Organic electroluminescent element, compound for use in the element, and light emitting device, display device, and illumination device using the element

Patent metadata

Field	Value
Publication number	US-11563178-B2
Application number	US-201715806660-A
Country	US
Kind code	B2
Filing date	Nov 8, 2017
Priority date	Nov 18, 2011
Publication date	Jan 24, 2023
Grant date	Jan 24, 2023

Abstract

The disclosure relates to organic electroluminescent elements, compounds for use in the elements, and devices using the elements, which include a compound represented by the following General Formula (1):

where R 1 to R 3 and R 6 to R 8 each independently represents a hydrogen atom, which may be a deuterium atom, or a substituent with a Hammett substituent constant σ p value of −0.15 or more, R 5 , R 9 and R 10 each independently represents a hydrogen atom or a substituent, L 1 represents a divalent linking group, DG 1 represents a donor group, and n1 represents 1 or 2, and where R 1 to R 3 , R 5 to R 10 , L 1 , and DG 1 are not bound to each other to form a ring.

First claim

The invention claimed is:

1. An organic electroluminescent element comprising:
a substrate;
a pair of electrodes including an anode and a cathode, disposed on the substrate; and
an organic layer disposed between the electrodes,
wherein the organic layer consists of a single host and at least one light emitting material represented by one of General Formula (5) to General Formula (7)

wherein, in General Formula (5),
R 1 to R 3 and R 6 to R 8 each independently represents a hydrogen atom, which may be a deuterium atom, or a substituent with a Hammett substituent constant σ p value of −0.15 or more,
R 5 and R 10 each independently represents a hydrogen atom or a substituent,
R 11 to R 14 each independently represents an alkyl group, an aryl group or a heteroaryl group,
X 1 to X 6 each independently represents CRz, wherein two adjacent CRzs may jointly form a five- or a six-membered ring, —N═, NRy, O or S, and Rz and Ry each independently represents a hydrogen atom or a substituent,
wherein R 1 to R 3 , R 5 to R 8 , R 10 to R 14 and X 1 to X 6 are not bound to each other to form a ring,
provided that when X 1 is O or S, then one of X 2 and X 3 is —N═ and the other of X 2 and X 3 is CRz; and
provided that when X 4 is O or S, then one of X 5 and X 6 is —N═ and the other of X 5 and X 6 is CRz;

wherein, in General Formula (6),
R 1 to R 3 and R 6 to R 8 each independently represents a hydrogen atom, which may be a deuterium atom, or a substituent with a Hammett substituent constant σ p value of −0.15 or more,
R 5 and R 10 each independently represents a hydrogen atom or a substituent,
R 11 to R 14 each independently represents an alkyl group, an aryl group or a heteroaryl group,
X 11 , X 13 , X 14 and X 16 to X 20 each independently represents CRz, wherein two adjacent CRzs may jointly form a five- or a six-membered ring, —N═, NRy, O or S, and Rz and Ry each independently represents a hydrogen atom or a substituent,
wherein R 1 to R 3 , R 5 to R 8 , R 10 to R 14 , X 11 , X 13 , X 14 and X 16 to X 20 are not bound to each other to form a ring,
provided that X 20 and X 16 are not both S, X 14 and X 19 are not both S, X 13 and X 17 are not both S, and X 11 and X 18 are not both S

wherein, in General Formula (7),
R 1 to R 3 and R 6 to R 8 each independently represents a hydrogen atom, which may be a deuterium atom, or a substituent with a Hammett substituent constant σ p value of −0.15 or more,
R 5 and R 10 each independently represents a hydrogen atom or a substituent,
R 11 to R 14 each independently represents an alkyl group, an aryl group or a heteroaryl group,
R 18 to R 21 each independently represents a hydrogen atom, a fluorine atom, an alkyl group, a silyl group, an aryl group, a heteroaryl group, —NY 21 Y 22 , —OY 23 or —SY 24 , wherein Y 21 to Y 24 each independently represents an alkyl group, an aryl group or a heteroaryl group, and which may have further substituents,
X 31 , X 33 , X 34 and X 36 to X 40 each independently represents CRz, wherein two adjacent CRzs may jointly form a five- or a six-membered ring, —N═, NRy, O or S, and Rz and Ry each independently represents a hydrogen atom or a substituent,
wherein R 1 to R 3 , R 5 to R 8 , R 10 to R 14 , R 18 to R 21 , X 31 , X 33 , X 34 and X 36 to X 40 are not bound to each other to form a ring
provided that at least one of conditions (i) and (ii) is true:
(i) at least one of X 31 , X 33 , X 34 and X 36 to X 40 represents CRz;
(ii) at least one of X 31 , X 33 , X 34 and X 36 to X 40 represents NRy, wherein Ry does not represent methyl or phenyl.

2. The organic electroluminescent element according to claim 1 , wherein in the General Formula (5) to General Formula (7) R 1 to R 3 and R 6 to R 8 each independently represents a hydrogen atom, which may be a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a silyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a halogen atom or a cyano group, and which may have further substituents.

3. The organic electroluminescent element according to claim 1 , wherein the organic layer is a light emitting layer formed by a vacuum deposition process.

4. The organic electroluminescent element according to claim 1 , wherein the organic layer is a light emitting layer formed by a wet process.

5. A device comprising the organic electroluminescent element according to claim 1 , wherein the device is a light emitting device, display device, or illumination device.

6. The electroluminescent element according to claim 1 , wherein the host has a hydrocarbon fused ring structure of 10 to 50 carbon atoms.

7. The electroluminescent element according to claim 6 , wherein the host is a naphthalene-based host, an anthracene-based host, a phenanthrene-based host, a triphenylene-based host, or a pyrene-based host.

8. The electroluminescent element according to claim 7 , wherein the host is an anthracene-based host.

9. The electroluminescent element according to claim 1 , wherein the host is selected from the group consisting of a carbazole or derivative thereof, a dibenzothiophene or derivative thereof, a dibenzofuran or derivative thereof, an arylamine or derivative thereof, and a metal complex.

10. The electroluminescent element according to claim 1 , wherein the organic layer contains light emitting material represented by one of General Formula (5) to General Formula (7) in the amount of 2% to 20% by mass, based on the total mass of the organic layer.

11. The electroluminescent element according to claim 10 , wherein the organic layer contains light emitting material represented by one of General Formula (5) to General Formula (7) in the amount of 3% to 10% by mass, based on the total mass of the organic layer.

Assignees

• Udc Ireland Ltd

Inventors

• Takaku Koji
• Yonekuta Yasunori
• Sotoyama Wataru
• Youfu Katsuyuki
• Hirai Yuki
• Kitamura Tetsu
• Watanabe Toru
• OUYANG Tianhua

Classifications

• H01L51/0067

  Electricity · mapped topic

• C07D307/91

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C07C2603/50

  Pyrenes; Hydrogenated pyrenes · CPC title

• H01L51/0054

  Electricity · mapped topic

• C07D263/48

  Nitrogen atoms not forming part of a nitro radical · CPC title