IP Library Granted Patent US 12,289,992
Granted Patent B2
US 12,289,992 · App. 17/250,808 · Granted Apr 29, 2025

Display apparatus and light absorber included in display apparatus

Inventors: Sanghyun Han (Hwaseong-si, KR); Jongwoo Kim (Hwaseong-si, KR); Eunjae Jeong (Hwaseong-si, KR); Dongjun Kim (Suwon-si, KR); Wonmin Yun (Yongin-si, KR); Young Kook Kim (Suwon-si, KR); Eung Seok Park (Seoul, KR); Yongchan Ju (Yongin-si, KR); Yisu Kim (Seoul, KR); Byoungduk Lee (Seongnam-si, KR); Seokhwan Hwang (Suwon-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/654C07D239/34C07D251/22C07D405/04H10K50/8445H10K50/865H10K85/615H10K85/622H10K85/623H10K85/6574H10K59/35H10K59/38
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Quick Facts
Patent No.
US 12,289,992
App. No.
17/250,808
Granted
Apr 29, 2025
Kind
B2
Abstract

A display apparatus according to an embodiment includes light-emitting devices and an encapsulation member, wherein the encapsulation member includes a light absorber including a hexagonal heterocycle containing two or more nitrogen atoms as ring-forming atoms, and first to third substituents substituted at the hexagonal heterocycle, the first to third substituents being different from one another, and thus can effectively block external light, thereby exhibiting improved reliability.

Claims (103)

1. A display apparatus comprising:

a light-emitting device comprising a first electrode, a second electrode facing the first electrode, and a plurality of organic layers between the first electrode and the second electrode; and

an encapsulation member on the light-emitting device and comprising a light absorber,

wherein the light absorber comprises a hexagonal heterocycle comprising two or more nitrogen atoms as ring-forming atoms, and first to third substituents substituted at the hexagonal heterocycle, the first to third substituents being different from one another,

the first substituent is a substituted phenyl group comprising at least one hydroxyl group, and

the second substituent is a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted pyrene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted dibenzofuran derivative, a substituted or unsubstituted carbazole derivative, or a substituted or unsubstituted fluorene derivative,

wherein a substituent of the substituted or unsubstituted dibenzofuran derivative, a substituent of the substituted or unsubstituted carbazole derivative, and a substituent of the substituted or unsubstituted fluorene derivative are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or adjacent groups are bonded to each other to form a ring, and

wherein when the hexagonal heterocycle comprises three nitrogen atoms as ring-forming atoms, then the third substituent is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms.

2. The display apparatus of claim 1 , wherein the encapsulation member comprises at least one organic film and at least one inorganic film, and the at least one organic film comprises the light absorber.

3. The display apparatus of claim 2 , wherein the at least one organic film and the at least one inorganic film are alternately laminated, and

the at least one organic film comprises:

a first organic film to absorb light in a first wavelength region; and

a second organic film to absorb light in a second wavelength region different from the light in the first wavelength region.

4. The display apparatus of claim 1 , wherein the encapsulation member covers the light-emitting device.

5. The display apparatus of claim 1 , further comprising a polarizing member on the encapsulation member.

6. The display apparatus of claim 1 , wherein the encapsulation member comprises:

a first inorganic film adjacent to the second electrode;

a second inorganic film on the first inorganic film; and

an organic film between the first inorganic film and the second inorganic film, the organic film comprising the light absorber,

wherein the organic film has a transmittance of 10% or less at about 405 nm wavelength, a transmittance of 70% or more at about 430 nm wavelength, and a transmittance of 97% or more at about 450 nm wavelength.

7. The display apparatus of claim 1 , wherein the plurality of organic layers comprises:

a hole transport region on the first electrode;

an emission layer on the hole transport region; and

an electron transport region on the emission layer.

8. The display apparatus of claim 1 , further comprising a light blocking layer on the encapsulation member.

9. The display apparatus of claim 1 , wherein the hexagonal heterocycle is triazine or pyrimidine.

10. The display apparatus of claim 1 , wherein the first substituent is represented by at least one among Formulae H1 to H5:

and

wherein R, in Formulae H4 and H5, is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

11. The display apparatus of claim 1 , wherein the light absorber is represented by Formula 1 or Formula 2:

and

wherein, in Formula 1 and Formula 2,

Ar is a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted pyrene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted dibenzofuran derivative, a substituted or unsubstituted carbazole derivative, or a substituted or unsubstituted fluorene derivative,

a substituent of the substituted or unsubstituted dibenzofuran derivative, a substituent of the substituted or unsubstituted carbazole derivative, and a substituent of the substituted or unsubstituted fluorene derivative are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or adjacent groups are bonded to each other to form a ring, and

R 2 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms,

in Formula 1, two among Y 1 to Y 3 are N and the remaining one among Y 1 to Y 3 is CH, and

R 1 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, and

in Formula 2, X is O or S, and

R 6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

12. The display apparatus of claim 11 , wherein Formula 1 is represented by at least one among Formula 1-1 to Formula 1-4:

wherein, in Formula 1-1 to Formula 1-4, Ar, Y 1 to Y 3 , R 1 , and R 4 are the same as defined in Formula 1.

13. The display apparatus of claim 11 , wherein Formula 2 is represented by at least one among Formula 2-1 to Formula 2-4:

and

wherein, in Formula 2-1 to Formula 2-4, X, Ar, R 4 , and R 6 are the same as defined in Formula 2.

14. The display apparatus of claim 11 , wherein Ar is represented by at least one among Ar-a to Ar-h:

and

wherein, in Ar-e to Ar-h, Z is O, S, NR a , or CR b R c , and

R a to R c are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

in Ar-a to Ar-h, R 11 to R 18 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

m1 to m8 are each independently an integer of 0 to 4.

