ORGANIC ELECTROLUMINESCENT APPARATUS

Abstract

The present invention relates to an organic electroluminescent device comprising a mixture comprising an electron-transporting host material and a hole-transporting host material, and to a formulation comprising a mixture of the host materials and to a mixture comprising the host materials. The electron-transporting host material corresponds to a compound of the formula (1) from the class of the fused carbazole derivatives containing an asymmetrically substituted pyrimidine or triazine unit.

Claims

1.-15. (canceled)

16. An organic electroluminescent device comprising an anode, a cathode and at least one organic layer, containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of the formula (1) as host material 1 and at least one compound of the formula (2) as host material 2 ##STR02046## where the symbols and indices used are as follows: X is the same or different at each instance and is CR.sup.0 or N, where at least two symbols X are N; X.sub.2 is the same or different at each instance and is CH, CR.sup.1 or N, where not more than 2 symbols X.sub.2 can be N; Y is the same or different at each instance and is selected from C(R).sub.2 and NR; L is the same or different at each instance and is a single bond or phenylene; R* at each instance is independently D or an aromatic or heteroaromatic ring system that has 6 to 18 ring atoms and may be partly or fully deuterated; R # is the same or different at each instance and is selected from the group consisting of D, F, Cl, Br, I, CN, NO.sub.2, C(═O)R.sup.2, P(═O)(Ar.sub.1).sub.2, P(Ar.sub.1).sub.2, B(Ar.sub.1).sub.2, Si(Ar.sub.1).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 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.2C═CR.sup.2, Si(R.sup.2).sub.2, C═O, C═S, 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 hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system that has 5 to 40 ring atoms and may be substituted in each case by one or more R.sup.2 radicals, an aryloxy or heteroaryloxy group that has 5 to 40 ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group that has 5 to 40 ring atoms and may be substituted by one or more R.sup.2 radicals; R is the same or different at each instance and is selected from a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms; at the same time, two substituents R may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R.sup.2 radicals; R.sup.1 is the same or different at each instance and is selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms; at the same time, it is possible for two substituents R.sup.1 bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R.sup.2 radicals; R.sup.0 and R.sup.2 are the same or different at each instance and are selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sub.1).sub.2, NH.sub.2, N(R.sup.3).sub.2, C(═O)Ar.sub.1, C(═O)H, C(═O)R.sup.3, P(═O)(Ar.sub.1).sub.2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 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 HC═CH, 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, NH, NR.sup.3, O, S, CONH or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system that has 5 to 60 ring atoms and may be substituted in each case by one or more R.sup.3 radicals, an aryloxy or heteroaryloxy group that has 5 to 60 ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems, where optionally two or more adjacent substituents R.sup.2 may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R.sup.3 radicals; 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 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, it is possible for two or more adjacent R.sup.3 substituents together to form a mono- or polycyclic, aliphatic ring system; Ar.sub.1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 ring atoms and may be substituted by one or more nonaromatic R.sup.3 radicals; at the same time, two Ar.sub.1 radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R.sup.3), C(R.sup.3).sub.2, O or S; Ar.sub.2 and Ar.sub.3 are different at each instance; Ar.sub.2 at each instance is a biphenyl, a dibenzofuranyl, a dibenzothiophenyl, a carbazol-N-yl or a carbazol-N-yl-phenyl group that may be substituted by one or more R* radicals; Ar.sub.3 at each instance is an aryl or heteroaryl group that has 5 to 40 ring atoms and may be substituted by one or more R.sup.2 radicals; A at each instance is independently a group of the formula (3) or (4), ##STR02047## Ar at each instance is in each case independently an aryl group which has 6 to 40 ring atoms and may be substituted by one or more R # radicals, or a heteroaryl group which has 5 to 40 ring atoms and may be substituted by one or more R # radicals; * indicates the binding site to the formula (2); a, b, c at each instance are each independently 0 or 1, where the sum total of the indices a+b+c at each instance is 1; e, f at each instance are each independently 0 or 1, where the sum total of the indices e+f at each instance is 1; n and m at each instance are independently 0, 1, 2, 3 or 4; and q, r, s, t at each instance are each independently 0 or 1.

17. The organic electroluminescent device according to claim 16, wherein the symbol Y in host material 1 is C(R).sub.2.

18. The organic electroluminescent device according to claim 16, wherein host material 2 conforms to one of the formulae (2a), (2b) or (2c) ##STR02048## where the symbols and indices A, R.sup.1, q, r and s used are as defined in claim 16.

19. The organic electroluminescent device according to claim 16, wherein, in the host material 1, X is N at three instances.

20. The organic electroluminescent device according to claim 16, wherein it is an electroluminescent device selected from 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).

21. The organic electroluminescent device according to claim 16, wherein it comprises, in addition to the light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL) and/or a hole blocker layer (HBL).

22. The organic electroluminescent device according to claim 16, wherein the light-emitting layer, as well as the at least one host material 1 and the at least one host material 2, contains at least one phosphorescent emitter.

23. The organic electroluminescent device according to claim 22, wherein the phosphorescent emitter conforms to the formula (IIIa) ##STR02049## where the symbols and indices for this formula (IIIa) are defined as follows: n+m is 3, n is 1 or 2, m is 2 or 1, X is N or CR, R is H, D, or a branched or linear alkyl group having 1 to 10 carbon atoms or a partly or fully deuterated branched or linear alkyl group having 1 to 10 carbon atoms or a cycloalkyl group which has 4 to 7 carbon atoms and may be partly or fully substituted by deuterium.

24. A process for producing a device according to claim 16, wherein the light-emitting layer is applied by gas phase deposition or from solution.

25. The process according to claim 24, wherein the at least one compound of the formula (1) and the at least one compound of the formula (2) are deposited from the gas phase successively or simultaneously from at least two material sources, optionally with the at least one phosphorescent emitter, and form the light-emitting layer.

26. The process according to claim 24, wherein the at least one compound of the formula (1) and the at least one compound of the formula (2) are deposited from the gas phase as a mixture, successively or simultaneously with the at least one phosphorescent emitter, and form the light-emitting layer.

27. The process according to claim 24, wherein the at least one compound of the formula (1) and the at least one compound of the formula (2) are applied from a solution together with the at least one phosphorescent emitter in order to form the light-emitting layer.

28. A mixture comprising at least one compound of the formula (1) as host material 1 and at least one compound of the formula (2) as host material 2 ##STR02050## where the symbols and indices used are as follows: X is the same or different at each instance and is CR.sup.0 or N, where at least two symbols X are N; X.sub.2 is the same or different at each instance and is CH, CR.sup.1 or N, where not more than 2 symbols X.sub.2 can be N; Y is the same or different at each instance and is selected from C(R).sub.2 and NR; L is the same or different at each instance and is a single bond or phenylene; R* at each instance is independently D or an aromatic or heteroaromatic ring system that has 6 to 18 ring atoms and may be partly or fully deuterated; R # at each instance is the same or different and is selected from the group consisting of D, F, Cl, Br, I, CN, NO.sub.2, C(═O)R.sup.2, P(═O)(Ar.sub.1).sub.2, P(Ar.sub.1).sub.2, B(Ar.sub.1).sub.2, Si(Ar.sub.1).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 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.2C═CR.sup.2, Si(R.sup.2).sub.2, C═O, C═S, 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 hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system that has 5 to 40 ring atoms and may be substituted in each case by one or more R.sup.2 radicals, an aryloxy or heteroaryloxy group that has 5 to 40 ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group that has 5 to 40 ring atoms and may be substituted by one or more R.sup.2 radicals; R is the same or different at each instance and is selected from a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms; at the same time, two substituents R may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R.sup.2 radicals; R.sup.1 is the same or different at each instance and is selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms; at the same time, it is possible for two substituents R.sup.1 bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R.sup.2 radicals; R.sup.0 and R.sup.2 are the same or different at each instance and are selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sub.1).sub.2, NH.sub.2, N(R.sup.3).sub.2, C(═O)Ar.sub.1, C(═O)H, C(═O)R.sup.3, P(═O)(Ar.sub.1).sub.2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 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 HC═CH, 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, NH, NR.sup.3, O, S, CONH or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system that has 5 to 60 ring atoms and may be substituted in each case by one or more R.sup.3 radicals, an aryloxy or heteroaryloxy group that has 5 to 60 ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems, where optionally two or more adjacent substituents R.sup.2 may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R.sup.3 radicals; 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 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, it is possible for two or more adjacent R.sup.3 substituents together to form a mono- or polycyclic, aliphatic ring system; Ar.sub.1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 ring atoms and may be substituted by one or more nonaromatic R.sup.3 radicals; at the same time, two Ar.sub.1 radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R.sup.3), C(R.sup.3).sub.2, O or S; Ar.sub.2 and Ar.sub.3 are different at each instance; Ar.sub.2 at each instance is a biphenyl, a dibenzofuranyl, a dibenzothiophenyl, a carbazol-N-yl or a carbazol-N-y-1phenyl group that may be substituted by one or more R* radicals; Ar.sub.3 at each instance is an aryl or heteroaryl group that has 5 to 40 ring atoms and may be substituted by one or more R.sup.2 radicals; A at each instance is independently a group of the formula (3) or (4), ##STR02051## Ar at each instance is in each case independently an aryl group which has 6 to 40 ring atoms and may be substituted by one or more R # radicals, or a heteroaryl group which has 5 to 40 ring atoms and may be substituted by one or more R # radicals; * indicates the binding site to the formula (2); a, b, c at each instance are each independently 0 or 1, where the sum total of the indices at each instance a+b+c is 1; e, f at each instance are each independently 0 or 1, where the sum total of the indices e+f at each instance is 1; n and m at each instance are independently 0, 1, 2, 3 or 4; and q, r, s, t at each instance are each independently 0 or 1.

29. The mixture according to claim 28, wherein the mixture consists of at least one compound of the formula (1), at least one compound of the formula (2) and a phosphorescent emitter.

30. A formulation comprising a mixture according to claim 28 and at least one solvent.

Description

EXAMPLE 1: PRODUCTION OF THE OLEDS

[0265] The examples which follow (see tables 8 to 10) present the use of the material combinations of the invention in OLEDs by comparison with material combinations from the prior art.

[0266] Pretreatment for Examples V1 to V15 and E1a to E5i and E6a-E15a:

[0267] Glass plates coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating, first with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plates form the substrates to which the OLEDs are applied.

[0268] 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 8. The materials required for production of the OLEDs, if they have not already been described before, are shown in table 10. The device data of the OLEDs are listed in table 9.

[0269] Examples V1 to V15 are comparative examples. Examples E1a to E5i and E6a-E15a show data for OLEDs of the invention.

[0270] All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer always consists of at least two matrix materials 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 E3:H3:TE2 (32%:60%:8%) mean here that the material E3 is present in the layer in a proportion by volume of 32%, H3 in a proportion of 60% and TE2 in a proportion of 8%. Analogously, the electron transport layer may also consist of a mixture of two materials.

[0271] 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 U10 in table 9 refers to the voltage which is required for a current density of 10 mA/cm.sup.2. EQE10 denotes the external quantum efficiency which is attained at 10 mA/cm.sup.2.

[0272] The lifetime LT is defined as the time after which luminance, measured in cd/m.sup.2 in forward direction, drops from the starting luminance to a certain proportion L1 in the course of operation with constant current density jo. A figure of L1=80% in table 9 means that the lifetime reported in the LT column corresponds to the time after which luminance in cd/m.sup.2 falls to 80% of its starting value.

[0273] Use of Mixtures of the Invention in OLEDs

[0274] The material combinations of the invention are used in examples E1a-k, E2a-k, E3a-k, E4a-k, E5a-i, E6a-E15a as matrix materials in the emission layer of green-phosphorescing OLEDs. As a comparison with the prior art, materials E55, E56, E57, E58, E59 and BCbz1 to BCbz6 are used in comparative examples V1 to V15. The combination of E58 with H9 in a light-emitting layer is disclosed, for example, in KR20180012499.

