IP Library › Granted Patent US 11,393,991
Granted Patent B2
US 11,393,991 · App. 16/037,937 · Granted Jul 19, 2022

Heterocyclic compound and organic electroluminescence device including the same

Inventors: Daeyup Shin (Suwon-si, KR); Seulong Kim (Cheonan-si, KR); Taekyung Kim (Yongin-si, KR); Jungsub Lee (Hwaseong-si, KR); Soon-ki Kwon (Jinju-si, KR); Yun-hi Kim (Jinju-si, KR); Yeonhee Ha (Jinju-si, KR); Jaeyoung Hwang (Jinju-si, KR)
Assignees: SAMSUNG DISPLAY CO., LTD.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY
H01L51/0094C07D209/86C07D209/88C07D401/14C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14C07D471/14C07D487/14C07D519/00C07F7/0812C07F7/10C09K11/06H01L51/0067H01L51/0072C09K2211/1007C09K2211/1014C09K2211/1018H01L51/5016H01L51/5056H01L51/5072H01L51/5088H01L51/5092
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Quick Facts
Patent No.
US 11,393,991
App. No.
16/037,937
Granted
Jul 19, 2022
Kind
B2
Abstract

Provided are a heterocyclic compound represented by Formula 1 below, and an organic electroluminescence device including the same in an emission layer. In Formula 1, X is a direct linkage or CR 2 R 3 , Z 1 to Z 8 are each independently CR 4 or N, at least two of Z 1 , Z 3 , Z 6 and Z 8 are each independently CR 5 , and R 5 is represented by Formula 2 or Formula 3 below.

Claims (92)

1. A heterocyclic compound represented by the following Formula 1:

wherein in Formula 1,

X is a direct linkage, or CR 2 R 3 ,

Z 1 to Z 8 are each independently CR 4 or N,

each of R 1 to R 4 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,

at least two of Z 1 , Z 3 , Z 6 and Z 8 are independently CR 5 , and

R 5 is represented by the following Formula 2 or Formula 3:

wherein in Formula 2,

Y is a direct linkage, CR 6 R 7 , SiR 8 R 9 , NR 10 , O, S or SO 2 ,

W 1 to W 8 are each independently CR 11 or N, and

each of R 6 to R 11 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,

except that

if Z 1 and Z 3 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 2 or Z 6 and Z 8 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 2 or Z 3 and Z 6 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 2, and

if X in Formula 1 is a direct linkage, and

if W 1 to W 8 in Formula 2 are each CR 11 ,

then Y in Formula 2 is not a direct linkage, and

wherein in Formula 3,

Q is NR 12 , O, or S,

U 1 to U 8 are each independently CR 13 or N,

one of U 1 to U 8 is a connecting part, and

each of R 12 and R 13 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,

except that

if Z 3 and Z 6 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 3, and

if X in Formula 1 is either a direct linkage or CR 2 R 3 wherein R 2 and R 3 are each an alkyl group,

then Q in Formula 3 is not NR 12 .

2. The heterocyclic compound of claim 1 , wherein Z 1 and Z 3 are each independently represented by CR 5 .

3. The heterocyclic compound of claim 2 , wherein Z 6 and Z 8 are each independently CR 4 wherein R 4 is hydrogen, or represented by CR 5 or one of the following structures:

4. The heterocyclic compound of claim 1 , wherein R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, or a substituted or unsubstituted carbazole group.

5. The heterocyclic compound of claim 1 , wherein R 1 is represented by one of the following structures:

6. The heterocyclic compound of claim 1 , wherein

either Z 1 and Z 8 , or Z 3 and Z 6 , are CR 5 , where R 5 is represented by Formula 3, and

if Z 1 and Z 8 are CR 5 , at least one of Z 3 and Z 6 is N, and if Z 3 and Z 6 are CR 5 , at least one of Z 1 and Z 8 is N.

7. The heterocyclic compound of claim 6 , wherein in Formula 3, Q is O, and at least one of U 2 and U 7 is N.

8. The heterocyclic compound of claim 1 , wherein in Formula 2, Y is a direct linkage, and

at least one of W 1 , W 3 , W 6 or W 8 is N.

9. The heterocyclic compound of claim 1 , wherein in Formula 2, Y is a direct linkage, and W 1 and W 3 , or W 6 and W 8 are N.