15. The display apparatus of claim 11 , wherein Formula 1 is represented by at least one among Formula 1-A to Formula 1-C:

and

wherein, in Formula 1-A to Formula 1-C, Y 1 to Y 3 , Ar, and R 1 to R 5 are the same as defined in Formula 1.

16. The display apparatus of claim 1 , wherein the light absorber comprises at least one among the compounds represented by Compound Group 1 and Compound Group 2:

17. A display apparatus comprising:

a light-emitting device comprising a first electrode, a second electrode facing the first electrode, and a plurality of organic layers between the first electrode and the second electrode; and

an encapsulation member on the light-emitting device and comprising an organic film comprising a light absorber,

wherein the organic film has a transmittance of 10% or less at about 405 nm wavelength, a transmittance of 70% or more at about 430 nm wavelength, and a transmittance of 97% or more at about 450 nm wavelength,

the light absorber comprises a hexagonal heterocycle comprising two or more N atoms as ring-forming atoms, and first to third substituents substituted at the hexagonal heterocycle, the first to third substituents being different from one another,

the second substituent is substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted pyrene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted dibenzofuran derivative, a substituted or unsubstituted carbazole derivative, or a substituted or unsubstituted fluorene derivative,

a substituent of the substituted or unsubstituted dibenzofuran derivative, a substituent of the substituted or unsubstituted carbazole derivative, and a substituent of the substituted or unsubstituted fluorene derivative are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or adjacent groups are bonded to each other to form a ring, and

when the hexagonal heterocycle comprises three N atoms as ring-forming atoms, then the third substituent is a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group.

18. The display apparatus of claim 17 , wherein the hexagonal heterocycle is triazine or pyrimidine.

19. The display apparatus of claim 17 , wherein the first substituent is a substituted phenyl group comprising at least one hydroxyl group.

20. The display apparatus of claim 17 , wherein the first substituent is represented by at least one among Formulae H1 to H5:

and

wherein R in Formulae H4 and H5 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

21. The display apparatus of claim 17 , wherein the second substituent is represented by at least one among Ar-a to Ar-h:

and

wherein, in Ar-e to Ar-h, Z is O, S, NR a , or CR b R c , and

R a to R c are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

in Ar-a to Ar-h, R 11 to R 18 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

m1 to m8 are each independently an integer of 0 to 4.

22. The display apparatus of claim 17 , wherein the third substituent is represented by at least one among S1 to S15:

23. The display apparatus of claim 17 , wherein the light absorber comprises at least one among the compounds represented by Compound Group 1 and Compound Group 2:

24. A light absorber represented by Formula 1 or Formula 2:

and

wherein, in Formula 1 and Formula 2,

Ar is a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted pyrene group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted dibenzofuran derivative, a substituted or unsubstituted carbazole derivative, or a substituted or unsubstituted fluorene derivative,

a substituent of the substituted or unsubstituted dibenzofuran derivative, a substituent of the substituted or unsubstituted carbazole derivative, and a substituent of the substituted or unsubstituted fluorene derivative are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or adjacent groups are bonded to each other to form a ring, and

R 2 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms,

in Formula 1, two among Y 1 to Y 3 are N and the remaining one among Y 1 to Y 3 is CH,

R 1 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, and

in Formula 2, X is O or S, and

R 6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

25. The light absorber of claim 24 , wherein Formula 1 is represented by at least one among Formula 1-1 to Formula 1-4:

and

wherein, in Formula 1-1 to Formula 1-4, Ar, Y 1 to Y 3 , R 1 , and R 4 are the same as defined in Formula 1.

26. The light absorber of claim 24 , wherein Formula 2 is represented by at least one among Formula 2-1 to Formula 2-4:

and

wherein, in Formula 2-1 to Formula 2-4, X, Ar, R 4 , and R 6 are the same as defined in Formula 1 and Formula 2.

27. The light absorber of claim 24 , wherein Formula 1 is represented by at least one among Formula 1-A to Formula 1-C:

and

wherein, in Formula 1-A to Formula 1-C, Y 1 to Y 3 , Ar, and R 1 to R 5 are the same as defined in Formula 1.

28. The light absorber of claim 24 , wherein Ar is represented by at least one among Ar-a to Ar-h:

and

wherein, in Ar-e to Ar-h, Z is O, S, NR a , or CR b R c , and

R a to R c are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

in Ar-a to Ar-h, R 11 to R 18 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

m1 to m8 are each independently an integer of 0 to 4.

29. The light absorber of claim 24 , wherein Ar is an unsubstituted anthracene, an unsubstituted phenanthrene, an unsubstituted pyrene, or an unsubstituted chrysene.

30. The light absorber of claim 24 , wherein R 1 is represented by at least one among S1 to S15:

31. The light absorber of claim 24 , wherein the light absorber represented by Formula 1 is at least one among the compounds represented by Compound Group 1 and Compound Group 2:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2021
From: HAN, SANGHYUN; KIM, JONGWOO; JEONG, EUNJAE; KIM, DONGJUN; YUN, WONMIN; KIM, YOUNG KOOK; PARK, EUNG SEOK; JU, YONGCHAN; KIM, YISU; LEE, BYOUNGDUK; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 055500/0739 →
Priority Claims (4)
KR 10-2018-0118701 · Oct 5, 2018 · national
KR 10-2018-0118704 · Oct 5, 2018 · national
KR 10-2018-0118707 · Oct 5, 2018 · national
KR 10-2019-0020685 · Feb 21, 2019 · national
Continuity (1)
Related Publication 20220158099A1 · May 19, 2022
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