[0275] On comparison of the inventive examples with the corresponding comparative examples, it is clearly apparent that the inventive examples each show a distinct advantage in device lifetime, with otherwise comparable performance data of the OLEDs.

TABLE-US-00008 TABLE 8 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness V1 SpMA1:PD1 SpMA1 SpMA2 E55:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1a SpMA1:PD1 SpMA1 SpMA2 E3:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1b SpMA1:PD1 SpMA1 SpMA2 E5:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1c SpMA1:PD1 SpMA1 SpMA2 E18:H7:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1d SpMA1:PD1 SpMA1 SpMA2 E42:H5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1e SpMA1:PD1 SpMA1 SpMA2 E48:H13:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1f SpMA1:PD1 SpMA1 SpMA2 E54:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1g SpMA1:PD1 SpMA1 SpMA2 E40:H5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1h SpMA1:PD1 SpMA1 SpMA2 E34:H18:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1i SpMA1:PD1 SpMA1 SpMA2 E32:H18:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1j SpMA1:PD1 SpMA1 SpMA2 E38:H4:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E1k SpMA1:PD1 SpMA1 SpMA2 E35:H6:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V2 SpMA1:PD1 SpMA1 SpMA2 E56:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2a SpMA1:PD1 SpMA1 SpMA2 E29:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2b SpMA1:PD1 SpMA1 SpMA2 E26:H15:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2c SpMA1:PD1 SpMA1 SpMA2 E25:H4:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2d SpMA1:PD1 SpMA1 SpMA2 E23:H20:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2e SpMA1:PD1 SpMA1 SpMA2 E11:H5:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2f SpMA1:PD1 SpMA1 SpMA2 E4O:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2g SpMA1:PD1 SpMA1 SpMA2 E19:H11:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2h SpMA1:PD1 SpMA1 SpMA2 E44:H8:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2i SpMA1:PD1 SpMA1 SpMA2 E4:H5:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2j SpMA1:PD1 SpMA1 SpMA2 E62:H5:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E2k SpMA1:PD1 SpMA1 SpMA2 E66:H20:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V3 SpMA1:PD1 SpMA1 SpMA2 E57:H5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3a SpMA1:PD1 SpMA1 SpMA2 E46:H5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3b SpMA1:PD1 SpMA1 SpMA2 E2:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3c SpMA1:PD1 SpMA1 SpMA2 E43:H1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3d SpMA1:PD1 SpMA1 SpMA2 E36:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3e SpMA1:PD1 SpMA1 SpMA2 E41:H12:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3f SpMA1:PD1 SpMA1 SpMA2 E33:H21:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3g SpMA1:PD1 SpMA1 SpMA2 E8:H11:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3h SpMA1:PD1 SpMA1 SpMA2 E9:H10:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3i SpMA1:PD1 SpMA1 SpMA2 E13:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3j SpMA1:PD1 SpMA1 SpMA2 E16:H5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E3k SpMA1:PD1 SpMA1 SpMA2 E63:H12:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V4 SpMA1:PD1 SpMA1 SpMA2 E58:H9:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4a SpMA1:PD1 SpMA1 SpMA2 E51:H9:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4b SpMA1:PD1 SpMA1 SpMA2 E40:H9:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4c