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Spirofluorene compound and organic electroluminescent device containing same

A compound, spirofluorene technology, applied in the direction of electric solid devices, electrical components, organic chemistry, etc., can solve the problems of development that has not been fully realized, and achieve the effects of excellent film phase stability, excellent life, and excellent hole migration ability.

Pending Publication Date: 2022-02-22
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of materials for stable and efficient organic material layers for organic electroluminescent devices has not been fully realized

Method used

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  • Spirofluorene compound and organic electroluminescent device containing same
  • Spirofluorene compound and organic electroluminescent device containing same
  • Spirofluorene compound and organic electroluminescent device containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0161] Embodiment 1: the synthesis of compound 1

[0162]

[0163] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol raw material A-1, 0.012mol raw material B-1, 0.03mol potassium tert-butoxide, 1×10 -4 mol Tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 , 1×10 -4 mol of triphenylphosphine, 150ml of toluene, heated to reflux for 12 hours, sampling point plate, showing that the reaction is complete. Natural cooling, filtration, rotary evaporation of the filtrate, passing through a silica gel column (silica gel 100-200 mesh, eluent: chloroform: n-hexane = 30:70 (volume ratio)) to obtain intermediate A-1. Elemental analysis structure (molecular formula C 31 h 21 N): Theoretical C 91.37; H 5.19; N 3.44; Tested: C 91.34; H 5.21; N 3.45. MS (m / z) (M+): theoretical value 407.17, found value 407.34.

[0164] In a 250ml three-neck flask, under nitrogen atmosphere, add 0.01mol raw material C-1, 0.024mol intermediate A-1, 0.03mol potassium tert-butoxide, ...

Embodiment 2

[0166] Embodiment 2: the synthesis of compound 85

[0167]

[0168] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol raw material A-1, 0.012mol raw material B-1, 0.03mol potassium tert-butoxide, 1×10 -4 mol Tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 , 1×10 -4 mol of triphenylphosphine, 150ml of toluene, heated to reflux for 12 hours, sampling point plate, showing that the reaction is complete. Natural cooling, filtration, rotary evaporation of the filtrate, passing through a silica gel column (silica gel 100-200 mesh, eluent: chloroform: n-hexane = 30:70 (volume ratio)) to obtain intermediate A-1. Elemental analysis structure (molecular formula C 31 h 21 N): Theoretical C 91.37; H 5.19; N 3.44; Tested: C 91.34; H 5.21; N 3.45. MS (m / z) (M+): theoretical value 407.17, found value 407.34.

[0169] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol raw material C-2, 0.012mol raw material D-1, 0.02mol sodium carbonat...

Embodiment 3

[0172] Embodiment 3: the synthesis of compound 14

[0173]

[0174] In a 250ml three-neck flask, under an atmosphere of nitrogen gas, add 0.01mol raw material A-1, 0.012mol raw material B-3, 0.03mol potassium tert-butoxide, 1×10 -4 mol Tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 , 1×10 -4 mol of triphenylphosphine, 150ml of toluene, heated to reflux for 12 hours, sampling point plate, showing that the reaction is complete. Natural cooling, filtration, rotary evaporation of the filtrate, passing through a silica gel column (silica gel 100-200 mesh, eluent: chloroform: n-hexane = 30:70 (volume ratio)) to obtain intermediate A-3. Elemental analysis structure (molecular formula C 37 h 28 NBO 2 ): theoretical value C84.26; H 4.97; N 2.66; test value: C84.31; H 4.96; N 2.63. MS (m / z) (M+): theoretical value 527.21, found value 527.37.

[0175] In a 250ml three-necked flask, add 0.01mol raw material A-1, 0.012mol raw material C-2, 0.03mol potassium tert-butoxide, 1×...

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Abstract

The invention provides a spirofluorene compound with a general formula (1) as defined in the specification, a preparation method of the spirofluorene compound, and application of the spirofluorene compound as a hole transport material in an organic electroluminescent device. The invention also relates to the organic electroluminescent device. The device sequentially comprises an anode, a hole transport region, a light emitting region, an electron transport region and a cathode from bottom to top, wherein the hole transport region comprises the spirofluorene compound as shown in the general formula (1). The invention further relates to a display device comprising the organic electroluminescent device.

Description

technical field [0001] The present invention relates to the technical field of semiconductors, more specifically, to a spirofluorene compound, its preparation method, and its use as a hole transport material in an organic electroluminescent device. An electroluminescent device, and a display device comprising the organic electroluminescent device. Background technique [0002] The carriers (holes and electrons) in the organic electroluminescent device (OLED) are respectively injected into the device by the two electrodes of the device under the drive of the electric field, and meet in the organic light-emitting layer to recombine and emit light. High-performance organic electroluminescent devices require various organic functional materials to have good photoelectric properties. For example, as a charge transport material, good carrier mobility is required. The injection and transport characteristics of hole injection layer materials and hole transport layer materials used...

Claims

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Application Information

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IPC IPC(8): C07C211/61H01L51/50H01L51/54
CPCC07C211/61C07C2603/94H10K85/624H10K85/633H10K50/15
Inventor 王芳尚书夏赵四杰张兆超崔明
Owner JIANGSU SUNERA TECH CO LTD
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