IP Library › Granted Patent US 11,223,019
Granted Patent B2
US 11,223,019 · App. 16/285,617 · Granted Jan 11, 2022

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

Inventors: Jinhyun Lui (Suwon-si, KR); Changwoo Kim (Suwon-si, KR); Dong Wan Ryu (Suwon-si, KR); Chang Ju Shin (Suwon-si, KR); Hyung Sun Kim (Suwon-si, KR); Seungjae Lee (Suwon-si, KR); Jihun Shin (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR); Ho Kuk Jung (Suwon-si, KR)
Assignee: Samsung SDI Co., Ltd.
H01L51/0067C07D405/14H01L51/0072H01L51/0073H01L51/0085H01L51/5012H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 11,223,019
App. No.
16/285,617
Granted
Jan 11, 2022
Kind
B2
Abstract

Disclosed are the compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1, a composition for an organic optoelectronic device including the compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. In Chemical Formula 1, each substituent is the same as defined in the specification.

Claims (59)

1. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes a light emitting layer, and the light emitting layer includes:

a first compound and a second compound, wherein the first compound and the second compound are each a host material for a phosphorescent dopant, wherein:

the first compound is represented by Chemical Formula 1-2, and

the second compound is represented by Chemical Formula 2; or a combination of Chemical Formula 3 and Chemical Formula 4,

wherein in Chemical Formula 1-2,

R 1 to R 4 are each hydrogen,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a group represented by Chemical Formula A, provided that at least one of Ar 1 and Ar 2 is a group represented by Chemical Formula A:

wherein, in Chemical Formula A,

X 1 is 0 or S,

R 5 to R 7 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C6 alkyl group, or a substituted or unsubstituted phenyl group, and

* is a linking point,

wherein, in Chemical Formula 2,

Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group,

R a and R 8 to R 11 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

m is 0, 1, or 2;

wherein, in Chemical Formulae 3 and 4,

Y 3 and Y 4 are each independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

adjacent two *'s of Chemical Formula 3 are C bonded with Chemical Formula 4,

other adjacent two of Chemical Formula 3 not being bonded with Chemical Formula 4 * are each independently C-L a -R b ,

L a , L 3 , and L 4 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

R b and R 12 to R 15 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

2. The organic optoelectronic device of claim 1 , wherein, in Chemical Formula 1-2, one of Ar 1 and Ar 2 is the group represented by Chemical Formula A and the other of Ar 1 and Ar 2 is a substituted or unsubstituted C6 to C30 aryl group.

3. The composition for an organic optoelectronic device of claim 1 , wherein, in Chemical Formula 1-2, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or the group represented by Chemical Formula A.

4. The organic optoelectronic device of claim 1 , wherein, in Chemical Formula 1-2, Ar 1 and Ar 2 are each independently one of groups of Group I:

Wherein, in Group I, * is a linking point.

5. The organic optoelectronic device of claim 1 , wherein the first compound is one of the compounds of Group 1 :

6. The organic optoelectronic device of claim 1 , wherein:

the second compound is represented by Chemical Formula 2, and Chemical Formula 2 is one of structures of Group II in which each * represents a linking point to a * in one of substituents of Group

Wherein, in Group II and Group III, * is a linking point.

7. The organic optoelectronic device of claim 6 , wherein Chemical Formula 2 is Chemical Formula C-8 or Chemical Formula C-17 of Group II in which each represents a linking point to a* in one of the substituents of Group III.

8. The organic optoelectronic device of claim 7 , wherein Chemical Formula 2 is Chemical Formula C-8 or Chemical Formula C-17 of Group II in which each * represents a linking point to a* in one of B-1, B-2, and B-3 of Group III.

9. The organic optoelectronic device of claim 1 , wherein:

the second compound is represented by Chemical Formula 2, and

Chemical Formula 2 is represented by Chemical Formula 2A:

Wherein, in Chemical Formula 2A,

Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group,

R 8 to R 11 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

10. The organic optoelectronic device of claim 1 , wherein:

the second compound is represented by a combination of Chemical Formula 3 and Chemical Formula 4, and

the second compound represented by a combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C:

wherein, in Chemical Formula 3C,

Y 3 and Y 4 are each independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

L a to La 2 , L 3 and L 4 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

R b1 to R b2 and R 12 to R 15 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

11. The organic optoelectronic device of claim 10 , wherein:

Y 3 and Y 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

R b1 to R b2 and R 12 to R 15 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

12. The organic optoelectronic device of claim 10 , wherein Y 3 and Y 4 are each independently selected from substituents cf Group IV:

Wherein in Group IV,

* is a linking point with L 3 and L 4 .

13. The organic optoelectronic device of claim 1 , wherein:

The second compound is represented by Chemical Formula 2A or Chemical Formula 3C:

wherein, in Chemical Formula 2A and Chemical Formula 3C,

Y 1 to Y 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

L 1 to L 4 , L a1 and L a2 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

R b1 , R b2 , and R 8 to R 15 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

14. A display device comprising the organic optoelectronic device of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2019
From: LUI, JINHYUN; KIM, CHANGWOO; RYU, DONG WAN; SHIN, CHANG JU; KIM, HYUNG SUN; LEE, SEUNGJAE; SHIN, JIHUN; JUNG, SUNG-HYUN; JUNG, HO KUK
To: SAMSUNG SDI CO., LTD.
Reel/Frame 048439/0239 →
Continuity (3)
Continuation 16269700 · Feb 7, 2019
Continuation In Part PCTKR2018006794 · Jun 15, 2018
Related Publication 20190198771A1 · Jun 27, 2019