IP Library › Granted Patent US 10,193,081
Granted Patent B2
US 10,193,081 · App. 14/864,288 · Granted Jan 29, 2019

Organic compound for optoelectric device and composition for optoelectric device and organic optoelectric device and display device

Inventors: Hyung-Sun Kim (Suwon-si, KR); Young-Kwon Kim (Suwon-si, KR); Dong-Wan Ryu (Suwon-si, KR); Youn-Hwan Kim (Suwon-si, KR); Eun-Sun Yu (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR)
Assignee: Samsung SDI Co., Ltd.
H01L51/0072C07D209/86C09K11/025C09K11/06H01L51/0054H01L51/0067C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/185H01L51/0059H01L51/0085H01L51/5016H01L51/5064H01L2251/5384
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Quick Facts
Patent No.
US 10,193,081
App. No.
14/864,288
Granted
Jan 29, 2019
Kind
B2
Abstract

Disclosed are a first compound for an organic optoelectric device represented by a combination of Chemical Formula I-1 and Chemical Formula I-2 and a composition for an organic optoelectric device including the first compound for an organic optoelectric device and at least one second compound for an organic optoelectric device having a moiety represented by Chemical Formula II, and an organic optoelectric device and a display device including the same. Chemical Formula I-1, Chemical Formula I-2 and Chemical Formula II are the same as described in the detailed description.

Claims (87)

1. A compound for an organic optoelectric device, the compound represented by a combination of Chemical Formula I-1 and Chemical Formula I-2 linked together:

wherein, in Chemical Formulae I-1 and I-2,

Y 1 to Y 8 are independently C or CR a ,

W 1 is N or NR b ,

one of Y 1 to Y 8 and W 1 of Chemical Formula I-2 is linked to L 1 of Chemical Formula I-1,

R 1 to R 12 , R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

L 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, and

n1 is an integer of 1 to 3,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

2. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is represented by Chemical Formulae I-A to I-E:

wherein, in Chemical Formulae I-A to I-E,

R 1 to R 12 and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

L 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, and

n1 is an integer of 1 to 3,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

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

wherein, in Chemical Formulae I-2a to I-2h,

Y 1 to Y 8 are independently C or CR a ,

W 1 is N or NR b ,

one of Y 1 to Y 8 and W 1 is linked to L 1 of Chemical Formula I-1,

R 6 to R 12 , R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

4. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is represented by Chemical Formulae I a to I e:

wherein, in Chemical Formulae I a to I e,

R 1 to R 12 and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

L 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, and

n1 is an integer of 1 to 3,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

5. The compound for an organic optoelectric device as claimed in claim 1 , wherein the L 1 is a substituted or unsubstituted phenylene listed in Group 1:

wherein, in Group 1,

indicates a linking point,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

6. The compound for an organic optoelectric device as claimed in claim 1 , wherein the compound is listed in Group 2:

7. A composition for an organic optoelectric device, the composition comprising

a first compound, the first compound being the compound for an organic optoelectric device as claimed in claim 1 , and

at least one second compound for an organic optoelectric device having a moiety represented by Chemical Formula II

wherein, in Chemical Formula II,

each Z is independently N, C or CR c , provided that at least one of Z is N,

R 13 to R 16 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a halogen, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, or a combination thereof,

L 2 to L 5 are each 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,

n2 to n5 are each independently one of integers of 0 to 5, and

indicates a linking point,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

8. The composition for an organic optoelectric device as claimed in claim 7 , wherein the second compound for an organic optoelectric device is represented by Chemical Formula II-A, or Chemical Formula II-B:

wherein, in Chemical Formulae II-A and II-B,

each Z is independently N, C or CR c , provided that at least one of Z is N,

X 1 to X 12 are each independently N, C or CR d ,

L 2 to L 8 are each 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,

n2 to n8 are each independently one of integers of 0 to 5, and

R 13 to R 18 , R c and R d are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heteroaryl group, or a combination thereof,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

9. The composition for an organic optoelectric device as claimed in claim 8 , wherein the second compound for an organic optoelectric device represented by Chemical Formula II-A is represented by Chemical Formula II-A1 or Chemical Formula II-A2:

wherein in Chemical Formula II-A 1 and II-A2,

each Z is independently N, C or CR c , provided that at least one of Z is N,

X 1 to X 12 are each independently N or CR d ,

R 13 to R 16 , R c and R d are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,

n2 to n6 are each independently 0 or 1,

n2+n3+n4+n5+n6≥1,

L 2 to L 5 are each 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

L 6 is a substituted or unsubstituted phenylene group 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 listed in Group 3,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group,

wherein in Group 3,

R 100 to R 127 are each independently hydrogen, deuterium, a C1 to C10 alkyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, an amine group, a C6 to C30 arylamine group, a C2 to C30 heteroarylamine group, a C1 to C30 alkoxy group, a halogen, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group or a combination thereof.

10. The composition for an organic optoelectric device as claimed in claim 8 , wherein the second compound for an organic optoelectric device represented by Chemical Formula II-A is one of compounds of Group 4:

11. The composition for an organic optoelectric device as claimed in claim 8 , wherein the second compound for an organic optoelectric device represented by Chemical Formula II-B is represented by at least one of Chemical Formula II-b1 to Chemical Formula II-b7:

wherein, in Chemical Formulae II-b1 to II-b7,

each Z is independently N, C or CR c , provided that at least one of Z is N,

each W 2 is independently N, C or CR e , and

R 15a to R 18a , R c and R e are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

12. The composition for an organic optoelectric device as claimed in claim 8 , wherein the second compound for an organic optoelectric device represented by Chemical Formula II-B is one of compounds of Group 6:

13. The composition for an organic optoelectric device as claimed in claim 7 , wherein the composition further comprises a phosphorescent dopant.

14. An organic optoelectric device comprising

an anode and a cathode facing each other, and

at least one 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 .

15. The organic optoelectric device as claimed in claim 14 , wherein the organic layer comprises an emission layer,

the emission layer comprises the compound for an organic optoelectric device.

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

the compound for an organic optoelectric device is a host of the emission layer, or

the organic layer further comprises a hole transport auxiliary layer, and the compound for an organic optoelectric device is in the hole transport auxiliary layer.

17. A display device comprising the organic optoelectric device as claimed in claim 14 .

18. An organic optoelectric device comprising

an anode and a cathode facing each other, and

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

wherein the organic layer includes the composition for an organic optoelectric device as claimed in claim 7 .

19. A display device comprising the organic optoelectric device as claimed in claim 18 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2015
From: KIM, HYUNG-SUN; KIM, YOUNG-KWON; RYU, DONG-WAN; KIM, YOUN-HWAN; YU, EUN-SUN; JUNG, SUNG-HYUN
To: SAMSUNG SDI CO., LTD.
Reel/Frame 036649/0797 →
Priority Claims (1)
KR 10-2014-0150601 · Oct 31, 2014 · national
Continuity (1)
Related Publication 20160126477A1 · May 5, 2016