# US 12,004,419 B2 · Electroactive compounds

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- Number: US 12,004,419 B2
- Document ID: US12004419B2
- Status: Granted
- Kind: B2
- Application number: 17/544,231
- Filed: 2021-12-07
- Published: 2022-03-24
- Granted: 2024-06-04
- Earliest claimed: 2016-11-23
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Hjalti Skulason; Viacheslav V. Diev; Giang Dong Vo; Weiying Gao; Weishi Wu; Norman Herron; Michael Henry Howard, Jr.; Kalindi Dogra; Yunlong Zou
- Web page: https://patentgrep.com/patent/US12004419B2

## CPC

- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07D 487/04: Ortho-condensed systems
- C07D 493/04: Ortho-condensed systems
- C07D 493/14: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C07C 2603/54: containing more than five condensed rings
- C09K 2211/1007: Non-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 85/622: {containing four rings, e.g. pyrene}
- H10K 85/624: {containing six or more rings}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

There is provided a compound having Formula I, Formula II, or Formula III. The variables are described in detail herein.

## Claims

### Claim 1

A compound having Formula I
wherein:
Ar1, Ar2, Ar4, and Ar6 are each independently hydrocarbon aryl, heteroaryl, or a substituted derivative thereof;
Ar3, and Ar5 each independently have Formula a
wherein in Formula a,
R8 is the same or different at each occurrence and each independently D, F, CN, alkyl, aryloxy, heteroaryl, alkoxy, siloxy, silyl, germyl, deuterated alkyl, deuterated aryloxy, deuterated heteroaryl, deuterated alkoxy, deuterated siloxane, deuterated silyl, or deuterated germyl;
p is the same or different at each occurrence and each independently an integer from 0-4;
q is an integer from 0-5;
wherein at least one of p or q is greater than 0;
r is 2 or 3; and
* indicates a point of attachment;
a and b are each independently 0 or 1;
m and n are 1; and
Core is Formula IA
where in Formula IA,
Y is the same or different at each occurrence and each independently O, S, Se, Te, NR2, CR3R4, or SiR5R6;
R2 is the same or different at each occurrence and each independently alkyl, hydrocarbon aryl, heteroaryl, or a substituted derivative thereof;
R3-R6 are each independently alkyl, silyl, germyl, hydrocarbon aryl, heteroaryl, or a substituted derivative thereof, where R3 and R4 and/or R5 and R6 are optionally joined together to form a cyclic group selected from cycloalkyl, silacycloalkyl, spirofluorenyl, silaspirofluorenyl, or a substituted derivative thereof;
a double dashed line between two rings indicates that the rings are fused together in any orientation; and
* indicates a point of attachment;
wherein the Core optionally has one or more substituents selected from the group consisting of D, alkyl, silyl, germyl, hydrocarbon aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germyl, deuterated hydrocarbon aryl, and deuterated heteroaryl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the Core is any one selected from the group consisting of Formula IA-a through Formula IA-t
where:
R1 is the same or different at each occurrence and each independently D, F, CN, alkyl, alkoxy, fluoroalkyl, hydrocarbon aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated hydrocarbon aryl, deuterated aryloxy, deuterated heteroaryl, deuterated heteroaryl deuterated silyl, deuterated siloxane, deuterated siloxy, or deuterated germyl;
c and d are each independently an integer of 0-3;
g and h are each independently an integer of 0-2; and
k is an integer of 0-4.

### Claim 3 (depends on 2)

The compound of claim 2, wherein the Core is any one selected from the group consisting of Formula IA-a1, Formula IA-a2, Formula IA-b1, Formula IA-b2, Formula IA-c, and Formula IA-c2

### Claim 4 (depends on 1)

The compound of claim 1, wherein Ar3 and Ar5 each independently have Formula b
wherein in Formula b, R8, p, q, r and * are same as defined in claim 1.

### Claim 5 (depends on 1)

The compound of claim 1, wherein p>0.

### Claim 6 (depends on 1)

The compound of claim 1, wherein q>0.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound is any one selected from the group consisting of Compounds IA-43, IA-44 and IA-45:

### Claim 8 (depends on 1)

An organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, wherein the photoactive layer comprises the compound according to claim 1.