IP Library › Granted Patent US 12,622,134
Granted Patent B2
US 12,622,134 · App. 18/281,336 · Granted May 5, 2026

Organic electroluminescent device, and electronic apparatus

Inventors: Takeshi Yamamoto (Tokyo, JP); Kouki Kase (Tokyo, JP); Eriko Chiba (Tokyo, JP); Yuta Hirayama (Tokyo, JP); Shuichi Hayashi (Tokyo, JP)
Assignee: Hodogaya Chemical Co., Ltd.
H10K50/844H10K50/11H10K50/15H10K50/16H10K50/85H10K85/636H10K85/6576
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 12,622,134
App. No.
18/281,336
Granted
May 5, 2026
Kind
B2
Abstract

An object of the present invention is to provide a compound with a high refractive index and a low extinction coefficient at a wavelength in range of 450 nm to 750 nm in a capping layer to improve light extraction efficiency of an organic electroluminescent device. The present invention was achieved by focusing on the fact that a specific arylamine based compound has excellent thin film stability and durability and is able improve the refractive index by adjusting the molecular structures, and planning molecule, and an organic electroluminescent device having excellent luminous efficiency was obtained by using this compound as a material for constituting a capping layer.

Claims (26)

1 . An organic electroluminescent device in this order including at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode, and a capping layer, and the organic electroluminescent device containing an amine compound as a material of the capping layer represented by the following general formula (1):

wherein Ar 1 and Ar 2 may be the same or different, each has a structure represent by the following general formula (A), and represents a monovalent group having a bonding site at any one of R 5 and R 6 , Ar 3 has a structure represented by the following general formula (A), and represents a monovalent group having a bonding site at any one of R 5 and R 6 , a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, L 1 and L 2 may be the same or different, each represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon group of 6 to 18 ring-forming carbon atoms, or a divalent group of a substituted or unsubstituted aromatic heterocyclic group of 6 to 18 ring-forming carbon atoms, L 3 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon group of 6 to 18 ring-forming carbon atoms, a divalent group of a substituted or unsubstituted aromatic heterocyclic group of 6 to 18 ring-forming carbon atoms, or a single bond,

wherein X represents an oxygen atom, or a sulfur atom, R 1 to R 4 may be the same or different, each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyl group of 5 to 10 carbon atoms that may have a substituent, a linear or branched alkenyl group of 2 to 6 carbon atoms that may have a substituent, a linear or branched alkyloxy group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyloxy group of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aryloxy group, R 1 to R 4 bonded to the same benzene ring may bind to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring, One of R 5 and R 6 represents a linking group as a bonding site, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyl group of 5 to 10 carbon atoms that may have a substituent, a linear or branched alkenyl group of 2 to 6 carbon atoms that may have a substituent, a linear or branched alkyloxy group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyloxy group of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group.

2 . The organic electroluminescent device according to claim 1 , wherein the general formula (A) has a structure represented by the following general formula (A-1):

wherein the dashed part is the binding site, X, R 1 to R 4 , and R 6 are the same as defined by the general formula (A).

3 . The organic electroluminescent device according to claim 1 , wherein the general formula (A) has a structure represented by the following general formula (A-2):

wherein the dashed part is the binding site, X, and R 1 to R 5 R 6 are the same as defined by the general formula (A).

4 . The organic electroluminescent device according to claim 1 , wherein L 1 and L 2 in the general formula (1) are divalent groups that result from the removal of two hydrogen atoms from unsubstituted benzene, divalent groups that result from the removal of two hydrogen atoms from unsubstituted naphthalene, or divalent groups that result from the removal of two hydrogen atoms from unsubstituted biphenyl.

5 . The organic electroluminescent device according to claim 1 , wherein the amine compound represented by the general formula (1) is represented by the following general formula (1-a):

wherein X, Ar 3 , L 3 , R 1 to R 4 , and R 6 are the same as defined by the general formula (1) and the general formula (A).

6 . The organic electroluminescent device according to claim 1 , wherein the amine compound represented by the general formula (1) is represented by the following general formula (1-b),

wherein X, Ar 3 , L 3 , and R 1 to R 5 are the same as defined by the general formula (1) and the general formula (A).

7 . The organic electroluminescent device according to claim 1 , wherein the thickness of the capping layer is within a range of 30 nm to 120 nm.

8 . The organic electroluminescent device according to claim 1 , wherein the refractive index of the capping layer is 1.85 or more within a wavelength range of 450 nm or more and 750 nm or less.

9 . An electronic apparatus comprising the organic electroluminescent device according to claim 1 .

10 . The organic electroluminescent device according to claim 2 , wherein the thickness of the capping layer is within a range of 30 nm to 120 nm.

11 . The organic electroluminescent device according to claim 3 , wherein the thickness of the capping layer is within a range of 30 nm to 120 nm.

12 . The organic electroluminescent device according to claim 4 , wherein the thickness of the capping layer is within a range of 30 nm to 120 nm.

13 . The organic electroluminescent device according to claim 5 , wherein the thickness of the capping layer is within a range of 30 nm to 120 nm.

14 . The organic electroluminescent device according to claim 2 , wherein the refractive index of the capping layer is 1.85 or more within a wavelength range of 450 nm or more and 750 nm or less.

15 . The organic electroluminescent device according to claim 3 , wherein the refractive index of the capping layer is 1.85 or more within a wavelength range of 450 nm or more and 750 nm or less.

16 . The organic electroluminescent device according to claim 4 , wherein the refractive index of the capping layer is 1.85 or more within a wavelength range of 450 nm or more and 750 nm or less.

17 . The organic electroluminescent device according to claim 5 , wherein the refractive index of the capping layer is 1.85 or more within a wavelength range of 450 nm or more and 750 nm or less.

18 . An electronic apparatus comprising the organic electroluminescent device according to claim 2 .

19 . An electronic apparatus comprising the organic electroluminescent device according to claim 3 .

20 . An electronic apparatus comprising the organic electroluminescent device according to claim 4 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2023
From: YAMAMOTO, TAKESHI; KASE, KOUKI; CHIBA, ERIKO; HIRAYAMA, YUTA; HAYASHI, SHUICHI
To: HODOGAYA CHEMICAL CO., LTD.
Reel/Frame 065402/0204 →
Priority Claims (1)
JP 2021-039784 · Mar 12, 2021 · national
Continuity (1)
Related Publication 20240179930A1 · May 30, 2024
References Cited (18)
US 10138201B2 · Kang · 2018 [cited by examiner]
US 20080125609A1 · Vestweber et al. · 2008 [cited by applicant]
US 20200395549A1 · Kase et al. · 2020 [cited by applicant]
US 20210053954A1 · Sun et al. · 2021 [cited by applicant]
US 20220017503A1 · Seok et al. · 2022 [cited by applicant]
US 20220119360A1 · Mochizuki et al. · 2022 [cited by applicant]
US 20220127277A1 · Ham et al. · 2022 [cited by applicant]
CN 111869326A · 2020 [cited by applicant]
JP 2021508729A · 2021 [cited by applicant]
KR 102059550B1 · 2019 [cited by applicant]
KR 20210052311A · 2021 [cited by applicant]
KR 20210128363A · 2021 [cited by applicant]
KR 20210128942A · 2021 [cited by applicant]
TW 202041503A · 2020 [cited by applicant]
WO 2022025647A1 · 2022 [cited by applicant]
WO 2022025648A1 · 2022 [cited by applicant]
WO 2022055321A1 · 2022 [cited by applicant]
The Office Action mailed Jun. 9, 2025, issued for the corresponding Taiwan patent application No. is 111108924. [cited by applicant]