# US 2019/0173020 A1 · Composition of matter for use in organic light-emitting diodes

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- Number: US 2019/0173020 A1
- Document ID: US20190173020A1
- Status: Published application
- Kind: A1
- Application number: 16/210,466
- Filed: 2018-12-05
- Published: 2019-06-06
- Earliest claimed: 2017-12-05
- Assignees: Kyulux, Inc.
- Applicants: Kyulux, Inc.
- Inventors: Yoshitake Suzuki; Shuo-Hsien Cheng; Yu Seok Yang; Jorge Aguilera-Iparraguirre; Rafael Gomez-Bombarelli; Timothy D. Hirzel
- Web page: https://patentgrep.com/patent/US20190173020A1

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/20: Delayed fluorescence emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present disclosure relates to compounds of Formula (I) as compounds capable of emitting delayed fluorescence, and uses of the compounds in organic light-emitting diodes.

## Claims

### Claim 1

A compound of Formula (I)
wherein
A is independently selected from CN,
R1, R2, R3, and R4 are independently selected from H, deuterium, Ph, and D;
D is independently selected from:
R11 to R18, R21 to R30, R31 to R38, and R41 to R46 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, CN, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted diarylamine;
each of R11 and R12, R12 and R13, R13 and R14, R15 and R16, R16 and R17, R17 and R18, L11 and R11, or L11 and R18 taken together can form a ring system;
each of R21 and R22, R22 and R23, R23 and R24, R24 and R25, R26 and R27, R27 and R28, R28 and R29, R29 and R30, L12 and R21, or L12 and R30 taken together can form a ring system;
each of R31 and R32, R32 and R33, R33 and R34, R35 and R36, R36 and R37, R37 and R38, L13 and R31, or L13 and R38 taken together can form a ring system;
each of R41 and R42, R42 and R43, R43 and R44, R45 and R46, L14 and R41, or L14 and R46 taken together can form a ring system;
L11 to L14 each independently represents a single bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene;
X represents O, S, a substituted or unsubstituted nitrogen atom, a substituted or unsubstituted carbon atom, a substituted or unsubstituted silicon atom, a carbonyl, a divalent substituted or unsubstituted ethylene having a bonding chain length of 2 atoms, a substituted or unsubstituted vinylene, a substituted or unsubstituted o-arylene, or a substituted or unsubstituted o-heteroarylene; and
Y represents C or N, provided that no more than one instance of Y is N;
provided that if an instance of Y is N, then the corresponding substituent selected from R31 to R34 is absent.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
D is independently selected from:
Z is independently selected from H, Me, t-Bu, and heteroaryl; and
heteroraryl is independently selected from

### Claim 3 (depends on 1)

The compound of claim 1, wherein A is CN.

### Claim 4 (depends on 1)

The compound of claim 1, wherein A is selected from A1, A2, A3, and A4.

### Claim 5 (depends on 1)

The compound of claim 1, wherein A is selected from A5, A6, A7, and A8.

### Claim 6 (depends on 1)

The compound of claim 1, wherein A is selected from A9, A10, A11, A12 and A13.

### Claim at position 7

-45. (canceled)

### Claim 46 (depends on 1)

The compound of claim 1, wherein at least one of R1, R2, R3, and R4 is H.

### Claim 47 (depends on 1)

The compound of claim 1, wherein at least one of R1, R2, R3, and R4 are Ph.

### Claim 48 (depends on 1)

The compound of claim 1, wherein R1, R2, R3, and R4 are D.

### Claim 49 (depends on 1)

The compound of claim 1, wherein at least two instances of D are the same.

### Claim 50 (depends on 1)

The compound of claim 1, wherein all instances of D are the same.

### Claim 51 (depends on 2)

The compound of claim 2, wherein at least one of R1, R2, R3, and R4 is independently selected from D1, D2, D3, D4, D5, D6, and D7.

### Claim 52 (depends on 2)

The compound of claim 2, wherein at least one of R1, R2, R3, and R4 is independently selected from D8, D9, D10, D11, D12, D13, and D14.

### Claim 53 (depends on 2)

The compound of claim 2, wherein at least one of R1, R2, R3, and R4 is independently selected from D15, D16, D17, D18, D19, D20, and D21.

### Claim 54 (depends on 2)

The compound of claim 2, wherein at least one of R1, R2, R3, and R4 is independently selected from D22, D23, D24, D25, D26, D27, and D28.

### Claim 55 (depends on 2)

The compound of claim 2, wherein at least one of R1, R2, R3, and R4 is independently selected from D29, D30, D31, D32, D33, D34, D35, D36, and D37.

### Claim 56

(canceled)

### Claim 57 (depends on 1)

The compound of claim 1, wherein at least two of D are the same.

### Claim 58 (depends on 1)

The compound of claim 1, wherein the compound is selected from

### Claim 59 (depends on 2)

The compound of claim 2, wherein the compound is

### Claim at position 22

-69. (canceled)

### Claim 70 (depends on 1)

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