ORGANIC MOLECULES FOR USE IN ORGANIC OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic molecule, in particular for use in organic optoelectronic devices. According to the invention, the organic molecule consists of a first chemical moiety with a structure of formula I,

##STR00001##

and two second chemical moieties, each at each occurrence independently from another, with a structure of formula II,

##STR00002##

wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond;
wherein
T, V is independently from another the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is hydrogen;
W, X, Y is independently from another the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF.sub.3;
wherein exactly one substituent selected of the group consisting of W, X, and Y is CN or CF.sub.3, and exactly two substituents selected of the group consisting of T, V, W, X and Y represent the binding sites connecting of a single bond linking the first chemical moiety to one of the two second chemical moieties.

Claims

1. An organic molecule, comprising a first chemical moiety comprising a structure of Formula I: ##STR00258## and two second chemical moieties, each independently from another comprising a structure of Formula II: ##STR00259## wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond; wherein T is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is hydrogen; V is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is hydrogen; W is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF.sub.3; X is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF.sub.3; Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of hydrogen, CN and CF.sub.3; # represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties; Z is at each occurrence independently from another selected from the group consisting of a direct bond, CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2; R.sup.1,R.sup.2 is independently form each other at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; and R.sup.a, R.sup.3 and R.sup.4 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R.sup.5).sub.2, OR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5; R.sup.5 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R.sup.6).sub.2, OR.sup.6, Si(R.sup.6).sub.3, B(OR.sup.6).sub.2, OSO.sub.2R.sup.6, CF.sub.3, CN, F, Br, I, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF.sub.3, CN, F, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-thioalkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-alkynyl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl).sub.2, and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); wherein the substituents R.sup.a, R.sup.3, R.sup.4 or R.sup.5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents Re, R.sup.3, R.sup.4 or R.sup.5; wherein exactly one substituent selected from the group consisting of W, X, and Y is CN or CF.sub.3, and exactly two substituents selected from the group consisting of T, V, W, X and Y represent the binding sites of a single bond linking the first chemical moiety and one of the two second chemical moieties.

2. The organic molecule according to claim 1, wherein R.sup.1 and R.sup.2 are independently from each other at each occurrence selected from the group consisting of H, methyl and phenyl.

3. The organic molecule according to claim 1, wherein W is CN.

4. The organic molecule according to claim 1, wherein the two second chemical moieties, each at each occurrence independently from another comprise a structure of Formula IIa: ##STR00260##

5. The organic molecule according to claim 1, wherein the two second chemical moieties, each at each occurrence independently from another comprise a structure of Formula IIb: ##STR00261## wherein R.sup.b is at each occurrence independently from another selected from the group consisting of deuterium, N(R.sup.5).sub.2, OR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5), CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CS, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

6. The organic molecule according to claim 1, wherein the two second chemical moieties, each at each occurrence independently from another comprise a structure of formula IIc: ##STR00262## wherein R.sup.b is at each occurrence independently from another selected from the group consisting of deuterium, N(R.sup.5).sub.2, OR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.4O-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

7. The organic molecule according to claim 5, wherein R.sup.b is at each occurrence independently from another selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; and N(Ph).sub.2.

8.-14. (canceled)

15. A composition comprising: (a) at least one organic molecule according to claim 1 as an emitter and/or host; (b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 1, and (c) optionally one or more dyes and/or one or more solvents.

16. An optoelectronic device comprising the organic molecule according to claim 1, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

17. The optoelectronic device according to claim 16, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is applied to the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

18. An optoelectronic device comprising the organic molecule according to claim 1, wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

19. The optoelectronic device according to claim 18, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

20. An optoelectronic device comprising the organic molecule according to claim 2, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

21. An optoelectronic device comprising the organic molecule according to claim 2, wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

22. The optoelectronic device according to claim 21, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

23. An optoelectronic device comprising the composition according to claim 15, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

24. The optoelectronic device according to claim 23, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is applied to the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.

25. A process for producing an optoelectronic device, comprising processing of the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

26. A process for producing an optoelectronic device, comprising processing of the composition according to claim 15 by a vacuum evaporation method or from a solution.

27. A process for preparing an organic molecule according to claim 1, comprising reacting a 2,4-R.sup.1-6-R.sup.2-substituted 3-bromo/chloro-5-cyanobenzotrifluoride with a difluoro-substituted, cyano/(trifluoromethyl)-phenylboronic acid ester or a difluoro-substituted, cyano/(trifluoromethyl)-phenylboronic acid.