SpMA1:PD1 SpMA1 SpMA2 E15:H10:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4d SpMA1:PD1 SpMA1 SpMA2 E31:H16:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4e SpMA1:PD1 SpMA1 SpMA2 E50:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4f SpMA1:PD1 SpMA1 SpMA2 E24:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4g SpMA1:PD1 SpMA1 SpMA2 E3O:H5:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4h SpMA1:PD1 SpMA1 SpMA2 E37:H4:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4i SpMA1:PD1 SpMA1 SpMA2 E14:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4j SpMA1:PD1 SpMA1 SpMA2 E39:H12:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (30%:58%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4k SpMA1:PD1 SpMA1 SpMA2 E65:H12:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (30%:58%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V5 SpMA1:PD1 SpMA1 SpMA2 E59:H1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5a SpMA1:PD1 SpMA1 SpMA2 E40:H1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5b SpMA1:PD1 SpMA1 SpMA2 E35:H1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5c SpMA1:PD1 SpMA1 SpMA2 E22:H4:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5d SpMA1:PD1 SpMA1 SpMA2 E10:H8:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5e SpMA1:PD1 SpMA1 SpMA2 E38:H11:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5f SpMA1:PD1 SpMA1 SpMA2 E53:H12:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5g SpMA1:PD1 SpMA1 SpMA2 E41:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5h SpMA1:PD1 SpMA1 SpMA2 E40:H3:TE3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5i SpMA1:PD1 SpMA1 SpMA2 E40:H3:TE4 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V6 SpMA1:PD1 SpMA1 SpMA2 E60:BCbz4:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E6a SpMA1:PD1 SpMA1 SpMA2 E60:H4:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V7 SpMA1:PD1 SpMA1 SpMA2 E38:BCbz4:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E7a SpMA1:PD1 SpMA1 SpMA2 E38:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V8 SpMA1:PD1 SpMA1 SpMA2 E39:BCbz1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E8a SpMA1:PD1 SpMA1 SpMA2 E39:H6:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V9 SpMA1:PD1 SpMA1 SpMA2 E52:BCbz2:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E9a SpMA1:PD1 SpMA1 SpMA2 E52:H3:TE1 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V10 SpMA1:PD1 SpMA1 SpMA2 E44:BCbz3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E10a SpMA1:PD1 SpMA1 SpMA2 E44:H8:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (38%:50%:12%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V11 SpMA1:PD1 SpMA1 SpMA2 E61:BCbz5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E11a SpMA1:PD1 SpMA1 SpMA2 E61:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V12 SpMA1:PD1 SpMA1 SpMA2 E61:BCbz6:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E12a SpMA1:PD1 SpMA1 SpMA2 E61:H5:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V13 SpMA1:PD1 SpMA1 SpMA2 E35:BCbz1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E13a SpMA1:PD1 SpMA1 SpMA2 E35:H8:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V14 SpMA1:PD1 SpMA1 SpMA2 E32:BCbz3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E14a SpMA1:PD1 SpMA1 SpMA2 E32:H11:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V15 SpMA1:PD1 SpMA1 SpMA2 E69:BCbz1:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E15a SpMA1:PD1 SpMA1 SpMA2 E69:H3:TE2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:60%:8%) 5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm

