# US 11,910,712 B2 · Compound, organic optoelectronic diode, and display device

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- Number: US 11,910,712 B2
- Document ID: US11910712B2
- Status: Granted
- Kind: B2
- Application number: 17/423,332
- Filed: 2020-01-22
- Published: 2022-06-02
- Granted: 2024-02-20
- Earliest claimed: 2019-01-25
- Assignees: Lt Materials Co., Ltd.
- Applicants: Lt Materials Co., Ltd.
- Inventors: Hye-Su Ji; Seong-Jong Park; Won-Jang Jeong
- Web page: https://patentgrep.com/patent/US11910712B2

## CPC

- C07D 401/14: containing three or more hetero rings
- C07D 215/06: having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
- C07D 471/04: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- 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}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/131: {with spacer layers between the electroluminescent layers}
- H10K 50/166: {comprising a multilayered structure}
- H10K 50/18: Carrier blocking layers
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present application relates to a compound represented by Chemical Formula 1, an organic optoelectronic diode and a display device.

## Claims

### Claim 1

A compound represented by the following Chemical Formula 1:
wherein, in Chemical Formula 1,
Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of Ar1 and Ar2 is a substituted or unsubstituted C2 to C60 heteroaryl group;
L1 and L2 are each independently a single bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 and n2 are each independently one of integers of 0 to 2; and
R1 to R9 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a substituted or unsubstituted C6 to C60 aryl group.

### Claim 2 (depends on 1)

The compound of claim 1, which is represented by the following Chemical Formula 2:
in Chemical Formula 2,
Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of Ar1 and Ar2 is a substituted or unsubstituted C2 to C60 heteroaryl group;
L1 and L2 are each independently a single bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 and n2 are each independently one of integers of 0 to 2; and
R1 to R9 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a substituted or unsubstituted C6 to C60 aryl group.

### Claim 3 (depends on 1)

The compound of claim 1, which is represented by the following Chemical Formula 3:
in Chemical Formula 3,
Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of Ar1 and Ar2 is a substituted or unsubstituted C2 to C60 heteroaryl group;
L1 and L2 are each independently a single bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 and n2 are each independently one of integers of 0 to 2; and
R1 to R9 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a substituted or unsubstituted C6 to C60 aryl group.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Ar1 is any one of the following Chemical Formula 4-1 to Chemical Formula 4-5:
in Chemical Formula 4-1 to Chemical Formula 4-5,
at least one of X1 to X5 is —N—, and the rest are —CH—, —CR—, or —CR10—;
at least one of X6 to X12 is —N—, and the rest are —CH—, —CR— or —CR11—;
at least one of X13 to X19 is —N—, and the rest are —CH—, —CR— or —CR12—;
X20 and X21 are each independently —N—, —CH— or —CR—, and at least one of X20 and X21 is —N—;
X22 and X23 are each independently —N—, —CH— or —CR—, and at least one of X22 and X23 is —N—,
Rs are each independently deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a substituted or unsubstituted C6 to C60 aryl group;
R10 to R12 are each independently any one of a phenyl group, a pyridinyl group and a substituent of the following Chemical Formula 5; and
R13 and R14 are each independently any one of hydrogen, deuterium, a phenyl group, a pyridinyl group and a substituent of the following Chemical Formula 5,
in Chemical Formula 4-1 to Chemical Formula 4-5 and Chemical Formula 5,
* means a bonding position.

### Claim 5 (depends on 4)

The compound of claim 4, wherein Ar1 is represented by Chemical Formula 4-1, and in Chemical Formula 4-1,
(1) X1 is —N—, and the rest are —CH—;
(2) X2 is —N—, and the rest are —CH—;
(3) X3 is —N—, and the rest are —CH—;
(4) X1 and X5 are —N—, X3 is —CH—, the rest are one of —CH— and —CR10— and R10 is a phenyl group or a pyridyl group;
(5) X1 and X3 are —N—, X5 is —CH—, the rest are one of —CH— and —CR10— and R10 is a phenyl group;
(6) X1 and X4 are —N—, and the rest are —CH—;
(7) X1, X3 and X5 are —N—, the rest are —CR10—, and R10 is a phenyl group; or
(8) X1, X3 and X5 are —N—, and the rest are —CH—.

### Claim 6 (depends on 4)

The compound of claim 4, wherein Ar1 is represented by Chemical Formula 4-2, and in Chemical Formula 4-2,
(1) X7 is —N—, and the rest are —CH—;
(2) X8 is —N—, and the rest are —CH—;
(3) X9 is —N—, and the rest are —CH—;
(4) X10 is —N—, and the rest are —CH—;
(5) X11 is —N—, and the rest are —CH—; or
(6) X12 is —N—, and the rest are —CH—.

### Claim 7 (depends on 4)

The compound of claim 4, wherein Ar1 is represented by Chemical Formula 4-3, and in Chemical Formula 4-3,
(1) X13 is —N—, and the rest are —CH—;
(2) X14 is —N—, and the rest are —CH—;
(3) X15 is —N—, and the rest are —CH—;
(4) X17 is —N—, and the rest are —CH—;
(5) X18 is —N—, and the rest are —CH—;
(6) X19 is —N—, and the rest are —CH—; or
(7) X13 and X19 are —N—, and the rest are —CH—.