Description

EXAMPLES

[0418] ##STR00069##

[0419] General Procedure for Synthesis AAV1:

##STR00070##

[0420] 3-bromo/chloro-5-cyanobenzotrifluoride E2 (1.00 equivalents), 4-cyano/(trifluoromethyl)-3,5-difluoro-boronic acid pinacol ester (1.10 equivalents), Pd.sub.2(dba).sub.3 (0.01 equivalent), 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (SPhos) (0.04 equivalents) and tribasic potassium phosphate (2.50 equivalents) are stirred under nitrogen atmosphere in a toluene/water mixture (ratio of 10:1, 2 mL toluene/mmol aryl bromide) at 110 C. until completion (usually 2-4 hours). Subsequently the reaction mixture is filtrated and the residue is washed with dichloromethane. The filtrate is dried over MgSO.sub.4, filtrated and concentrated in vacuo. The crude product obtained is purified by recrystallisation from an appropriate solvent (ethanol, toluene, n-hexane) or by flash chromatography. The product is obtained as solid.

[0421] Instead of a boronic acid ester a corresponding boronic acid may be used.

[0422] General Procedure for Synthesis AAV2:

##STR00071##

[0423] The synthesis of Z2 is carried out according to AAV1, wherein 3-bromo-5-cyanobenzotrifluoride E2 reacts with 3-cyano/(trifluoromethyl)-2,4-difluoro-boronic acid pinacol ester.

[0424] General Procedure for Synthesis AAV3:

##STR00072##

[0425] The synthesis of Z3 is carried out according to AAV1, wherein 3-bromo-5-cyanobenzotrifluoride E2 reacts with 4-cyano/(trifluoromethyl)-2,6-difluoro-boronic acid pinacol ester.

[0426] General Procedure for Synthesis AAV4:

##STR00073##

[0427] The synthesis of Z4 is carried out according to AAV1, wherein 3-bromo-5-cyanobenzotrifluoride E2 reacts with 4-cyano/(trifluoromethyl)-2,5-difluoro-boronic acid pinacol ester.

[0428] General Procedure for Synthesis AAV5:

##STR00074##

[0429] The synthesis of Z5 is carried out according to AAV1, wherein 3-bromo-5-cyanobenzotrifluoride E2 reacts with 2-cyano/(trifluoromethyl)-4,5-difluoro-boronic acid pinacol ester.

[0430] General Procedure for Synthesis AAV6:

##STR00075##

[0431] The synthesis of Z6 is carried out according to AAV1, wherein 3-bromo-5-cyanobenzotrifluoride E2 reacts with 3-cyano/(trifluoromethyl)-4,5-difluoro-boronic acid pinacol ester.

[0432] General Procedure for Synthesis AAV7:

##STR00076## ##STR00077## ##STR00078##

[0433] Z1, Z2, Z3, Z4, Z5 or Z6 (1 equivalent each), the corresponding donor molecule D-H (2.00 equivalents) and tribasic potassium phosphate (4.00 equivalents) are suspended under nitrogen atmosphere in DMSO and stirred at 120 C. until completion (usually 4-16 h). After chilling to rt the reaction mixture is poured into water. The precipitated crude product is filtered off, washed with water and dissolved in dichloromethane. The resulting solution is dried over MgSO.sub.4, filtered and concentrated in vacuo. The crude product is purified by recrystallization from an appropriate solvent (toluene, ethanol, n-hexane) or by flash chromatography. The product is obtained as a solid.

[0434] In particular, the donor molecule D-H is a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-tert-butylcarbazole), or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butycarbazole).

[0435] Exemplarily a halogen-substituted carbazole, particularly 3-bromocarbazole, can be used as D-H.

[0436] In a subsequent reaction a boronic acid ester functional group or boronic acid functional group may be exemplarily introduced at the position of the one or more halogen substituents, which was introduced via D-H, to yield the corresponding carbazol-3-ylboronic acid ester or carbazol-3-ylboronic acid, e.g., via the reaction with bis(pinacolato)diboron (CAS No. 73183-34-3). Subsequently, one or more substituents R.sup.a may be introduced in place of the boronic acid ester group or the boronic acid group via a coupling reaction with the corresponding halogenated reactant R.sup.a-Hal, preferably R.sup.aCl and R.sup.aBr.

[0437] Alternatively, one or more substituents R.sup.a may be introduced at the position of the one or more halogen substituents, which was introduced via D-H, via the reaction with a boronic acid of the substituent R.sup.a [R.sup.aB(OH).sub.2] or a corresponding boronic acid ester.

