IP Library › Granted Patent US 10,050,212
Granted Patent B2
US 10,050,212 · App. 14/302,464 · Granted Aug 14, 2018

Organic optoelectric device and display device

Inventors: Pyeong-Seok Cho (Uiwang-si, KR); Gi-Wook Kang (Uiwang-si, KR); Eui-Su Kang (Uiwang-si, KR); Youn-Hwan Kim (Uiwang-si, KR); Hun Kim (Uiwang-si, KR); Yong-Tak Yang (Uiwang-si, KR); Jae-Jin Oh (Uiwang-si, KR); Eun-Sun Yu (Uiwang-si, KR); Nam-Heon Lee (Uiwang-si, KR); Sang-Shin Lee (Uiwang-si, KR); Han-Ill Lee (Uiwang-si, KR)
Assignee: Cheil Industries, Inc.
H01L51/0067C09B57/00H01L51/0054H01L51/0072H01L51/0073H01L51/0074H01L51/5012H01L51/5016H01L51/5056
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Quick Facts
Patent No.
US 10,050,212
App. No.
14/302,464
Granted
Aug 14, 2018
Kind
B2
Abstract

Disclosed is an organic optoelectric device, including an anode and a cathode facing each other, an emission layer interposed between the anode and the cathode, a hole transport layer interposed between the anode and the emission layer, and a hole transport auxiliary layer interposed between the hole transport layer and the emission layer. The emission layer includes at least one first compound represented by Chemical Formula 1: The emission layer further includes at least one second compound represented by Chemical Formula 2: The hole transport auxiliary layer includes a third compound represented by Chemical Formula 2, the third compound being the same as or different from the second compound.

Claims (49)

1. An organic optoelectric device, comprising:

an anode and a cathode facing each other,

an emission layer interposed between the anode and the cathode,

a hole transport layer interposed between the anode and the emission layer, and

a hole transport auxiliary layer interposed between the hole transport layer and the emission layer,

the emission layer including at least one first compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

Z is independently N or CR a ,

at least one of Z is N,

R 1 to R 10 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a combination thereof,

the total number of 6-membered rings substituted on the triphenylenyl group is less than or equal to 6,

L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted terphenylene group, wherein a substituent of the substituted phenylene group, the substituted biphenylene group, and the substituted terphenylene group is a C1 to C30 alkyl group, a C6 to C30 aryl group, or a cyano group,

n1 to n3 are independently 0 or 1, and

n1+n2+n3≥1;

the emission layer further including at least one second compound represented by Chemical Formula 2:

wherein, in Chemical Formula 2,

Y 1 is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R 11 to R 14 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof, and

at least one of R 11 to R 14 and Ar 1 includes a substituted or unsubstituted triphenylenyl group or a substituted or unsubstituted carbazolyl group; and

the hole transport auxiliary layer including a third compound represented by Chemical Formula 2, the third compound being the same as or different from the second compound.

2. The organic optoelectric device as claimed in claim 1 , wherein the first compound is represented by Chemical Formula 1-I or Chemical Formula 1-II:

wherein, in Chemical Formula 1-I or 1-II,

Z is independently N or CR a ,

at least one of Z is N,

R 1 to R 10 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a combination thereof,

the total number of 6-membered rings substituted on the triphenylenyl group is less than or equal to 6,

L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted terphenylene group, a substituent of the substituted phenylene group, the substituted biphenylene group, and the substituted terphenylene group is a C1 to C30 alkyl group, a C6 to C30 aryl group, or a cyano group,

n1 to n3 are independently 0 or 1, and

n1+n2+n3≥1.

3. The organic optoelectric device as claimed in claim 1 , wherein L of Chemical Formula 1 is a single bond, a substituted or unsubstituted phenylene having a kink structure, a substituted or unsubstituted biphenylene group having a kink structure, or a substituted or unsubstituted terphenylene group having a kink structure, and a substituent of the substituted phenylene group, the substituted biphenylene group, and the substituted terphenylene group is a C1 to C30 alkyl group, a C6 to C30 aryl group or a cyano group.

4. The organic optoelectric device as claimed in claim 3 , wherein L of Chemical Formula 1 is a single bond or a substituted or unsubstituted group selected from Group 1:

wherein, in the Group 1,

R 15 to R 42 are independently hydrogen, C1 to C10 alkyl group, C6 to C30 aryl group, a cyano group.

5. The organic optoelectric device as claimed in claim 1 , wherein the first compound has at least two kink structures.

6. The organic optoelectric device as claimed in claim 1 , wherein the first compound is a compound selected from Group 2:

7. The organic optoelectric device as claimed in claim 1 , wherein the second compound and the third compound are independently represented by at least one of Chemical Formula 2-I to Chemical Formula 2-III:

wherein, in Chemical Formulae 2-I to 2-III,

Y 1 to Y 3 are independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

Ar 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

R 11 to R 14 and R 43 to R 54 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof.

8. The organic optoelectric device as claimed in claim 7 , wherein Ar 1 and Ar 2 of Chemical Formula 2-I are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

9. The organic optoelectric device as claimed in claim 7 , wherein the compound represented by Chemical Formula 2-I is selected from Group 4:

10. The organic optoelectric device as claimed in claim 7 , wherein the compound represented by Chemical Formula 2-II is selected from Group 5:

11. The organic optoelectric device as claimed in claim 7 , wherein the compound represented by Chemical Formula 2-III is selected from Group 6:

12. The organic optoelectric device as claimed in claim 1 , wherein the hole transport auxiliary layer is in contact with the hole transport layer and the emission layer.

13. The organic optoelectric device as claimed in claim 1 , wherein the emission layer includes the first compound and the second compound in a weight ratio of about 1:10 to about 10:1.

14. The organic optoelectric device as claimed in claim 1 , wherein the emission layer further includes a phosphorescent dopant.

15. A display device including the organic optoelectric device as claimed in claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2014
From: CHO, PYEONG-SEOK; KANG, GI-WOOK; KANG, EUI-SU; KIM, YOUN-HWAN; KIM, HUN; YANG, YONG-TAK; OH, JAE-JIN; YU, EUN-SUN; LEE, NAM-HEON; LEE, SANG-SHIN; LEE, HAN-ILL
To: CHEIL INDUSTRIES, INC.
Reel/Frame 033084/0419 →
Priority Claims (1)
KR 10-2013-0121466 · Oct 11, 2013 · national
Continuity (1)
Related Publication 20150102301A1 · Apr 16, 2015
Cited By (2)
US 12,402,528 US 12,628,249