TABLE-US-00009 TABLE 9 Data of the OLEDs CIE x/y at U10 EQE10 1000 j.sub.0 L1 LT Ex. (V) (%) cd/m.sup.2 (mA/cm.sup.2) (%) (h) V1 4.5 21.6 0.35/0.63 40 80 390 E1a 4.4 23.2 0.35/0.63 40 80 505 E1b 4.3 23.5 0.35/0.63 40 80 845 E1c 4.7 22.4 0.35/0.63 40 80 590 E1d 4.4 23.6 0.35/0.63 40 80 920 E1e 4.3 23.9 0.35/0.63 40 80 530 E1f 4.3 22.8 0.35/0.63 40 80 705 E1g 4.4 21.4 0.35/0.63 40 80 1080 E1h 4.5 22.1 0.35/0.63 40 80 700 E1i 4.4 22.5 0.35/0.63 40 80 1060 E1j 4.4 23.0 0.35/0.63 40 80 840 E1k 4.3 22.8 0.35/0.63 40 80 960 V2 5.1 18.1 0.34/0.62 40 80 610 E2a 5.1 19.0 0.34/0.62 40 80 815 E2b 5.4 18.6 0.34/0.62 40 80 715 E2c 5.3 19.2 0.33/0.63 40 80 730 E2d 5.1 17.5 0.34/0.62 40 80 790 E2e 5.2 19.1 0.34/0.62 40 80 660 E2f 5.4 19.6 0.34/0.62 40 80 675 E2g 5.3 19.4 0.34/0.62 40 80 840 E2h 5.2 18.7 0.33/0.63 40 80 800 E2i 5.1 18.5 0.33/0.63 40 80 975 E2j 5.5 19.3 0.34/0.62 40 80 690 E2k 5.3 18.1 0.34/0.62 40 80 715 V3 4.4 23.4 0.35/0.62 40 80 410 E3a 4.6 23.0 0.34/0.63 40 80 950 E3b 4.5 23.2 0.35/0.63 40 80 605 E3c 4.7 22.6 0.35/0.63 40 80 590 E3d 4.6 21.6 0.35/0.62 40 80 760 E3e 4.5 23.0 0.34/0.63 40 80 1020 E3f 4.4 22.1 0.35/0.62 40 80 815 E3g 4.6 22.4 0.35/0.62 40 80 840 E3h 4.5 22.8 0.35/0.62 40 80 755 E3i 4.7 22.0 0.34/0.63 40 80 490 E3j 4.4 22.2 0.35/0.63 40 80 780 E3k 4.7 22.8 0.35/0.63 40 80 1035 V4 4.9 18.0 0.34/0.62 40 80 665 E4a 4.8 18.5 0.33/0.63 40 80 960 E4b 4.6 18.1 0.33/0.63 40 80 1760 E4c 4.7 19.3 0.33/0.63 40 80 1330 E4d 4.9 19.5 0.33/0.63 40 80 1540 E4e 4.6 19.3 0.33/0.63 40 80 1150 E4f 4.9 18.7 0.34/0.62 40 80 1030 E4g 4.8 19.0 0.33/0.63 40 80 885 E4h 4.9 19.4 0.34/0.62 40 80 1070 E4i 4.7 18.7 0.34/0.62 40 80 885 E4j 4.8 18.9 0.34/0.62 40 80 1610 E4k 5.0 18.8 0.34/0.63 40 80 1450 V5 4.6 20.7 0.35/0.63 40 80 810 E5a 4.6 20.3 0.34/0.63 40 80 1330 E5b 4.5 21.2 0.34/0.63 40 80 1145 E5c 4.7 20.7 0.35/0.63 40 80 1020 E5d 4.7 20.4 0.35/0.63 40 80 950 E5e 4.7 20.5 0.35/0.63 40 80 1080 E5f 4.7 20.3 0.35/0.63 40 80 1160 E5g 4.5 21.0 0.35/0.63 40 80 1250 E5h 4.9 20.1 0.35/0.63 40 80 1475 E5i 4.8 19.3 0.35/0.63 40 80 960 V6 4.4 22.4 0.34/0.63 40 80 615 E6a 4.5 22.2 0.35/0.63 40 80 680 V7 4.3 23.6 0.35/0.63 40 80 735 E7a 4.4 23.0 0.35/0.63 40 80 870 V8 4.3 23.3 0.35/0.63 40 80 820 E8a 4.4 22.9 0.35/0.63 40 80 910 V9 5.0 18.9 0.34/0.62 40 80 640 E9a 5.0 19.4 0.34/0.62 40 80 910 V10 4.4 20.8 0.35/0.63 40 80 915 E10a 4.6 20.4 0.34/0.63 40 80 1080 V11 4.3 23.7 0.34/0.63 40 80 755 E11a 4.3 23.2 0.34/0.63 40 80 875 V12 4.1 23.6 0.34/0.63 40 80 735 E12a 4.3 23.4 0.34/0.63 40 80 900 V13 4.2 23.5 0.35/0.63 40 80 845 E13a 4.4 23.0 0.35/0.63 40 80 930 V14 4.2 23.6 0.35/0.63 40 80 875 E14a 4.3 22.9 0.35/0.63 40 80 1005 V15 4.1 23.9 0.34/0.63 40 80 960 E15a 4.3 23.8 0.35/0.63 40 80 1115

