IP Library › Granted Patent US 11,515,480
Granted Patent B2
US 11,515,480 · App. 16/721,777 · Granted Nov 29, 2022

Organic light emitting device

Inventors: Heejun Park (Paju-si, KR); Seonkeun Yoo (Gunpo-si, KR); Soyoung Jang (Seoul, KR); Jicheol Shin (Gimpo-si, KR); Sangbeom Kim (Paju-si, KR); Sunghoon Kim (Seoul, KR); Tae Wan Lee (Seoul, KR); Dong Hun Lee (Seoul, KR); Jeonghoe Heo (Seoul, KR)
Assignee: LG Display Co., Ltd.
H01L51/0061C07D333/76H01L51/006H01L27/1255H01L27/3244H01L29/7869H01L51/001H01L51/0056H01L51/0074H01L51/5012H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5253H01L51/56H01L2251/558
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Quick Facts
Patent No.
US 11,515,480
App. No.
16/721,777
Granted
Nov 29, 2022
Kind
B2
Abstract

The present disclosure provides an organic light-emitting device comprising a novel compound. When the novel compound is applied as a hole transport material to an organic light emitting device, the novel compound allows the device to have improved drive voltage, efficiency and lifespan characteristics.

Claims (64)

1. An organic light-emitting device, comprising:

a first electrode;

a second electrode; and

at least one organic material layer between the first and second electrodes,

wherein the at least one organic material layer contains a compound represented by the following Chemical Formula 1:

wherein:

X represents O or S,

each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,

a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding R1s are bonded to each other to form a ring,

b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,

n is 0 or 1, n=0 representing a direct bond,

m is an integer of 1 to 3,

each of c and d is independently an integer of 0 or 1,

m, c and d are selected such that when m is 1, c+d=2, when m is 2, c+d=1, and when m is 3, c+d=0, and

each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms,

wherein the at least one organic material layer includes at least one layer selected from the group consisting of a hole transport layer and an auxiliary hole transport layer, and

wherein the at least one layer contains at least two types of the compounds represented by Chemical Formula 1.

2. An organic light-emitting device, comprising:

a first electrode;

a second electrode; and

at least one organic material layer between the first and second electrodes,

wherein the at least one organic material contains a.A compound represented by the following Chemical Formula 1-1:

wherein:

X represents S,

each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,

a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding Rls are bonded to each other to form a ring,

b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,

n is 0 or 1, n=0 representing a direct bond,

m is an integer of 1 to 3,

each of c and d is independently an integer of 0 or 1,

m, c and d are selected such that m+c+d=3, and

each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms,

with the proviso that each of R1, R2, Ar1 and Ar2 is independently not carbazole or free of a carbazole substituent,

wherein the at least one organic material layer includes at least one layer selected from the group consisting of a hole transport layer and an auxiliary hole transport layer, and

wherein the at least one layer contains at least two types of the compounds represented by Chemical Formula 1-1.

3. The organic light-emitting device of claim 1 , wherein the compound is represented by the following Chemical Formula 2:

wherein:

X represents O or S,

each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,

a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding R1s are bonded to each other to form a ring,

b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,

m is an integer of 1 to 3,

each of c and d is independently an integer of 0 or 1,

m, c and d are selected such that when m is 1, c+d=2, when m is 2, c+d=1, and when m is 3, c+d=0, and

each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

4. The organic light-emitting device of claim 1 , wherein the compound is represented by one of the following Chemical Formulas 3 to 5:

wherein:

X represents 0 or S,

each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,

a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding Rls are bonded to each other to form a ring,

b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,

m is an integer of 1 to 3,

each of c and d is independently an integer of 0 or 1,

m, c and d are selected such that when m is 1, c+d=2, when m is 2, c+d=1, and when m is 3, c+d=0, and

each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

5. The organic light-emitting device of claim 1 , wherein each of Ar1 and Ar2 of the Chemical Formula 1 is independently selected from the following substituents:

6. The organic light-emitting device of claim 1 , wherein the compound is represented by one of the following Chemical Formulas:

7. The organic light-emitting device of claim 1 , wherein the organic material layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an auxiliary hole transport layer, a light-emitting layer, an auxiliary electron transport layer, an electron transport layer, and an electron injection layer.

8. The organic light-emitting device of claim 1 , wherein the organic light-emitting device further comprises an encapsulating layer formed on the second electrode, and a barrier layer formed on the encapsulating layer.

9. The organic light-emitting device of claim 8 , wherein the encapsulating layer is formed on entire faces of the second electrode.

10. The organic light-emitting device of claim 8 , wherein the barrier layer is bonded to the encapsulating layer via an adhesive.

11. The organic light-emitting device of claim 1 , wherein the organic light-emitting device further comprises a driving thin-film transistor including an active layer electrically connected to the first electrode.

12. The organic light-emitting device of claim 11 , wherein the active layer includes an oxide semiconductor layer.

13. The organic light-emitting device of claim 11 , wherein the driving thin-film transistor includes a gate insulating film formed on the active layer, and a gate electrode formed on the gate insulating film.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 30, 2019
From: PARK, HEEJUN; YOO, SEONKEUN; JANG, SOYOUNG; SHIN, JICHEOL; KIM, SANGBEOM; KIM, SUNGHOON; LEE, TAE WAN; LEE, DONG HUN; HEO, JEONGHOE
To: LG DISPLAY CO., LTD.
Reel/Frame 051389/0985 →
Priority Claims (1)
KR 10-2018-0167668 · Dec 21, 2018 · national
Continuity (1)
Related Publication 20200203619A1 · Jun 25, 2020