Deuterated organic compound, mixture and composition containing said compound, and organic electronic device

Patent metadata

Field	Value
Publication number	US-10323180-B2
Application number	US-201515532876-A
Country	US
Kind code	B2
Filing date	Dec 3, 2015
Priority date	Dec 4, 2014
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

The present disclosure discloses a deuterated organic compound and a formulation and an organic electronic device containing the same, wherein the deuterated organic compound has the following structural formula:

wherein Ar is an aromatic or heteroaromatic structural unit, D is an electron donor group, A is an electron acceptor group, n and m are an integer between 1 and 6; and wherein for the organic compound, (S1−T1)≤0.25 eV, and at least one H atom of the organic compound is substituted by deuterium. The present disclosure achieves the improvement of the electroluminescence quantum efficiency and the lifetime of the organic compound by replacing the H atom in the organic compound with deuterium and having (S1−T1)≤0.35 eV, and the material of the present disclosure has a great application potential and application range due to its low cost and relatively simple synthesis process.

First claim

What is claimed is:

1. An organic compound having the following structural formula (I):

wherein Ar is an aromatic or heteroaromatic structural unit,
n and m are each an integer between 1 and 6,
D is an electron donor group, wherein when m>1, each D is independently selected from the same or different electron donor groups,
A is an electron acceptor group, wherein when n>1, each A is independently selected from the same or different electron acceptor groups,
wherein for the organic compound, (S1−T1)≤0.35 eV and at least one H atom of the organic compound is substituted by deuterium, and
wherein (S1−T1) refers to a difference between singlet energy level (S1) and triplet energy level (T1).

2. The organic compound according to claim 1 , wherein (S1−T1)≤0.25 eV.

3. The organic compound according to claim 1 , wherein at least one H atom in at least one electron donor group D is substituted by deuterium.

4. The organic compound according to claim 1 , wherein at least one H atom in at least one electron acceptor group A is substituted by deuterium.

5. The organic compound according to claim 1 , wherein at least one H atom in Ar is substituted by deuterium.

6. The organic compound according to claim 1 , wherein the electron donor group D comprises any of the following groups:

7. The organic compound according to claim 1 , wherein the electron acceptor group A is selected from F, cyano, and groups comprising any of the following:

wherein n is an integer between 1 to 3, X 1 -X 8 are selected from CR 1 or N, and at least one of X 1 -X 8 is N, and wherein R 1 is selected from any of the following groups: hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, heteroalkyl, aryl, and heteroaryl.

8. The organic compound according to claim 1 , wherein Ar is selected from any of the following groups:

wherein z is O or S.

9. The organic compound according to claim 1 , wherein more than 20% of the H atoms are substituted by deuterium.

10. The organic compound according to claim 1 , selected from the table listed below, wherein one or more H are substituted by deuterium:

11. A mixture comprising at least one organic compound according to claim 1 and further an organic functional material selected from a hole-injection or hole-transport material, a hole-blocking material, an electron-injection or electron-transport material, an electron-blocking material, an organic host material, a singlet emitter, and a triplet emitter.

12. A formulation comprising an organic compound having the following structural formula (I):

wherein Ar is an aromatic or heteroaromatic structural unit,
n and m are each an integer between 1 and 6,
D is an electron donor group, wherein when m>1, each D is independently selected from the same or different electron donor groups,
A is an electron acceptor group, wherein when n>1, each A is independently selected from the same or different electron acceptor groups,
wherein for the organic compound, (S1−T1)≤0.35 eV and at least one H atom of the organic compound is substituted by deuterium, and at least one organic solvent, and
wherein (S1−T1) refers to a difference between singlet energy level (S1) and triplet energy level (T1).

13. The formulation according to claim 12 , wherein the organic solvent selecting from methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxahexane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthane, indene and/or a mixture thereof.

14. The formulation according to claim 13 , wherein the formulation includes the organic compound with a weight percentage from 0.01 to 20%.

15. The formulation according to claim 13 , wherein the formulation includes the organic compound with a weight percentage from 0.1 to 15%.

16. The formulation according to claim 13 , wherein the formulation includes the organic compound with a weight percentage from 0.2 to 10%.

17. The formulation according to claim 13 , wherein the formulation includes the organic compound with a weight percentage from 0.25 to 5%.

Assignees

• Guangzhou Chinaray Optoelectronic Mat Ltd

Inventors

• Pan Junyou
• Yan Xiaolin
• Huang Hong

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C07D221/20

  Spiro-condensed ring systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0059

  Electricity · mapped topic