# US 9,006,503 B2 · Organic electroluminescence devices containing substituted benzo[C]phenanthrenes

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- Number: US 9,006,503 B2
- Document ID: US9006503B2
- Status: Granted
- Kind: B2
- Application number: 14/146,106
- Filed: 2014-01-02
- Published: 2014-04-24
- Granted: 2015-04-14
- Earliest claimed: 2009-01-23
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Amir Hossain Parham; Arne Buesing; Holger Heil; Philipp Stoessel
- Web page: https://patentgrep.com/patent/US9006503B2

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C09B 1/00: Dyes with anthracene nucleus not condensed with any other ring
- C09B 3/02: Benzathrones
- C09B 3/78: Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 57/008: {Triarylamine dyes containing no other chromophores}
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1416: Condensed systems
- C09K 2211/1433: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1466: containing nitrogen as the only heteroatom
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to substituted benzo[c]phenanthrene derivatives and to the production and to the use thereof in electronic devices, and to the electronic devices themselves. The present invention relates in particular an electronic device containing 10-benzo[c]phenanthrene derivatives of, e.g., formula (II) substituted with at least one aromatic unit or at least one diarylamino unit.

## Claims

### Claim 1

An electronic device comprising at least one compound of formula (II):
wherein
R2 is selected from the group consisting of Ar and N(Ar)2;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R13, where, in the case where two Ar are bonded to the same N or P atom, the two Ar may be linked to one another by a single covalent bond or a divalent group selected from the group consisting of BR13, C(R13)2, Si(R13)2, C═O, C═NR13, C═C(R13)2, O, S, S═O, SO2, NR13, PR13 and P(═O)R13;
with the proviso that Ar, if it is bonded directly to the aromatic skeleton of the formula (II), is different from triarylamine;
R1 and R12 are H;
R13 is identical or different on each occurrence and is selected from the group consisting of H, D, F, Cl, Br, I, CHO, N(R14)2, CN, NO2, Si(R14)3, B(OR14)2, OSO2R14, straight-chain alkyl, alkenyl, alkoxy and thioalkoxy groups having 1 to 40 C atoms and branched, monocyclic or polycyclic alkyl, alkenyl, alkoxy and thioalkoxy groups having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R14, where one or more non-adjacent CH2 groups are optionally replaced by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14 and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, and aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R14, and aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms which are optionally substituted by one or more radicals R14, and a combination of these systems, where two or more adjacent substituents R13 optionally define a monocyclic or polycyclic, aliphatic or aromatic ring system with one another;
R14 is identical or different on each occurrence and is selected from the group consisting of H and an aliphatic hydrocarbon radical having 1 to 20 carbon atoms, where one or more H atoms of the aliphatic hydrocarbon radical are optionally replaced by F; where, in the case where two or more substituents R14 are adjacent, these optionally define a monocyclic or polycyclic aliphatic ring system;
with the proviso that the following compounds are excluded:

### Claim 2 (depends on 1)

The electronic device of claim 1, wherein said electronic device is selected from the group consisting of organic electroluminescent devices, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic integrated circuits, organic solar cells, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, and organic photoreceptors.

### Claim 3 (depends on 2)

The electronic device of claim 2, wherein the at least one compound of formula (II) is comprised in a hole transport layer, in a hole injection layer, in an electron transport layer, or in an emitting layer.

### Claim 4 (depends on 1)

The electronic device of claim 1, wherein in formula (II), Ar is on each occurrence, identically or differently, one or more unit(s) selected from the group consisting of naphthyl, anthracene, phenanthrene, 1,3,5-triazine, benzimidazole, phenothiazine, fluorene, carbazole, spirobifluorene, and combinations thereof, which is optionally substituted by one or more radicals R13; and wherein, in the case where two Ar are bonded to the same N atom, the two Ar are optionally linked to one another by a single covalent bond or a divalent group selected from the group consisting of C(R13)2, C═O, O, S, NR13 and PR13.

### Claim 5 (depends on 1)

The electronic device of claim 1, wherein in formula (II), the group Ar is selected from the groups of the formula (VII), formula (IX), formula (XI), or formula (XII),
wherein the dashed bond denotes the link to the benzo[c]phenanthrene unit;
Ar1 is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, optionally substituted by one or more radicals R14;
Ar2 is an aryl or heteroaryl group having 5 to 20 aromatic ring atoms which are optionally substituted by one or more radicals R14; and
q is 1.

### Claim 6 (depends on 1)

The electronic device of claim 1, wherein in formula (II), R13, identically or differently on each occurrence, is selected from the group consisting of H, a straight-chain alkyl or alkenyl group having 1 to 9 carbon atoms, a C6-10-aryl group, and a 5- to 14-membered heteroaryl group, where one or more H atoms of the straight-chain alkyl or alkenyl group are optionally replaced by F.

### Claim 7

An electronic device comprising at least one compound of formula (I)
wherein
R1, R2, R3, R4, R6, R7, R8, R9, R10, R11 and R12 are H; and
R5 is 10-phenylanthracen-9-yl.