# US 2019/0375757 A1 · Bisbenzofuran-fused indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled)

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- Number: US 2019/0375757 A1
- Document ID: US20190375757A1
- Status: Published application
- Kind: A1
- Application number: 16/463,507
- Filed: 2017-11-22
- Published: 2019-12-12
- 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/US20190375757A1

## CPC

- C07D 493/04: Ortho-condensed systems
- 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 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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 indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLEDs).

## Claims

### Claim at position 1

1-15. (canceled)

### Claim 16

A compound of formula (1):
wherein
Z is on each occurrence, identically or differently, CR or N; or Z is C when Z 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 V is bonded to a group Z or to a group E; and wherein at least two adjacent groups V, in each 6-membered ring comprising groups V in formula (1), define a group of formula (V-1):
where the dashes indicate 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 and R0
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 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R2;
R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, 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 R1 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R2;
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 define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally 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 17 (depends on 16)

The compound of claim 16, wherein the compound is selected from the group consisting of compounds of formulae (1-1) through (1-18):

### Claim 18 (depends on 16)

The compound of claim 16, wherein X is O or S.

### Claim 19 (depends on 16)

The compound of claim 16, wherein E is —C(R0)2— or —Si(R0)2—.

### Claim 20 (depends on 16)

The compound of claim 16, wherein within formula (1), at least one group V in each 6-membered ring comprising groups V is a group CR1, wherein R1 is 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.

### Claim 21 (depends on 16)

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

### Claim 22 (depends on 16)

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

### Claim 23 (depends on 16)

The compound of claim 16, wherein when R1 is an aromatic or heteroaromatic ring system, then R1 is selected on each occurrence, identically or differently, from the group consisting of formula (R1-1):
wherein the dashes denotes the bond to the structure of formula (1);
Ar3 and Ar4
are selected on each occurrence, identically or differently, 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, indenocarbazole, pyridine, quinoline, pyrazole, indazole, imidazole, benzimidazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, pyrazine, quinoxaline, 1,3,5-triazine, 1,2,4-triazine, and 1,2,3-triazine, which in each case are optionally substituted by one or more radicals R2; and
n is an integer from 0 to 20.

### Claim 24 (depends on 23)

The compound of claim 23, wherein Ar3 and Ar4 are on each occurrence, identically or differently, selected 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.

### Claim 25 (depends on 16)

The compound of claim 16, 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, 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 26 (depends on 16)

The compound of claim 16, wherein R0 is on each occurrence, identically or differently, for 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 was optionally substituted by one or more radicals R2, and wherein in each case one or more H atoms is optionally replaced by F.

### Claim 27 (depends on 16)

An oligomer, polymer, or dendrimer comprising one or more compounds of claim 16, 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 28 (depends on 16)

A formulation comprising at least one compound of claim 16 and at least one solvent.

### Claim 29 (depends on 27)

A formulation comprising at least one oligomer, polymer, or dendrimer of claim 27 and at least one solvent.

### Claim 30 (depends on 16)

An electronic device comprising at least one compound of claim 16, 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 31 (depends on 27)

An electronic device comprising at least one oligomer, polymer, or dendrimer of claim 27, 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 32 (depends on 30)

The electronic device of claim 30, 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.

### Claim 33 (depends on 31)

The electronic device of claim 31, 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.