BISBENZOFURAN-FUSED 2,8-DIAMINOINDENO[1,2-B]FLUORENE DERIVATIVES AND RELATED COMPOUNDS AS MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES (OLED)

• US 20190315764A1
• Filed: 11/21/2017
• Published: 10/17/2019
• Est. Priority Date: 11/25/2016
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Linge, Rouven, Rodriguez, Lara-Isabel, Meyer, Sebastian, Heil, Holger
• Granted Patent: US 11,584,753 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 15/20 Polycyclic condensed hydrocarbons
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 2603/44 Naphthacenes; Hydrogenated naphthacenes
• CPC Class Codes: C07C 2603/54 containing more than five condensed rings
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C07D 493/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07F 7/0816 said ring comprising Si as a ring atom
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention relates to bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds of formula (1) as materials for organic electroluminescent devices (OLEDs).

Claims

1-14. -14. (canceled)

15. A compound of formula (1):

16. The compound of claim 15, wherein the compound is selected from the group consisting of compounds of formulae (1-1) through (1-6):

17. The compound of claim 15, wherein X is selected from O or S.

18. The compound of claim 15, wherein E is selected from —

C(R⁰)₂—

or —

Si(R⁰)₂—

.

19. The compound of claim 15, wherein the compound is selected from the group consisting of compounds of formulae (1-la) through (1-6b):

20. The compound of claim 15, wherein the groups Ar¹ and Ar² are selected, identically or differently, on each occurrence from the group consisting of benzene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, fluorene, benzofluorene, spirobifluorene, cis-indenofluorene, trans-indenofluorene, cis-benzindenofluorene, trans-benzindenofluorene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, indole, carbazole, indolocarbazole, and indenocarbazole, which in each case is optionally substituted by one or more radicals R²;

and wherein Ar¹ and Ar² are also optionally connected to one another via a group E⁰.

21. The compound of claim 15, wherein the groups Ar¹ and Ar² are selected, identically or differently, on each occurrence from the group consisting of benzene, naphthalene, biphenyl, fluorene, dibenzofuran, dibenzothiophene, and carbazole, which in each case is optionally substituted by one or more radicals R²;

and wherein Ar¹ and Ar² are also optionally connected to one another via a group E⁰.

22. The compound of claim 15, wherein when R⁰ is on each occurrence, identically or differently, H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R², wherein in each case one or more H atoms are optionally replaced by F, or an aryl or heteroaryl group having 5 to 25 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R², and wherein two adjacent substituents R⁰ optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R².

23. The compound of claim 15, wherein R⁰ is on each occurrence, identically or differently, H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R², and wherein in each case one or more H atoms is optionally replaced by F.

24. An oligomer, polymer, or dendrimer comprising one or more compounds of claim 15, wherein the bond(s) to the polymer, oligomer, or dendrimer are located at any desired position in formula (1) substituted by R or R¹.

25. A formulation comprising at least one compound of claim 15 and at least one solvent.

26. A formulation comprising at least one oligomer, polymer, or dendrimer of claim 24 and at least one solvent.

27. An electronic device comprising at least one compound of claim 15, 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, dye-sensitised organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, and organic plasmon emitting devices.

28. An electronic device comprising at least one oligomer, polymer, or dendrimer of claim 24, 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, dye-sensitised organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, and organic plasmon emitting devices.

29. The electronic device of claim 27, wherein the electronic device is an organic electroluminescent device and the at least one compound is employed as a fluorescent emitter or as a matrix material for fluorescent emitters or as a hole-transport material.

30. The electronic device of claim 28, wherein the electronic device is an organic electroluminescent device and the at least one oligomer, polymer, or dendrimer is employed as a fluorescent emitter or as a matrix material for fluorescent emitters or as a hole-transport material.