IP Library › Granted Patent US 12,559,467
Granted Patent B2
US 12,559,467 · App. 17/617,579 · Granted Feb 24, 2026

Organic light emitting device

Inventors: Hojung Lee (Daejeon, KR); Wanpyo Hong (Daejeon, KR); Jae Seung Ha (Daejeon, KR); Ji Young Choi (Daejeon, KR); Woochul Lee (Daejeon, KR); Joo Ho Kim (Daejeon, KR); Hoon Jun Kim (Daejeon, KR); Seonwoo Kim (Daejeon, KR)
Assignee: LG CHEM, LTD.
C07D307/91C07C15/28C07F5/027C07F7/0812C09K11/06H10K85/00H10K85/40H10K85/615H10K85/626H10K85/657H10K85/6572H10K85/6574H10K85/658C07B2200/05C07C2603/24C09K2211/1007C09K2211/1011C09K2211/1018H10K50/11H10K50/12H10K2101/90
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Quick Facts
Patent No.
US 12,559,467
App. No.
17/617,579
Granted
Feb 24, 2026
Kind
B2
Abstract

An organic light emitting device including a light emitting layer, which comprises one or more of compounds represented by Formulae 1-1 to 1-3; and a compound represented by Formula 2.

Claims (50)

1 . An organic light emitting device comprising:

an anode;

a cathode; and

an organic material layer comprising a light emitting layer provided between the anode and the cathode,

wherein the light emitting layer comprises one or more of compounds represented by the following Formulae 1-1 to 1-3; and a compound represented by the following Formula 2:

wherein, in Formulae 1-1 to 1-3 and 2,

L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group,

D is deuterium, n11, n21, and n31 are each an integer from 0 to 6, n12, n13, n22, n32, and n33 are each an integer from 0 to 7, and n23 is an integer from 0 to 5,

Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,

Ar12, Ar13, Ar23, Ar24, Ar31, and Ar32 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

m11 and m21 are an integer from 0 to 4, m22 is an integer from 0 to 5, and substituents in the parenthesis are the same as or different from each other provided that when m11, m21, and m22 are each 2 or higher,

the compounds of Formulae 1-1 to 1-3 each have at least one or more deuteriums,

R1 to R3, R6, and R7 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or a group represented by the following Formula 2-A or 2-B, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,

r1 and r2 are an integer from 0 to 4, r3 is an integer from 0 to 3, r6 and r7 are an integer from 0 to 5, and substituents in the parenthesis are the same as or different from each other provided that when r1 to r3, r6, and r7 are each 2 or higher,

wherein, in Formulae 2-A and 2-B,

* is a bonding site,

T11 to T19 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,

at least one of T17 to T19 is a substituted or unsubstituted aryl group, and at least one of the remaining T17 to T19 is a substituted or unsubstituted alkyl group,

A11 to A14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted aliphatic hydrocarbon ring,

L11 is a direct bond; or a substituted or unsubstituted arylene group,

p1 is 0 or 1, and

Y1 is C or Si,

wherein one or more of R1 to R3, R6, and R7 are a group represented by Formula 2-A or 2-B, or

wherein two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, two of adjacent R6's, or two of adjacent R7's are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring comprising 5 or more carbon atoms.

2 . The organic light emitting device of claim 1 , wherein the compounds of Formulae 1-1 to 1-3 are deuterated by 30% or more.

3 . The organic light emitting device of claim 1 , wherein n11, n21, and n31 are 1 or higher.

4 . The organic light emitting device of claim 1 , wherein the light emitting layer comprises two types of compounds each represented by any one of Formulae 1-1 to 1-3 as hosts.

5 . The organic light emitting device of claim 1 , wherein the compound of Formula 1-1 is represented by any one selected from the following Formulae 101 to 104:

wherein, in Formulae 101 to 104, Ar11 to Ar13, D, n11 to n13, m11, and L1 are the same as defined in Formula 1-1.

6 . The organic light emitting device of claim 1 , wherein the compound of Formula 1-2 is represented by any one selected from the following Formulae 111 to 114:

wherein, in Formulae 111 to 114, D, n21 to n23, Ar21 to Ar24, m21, m22, and L2 are the same as defined in Formula 1-2.

7 . The organic light emitting device of claim 1 , wherein the compound of Formula 1-3 is represented by any one selected from the following Formulae 121 to 124:

wherein, in Formulae 121 to 124, Ar31, Ar32, D, n31 to n33, and L3 are the same as defined in Formula 1-3.

8 . The organic light emitting device of claim 1 , wherein the compound of Formula 2 comprises at least one deuterium.

