IP Library › Granted Patent US 10,516,114
Granted Patent B2
US 10,516,114 · App. 15/677,405 · Granted Dec 24, 2019

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); Jun Seok Kim (Suwon-si, KR); Hyung Sun Kim (Suwon-si, KR); Chang Ju Shin (Suwon-si, KR); Eun Sun Yu (Suwon-si, KR); Yuna Jang (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR)
Assignees: Samsung SDI Co., Ltd.; Samsung Electronics Co., Ltd.
H01L51/0072C07D209/86C07D251/24H01L51/0052H01L51/0054H01L51/0067H01L51/0085H01L51/5016H01L51/5056H01L51/5088H01L51/5096H01L51/5206H01L51/5221H01L2251/5384
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Quick Facts
Patent No.
US 10,516,114
App. No.
15/677,405
Granted
Dec 24, 2019
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 (71)

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

wherein, in Chemical Formula 1,

R 1 is a substituted or unsubstituted C6 to C30 aryl group,

R 2 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

R 3 is hydrogen or deuterium,

R 4 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

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

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

2. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is represented by one of Chemical Formula 1-1 to Chemical Formula 1-3:

wherein, in Chemical Formula 1,

R 1 is a substituted or unsubstituted C6 to C30 aryl group,

R 2 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

R 3 is hydrogen or deuterium,

R 4 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

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.

3. The compound for an organic optoelectric device as claimed in 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group,

R 2 and R 4 are independently hydrogen, deuterium, 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, or a substituted or unsubstituted triphenylene group, and

R 3 is hydrogen or deuterium.

4. 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, or a substituted or unsubstituted triphenylene group,

R 3 is hydrogen or deuterium, and

R 4 is hydrogen, deuterium, 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, or a substituted or unsubstituted triphenylene group.

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

R 1 is selected from substituents of Group I,

R 2 and R 4 are independently hydrogen or selected from substituents of Group I:

wherein, in Group I, * is a linking point with an adjacent atom, and

R 3 is hydrogen.

6. The compound for an organic optoelectric device as claimed in claim 1 , wherein Ar 1 and Ar 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 triphenylene group, or a combination thereof.

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

at least one of R 1 and R 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group, and

Ar 1 and Ar 2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl 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:

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

a second compound for an organic optoelectric device represented by Chemical Formula 2:

wherein, in Chemical Formula 2 ,

Z 1 to Z 3 are independently N or CR a , provided that at least two of Z 1 to Z 3 are N,

R a 's are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, wherein the R a 's are independently present or adjacent groups are linked with each other to provide 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,

Ar 3 to Ar 5 are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

L 1 to L 3 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.

10. The composition for an organic optoelectric device as claimed in claim 9 , wherein Chemical Formula 2 is represented by Chemical Formula 2-1, Chemical Formula 2-2, or Chemical Formula 2-3:

wherein, in each of respective Chemical Formulae 2-1 to 2-3,

Z 1 to Z 6 are independently N or CR a , provided that at least two of Z 1 to Z 3 are N and at least two of Z 4 to Z 6 are N,

Ar 3 to Ar 7 are independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R a and R 5 to R 8 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

X is O or S.

11. The composition for an organic optoelectric device as claimed in claim 9 , wherein Ar 3 to Ar 5 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 phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl 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 indolocarbazolyl group, a substituted or unsubstituted indolobenzofuranyl group, a substituted or unsubstituted indolobenzothiophenyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group.

12. An organic optoelectric device, comprising:

an anode and a cathode facing each other, and

an organic layer disposed between the anode and the cathode,

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

13. The organic optoelectric device as claimed in claim 12 , 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.

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

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

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

15. A display device comprising the organic optoelectric device as claimed in claim 12 .

16. An organic optoelectric device, comprising:

an anode and a cathode facing each other, and

an organic layer disposed between the anode and the cathode,

wherein the organic layer includes the composition for an organic optoelectric device as claimed in claim 9 .

17. The organic optoelectric device as claimed in 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 auxiliary layer adjacent to the light emitting layer, and

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

19. A display device comprising the organic optoelectric device as claimed in 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; KIM, JUN SEOK; KIM, HYUNG SUN; SHIN, CHANG JU; YU, EUN SUN; JANG, YUNA; JUNG, SUNG-HYUN
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 043296/0777 →
Priority Claims (1)
KR 10-2016-0125110 · Sep 28, 2016 · national
Continuity (1)
Related Publication 20180090689A1 · Mar 29, 2018