TABLE-US-00010 TABLE 10 Structural formulae of the materials of the OLEDs used, if not already described before: [01920] PD1 (CAS Reg. No. 1224447-88-4) [01921] SpMA1 [01922] SpMA2 [01923] ST2 [01924] LiQ [01925] TE1 [01926] TE2 [01927] TE3 [01928] TE4 [01929] BCbz1 [01930] BCbz2 [01931] BCbz3 [01932] BCbz4 [01933] BCbz5 [01934] BCbz6 [01935] E55 [01936] E56 [01937] E57 [01938] E58 [01939] E59 [01940] E60.

[0276] E55 and E56 are described in WO2015014435; E57 is described in WO2011088877; E58 is described in KR20180012499; E59 is described in US20100187977; E60 is described in US20170117488.

[0277] 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. The respective figures in square brackets or the numbers quoted for individual compounds relate to the CAS numbers of the compounds known from the literature.

Preparation of the Compounds

[0278] E5 (117):

##STR01941##

[0279] 7,7-Dimethyl-5H-indeno[2,1-b]carbazole [CAS-1257220-47-5] (28.34 g, 100.0 mmol) is initially charged under inert atmosphere in 600 ml of dried DMF. At room temperature, sodium hydride suspension (60% in paraffin oil) (4.19 g, 105.0 mmol) is added gradually, and the mixture is stirred at room temperature for 1 h. Subsequently, 2-chloro-4-dibenzofuran-3-yl-6-phenyl-1,3,5-triazine [2142681-84-1] (37.57 g, 105.0 mmol) is added cautiously, and the reaction mixture is stirred at room temperature overnight. 500 ml of water is added dropwise and the mixture is stirred for a further 1 h, then the solids are filtered off with suction and washed 3× with 250 ml of water and 3× with 250 ml of ethanol. The crude product is subjected to basic hot extraction twice with toluene/heptane (3:1) over aluminium oxide, then recrystallized three times from ethyl acetate and finally sublimed under high vacuum. Yield: 27.4 g (45.3 mmol, 45%); purity: >99.9% by HPLC.

[0280] The following compounds can be prepared analogously: Purification can also be effected using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl pyrrolidone, etc.

TABLE-US-00011 Reactant 1 Reactant 2 Product Yield [01942]   CAS-1024598-06-8 [01943]   CAS-1618107-00-8 [01944]   E2 (63) 46% [01945]   CAS-1024598-06-8 [01946]   CAS- 2226747-65-3 [01947] 41% 1278 [01948]   CAS-1257220-47-5 [01949]   CAS-1472062-94-4 [01950] 55% E39 (766) [01951]   CAS-1257220-47-5 [01952]   CAS-2260688-95-5 [01953] 47% E44 (897) [01954]   CAS-1316311-27-9 [01955]   CAS-2142681-84-1 [01956] 40% E11 (159) [01957]   CAS-1257220-52-2 [01958]   CAS-1472729-25-1 [01959]   E14 (194) 44% [01960]   CAS-1615703-28- [01961]   CAS-1268244-56-9 [01962] 38% E54 (1237) [01963]   CAS-1637752-63- [01964]   CAS-2226747-84-6 [01965]   E23 (316) 36% [01966]   CAS-1257220-47-5 [01967]   CAS-2170887-83-7 [01968] 41% E32 (567) [01969]   CAS-1257220-47-5 [01970]   CAS-1476735-48-4 [01971]   E15 (223) 55% [01972]   CAS-1615703-28- [01973]   CAS-1472062-94-4 [01974] 45% E41 (771) [01975] [01976] [01977] 52% E61