### Claim 8 (depends on 4)

The compound of claim 4, wherein Ar1 is represented by Chemical Formula 4-4, and in Chemical Formula 4-4,
(1) X20 is —N—, X21 is —CH—, and R13 is hydrogen; or
(2) X20 and X21 are —N—, and R13 is hydrogen or deuterium.

### Claim 9 (depends on 4)

The compound of claim 4, wherein Ar1 is represented by Chemical Formula 4-5, and in Chemical Formula 4-5,
(1) X22 is —N—, X23 is —CH—, and R14 is hydrogen; or
(2) X22 and X23 are and R14 is one of hydrogen, deuterium and a phenyl group.

### Claim 10 (depends on 1)

The compound of claim 1, wherein Ar2 is any one of the following Chemical Formula 6-1 to Chemical Formula 6-8:
in Chemical Formula 6-1 to Chemical Formula 6-8,
X1 to X5 are each independently —N—, —CH—, —CR— or —CR10—;
X6 to X12 are each independently —N—, —CH—, —CR— or —CR11—,
X13 to X19 are each independently —N—, —CH—, —CR— or —CR12—;
X20 and X21 are each independently —N—, —CH— or —CR—;
X22 and X23 are each independently —N—, —CH— or —CR—;
Rs are each independently deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a substituted or unsubstituted C6 to C60 aryl group;
R10 to R12 are each independently any one of a phenyl group, a pyridinyl group and a substituent of the following Chemical Formula 5; and
R13 to R15 are each independently any one of hydrogen, deuterium, a phenyl group, a pyridinyl group and a substituent of the following Chemical Formula 5,
in Chemical Formula 6-1 to Chemical Formula 6-8 and Chemical Formula 5,
* means a bonding site.

### Claim 11 (depends on 10)

The compound of claim 10, wherein Ar2 is represented by Chemical Formula 6-1, and in Chemical Formula 6-1,
(1) X1 to X5 are —CH—;
(2) X1, X3 and X5 are —CH—, the rest are —CR10—, and R10 is a phenyl group or a pyridinyl group;
(3) X1 is —N—, and the rest are —CH—;
(4) X2 is —N—, and the rest are —CH—;
(5) X1 and X5 are —N—, X3 is —CH—, the rest are one of —CH— and —CR10— and R10 is a phenyl group or the substituent of Chemical Formula 5;
(6) X1 and X3 are —N—, X5 is —CH—, the rest are one of —CH— and —CR10— and R10 is a phenyl group or the substituent of Chemical Formula 5;
(7) X1, X3 and X5 are —N—, the rest are one of —CH— and —CR10—, and R10 is the substituent of Chemical Formula 5; or
(8) X1, X3 and X5 are —N—, the rest are one of —CH— and —CR10—, and R10 is a phenyl group.

### Claim 12 (depends on 10)

The compound of claim 10, wherein Ar2 is represented by Chemical Formula 6-2, and in Chemical Formula 6-2,
(1) X6 to X12 are —CH—;
(2) X9 is —N—, and the rest are —CH—;
(3) X11 is —N—, and the rest are —CH—; or
(4) X12 is —N—, and the rest are —CH—.

### Claim 13 (depends on 10)

The compound of claim 10, wherein Ar2 is represented by Chemical Formula 6-3, and in Chemical Formula 6-3,
(1) X13 to X19 are —CH—;
(2) X15 is —N—, and the rest are —CH—;
(3) X17 is —N—, and the rest are —CH—; or
(4) X18 is —N—, and the rest are —CH—.

### Claim 14 (depends on 10)

The compound of claim 10, wherein Ar2 is represented by Chemical Formula 6-4, and in Chemical Formula 6-4,
(1) X20 and X21 are —CH—, and R13 and R14 are each independently hydrogen or deuterium;
(2) X20 and X21 are —N—, and R13 and R14 are each independently hydrogen or deuterium;
(3) X20 and X21 are —N—, and R13 and R14 are a phenyl group; or
(4) X20 and X21 are —N—, any one of R13 and R14 is a phenyl group, and the rest is hydrogen or deuterium.

### Claim 15 (depends on 10)

The compound of claim 10, wherein Ar2 is represented by Chemical Formula 6-5, and in Chemical Formula 6-5,
(1) X22 and X23 are —N—, and R15 is hydrogen or deuterium; or
(2) X22 and X23 are —N—, and R15 is a phenyl group.

### Claim 16 (depends on 2)

The compound of claim 2, wherein the compound represented by Chemical Formula 2 is any one of compounds of the following Group II:

### Claim 17 (depends on 3)

The compound of claim 3, wherein the compound represented by Chemical Formula 3 is any one of compounds of the following Group Ill:
[Group III]

### Claim 18 (depends on 1)

An organic optoelectronic diode comprising:
an anode and a cathode facing each other; and
at least one organic layer disposed between the anode and the cathode,
wherein the organic layer includes the compound of claim 1.

### Claim 19 (depends on 18)

The organic optoelectronic diode of claim 18, wherein the organic layer includes a charge generation layer or a hole blocking layer, and the charge generation layer or the hole blocking layer includes the compound.

### Claim 20 (depends on 18)

A display device comprising the organic optoelectronic diode of claim 18.