Pyrene-triazine derivative and applications thereof in organic electronic component

Patent metadata

Field	Value
Publication number	US-11672174-B2
Application number	US-201716467423-A
Country	US
Kind code	B2
Filing date	Dec 8, 2017
Priority date	Dec 8, 2016
Publication date	Jun 6, 2023
Grant date	Jun 6, 2023

Abstract

A pyrene-triazine compound, a mixture containing same, a formulation, an organic electronic component, and applications. The pyrene-triazine compound comprises a triazine structure of three strong electron affinity nitrogen atoms and a pyrene fused ring structure. Because the triazine structure has great optoelectronic performance and a planar structured pyrene derivative has great carrier transport performance and optoelectronic performance, the application of the pyrene-triazine compound in the organic electronic component produces a light-emitting component having high efficiency and an extended service life.

First claim

What is claimed is:

1. A pyrene-triazine compound represented by general formula (1):

wherein
Ar 1 and Ar 3 each is a heterocyclic aromatic group having a nitrogen atom selected from the following structures:

Ar 2 and Ar 4 are selected from the following structures:

X is CR 13 or N, but two adjacent X are not simultaneously N; R 1 to R 7 and R 13 are selected from group consisting of H, D, F, —CN, —NO 2, —CF 3, alkenyl, alkynyl, amino, acyl, amide group, cyano, isocyano, alkoxy, hydroxy, carbonyl, sulfonyl, an alkyl group containing 1 to 60 carbon atoms, a cycloalkyl group containing 3 to 60 carbon atoms, an aromatic group containing 6 to 60 carbon atoms, and a heterocyclic aromatic group containing 3 to 60 carbon atoms; and
m, n, p, and q are integers from 0 to 20.

2. A mixture comprising the pyrene-triazine compound of claim 1 , and at least one organic solvent or at least one organic functional material, which is selected from a hole injection material, a hole transport material, a hole blocking material, an electron injection material, an electron transport material, an electron blocking material, a light-emitting host material, a fluorescent emitter, a phosphorescent emitter, a thermally activated delayed fluorescent material or an organic dye.

3. An organic electronic device comprising the pyrene-triazine compound of claim 1 .

4. The organic electronic device according to claim 3 , wherein the organic electronic device is an organic light emitting diode, an organic photovoltaic cell, an organic light-emitting electrochemical cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor or an organic plasmon emitting diode.

5. The organic electronic device according to claim 3 , wherein the organic electronic device is an organic electroluminescence device, and the organic electronic device comprises an electron transport layer, an electron injection layer or a light-emitting layer, the electron transport layer, the electron injection layer or the light-emitting layer comprising the pyrene-triazine compound.

6. The pyrene-triazine compound according to claim 1 , wherein the lowest unoccupied molecular orbital energy level (LUMO) is less than or equal to −3.05 eV.

7. The pyrene-triazine compound according to claim 1 , wherein the highest occupied molecular orbital energy level (HOMO) is less than or equal to −6.0 eV.

8. The pyrene-triazine compound according to claim 1 , wherein the triplet excited state energy level (T1) is greater than or equal to 1.8 eV.

9. The pyrene-triazine compound according to claim 1 , wherein the ΔHOMO is greater than or equal to 0.5 eV, Δ HOMO=|(HOMO−1)−HOMO|, (HOMO−1) represents the second highest occupied molecular orbital energy level, HOMO represents the highest occupied molecular orbital energy level.

Assignees

• Guangzhou Chinaray Optoelectronic Mat Ltd

Inventors

• Hu Guang
• Yang Xi
• Pan Junyou

Classifications

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• Y02P70/50

  Manufacturing or production processes characterised by the final manufactured product · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title

• H10K85/656 Primary

  comprising two or more different heteroatoms per ring (H10K85/652 takes precedence) · CPC title