IP Library › Granted Patent US 10,096,784
Granted Patent B2
US 10,096,784 · App. 15/677,491 · Granted Oct 9, 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); Jinhyun Lui (Suwon-si, KR); Bum Woo Park (Suwon-si, KR); Eun Sun Yu (Suwon-si, KR); Yuna Jang (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR); Pyeongseok Cho (Suwon-si, KR)
Assignees: Samsung SDI Co., Ltd.; Samsung Electronics Co., Ltd.
H01L51/0072C07D491/048C07D495/04H01L51/0067H01L51/0071H01L51/0073H01L51/0074
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Quick Facts
Patent No.
US 10,096,784
App. No.
15/677,491
Granted
Oct 9, 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 (76)

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

wherein, in Chemical Formula 1,

X is O, S, CR 6 R 7 , or SiR 8 R 9 ,

R 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 2 to R 9 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 is 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 of claim 1 , wherein R 1 is 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 phenanthrenyl group, a substituted or unsubstituted triphenylene 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 benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, or a substituted or unsubstituted phenanthrolinyl group.

3. The compound for an organic optoelectric device of claim 1 , wherein R 1 is selected from substituents of Group I:

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

4. The compound for an organic optoelectric device of claim 1 , wherein X is O or S,

R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl 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,

L is a single bond, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted dibenzofuranpyrimidinylene group, or a substituted or unsubstituted dibenzothiophenepyrimidinylene group,

R 2 to R 5 are 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 naphthyl group, a phenanthrenyl group, a triphenylene group, a fluoranthenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, or triazinyl group.

5. The compound for an organic optoelectric device of claim 1 , wherein the compound is represented by Chemical Formula 1A or Chemical Formula 1B:

wherein, in Chemical Formula 1A and Chemical Formula 1B,

X is O, or S,

ET 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 benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, or a substituted or unsubstituted phenanthrolinyl group,

HT is 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 phenanthrenyl group, a substituted or unsubstituted triphenylene 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, or a substituted or unsubstituted dibenzothiophenyl group,

R 2 to R 9 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 is 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.

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

7. A composition for an organic optoelectric device, comprising

a first compound for an organic optoelectric device being the compound of 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 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 10 to R 15 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 16 to R 19 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 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.

8. The composition for an organic optoelectric device of claim 7 , 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.

9. The composition for an organic optoelectric device of claim 7 , 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.

10. The composition for an organic optoelectric device of claim 9 , wherein:

Chemical Formula 2 includes the structure represented by C-8 of Group III, and

the moieties *—Y 1 —Ar 1 and *—Y 2 —Ar 2 of Chemical Formula 2 are independently represented by one of B-1 to B-4 of Group IV.

11. 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 of claim 1 .

12. The organic optoelectric device of claim 11 , wherein:

the organic layer includes a light emitting layer,

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

13. A display device comprising the organic optoelectric device of claim 11 .

14. A composition for an organic optoelectric device, comprising

a first compound for an organic optoelectric device represented by Chemical Formula 1A; and

a second compound for an organic optoelectric device represented by Chemical Formula 1B:

wherein, in Chemical Formula 1A and Chemical Formula 1B,

X is O, or S,

ET 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 benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, or a substituted or unsubstituted phenanthrolinyl group,

HT is 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 phenanthrenyl group, a substituted or unsubstituted triphenylene 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, or a substituted or unsubstituted dibenzothiophenyl group,

R 2 to R 9 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 is 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.

15. The composition for an organic optoelectric device of claim 14 , wherein:

ET is a substituted or unsubstituted quinazolinyl group,

HT is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

R 2 to R 9 are 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 naphthyl group, a phenanthrenyl group, a triphenylene group, a fluoranthenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, or a triazinyl group.

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 14 .

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. A display device comprising the organic optoelectric device of claim 16 .

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 15, 2017
From: KIM, BYUNGKU; KANG, DONG MIN; LUI, JINHYUN; PARK, BUM WOO; YU, EUN SUN; JANG, YUNA; JUNG, SUNG-HYUN; CHO, PYEONGSEOK
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 043297/0453 →
Priority Claims (1)
KR 10-2016-0120645 · Sep 21, 2016 · national
Continuity (1)
Related Publication 20180083202A1 · Mar 22, 2018