9 . The organic light emitting device of claim 1 , wherein the compound represented by Formula 1-1 is any one selected from the following compounds:

10 . The organic light emitting device of claim 1 , wherein the compound represented by Formula 1-2 is any one selected from the following compounds:

11 . The organic light emitting device of claim 1 , wherein the compound represented by Formula 1-3 is any one selected from the following compounds:

12 . An organic light emitting device comprising:

an anode;

a cathode; and

an organic material layer comprising a light emitting layer provided between the anode and the cathode,

wherein the light emitting layer comprises one or more of compounds represented by the following Formulae 1-1 to 1-3; and a compound any one selected from the following Group 1:

wherein, in Formulae 1-1 to 1-3,

L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group,

D is deuterium, n11, n21, and n31 are each an integer from 0 to 6, n12, n13, n22, n32, and n33 are each an integer from 0 to 7, and n23 is an integer from 0 to 5,

Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,

Ar12, Ar13, Ar23, Ar24, Ar31, and Ar32 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

m11 and m21 are an integer from 0 to 4, m22 is an integer from 0 to 5, and substituents in the parenthesis are the same as or different from each other provided that when m11, m21, and m22 are each 2 or higher,

the compounds of Formulae 1-1 to 1-3 each have at least one or more deuteriums, and

[Group 1]

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2021
From: LEE, HOJUNG; HONG, WANPYO; HA, JAE SEUNG; CHOI, JI YOUNG; LEE, WOOCHUL; KIM, JOO HO; KIM, HOON JUN; KIM, SEONWOO
To: LG CHEM, LTD.
Reel/Frame 058341/0596 →
Priority Claims (3)
KR 10-2019-0157386 · Nov 29, 2019 · national
KR 10-2019-0157398 · Nov 29, 2019 · national
KR 10-2019-0157427 · Nov 29, 2019 · national
Continuity (1)
Related Publication 20230084250A1 · Mar 16, 2023
References Cited (40)
US 9634254B2 · Hamada · 2017 [cited by applicant]
US 20100187983A1 · Herron et al. · 2010 [cited by applicant]
US 20150108448A1 · Dai et al. · 2015 [cited by applicant]
US 20150236274A1 · Hatakeyama et al. · 2015 [cited by applicant]
US 20170025608A1 · Herron et al. · 2017 [cited by applicant]
US 20180094000A1 · Hatakeyama et al. · 2018 [cited by applicant]
US 20180301629A1 · Hatakeyama et al. · 2018 [cited by applicant]
US 20190115538A1 · Lim et al. · 2019 [cited by applicant]
US 20190181350A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20190207112A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20190305227A1 · Yoon et al. · 2019 [cited by applicant]
US 20200052212A1 · Tasaki et al. · 2020 [cited by applicant]
US 20200058885A1 · Hong et al. · 2020 [cited by applicant]
US 20200176679A1 · Jeong et al. · 2020 [cited by applicant]
US 20200185626A1 · Yuuki · 2020 [cited by applicant]
US 20200220083A1 · Hatakeyama et al. · 2020 [cited by applicant]
US 20210036233A1 · Joo et al. · 2021 [cited by applicant]
US 20210050547A1 · Li et al. · 2021 [cited by applicant]
US 20210167293A1 · Joo et al. · 2021 [cited by applicant]
US 20210184121A1 · Suh et al. · 2021 [cited by applicant]
US 20220006019A1 · Kim et al. · 2022 [cited by applicant]
CN 110492009A · 2019 [cited by applicant]
CN 111647010A · 2020 [cited by applicant]
JP 2018043984A · 2018 [cited by applicant]
KR 1020110126950A · 2011 [cited by applicant]
KR 1020120058602A · 2012 [cited by applicant]
KR 1020150011347A · 2015 [cited by applicant]
KR 1020180112721A · 2018 [cited by applicant]
KR 1020190051867A · 2019 [cited by applicant]
KR 1020190078541A · 2019 [cited by applicant]
KR 1020190101900A · 2019 [cited by applicant]
KR 1020190113498A · 2019 [cited by applicant]
KR 1020190127529A · 2019 [cited by applicant]
KR 1020200003741A · 2020 [cited by applicant]
KR 1020200090158A · 2020 [cited by applicant]
WO 2019102936A1 · 2019 [cited by applicant]
WO 2019218969A1 · 2019 [cited by applicant]
WO 2020054676A1 · 2020 [cited by applicant]
WO 2020080872A · 2020 [cited by applicant]
WO WO2020085829A1 · 2020 [cited by examiner]