least one compound according to claim 1 and at least one solvent.

15. An electronic device as host material, hole conductor material or electron transport material which comprises the compound according to claim 1.

16. A process for preparing the compound according to claim 1 which comprises a coupling reaction, joining a compound comprising at least one nitrogen-containing heterocyclic group to a compound comprising at least one aromatic or heteroaromatic group.

17. An electronic device comprising at least one compound according to claim 1.

18. The electronic device as claimed in claim 17, wherein the electronic device is 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, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells and organic laser diodes.

Description

EXAMPLES

(1) The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The reactants can be sourced from ALDRICH. The numbers for the reactants known from the literature, some of which are stated in square brackets, are the corresponding CAS numbers.

Synthesis Examples

a) Benzo[kl]xanthen-9-yl-(2-chlorophenyl)amine

(2) ##STR00226##

(3) 40 g (137 mmol) of 9-bromobenzo[kl]xanthene, 17.9 g (140 mmol) of 2-chloroaniline, 68.2 g (710 mmol) of sodium tert-butoxide, 613 mg (3 mmol) of palladium(II) acetate and 3.03 g (5 mmol) of dppf are dissolved in 1.3 l 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: 39 g (109 mmol); 83% of theory.

(4) The following compounds can be prepared in an analogous manner:

(5) TABLE-US-00002 Reactant 1 Reactant 2 Product Yield 1a 81% 2a 0 75% 3a 76% 4a 72% 5a 0 79% 6a 71% 7a 73% 8a 0 77% 9a 70% 10a 70% 11a 71% 12a 0 76% 13a 70% 14a 69% 15a 0 71% 16a 67% 17a 71%

b) Cyclization

(6) ##STR00278##

(7) 35 g (102 mmol) of benzo[kl]xanthen-9-yl-(2-chlorophenyl)amine, 56 g (409 mmol) of potassium carbonate, 4.5 g (12 mmol) of tricyclohexylphosphine tetrafluoroborate and 1.38 g (6 mmol) of palladium(II) acetate are suspended in 500 ml of dimethylacetamide and stirred under reflux for 6 h. After cooling, the reaction mixture is admixed with 300 ml of water and 400 ml of ethyl acetate. The mixture is stirred for a further 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. Yield: 28 g (229 mmol) of the A+B mixture; 90% of theory; purity: 98.0% by HPLC. After recrystallization from ethyl acetate/toluene (1:2), 62% A and 23% B are obtained.

(8) The following compounds can be prepared in an analogous manner:

(9) TABLE-US-00003 Reactant 1 Product 1b 0 2b 3b 4b 5b 6b 0 7b 8b 9b 10b 11b 00 12b 01 02 13b 03 04 14b 05 06 15b 07 08 16b 09 0 Product Yield 1b 60%/19% 2b 72% 3b 54%/22% 4b 59%/18% 5b 67% 6b 56%/20% 7b 53%/19% 8b 50%/21% 9b 59%/11% 10b 50%/20% 11b 77% 12b 61%/15% 13b 0 59%/16% 14b 72% 15b 55%/22% 16b 41%/24%

c) Buchwald

(10) ##STR00323##

(11) 4.3 g of NaH (107 mmol), 60% in mineral oil, are dissolved in 300 ml of dimethylformamide under a protective atmosphere. 32 g (107 mmol) of carbazole derivative (A) 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%. The yield is 38 g (70 mmol); 66% of theory.

(12) The following compounds can be prepared in an analogous manner:

(13) TABLE-US-00004 Reactant 1 Reactant 2 1c 2c 3c 4c 0 5c 6c 7c 8c 9c 0 10c 11c 12c 13c 14c 0 15c 16c 17c 18c 19c 0 20c 21c 22c 23c 24c 0 25c 26c 27v 28c 29c 0 30c 31c 32c 33c 34c 0 Product Yield 1c 66% 2c 62% 3c 64% 4c 57% 5c 61% 6c 63% 7c 60% 8c 68% 9c 00 65% 10c 01 69% 11c 02 67% 12c 03 64% 13c 04 63% 14c 05 68% 15c 06 65% 16c 07 62% 17c 08 65% 18c 09 71% 19c 0 69% 20c 73% 21c 70% 22c 63% 23c 60% 24c 71% 25c 7% 26c 69% 27v 63% 28c 64% 29c 0 70% 30c 76% 31c 65% 32c 69% 33c 72% 34c 74%

(14) Production of the OLEDs

(15) In examples I1 to I19 which follow, the data of various OLEDs are presented.

(16) Pretreatment for Examples I1-I19:

(17) 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.

(18) 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.

(19) 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 IC5:1C3:TEG2 (55%:35%:10%) mean here that the material 105 is present in the layer in a proportion by volume of 55%, IC3 in a proportion of 35% and TEG2 in a proportion of 10%. Analogously, the electron transport layer may also consist of a mixture of two materials.

(20) The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming Lambertian emission characteristics, and also the lifetime are determined. 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.

(21) Use of Mixtures of the Invention in the Emission Layer of Phosphorescent OLEDs

(22) The materials of the invention can be used in the emission layer in phosphorescent red OLEDs. The inventive material EG1 is used in Example I1 as matrix material in combination with the phosphorescent emitter TEG5. At a luminance of 1000 cd/m.sup.2, the OLED has colour coordinates of CIEx=0.67 and CIEy=0.33. In examples I2 to I13 too, the OLED emits light with the colour coordinates CIEx=0.67 and CIEy=0.33. This shows that the inventive compounds EG1-EG13 are suitable for use as matrix material in OLEDs.

(23) Use of Mixtures of the Invention in the Electron Transport Layer of Phosphorescent OLEDs

(24) The materials of the invention can also be used in the electron transport layer in OLEDs. In Examples 114 to 119, the inventive materials EG14 to EG19 are used in the electron transport layer. In examples I14 to I19, the OLED emits light with the colour coordinates CIEx=0.67 and CIEy=0.33. This shows that the inventive compounds EG14 to EG19 are suitable for use as electron transport material in OLEDs.

(25) TABLE-US-00005 TABLE 1 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness I1 HATCN SpMA1 SpMA3 EG1:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I2 HATCN SpMA1 SpMA3 EG2:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I3 HATCN SpMA1 SpMA3 EG3:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I4 HATCN SpMA1 SpMA3 EG4:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I5 HATCN SpMA1 SpMA3 EG5:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I6 HATCN SpMA1 SpMA3 EG6:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I7 HATCN SpMA1 SpMA3 EG7:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I8 HATCN SpMA1 SpMA3 EG8:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I9 HATCN SpMA1 SpMA3 EG9:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I10 HATCN SpMA1 SpMA3 EG10:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I11 HATCN SpMA1 SpMA3 EG11:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I12 HATCN SpMA1 SpMA3 EG12:TER5 ST2:LiQ 5 nm 125 nm 10 nm (95%:5%) (50%:50%) 40 nm 35 nm I13 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG13 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm I14 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG14 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm I15 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG15 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm I16 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG16 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm I17 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG17 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm I18 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG18 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm I19 HATCN SpMA1 SpMA3 EG1:TER5 ST2 ST2:EG19 LiQ 5 nm 125 nm 10 nm (95%:5%) 5 nm (50%:50%) 3 nm 40 nm 30 nm

(26) TABLE-US-00006 TABLE 2 Structural formulae of the materials for the OLEDs HATCN SpMA1 SpMA3 ST2 0 TER5 LiQ EG1 EG2 EG3 EG4 EG5 EG6 EG7 EG8 0 EG9 EG10 EG11 EG12 EG13 EG14 EG15 EG16 EG17 EG18 0 EG19