# US 11,440,901 B2 · Composition of matter for use in organic light-emitting diodes

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- Number: US 11,440,901 B2
- Document ID: US11440901B2
- Status: Granted
- Kind: B2
- Application number: 16/568,516
- Filed: 2019-09-12
- Published: 2020-03-12
- Granted: 2022-09-13
- Earliest claimed: 2018-09-12
- Assignees: Kyulux, Inc.
- Applicants: Kyulux, Inc.
- Inventors: YuSeok Yang; Yong Joo Cho; Yoshitake Suzuki; Shuo-Hsien Cheng; Jorge Aguilera-Iparraguirre
- Web page: https://patentgrep.com/patent/US11440901B2

## CPC

- C07D 403/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07F 7/0816: {said ring comprising Si as a ring atom}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/81: Anodes
- H10K 50/82: Cathodes
- 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)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present disclosure relates to compounds of Formula (1) as useful materials for OLEDs. A is CN, cyanoaryl, or heteroaryl having at least one nitrogen atom as a ring-constituting atom; and D1, D2 and D3 are diarylamino or carbazolyl.

## Claims

### Claim 1

A compound of Formula (I):
wherein:
A is selected from CN, aryl that is substituted with at least one cyano, and a group represented by Formula (III):
wherein:
one of X1, X2 and X3 is N,
the other two of X1, X2 and X3 are independently N or C(R13),
R11, R12 and R13 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl, and
* represents a point of attachment to Formula (I); and
D1, D2 and D3 are independently selected from substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, and group represented by Formula (II):
wherein:
R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; or two or more instances of R1, R2, R3, R4, R5, R6, R7 and R8 taken together can form a ring system, or R5 and R6 taken together can form single bond, and
L1 is selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene.

### Claim 2 (depends on 1)

The compound of claim 1, wherein D1, D2 and D3 are the same.

### Claim 3 (depends on 1)

The compound of claim 1, wherein two of D1, D2 and D3 are the same.

### Claim 4 (depends on 1)

The compound of claim 1, wherein D1 and D3 are the same.

### Claim 5 (depends on 1)

The compound of claim 1, wherein at least one of D1, D2 and D3 has at least one carbazole ring.

### Claim 6 (depends on 5)

The compound of claim 5, wherein the carbazole ring is substituted by at least one selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.

### Claim 7 (depends on 5)

The compound of claim 5, wherein the carbazole ring is substituted at 3-position, 6-position, or 3- and 6-positions.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R1 and R2, R2 and R3, R3 and R4, or R4 and R5 are taken together to form a ring system.

### Claim 9 (depends on 1)

The compound of claim 1, wherein at least one of R1, R2, R3 and R4 is substituted or unsubstituted carbazolyl.

### Claim 10 (depends on 1)

The compound of claim 1, wherein A is CN.

### Claim 11 (depends on 1)

The compound of claim 1, wherein when D1, D2 and D3 are independently substituted or unsubstituted 9-carbazolyl, then A is substituted or unsubstituted cyanoaryl, or group represented by Formula (III).

### Claim 12 (depends on 1)

The compound of claim 1, wherein when D1, D2 and D3 are independently substituted or unsubstituted 9-carbazolyl, and A is cyano, then all of D1, D2 and D3 are not the same.

### Claim 13 (depends on 1)

The compound of claim 1, wherein when D1, D2 and D3 are independently substituted or unsubstituted 9-carbazolyl, and A is cyano, then at least one of D1, D2 and D3 is 9-carbazolyl substituted with at least one selected from substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl.

### Claim 14 (depends on 1)

An organic light-emitting diode (OLED) comprising the compound of claim 1.

### Claim 15 (depends on 14)

An organic light-emitting diode (OLED) of claim 14, wherein light emission of the OLED occurs mainly in the compound.

### Claim 16 (depends on 14)

The organic light-emitting diode (OLED) of claim 14, comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host material and the compound.

### Claim 17 (depends on 14)

The organic light-emitting diode (OLED) of claim 14, comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises the compound and a light-emitting material, and light emission of the OLED occurs mainly in the light-emitting material.

### Claim 18 (depends on 14)

The organic light-emitting diode (OLED) of claim 14, comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host material, an assistant dopant and a light-emitting material, and the assistant dopant is the compound.

### Claim 19 (depends on 1)

A screen or a display comprising the compound of claim 1.