IP Library › Granted Patent US 10,096,777
Granted Patent B2
US 10,096,777 · App. 15/794,087 · Granted Oct 9, 2018

Composition for organic optoelectric device and organic optoelectric device and display device

Inventors: Sangshin Lee (Suwon-si, KR); Dong Wan Ryu (Suwon-si, KR); Joohee Seo (Suwon-si, KR); Eun Sun Yu (Suwon-si, KR); Seungjae Lee (Suwon-si, KR); Chunkeun Jang (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR)
Assignees: Samsung SDI Co., Ltd.; Samsung Electronics Co., Ltd.
H01L51/0045H01L27/3237H01L51/50
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Quick Facts
Patent No.
US 10,096,777
App. No.
15/794,087
Granted
Oct 9, 2018
Kind
B2
Abstract

Disclosed are a composition for an organic optoelectric device including at least one first compound for an organic optoelectric device represented by Chemical Formula 1; and at least one second compound for an organic optoelectric device including a carbazole moiety represented by Chemical Formula 2, an organic optoelectric device include the same, and a display device. Details of Chemical Formula 1 and Chemical Formula 2 are the same as defined in the specification.

Claims (77)

1. A composition for an organic optoelectric device, comprising:

at least one first compound for an organic optoelectric device represented by Chemical Formula 1; and

at least one second compound for an organic optoelectric device including a carbazole moiety represented by Chemical Formula 2:

wherein, in Chemical Formula 1,

X 1 and X 2 are independently N-L a -R a , O, or S,

at least one of X 1 and X 2 is N-L a -R a ,

R a is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

at least one of R a is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group except a carbazolyl group,

R 1 to R 7 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

adjacent groups of R 1 to R 4 are linked with each other to form at least one of a substituted or unsubstituted aliphatic, aromatic, or heteroaromatic monocyclic ring or a substituted or unsubstituted aliphatic, aromatic, or heteroaromatic polycyclic ring, and

L a is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group;

wherein, in Chemical Formula 2,

Y 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

A 1 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R 12 to R 17 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

R 14 to R 17 are independently present or adjacent groups of R 14 to R 17 are linked with each other to form a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring;

wherein “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.

2. The composition as claimed in claim 1 , wherein R 1 and R 2 of Chemical Formula 1 are linked with each other; R 3 and R 4 are linked with each other; or R 1 and R 2 are linked with each other and R 3 and R 4 are linked with each other to form at least one of a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring.

3. The composition as claimed in claim 1 , wherein Chemical Formula 1 is represented by one of Chemical Formula 1A to Chemical Formula 1C:

wherein, in Chemical Formula 1A to Chemical Formula 1C,

X 1 and X 2 are independently N-L a -R a , O, or S,

at least one of X 1 and X 2 is N-L a -R a ,

R a is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

at least one of R a is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group except a carbazolyl group,

R 1 to R 11 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

L a is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group.

4. The composition as claimed in claim 1 , wherein:

at least one of R a of Chemical Formula 1 is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group except a carbazolyl group, and

the substituted or unsubstituted N-containing C2 to C30 heterocyclic group except the carbazolyl group is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group.

5. The composition as claimed in claim 1 , wherein:

at least one of R a of Chemical Formula 1 is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group except a carbazolyl group, and

the substituted or unsubstituted N-containing C2 to C30 heterocyclic group except the carbazolyl group is selected from substituents of Group I:

wherein, in Group I,

* is a linking point.

6. The composition as claimed in claim 1 , wherein Chemical Formula 1 is represented by one of Chemical Formula 1A-I, Chemical Formula 1B-I and Chemical Formula 1C-I:

wherein, in Chemical Formula 1A-I, Chemical Formula 1B-I and Chemical Formula 1C-I,

R a1 and R a2 are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group,

one of R a1 and R a2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group,

R 1 to R 11 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

L a1 and L a2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group.

7. The composition as claimed in claim 1 , wherein Chemical Formula 1 is represented by one of Chemical Formula 1A-II, Chemical Formula 1A-III, Chemical Formula 1A-IV, Chemical Formula 1A-V, Chemical Formula 1B-II, Chemical Formula 1B-III, Chemical Formula 1B-IV, Chemical Formula 1B-V, Chemical Formula 1C-II, Chemical Formula 1C-III, Chemical Formula 1C-IV, and Chemical Formula 1C-V:

wherein, in Chemical Formula 1A-II, Chemical Formula 1A-III, Chemical Formula 1A-IV, Chemical Formula 1A-V, Chemical Formula 1B-II, Chemical Formula 1B-III, Chemical Formula 1B-IV, Chemical Formula 1B-V, Chemical Formula 1C-II, Chemical Formula 1C-III, Chemical Formula 1C-IV, and Chemical Formula 1C-V,

R a1 and R a2 are independently a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group,

R 1 to R 11 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

L a1 and L a2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group.

8. The composition as claimed in claim 1 , wherein Chemical Formula 2 is represented by Chemical Formula 2A, Chemical Formula 2B, or Chemical Formula 2C:

wherein, in Chemical Formula 2A, Chemical Formula 2B, and Chemical Formula 2C,

Y 1 to Y 3 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

A 1 to A 3 are independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R 12 , R 13 , and R 18 to R 23 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

n is one of integers of 0 to 2.

9. The composition as claimed in claim 8 , wherein A 1 and A 2 of Chemical Formula 2A are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group.

10. The composition as claimed in claim 8 , wherein:

Chemical Formula 2A is one of structures of Group II, and

*—Y 1 -A 1 and *—Y 2 -A 2 are one of substituents of Group III,

wherein, in Groups II and III, * is a linking point.

11. The composition as claimed in claim 8 , wherein at least one of A 1 and A 3 of Chemical Formula 2B and Chemical Formula 2C is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group except a carbazolyl group.

12. The composition as claimed in claim 1 , wherein:

the first compound for an organic optoelectric device is represented by Chemical Formula 1C-I or Chemical Formula 1C-III, and

the second compound for an organic optoelectric device is represented by Chemical Formula 2A-a, Chemical Formula 2B, or Chemical Formula 2C:

wherein, in Chemical Formula 1C-I, Chemical Formula 1C-II, and Chemical Formula 1C-III,

R a1 and R a2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted quinazolinyl group,

R 5 to R 11 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

L a1 and L a2 are independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group;

wherein, in Chemical Formula 2A-a, Chemical Formula 2B, and Chemical Formula 2C,

Y 1 to Y 3 are independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

A 1 and A 2 of Chemical Formula 2A-a are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group,

A 1 and A 3 of Chemical Formula 2B and Chemical Formula 2C are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group, and

one of A 1 and A 3 of Chemical Formula 2B and Chemical Formula 2C is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group.

13. An organic optoelectric device, comprising

an anode and a cathode facing each other, and

at least one organic layer interposed between the anode and the cathode,

wherein the composition for an organic optoelectric device as claimed in claim 1 .

14. The organic optoelectric device as claimed in claim 13 , wherein

the organic layer includes a light emitting layer, and

the composition for an organic optoelectric device is included as a host of the light emitting layer.

15. A display device comprising the organic optoelectric device as claimed in claim 13 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2019
From: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 051338/0532 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2017
From: LEE, SANGSHIN; RYU, DONG WAN; SEO, JOOHEE; YU, EUN SUN; LEE, SEUNGJAE; JANG, CHUNKEUN; JUNG, SUNG-HYUN
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 043953/0663 →
Priority Claims (1)
KR 10-2016-0176859 · Dec 22, 2016 · national
Continuity (1)
Related Publication 20180182970A1 · Jun 28, 2018