# US 2019/0378989 A1 · High-molecular-weight compound having substituted triarylamine skeleton

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- Number: US 2019/0378989 A1
- Document ID: US20190378989A1
- Status: Published application
- Kind: A1
- Application number: 16/487,554
- Filed: 2018-03-09
- Published: 2019-12-12
- Earliest claimed: 2017-03-15
- Assignees: Hodogaya Chemical Co., Ltd.
- Applicants: Hodogaya Chemical Co., Ltd.
- Inventors: Kazunori TOGASHI; Hideyoshi KITAHARA; Junichi IZUMIDA; Mari KANEKO
- Web page: https://patentgrep.com/patent/US20190378989A1

## CPC

- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G 61/121: {derived from organic halides}
- C09K 11/06: containing organic luminescent materials
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/151: {Copolymers}
- C08G 2261/124: alternating
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/148: Side-chains having aromatic units
- C08G 2261/1646: comprising aromatic or heteroaromatic end groups
- C08G 2261/18: conjugated
- C08G 2261/228: Polymers, i.e. more than 10 repeat units
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3162: Arylamines
- C08G 2261/3325: derived from other polycyclic systems
- C08G 2261/512: Hole transport
- C08G 2261/95: Use in organic luminescent diodes
- C09K 2211/1416: Condensed systems
- C09K 2211/1425: Non-condensed systems
- C09K 2211/1433: bridged by heteroatoms, e.g. N, P, Si or B
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/181: {Electron blocking layers}
- H10K 2101/10: Triplet emission
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A high molecular weight compound according to the present invention includes a substituted triarylamine structural unit represented by a general formula (1) below, where Ar1 and Ar2 are a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, R1 and R2 represent a hydrogen atom, a heavy hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkyloxy group, or a cycloalkyloxy group, X, Y and Z are, on the condition that at least one of them is an aryl group or a heteroaryl group, an aryl group, a heteroaryl group, or a group similar to the groups represented by R1 and R2 above.

## Claims

### Claim 1

A high molecular weight compound comprising a substituted triarylamine structural unit represented by a general formula (1) below,
where Ar1 and Ar2 are each a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group,
R1 and R2 each represent a hydrogen atom, a heavy hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group with 1 to 8 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkyloxy group with 1 to 6 carbon atoms, or a cycloalkyloxy group with 5 to 10 carbon atoms, and
X, Y and Z are, on the condition that at least one of them is an aryl group or a heteroaryl group, an aryl group, a heteroaryl group, or a group similar to the groups represented by R1 and R2 above.

### Claim 2 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein the high molecular weight compound is a polymer comprising the structural unit above-mentioned as a repeating unit, and has a weight average molecular weight of 10,000 or more and less than 1,000,000 on a polystyrene conversion basis.

### Claim 3 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein, in the general formula (1) above, X and Y are an aryl group or a heteroaryl group.

### Claim 4 (depends on 3)

The high molecular weight compound as set forth in claim 3, wherein the aryl group and the heteroaryl group have no substituent group.

### Claim 5 (depends on 4)

The high molecular weight compound as set forth in claim 4, wherein, in the general formula (1) above, X and Y are a phenyl group, a biphenylyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a naphthyl phenyl group, or a triphenylenyl group.

### Claim 6 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein, in the general formula (1) above, R1, R2 and Z are a hydrogen atom or a heavy hydrogen atom.

### Claim 7 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein, in the general formula (1) above, X and Z are an aryl group or a heteroaryl group.

### Claim 8 (depends on 7)

The high molecular weight compound as set forth in claim 7, wherein the aryl group and the heteroaryl group have no substituent group.

### Claim 9 (depends on 8)

The high molecular weight compound as set forth in claim 8, wherein, in the general formula (1) above, X and Z are a phenyl group, a biphenylyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a naphthyl phenyl group, or a triphenylenyl group.

### Claim 10 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein, in the general formula (1) above, R1, R2 and Y are a hydrogen atom or a heavy hydrogen atom.

### Claim 11 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein, in the general formula (1) above, all of X, Y and Z are an aryl group or a heteroaryl group.

### Claim 12 (depends on 11)

The high molecular weight compound as set forth in claim 11, wherein the aryl group or the heteroaryl group has no substituent group.

### Claim 13 (depends on 12)

The high molecular weight compound as set forth in claim 12, wherein, in the general formula (1) above, all of X, Y and Z are a phenyl group, a biphenylyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a naphthyl phenyl group, or a triphenylenyl group.

### Claim 14 (depends on 1)

The high molecular weight compound as set forth in claim 1, wherein, in the general formula (1) above, R1 and R2 are a hydrogen atom or a heavy hydrogen atom.

### Claim 15 (depends on 1)

The high molecular weight compound as set forth in claim 1, comprising a structural unit that has a group having at least one aromatic hydrocarbon ring, or a structural unit that has a triarylamine skeleton, in addition to the unit represented by the general formula (1) above.

### Claim 16 (depends on 1)

An organic electroluminescent element comprising:
a pair of electrodes; and
at least one organic layer interposed between the pair of electrodes,
wherein the organic layer contains the high molecular weight compound as set forth in claim 1.

### Claim 17 (depends on 16)

The organic electroluminescent element as set forth in claim 16, wherein the organic layer is a hole transport layer.

### Claim 18 (depends on 16)

The organic electroluminescent element as set forth in claim 16, wherein the organic layer is an electron blocking layer.

### Claim 19 (depends on 16)

The organic electroluminescent element as set forth in claim 16, wherein the organic layer is a hole injection layer.

### Claim 20 (depends on 16)

The organic electroluminescent element as set forth in claim 16, wherein the organic layer is a light emitting layer.