Synthesis of E38

[0281] ##STR01978##

[0282] An initial charge of 7,7-dimethyl-5H-indeno[2,1-b]carbazole [CAS-1257220-47-5] (28.34 g, 100.0 mmol), 2-[1,1′-biphenyl]-4-yl-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine [2085262-87-7] (46.19 g, 110 mmol) and sodium tert-butyloxide (19.22 g, 200 mmol) in toluene (900 ml) is inertized for 30 min. Subsequently, XPhos (3.28 g, 6.88 mmol) and Pd.sub.2(dba).sub.3 (1.26 g, 1.38 mmol) are added successively and the reaction mixture is heated under reflux for 16 h. The mixture is worked up by extraction with toluene/water, the combined organic phases are dried over Na.sub.2SO.sub.4, and the filtrate is concentrated to dryness. The residue is suspended in ethanol (700 ml) and boiled under reflux for 2 h. The solids are filtered off with suction and washed with ethanol. The crude product is subjected to hot extraction three times with toluene/heptane (1:2), then recrystallized twice from ethyl acetate and finally sublimed under high vacuum. Yield: 34.6 g (51.9 mmol, 52%); purity: >99.9% by HPLC.

[0283] The following compounds can be prepared analogously: The catalyst system used here (palladium source and ligand) may also be Pd.sub.2(dba).sub.3 with SPhos [657408-07-6] or Pd(OAc).sub.2 with S-Phos or Pd.sub.2(dba).sub.3 with PtBu.sub.3 or Pd(OAc).sub.2 with P.sup.tBu.sub.3 (tBu means tert-butyl). Purification can also be effected using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

TABLE-US-00012 Reactant 1 Reactant 2 Product Yield [01979]   CAS-1024598-06-8 [01980]   CAS-1472062-94-4 [01981] 28% E40 (767) [01982]   CAS-1615703-28-0 [01983]   CAS-2286234-09-9 [01984] 45% E48 (1070) [01985]   CAS-1448296-00-1 [01986]   CAS-2102445-23-6 [01987] 56% E43 (837) [01988]   CAS-1257220-47 [01989] [01990] 24% E3 (111) [01991]   CAS-1346571-68-3 [01992]   CAS-2172889-30-2 [01993] 52% E9 (149) [01994]   CAS-1257220-47 [01995]   CAS-2260689-00-5 [01996] 58% E51 (1228) [01997]   CAS-1615703-28-0 [01998]   CAS-2260689-12-9 [01999]   E34 (619) 50% [02000]   CAS-1615703-28-0 [02001] [02002] 36% E63 (1294) [02003]   CAS-1346571-68-3 [02004] [02005] 48% E66 (1317)

##STR02006##

[0284] To an initial charge of 9-[1,1′-biphenyl]-3-yl-3-bromo-9H-carbazole (59.88 g, 150.3 mmol) [CAS-1428551-28-3], 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (51.1 g, 147.3 mmol) [CAS-1454807-26-1] in toluene (1200 ml), 1,4-dioxane (1200 ml) and water (600 ml) under inert atmosphere are added K.sub.3PO.sub.4 (95.7 g, 451 mmol), tri(ortho-tolyl)phosphine (2.33 g, 7.52 mmol) and Pd(OAc).sub.2 (840 mg, 3.76 mmol), and the mixture is stirred under reflux for 32 h. After cooling, the mixture is worked up by extraction with toluene/water, the aqueous phase is extracted three times with toluene (500 ml each time), and the combined organic phases are dried over Na.sub.2SO.sub.4. The crude product is first extracted by stirring in EtOH (1500 ml). The solids filtered off with suction are subjected to extraction with hot heptane/toluene twice, recrystallized from DMAc twice and finally sublimed under high vacuum.

[0285] Yield: 40.5 g (72.5 mmol, 48%); purity: >99.9% by HPLC.

[0286] The following compounds can be prepared analogously. The catalyst system used here (palladium source and ligand) may also be Pd.sub.2(dba).sub.3 with SPhos [657408-07-6], or tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Purification can also be accomplished using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

TABLE-US-00013 Reactant 1 Reactant 2 Product Yield [02007] [02008] [02009] 47% [02010] [02011] [02012] 59% [02013] [02014] [02015] 64% [02016] [02017] [02018] 55% [02019] [02020] [02021] 50% [02022] [02023] [02024] 51% [02025] [02026] [02027] 58% [02028] [02029] [02030] 62% [02031] [02032] [02033] 38% [02034] [02035] [02036] 46% [02037] [02038] [02039] 40% [02040] [02041] [02042] 52% [02043] [02044] [02045] 41%