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Novel hole injection and hole transport compound and organic light-emitting element comprising same

A technology of hole transport and hole injection, which is applied in the direction of household components, electrical components, luminescent materials, etc., can solve the problems of low efficiency, high driving voltage, short life, etc., and achieve excellent hole transport characteristics, high efficiency, excellent The effect of low voltage

Active Publication Date: 2016-09-07
DONGJIN SEMICHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] A large number of amine derivatives having a carbazole skeleton have been studied so far as hole injection / hole transport materials used in such organic light-emitting devices, but they have been limited in practical use due to high driving voltage, low efficiency, and short lifetime. there are many difficulties

Method used

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  • Novel hole injection and hole transport compound and organic light-emitting element comprising same
  • Novel hole injection and hole transport compound and organic light-emitting element comprising same
  • Novel hole injection and hole transport compound and organic light-emitting element comprising same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0164] Embodiment 1: the synthesis of compound 1

[0165]

[0166]

[0167] 20.0g of 4-bromo-N,N-diphenylaniline, 20.36g of bis(pinacolate) diboron, 0.2g of Pd(dppf)Cl 2 18.1 g of KOAc was dissolved in 400 ml of toluene, and stirred under reflux. The reaction was confirmed by TLC, and water was added, and then the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and purified on a column to obtain 19.5 g of intermediate OP1 (yield 85%).

[0168] In a round bottom flask, 4.0 g of the above intermediate 1A-1, 3.7 g of OP1 were dissolved in 70 ml of toluene, and 12 ml of K 2 CO 3 (2M) and 0.3g of Pd(PPh 3 ) 4 , and then reflux stirring. The reaction was confirmed by TLC, and water was added, and then the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and purified on a column to obtain 2.0 g of compound 1 (yield 72%).

[0169] m / z: 644.28 (100.0%), 645.29 (51.3%), 646...

Embodiment 2

[0170] Embodiment 2: the synthesis of compound 2

[0171]

[0172] Compound 2 was synthesized by the same method as Compound 1 except that Intermediate 2A-1 was used instead of Intermediate 1A-1 (yield 64%).

[0173] m / z: 694.30 (100.0%), 695.30 (56.4%), 696.31 (15.2%), 697.31 (2.8%)

Embodiment 3

[0174] Embodiment 3: the synthesis of compound 3

[0175]

[0176] Using N-(4-bromophenyl)-N-phenylnaphthalene-1-amine instead of 4-bromo-N,N-diphenylaniline for the reaction, synthesized by the same method as OP1 OP2 (60% yield).

[0177] Compound 3 was synthesized by the same method as Compound 1 except that Intermediate 2A-1 and OP2 were reacted (yield 68%).

[0178] m / z: 744.31 (100.0%), 745.32 (60.0%), 746.32 (17.9%), 747.32 (3.6%)

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Abstract

A hole injection and hole transport compound according to the present invention has a HOMO energy level facilitating hole injection, high LUMO energy level capable of blocking electrons, a superb hole transport characteristic, and when applied to a hole injection layer or hole transport layer of an organic light-emitting element, can impart stability and extended lifespan thereto due to superbly low voltage, high efficiency and high Tg.

Description

technical field [0001] The present invention relates to a novel hole injecting and hole transporting compound and an organic light-emitting device comprising the same. Background technique [0002] Recently, self-illuminating organic light-emitting elements that can be driven at low voltages have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs) that are the mainstream of flat panel display elements. Lightweight and thin, it is also advantageous in terms of power consumption, and the color reproduction range is wide, so it is attracting attention as a next-generation display element. [0003] Materials used as organic layers in organic light-emitting devices can be roughly classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials according to their functions. [0004] A large number of amine derivatives having a carbazole skeleton hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/50
CPCC09K11/06C07D307/91Y10S428/917H10K50/171H10K50/16H10K50/15H10K50/11
Inventor 咸昊完金奉记安贤哲金成勋金东骏韩政佑金槿泰李萤振安慈恩
Owner DONGJIN SEMICHEM CO LTD
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