IP Library Granted Patent US 11,818,950
Granted Patent B2
US 11,818,950 · App. 16/063,156 · Granted Nov 14, 2023

Organic electroluminescence element

Inventors: Masashi Tada (Tokyo, JP); Kazuaki Yoshimura (Tokyo, JP); Atsushi Kawada (Tokyo, JP); Katsuhide Noguchi (Tokyo, JP); Yuta Sagara (Tokyo, JP); Junya Ogawa (Tokyo, JP)
Assignee: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
H10K85/6572C07D487/04C07D519/00C09K11/06C09K2211/1018H10K50/11H10K2101/90
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Quick Facts
Patent No.
US 11,818,950
App. No.
16/063,156
Granted
Nov 14, 2023
Kind
B2
Abstract

Provided is a thermally activated delayed fluorescent organic electroluminescent device having a low driving voltage, high luminous efficiency, and a long lifetime. The organic electroluminescent device includes light-emitting layers between an anode and a cathode opposite to each other, and at least one of the light-emitting layers contains a thermally activated delayed fluorescent material, or the thermally activated delayed fluorescent material and a host material. The thermally activated delayed fluorescent material is represented by the following general formula (1) where A represents an electron-withdrawing group, such as a CN group, and D 1 and D 2 each represent an electron-donating group having an indole ring structure.

Claims (11)

1. An organic electroluminescent device, comprising one or more light-emitting layers between an anode and a cathode opposite to each other, wherein at least one of the light-emitting layers contains a thermally activated delayed fluorescent material represented by the following general formula (1) as a light-emitting dopant:

where D 1 and D 2 each independently represent a nitrogen-containing heterocycle represented by the formula (1a), a ring Y in the formula (1a) of one of D 1 or D 2 is represented by formula (1 a-1), and the ring Y in the formula (1a) of the other of D 1 or D 2 is represented by the formula (1 a-2) or (1 a-3), and when the ring Y is represented by the formula (1 a-2), the ring Y is fused at a position d, and when the ring Y is represented by the formula (1a-3), the ring Y is fused at a position g, h, or i, X 1 and X 2 each independently represent O, S, or N—R 6 , R 1 to R 6 each independently represent an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms, A represents a cyano group, a, b, c, and e each independently represent an integer of from 0 to 4, and f represents an integer of from 0 to 2.

2. An organic electroluminescent device according to claim 1 , wherein the ring Y in the formula (1a) of the other of D 1 or D 2 is represented by the formula (1a-3).

3. An organic electroluminescent device according to claim 2 , wherein X 2 in the formula (1a-3) represents N—R 6.

4. An organic electroluminescent device according to any one of claims 1 , 2 and 3 , wherein the light-emitting layer containing the thermally activated delayed fluorescent material contains a host material.

5. An organic electroluminescent device according to claim 4 , wherein the host material comprises a compound represented by the following general formula (2):

where L represents a p-valent group produced from benzene, dibenzofuran, dibenzothiophene, carborane, or a compound obtained by linking two or three of groups selected each independently from benzene, dibenzofuran, dibenzothiophene, and carborane, p represents an integer of 1 or 2, and q represents an integer of from 0 to 4, provided that when L represents a p-valent group produced from a single benzene, q represents an integer of from 1 to 4.

6. An organic electroluminescent device according to claim 5 , wherein the host material includes a first host and a second host selected from compounds each having a singlet excitation energy (S 1) larger than that of the first host, and at least one of the first host or the second host comprises a compound represented by the general formula (2).

7. An organic electroluminescent device according to claim 5 , wherein the light-emitting layer contains at least two kinds of host materials each represented by the general formula (2).

8. An organic electroluminescent device according to claim 4 , wherein an ionization potential of the thermally activated delayed fluorescent material is smaller than an ionization potential of the host material.

9. An organic electroluminescent device according to claim 1 , wherein the thermally activated delayed fluorescent material has an emission maximum wavelength in a range of from 440 nm to 470 nm.

Assignments (3)
CHANGE OF ADDRESS Recorded Nov 13, 2019
From: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
Reel/Frame 050998/0200 →
CHANGE OF NAME Recorded Dec 18, 2018
From: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
Reel/Frame 047805/0595 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2018
From: TADA, MASASHI; YOSHIMURA, KAZUAKI; KAWADA, ATSUSHI; NOGUCHI, KATSUHIDE; SAGARA, YUTA; OGAWA, JUNYA
To: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
Reel/Frame 046104/0485 →