[0438] HPLC-MS:

[0439] HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL). A reverse phase column 4.6 mm150 mm, particle size 5.0 m from Waters (without pre-column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) with the solvents acetonitrile, water and THF in the following concentrations:

TABLE-US-00001 solvent A: H.sub.2O (90%) MeCN (10%) solvent B: H.sub.2O (10%) MeCN (90%) solvent C: THF (50%) MeCN (50%)

[0440] From a solution with a concentration of 0.5 mg/ml an injection volume of 15 L is taken for the measurements. The following gradient is used:

TABLE-US-00002 Flow rate [ml/min] time [min] A[%] B[%] C[%] 3 0 40 50 10 3 10 15 25 60 3 14 15 25 60 3 14.01 40 50 10 3 18 40 50 10 3 19 40 50 10

[0441] Ionisation of the probe is performed by APCI (atmospheric pressure chemical ionization).

[0442] Cyclic Voltammetry

[0443] Cyclic voltammograms are measured from solutions having concentration of 10.sup.3 mol/l of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/l of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp.sub.2/FeCp.sub.2.sup.+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against SCE.

[0444] Density Functional Theory Calculation

[0445] Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.

[0446] Photophysical Measurements

[0447] Sample pretreatment: Spin-coating

[0448] Apparatus: Spin150, SPS euro.

[0449] The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

[0450] Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 s at 4000 U/min at 1000 Upm/s. After coating, the films are dried at 70 C. for 1 min.

[0451] Photoluminescence spectroscopy and TCSPC (Time-correlated single-photon counting) Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.

[0452] Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[0453] Excitation Sources:

[0454] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

[0455] NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

[0456] SpectraLED 310 (wavelength: 314 nm)

[0457] SpectraLED 355 (wavelength: 355 nm).

[0458] Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

[0459] Photoluminescence Quantum Yield Measurements

[0460] For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.

[0461] Emission maxima are given in nm, quantum yields 0 in % and CIE coordinates as x,y values. PLQY is determined using the following protocol: [0462] 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference [0463] 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength [0464] 3) Measurement [0465] Quantum yields are measured for sample of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

[00001]${}_{P.Math.L}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\right)\right].Math.d.Math..Math.}{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\right)\right].Math.d.Math..Math.}$ [0466] wherein n.sub.photon denotes the photon count and Int. the intensity.

[0467] Production and Characterization of Organic Electroluminescence Devices

[0468] OLED devices comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100%, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100%.

[0469] The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50% of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80% of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95% of the initial luminance etc. Accelerated lifetime measurements are performed (e.g. applying increased current densities). Exemplarily LT80 values at 500 cd/m.sup.2 are determined using the following equation:

[00002]$\mathrm{LT}.Math..Math.80.Math.\left(500.Math.\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}.Math..Math.80.Math.\left(L_0\right).Math.{\left(\frac{L_0}{500.Math.\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$

[0470] wherein L.sub.0 denotes the initial luminance at the applied current density.

[0471] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given. Figures show the data series for one OLED pixel.

Example 1

[0472] ##STR00079##

[0473] Example 1 was synthesized according to AAV1 (64% yield) and AAV7 (75% yield). MS (HPLC-MS), m/z (retention time): 602.41 (7.07 min).

[0474] FIG. 1 depicts the emission spectrum of example 1 (10% by weight in PMMA). The emission maximum is at 465 nm. The photoluminescence quantum yield (PLQY) is 82% and the full width at half maximum is 0.44 eV. The resulting CIE, coordinate is determined at 0.16 and the CIE, coordinate at 0.21.

Example 2

[0475] ##STR00080##

[0476] Example 2 was synthesized according to AAV1 (64% yield) and AAV7 (48% yield). MS (HPLC-MS), m/z (retention time): 754.29 (8.81 min).

[0477] FIG. 2 depicts the emission spectrum of example 2 (10% by weight in PMMA). The emission maximum is at 484 nm. The photoluminescence quantum yield (PLQY) is 79%, the full width at half maximum is 0.45 eV and the emission lifetime is 45.5 s. The resulting CIE, coordinate is determined at 0.21 and the CIE, coordinate at 0.36.

[0478] Device D1

[0479] Example 2 was tested in an OLED-device D1 with the following layer structure:

##STR00081##

TABLE-US-00003 Layer # Thickness 9 100 nm Al 8 2 nm Liq 7 10 nm MAT1 6 20 nm NBPhen 5 50 nm Example 2 (20%):mCBP (80%) 4 10 nm mCBP 3 10 nm TCTA 2 45 nm NPB 1 50 nm ITO Substrate Glass

[0480] For D1 an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 22.6% and a LT80-value at 500 cd/m.sup.2 of 432 h from accelerated lifetime measurements were determined. The emission maximum is at 486 nm and CIEy is 0.38 at 7 V.

[0481] Additional Examples of Organic Molecules of the Invention

##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132##

##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184##

##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221##

##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257##

FIGURES

[0482] FIG. 1 Emission spectrum of example 1 (10% by weight) in PMMA.

[0483] FIG. 2 Emission spectrum of example 2 (10% by weight) in PMMA.