# US 2019/0315764 A1 · Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled)

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- Number: US 2019/0315764 A1
- Document ID: US20190315764A1
- Status: Published application
- Kind: A1
- Application number: 16/463,448
- Filed: 2017-11-21
- Published: 2019-10-17
- Earliest claimed: 2016-11-25
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Rouven Linge; Lara-Isabel Rodriguez; Sebastian Meyer; Holger Heil
- Web page: https://patentgrep.com/patent/US20190315764A1

## CPC

- C07D 493/04: Ortho-condensed systems
- C07C 15/20: Polycyclic condensed hydrocarbons
- C07C 211/54: having amino groups bound to two or three six-membered aromatic rings
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 493/22: in which the condensed system contains four or more hetero rings
- C07F 7/0816: {said ring comprising Si as a ring atom}
- C09K 11/06: containing organic luminescent materials
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C07C 2603/44: Naphthacenes; Hydrogenated naphthacenes
- C07C 2603/54: containing more than five condensed rings
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## 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

### Claim at position 1

1-14. (canceled)

### Claim 15

A compound of formula (1):
wherein
Z is on each occurrence, identically or differently, CR or N; or Z is C when it is bonded to a group V or to a group E;
V is on each occurrence, identically or differently, CR1 or N; or V is C when it is bonded to a group Z, to a group E, or to a group —NAr1Ar2; and wherein two adjacent groups V, in each 6-membered ring comprising groups V in formula (1), define a group of formula (V-1):
wherein the dashes denote the bonds to the structure of formula (1);
E is on each occurrence, identically or differently, selected from the group consisting of —BR0—, —C(R0)2—, —C(R0)2—C(R0)2—, —C(R0)2—O—, —C(R0)2—S—, —R0C═CR0—, —R0C═N—, —Si(R0)2 , —Si(R0)2—Si(R0)2—, Ge(R0)2, —C(═O)—, —C(═NR0)—, ˜C(═C(R0)2)—, —O—, —S—, —Se—, —S(═O)—, —SO2—, —N(R0)—, —P(R0)—, and —P((═O)R0)—; and wherein two groups E are optionally in a cis- or trans-position relative to each other;
X is on each occurrence, identically or differently, selected from the group consisting of —O—, —S—, —S(═O)—, —SO2—, —N(R0)—, —BR0—, Si(R0)2, —P(R0)—, and —P((═O)R0)—;
W is on each occurrence, identically or differently, CR or N;
R, R0, and R1
are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, NO2, Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, wherein in each case one or more non-adjacent CH2 groups are optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, P(═O)(R2), SO, SO2, O, S, or CONR2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R2, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, and wherein two adjacent substituents R and/or two adjacent substituents R0 and/or two adjacent substituents R1 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R2;
Ar1 and Ar2
are on each occurrence, identically or differently, selected from the group consisting of aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, 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 by a group E0 and define a group of formula (E0-1):
wherein the dashes indicate the bond to the structure of formula (1);
E0 is on each occurrence, identically or differently, a single bond, N(R0), O, S, C(R0)2, C(R0)2—C(R0)2, C(R0)═C(R0), Si(R0)2, or B(R0);
R2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, NO2, Si(R3)3, B(OR3)2, OSO2R3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R3, wherein in each case one or more non-adjacent CH2 groups are optionally replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, P(═O)(R3), SO, SO2, O, S, or CONR3 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R3, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, and wherein two adjacent substituents R2 optionally a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R3;
R3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, wherein in each case one or more non-adjacent CH2 groups are optionally replaced by SO, SO2, O, S and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms; and
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R3.

### Claim 16 (depends on 15)

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

### Claim 17 (depends on 15)

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

### Claim 18 (depends on 15)

The compound of claim 15, wherein E is selected from —C(R0)2— or —Si(R0)2—.

### Claim 19 (depends on 15)

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

### Claim 20 (depends on 15)

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.

### Claim 21 (depends on 15)

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.

### Claim 22 (depends on 15)

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.

### Claim 23 (depends on 15)

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.

### Claim 24 (depends on 15)

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.

### Claim 25 (depends on 15)

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

### Claim 26 (depends on 24)

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

### Claim 27 (depends on 15)

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.

### Claim 28 (depends on 24)

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.

### Claim 29 (depends on 27)

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.

### Claim 30 (depends on 28)

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.