IP Library Granted Patent US 10,844,065
Granted Patent B2
US 10,844,065 · App. 15/963,036 · Granted Nov 24, 2020

Heterocyclic compound, and organic electroluminescence device and organic electroluminescence display device including the same

Inventors: Jimyoung Ye (Suwon-si, KR); Myeongsuk Kim (Hwaseong-si, KR); Seulong Kim (Hwaseong-si, KR); Byeongwook Yoo (Hwaseong-si, KR); Jaehoon Hwang (Seoul, KR); Soo-byung Ko (Yongin-si, KR); Jihwan Yoon (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
C07D487/04C07D403/14C07D409/14C07D413/14C07D417/14C07D487/02H01L51/0061H01L51/0072H01L51/5024H01L27/3213H01L51/0074H01L51/5012
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,844,065
App. No.
15/963,036
Granted
Nov 24, 2020
Kind
B2
Abstract

Provided are a heterocyclic compound represented by Formula 1 and an organic electroluminescence device and an organic electroluminescence display device including the heterocyclic compound represented by Formula 1 in an emission layer. In Formula 1, A is represented by Formula 2, D 1 is represented by Formula 3, and D 2 is represented by Formula 4.

Claims (86)

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

D 1 -A-D 2   Formula 1

wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:

wherein in Formulae 2 to 4,

q and r are each independently an integer of 0 to 3,

p is 0 or 1,

X 1 and X 2 are each independently CR′ or N,

R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,

L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,

Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

at least one of Y 1 or Y 2 is an electron-donating group,

in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:

wherein in Formula 5,

R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and

m is an integer of 0 to 6, and

wherein the heterocyclic compound emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm.

2. The heterocyclic compound of claim 1 , wherein p is 1, and X 1 and X 2 are N.

3. The heterocyclic compound of claim 1 , wherein at least one of Y 1 or Y 2 is represented by one of the above Formula 5, the following Formula 6 or the following Formula 7:

wherein in Formula 6,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,

wherein in Formula 7,

Z is a direct linkage, O, S, or NR 8 ,

R 6 to R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

a and b are each independently an integer of 0 to 4.

4. The heterocyclic compound of claim 1 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

5. The heterocyclic compound of claim 4 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

6. The heterocyclic compound of claim 1 , wherein D 1 and D 2 are symmetric about A.

7. The heterocyclic compound of claim 6 , wherein X 1 and X 2 are the same.

8. The heterocyclic compound of claim 1 , wherein L 1 and L 2 are each independently represented by one of the following Formulae 8-1 to 8-4:

wherein in Formulae 8-2 and 8-3,

W 1 and W 2 are each independently NR 9 , S, or O, and

R 9 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

9. The heterocyclic compound of claim 1 , wherein Y 1 and Y 2 are different from each other.

10. 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:

11. 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:

D 1 -A-D 2   Formula 1

wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:

wherein in Formulae 2 to 4,

q and r are each independently an integer of 0 to 3,

p is 0 or 1,

X 1 and X 2 are each independently CR′ or N,

R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,

L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,

Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

at least one of Y 1 or Y 2 is an electron-donating group,

in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:

wherein in Formula 5,

R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and

m is an integer of 0 to 6,

wherein the emission layer comprises a host and a dopant and emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm, and

wherein the dopant comprises the heterocyclic compound.

12. The organic electroluminescence device of claim 11 , wherein p is 1, and X 1 and X 2 are N.

13. The organic electroluminescence device of claim 11 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

14. The organic electroluminescence device of claim 11 , wherein D 1 and D 2 are symmetric about A.

15. The organic electroluminescence device of claim 11 , wherein the heterocyclic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1:

16. An organic electroluminescence display device, comprising:

a first pixel comprising a first organic light emitting diode which emits first visible rays;

a second pixel comprising a second organic light emitting diode which emits second visible rays;

a third pixel comprising a third organic light emitting diode which emits third visible rays; and

a fourth pixel comprising a fourth organic light emitting diode which emits near-infrared rays;

wherein the fourth organic light emitting diode comprises an emission layer comprising a heterocyclic compound represented by the following Formula 1:

D 1 -A-D 2   Formula 1

wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:

wherein in Formulae 2 to 4,

q and r are each independently an integer of 0 to 3,

p is 0 or 1,

X 1 and X 2 are each independently CR′ or N,

R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,

L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,

Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

at least one of Y 1 or Y 2 is an electron-donating group,

in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:

wherein in Formula 5,

R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and

m is an integer of 0 to 6.

17. The organic electroluminescence display device of claim 16 , wherein the fourth organic light emitting diode emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm.

18. The organic electroluminescence display device of claim 16 , wherein D 1 and D 2 are symmetric about A,

p is 1, X 1 and X 2 are N, and

at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

19. The organic electroluminescence display device of claim 16 , wherein the heterocyclic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2018
From: YE, JIMYOUNG; KIM, MYEONGSUK; KIM, SEULONG; YOO, BYEONGWOOK; HWANG, JAEHOON; KO, SOO-BYUNG; YOON, JIHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 045681/0401 →
Priority Claims (1)
KR 10-2017-0122054 · Sep 21, 2017 · national
Continuity (1)
Related Publication 20190084986A1 · Mar 21, 2019