10. The heterocyclic compound of claim 1 , wherein Formula 1 is represented by the following Formula 5:

wherein in Formula 5,

each R 5 is independently represented by Formula 2 or Formula 3,

R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, or a substituted or unsubstituted carbazole group, and

X, Z 6 and Z 8 are the same as defined in Formula 1,

except that

if each R 5 in Formula 5 is represented by Formula 2 or Z 6 and Z 8 in Formula 5 are each independently CR 5 wherein R 5 is represented by Formula 2 or Z 6 in Formula 5 is CR 5 wherein R 5 is represented by Formula 2 and the R 5 in Formula 5 that is bonded at a para-position to the N in Formula 5 is represented by Formula 2, and

if X in Formula 5 is a direct linkage, and

if W 1 to W 8 in Formula 2 are each CR 11 ,

then Y in Formula 2 is not a direct linkage, and

except that

if Z 6 in Formula 5 is CR 5 wherein R 5 is represented by Formula 3 and the R 5 in Formula 5 that is bonded at a para-position to the N in Formula 5 is represented by Formula 3, and

if X in Formula 1 is either a direct linkage or CR 2 R 3 wherein R 2 and R 3 are each an alkyl group,

then Q in Formula 3 is not NR 12 .

11. The heterocyclic compound of claim 1 , wherein X is a direct linkage, and

a torsional angle of a single bond connecting Formula 1 with Formula 2 or Formula 3 is about 50 degrees or more.

12. The heterocyclic compound of claim 1 , wherein X is CR 2 R 3 , and

a torsional angle of a single bond connecting Formula 1 with Formula 2 or Formula 3 is about 70 degrees or more.

13. The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Formula 1 is one selected from compounds represented in the following Compound Group 1:

14. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region provided on the first electrode;

an emission layer provided on the hole transport region;

an electron transport region provided on the emission layer; and

a second electrode provided on the electron transport region,

wherein the emission layer comprises a heterocyclic compound represented by the following Formula 1:

wherein in Formula 1,

X is a direct linkage, or CR 2 R 3 ,

Z 1 to Z 8 are each independently CR 4 or N,

each of R 1 to R 4 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,

at least two of Z 1 , Z 3 , Z 6 and Z 8 are CR 5 , and

R 5 is represented by the following Formula 2 or Formula 3:

wherein in Formula 2,

Y is a direct linkage, CR 6 R 7 , SiR 8 R 9 , NR 10 , O, S or SO 2 ,

each of W 1 to W 8 is independently CR 11 or N, and

each of R 6 to R 11 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,

except that

if Z 1 and Z 3 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 2 or Z 6 and Z 8 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 2 or Z 3 and Z 6 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 2, and

if X in Formula 1 is a direct linkage, and

if W 1 to W 8 in Formula 2 are each CR 11 ,

then Y in Formula 2 is not a direct linkage, and

wherein in Formula 3,

Q is NR 12 , O, or S,

U 1 to U 8 are each independently CR 13 or N,

one of U 1 to U 8 is a connecting part, and

each of R 12 and R 13 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms for forming a ring,

except that

if Z 3 and Z 6 in Formula 1 are each independently CR 5 wherein R 5 is represented by Formula 3, and

if X in Formula 1 is either a direct linkage or CR 2 R 3 wherein R 2 and R 3 are each an alkyl group,

then Q in Formula 3 is not NR 12 .

15. The organic electroluminescence device of claim 14 , wherein each of Z 1 and Z 3 is independently represented by CR 5 .

16. The organic electroluminescence device of claim 14 , wherein R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, or a substituted or unsubstituted carbazole group.

17. The organic electroluminescence device of claim 14 , wherein the emission layer comprises a host and a dopant, and

the host comprises the heterocyclic compound represented by Formula 1.

18. The organic electroluminescence device of claim 17 , wherein the host is a phosphorescence host or a thermally activated delayed fluorescence host.

19. The organic electroluminescence device of claim 14 , wherein the heterocyclic compound represented by Formula 1 is at least one selected from compounds represented in the following Formula Compound Group 1:

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE INFORMATION PREVIOUSLY RECORDED ON REEL 046569 FRAME 0081. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 23, 2018
From: SHIN, DAEYUP; KIM, SEULONG; KIM, TAEKYUNG; LEE, JUNGSUB; KWON, SOON-KI; KIM, YUN-HI; HA, YEONHEE; HWANG, JAEYOUNG
To: SAMSUNG DISPLAY CO., LTD.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY
Reel/Frame 046922/0795 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2018
From: SHIN, DAEYUP; KIM, SEULONG; KIM, TAEKYUNG; LEE, JUNGSUB; KWON, SOON-KI; KIM, YUN-HI; HA, YEONHEE; HWANG, JAEYOUNG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 046569/0081 →
Priority Claims (1)
KR 10-2017-0097829 · Aug 1, 2017 · national
Continuity (1)
Related Publication 20190044076A1 · Feb 7, 2019
Cited By (2)
US 12,193,320 US 12,543,498