IP Library › Granted Patent US 10,032,999
Granted Patent B2
US 10,032,999 · App. 15/678,397 · Granted Jul 24, 2018

Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device

Inventors: Byungku Kim (Suwon-si, KR); Dong Min Kang (Suwon-si, KR); Changwoo Kim (Suwon-si, KR); Jaejin Oh (Suwon-si, KR); Eun Sun Yu (Suwon-si, KR); Yuna Jang (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR); Jinseok Hong (Suwon-si, KR)
Assignees: Samsung SDI Co., Ltd.; Samsung Electronics Co., Ltd.
H01L51/0072C07D487/04C07D519/00C09K11/025C09K11/06H01L51/0052H01L51/0054H01L51/0067H01L51/0073H01L51/0074H01L51/0085C09K2211/1007C09K2211/1029C09K2211/185H01L51/5016H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 10,032,999
App. No.
15/678,397
Granted
Jul 24, 2018
Kind
B2
Abstract

Disclosed are a compound for an organic optoelectric device represented by Chemical Formula 1, a composition for an organic optoelectric device, an organic optoelectric device including the same, and a display device. Details of Chemical Formula 1 are the same as those defined in the specification.

Claims (84)

1. A compound for an organic optoelectric device represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

R 1 and R 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,

R 3 to R 6 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

L 1 and L 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and

the “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group.

2. The compound for an organic optoelectric device as claimed in claim 1 , wherein R 1 and R 2 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 phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group(naphthyridinyl), a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted benzoquinazolinyl group.

3. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is represented by Chemical Formula 1A:

wherein, in Chemical Formula 1A,

R 1a and R 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 naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, or a substituted or unsubstituted benzoquinazolinyl group,

at least one of R 1a and R 2a is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzoquinazolinyl group,

R 3 to R 6 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

L 1 and L 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof.

4. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is represented by Chemical Formula 1B:

wherein, in Chemical Formula 1B,

R 1b and R 2b 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 phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group,

R 3 to R 6 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

L 1 and L 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof.

5. The compound for an organic optoelectric device as claimed in claim 1 , wherein R 1 and R 2 are independently selected from substituents of Group I:

wherein, in Group I, * is a binding site with an adjacent atom.

6. The compound for an organic optoelectric device as claimed in claim 1 , wherein L 1 and L 2 are independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

7. The compound for an organic optoelectric device as claimed in claim 1 , wherein:

R 1 and R 2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group,

L 1 and L 2 are independently a single bond, or phenylene group,

R 3 to R 6 are all hydrogen, and

the “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C4 alkyl group, a phenyl group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

8. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is selected from compounds of Group 1:

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

the compound for an organic optoelectric device as claimed in claim 3 as a first compound; and

a compound represented by Chemical Formula 1B as a second compound,

wherein, in Chemical Formula 1B,

R 1b and R 2b 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 phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group,

R 3 to R 6 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

L 1 and L 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof.

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

a first compound that is the compound for an organic optoelectric device as claimed in claim 1 ; and

at least one second compound for an organic optoelectric device selected from a compound represented by Chemical Formula 2 and a compound consisting of a combination of a moiety represented by Chemical Formula 3 and a moiety represented by Chemical Formula 4:

wherein, in Chemical Formula 2,

Y 1 and Y 2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

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

R 7 to R 12 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof, and

m is an integer of 0 to 2;

wherein, in Chemical Formulae 3 and 4,

Y 3 and Y 4 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

Ar 3 and Ar 4 are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R 13 to R 16 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,

two adjacent *'s of Chemical Formula 3 are C bound to two adjacent *'s of Chemical Formula 4 to provide a fused ring and *'s of not providing the fused ring in Chemical Formula 3 are independently CR a , and

R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or a combination thereof;

wherein the “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group.

11. The composition for an organic optoelectric device as claimed in claim 10 , wherein Ar 1 and Ar 2 of Chemical Formula 2 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 triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolyl group, a substituted or unsubstituted isoquinazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.

12. The composition for an organic optoelectric device as claimed in claim 10 , wherein:

Chemical Formula 2 includes one of structures of Group III, and

the moieties *—Y 1 —Ar 1 and *—Y 2 —Ar 2 of Chemical Formula 2 are independently one of substituents of Group IV,

wherein, in Group III and Group IV, * is a linking point.

13. An organic optoelectric device, comprising:

an anode and a cathode facing each other, and

an organic layer between the anode and the cathode,

wherein the organic layer includes the compound for an organic optoelectric device as claimed in claim 1 .

14. The organic optoelectric device of claim 13 , wherein:

the organic layer includes a light emitting layer, and

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

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

the organic layer further includes a hole transport auxiliary layer adjacent to the light emitting layer, and

the hole transport auxiliary layer includes the compound for an organic optoelectric device.

16. An organic optoelectric device, comprising:

an anode and a cathode facing each other, and

an organic layer between the anode and the cathode,

wherein the organic layer includes the composition for an organic optoelectric device of claim 9 .

17. The organic optoelectric device of claim 16 , 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.

18. The organic optoelectric device as claimed in claim 17 , wherein:

the organic layer further includes a hole transport auxiliary layer adjacent to the light emitting layer, and

the hole transport auxiliary layer includes the composition for an organic optoelectric device.

19. An organic optoelectric device, comprising:

an anode and a cathode facing each other, and

an organic layer between the anode and the cathode,

wherein the organic layer includes the composition for an organic optoelectric device of claim 10 .

20. The organic optoelectric device of claim 19 , 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.

21. The organic optoelectric device as claimed in claim 20 , wherein:

the organic layer further includes a hole transport auxiliary layer adjacent to the light emitting layer, and

the hole transport auxiliary layer includes the composition for an organic optoelectric device.

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 Aug 16, 2017
From: KIM, BYUNGKU; KANG, DONG MIN; KIM, CHANGWOO; OH, JAEJIN; YU, EUN SUN; JANG, YUNA; JUNG, SUNG-HYUN; HONG, JINSEOK
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 043305/0808 →
Priority Claims (1)
KR 10-2016-0125668 · Sep 29, 2016 · national
Continuity (1)
Related Publication 20180090690A1 · Mar 29, 2018