# US 2021/0280786 A1 · Organic electroluminescence device and diamine compound for organic electroluminescence device

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- Number: US 2021/0280786 A1
- Document ID: US20210280786A1
- Status: Published application
- Kind: A1
- Application number: 17/097,647
- Filed: 2020-11-13
- Published: 2021-09-09
- Earliest claimed: 2020-02-20
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., LTD.
- Inventors: XiuLan JIN
- Web page: https://patentgrep.com/patent/US20210280786A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07B 59/00: Introduction of isotopes of elements into organic compounds {; Labelled organic compounds per se}
- C07C 211/58: Naphthylamines; N-substituted derivatives thereof
- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C07C 2603/26: Phenanthrenes; Hydrogenated phenanthrenes
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- 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}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic electroluminescence device is provided, which may include a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region. The hole transport region may include a diamine compound represented by Formula 1, thereby exhibiting high light emission efficiency.

## Claims

### Claim 1

An organic electroluminescence device comprising:
a first electrode;
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region;
an electron transport region disposed on the emission layer; and
a second electrode disposed on the electron transport region,
wherein the hole transport region comprises a diamine compound represented by Formula 1:
wherein in Formula 1,
a1 to a4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a group represented by Formula 2-1,
one of a1 to a4 is a group represented by Formula 2-1,
another one of a1 to a4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms,
a5 to a8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a group represented by Formula 2-2 below,
one of a5 to a8 is a group represented by Formula 2-2, and
another one of a5 to a8 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms:
wherein in Formula 2-1 and Formula 2-2,
L1 and L2 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
m and n are each independently an integer from 0 to 4, and
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and
when a1 is a group represented by Formula 2-1, a5 is a group represented by Formula 2-2, and a7 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then one of a2 to a4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and at least one of Ar1 to Ar4 is a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

### Claim 2 (depends on 1)

The organic electroluminescence device of claim 1, wherein
when one of a1 to a4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms is a group represented by Formula 2-3, and
when one of a5 to a8 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms is a group represented by Formula 2-4:
wherein in Formula 2-3 and Formula 2-4,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or bonded to an adjacent group to form a ring, and
o and p are each independently an integer from 0 to 5.

### Claim 3 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1 is represented by Formula 3-1 or Formula 3-2:
wherein in Formula 3-1 and Formula 3-2,
a6 to a8 are each independently a hydrogen atom or a deuterium atom,
R3 is a hydrogen atom or a deuterium atom,
q is an integer from 0 to 2, and
Ar1 to Ar4, L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 4 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1 is represented by Formula 4:
wherein in Formula 4,
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
at least one of Ar1 to Ar4 is a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
a6 and a8 are each independently a hydrogen atom or a deuterium atom,
R3 is a hydrogen atom or a deuterium atom,
q is an integer from 0 to 2, and
L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 5 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1 is represented by one of Formula 5 to Formula 7:
wherein in Formula 5 to Formula 7,
R3 and R4 are each independently a hydrogen atom or a deuterium atom,
q and r are each independently an integer from 0 to 2, and
Ar1 to Ar4, L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 6 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1 is represented by one of Formula 8 to Formula 11:
wherein in Formula 8 to Formula 11,
R3 and R4 are each independently a hydrogen atom or a deuterium atom,
q and r are each independently an integer from 0 to 2, and
Ar1 to Ar4, L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 7 (depends on 1)

The organic electroluminescence device of claim 1, wherein L1 and L2 are each independently a direct linkage, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

### Claim 8 (depends on 1)

The organic electroluminescence device of claim 1, wherein the hole transport region comprises:
a hole injection layer disposed on the first electrode; and
a hole transport layer disposed on the hole injection layer,
wherein the hole transport layer comprises a diamine compound represented by Formula 1.

### Claim 9 (depends on 5)

The organic electroluminescence device of claim 5, wherein Formula 6 is represented by Formula 6-1 or Formula 6-2:
wherein in Formula 6-1 and Formula 6-2,
Ar1 to Ar4, L1, L2, R1 to R4, and m to r are the same as defined in Formula 6.

### Claim 10 (depends on 6)

The organic electroluminescence device of claim 6, wherein Formula 9 is represented by Formula 9-1:
wherein in Formula 9-1,
Ar1 to Ar4, L1, L2, R1 to R4, and m to r are the same as defined in Formula 9.

### Claim 11 (depends on 6)

The organic electroluminescence device of claim 6, wherein Formula 10 is represented by one of Formula 10-1 to Formula 10-3:
wherein in Formula 10-1 to Formula 10-3,
Ar1 to Ar4, L1, L2, R1 to R4, and m to r are the same as defined in Formula 10.

### Claim 12 (depends on 1)

The organic electroluminescence device of claim 1, wherein the diamine compound represented by Formula 1 is one selected from Compound Group 1:

### Claim 13

A diamine compound represented by Formula 1:
wherein in Formula 1,
a1 to a4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a group represented by Formula 2-1,
one of a1 to a4 is a group represented by Formula 2-1,
another one of a1 to a4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms,
a5 to a8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a group represented by Formula 2-2,
one of a5 to a8 is a group represented by Formula 2-2, and
another one of a5 to a8 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms:
wherein in Formula 2-1 and Formula 2-2,
L1 and L2 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
m and n are each independently an integer from 0 to 4, and
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and
when a1 is a group represented by Formula 2-1, a5 is a group represented by Formula 2-2, and a7 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then one of a2 to a4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and at least one of Ar1 to Ar4 is a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

### Claim 14 (depends on 13)

The diamine compound of claim 13, wherein
when one of a1 to a4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms is a group represented by Formula 2-3, and
when one of a5 to a8 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms is a group represented by Formula 2-4:
wherein in Formula 2-3 and Formula 2-4,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or bonded to an adjacent group to form a ring, and
o and p are each independently an integer from 0 to 5.

### Claim 15 (depends on 14)

The diamine compound of claim 14, wherein Formula 1 is represented by Formula 3-1 or Formula 3-2:
wherein in Formula 3-1 and Formula 3-2,
a6 to a8 are each independently a hydrogen atom or a deuterium atom,
R3 is a hydrogen atom or a deuterium atom,
q is an integer from 0 to 2, and
Ar1 to Ar4, L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 16 (depends on 14)

The diamine compound of claim 14, wherein Formula 1 is represented by Formula 4:
wherein in Formula 4,
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
at least one of Ar1 to Ar4 is a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
a6 and a8 are each independently a hydrogen atom or a deuterium atom,
R3 is a hydrogen atom or a deuterium atom,
q is an integer from 0 to 2, and
L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 17 (depends on 14)

The diamine compound of claim 14, wherein Formula 1 is represented by one of Formula 5 to Formula 7:
wherein in Formula 5 to Formula 7,
R3 and R4 are each independently a hydrogen atom or a deuterium atom,
q and r are each independently an integer from 0 to 2, and
Ar1 to Ar4, L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 18 (depends on 14)

The diamine compound of claim 14, wherein Formula 1 is represented by one of Formula 8 to Formula 11:
wherein in Formula 8 to Formula 11,
R3 and R4 are each independently a hydrogen atom or a deuterium atom,
q and r are each independently an integer from 0 to 2, and
Ar1 to Ar4, L1, L2, R1, R2, and m to p are the same as defined in Formula 1 and Formula 2-1 to Formula 2-4.

### Claim 19 (depends on 13)

The diamine compound of claim 13, wherein L1 and L2 are each independently a direct linkage, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

### Claim 20 (depends on 13)

The diamine compound of claim 13, wherein the diamine compound represented by Formula 1 is one selected from Compound Group 1: