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Dibenzazepine compound used in organic layer of OLED device and organic electroluminescent device

A benzonitride and compound technology, which is applied in the field of organic electroluminescent materials, can solve the problems of small lateral resistance, color crosstalk, and decrease, and achieve the effects of large lateral resistance, low operating voltage, and improved color rendering effect.

Pending Publication Date: 2021-12-28
BOE TECH GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, OLED devices generally use HT material and P-type dopant to co-evaporate to obtain the hole transport layer (HIL). Color>Green>Red relationship, which leads to the fact that when the blue light device is lit, the charge will flow laterally to the red and green sub-pixels through the P-type doped HTL layer, so the red and green pixels are lit, or work in the green pixel When , charge flows laterally to the red pixel, and red is lit, causing color crosstalk

Method used

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  • Dibenzazepine compound used in organic layer of OLED device and organic electroluminescent device
  • Dibenzazepine compound used in organic layer of OLED device and organic electroluminescent device
  • Dibenzazepine compound used in organic layer of OLED device and organic electroluminescent device

Examples

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preparation example Construction

[0088] The second aspect of the present invention also provides a synthesis method of the dibenzoazepine compound, comprising the following steps:

[0089] S1, in an inert atmosphere, dissolve compound a and organoboron reagent b in a solvent, add potassium tert-butoxide, palladium acetate, and 2-(dicyclohexylphosphine)-biphenyl, and heat to react to obtain compound c;

[0090]

[0091] S2, in an inert atmosphere, dissolve compound c and amine compound d in a solvent, add tetrakis(triphenylphosphine)palladium and potassium carbonate aqueous solution, heat and reflux for reaction, and obtain the compound shown in formula 1 or formula 2 or formula 3;

[0092]

[0093] Among them, R represents the removal of the group -L-NAr in formula 1 6Ar 7 Structures other than Formula 2 remove the group -L-NAr 6 Ar 7 Remove the group -L-NAr in structures other than formula 3 6 Ar 7 outside the structure;

[0094] X is Br or I;

[0095] n is an integer of 1-3;

[0096] L. Ar 6 ...

Synthetic example 1

[0119] Synthesis of compound A-1

[0120] In the reaction flask, add 4-bromophenylboronic acid [CAS: 5467-74-3] (70 mg, 0.35 mmol), compound iminodibenzyl [CAS: 494-19-9] (132 mg, 0.68 mmol), tert-butyl Potassium alkoxide (112mg, 1mmol), palladium acetate (10mg), 2-(dicyclohexylphosphine)-biphenyl (30mg) and 10ml of toluene were added to 80°C for 4 hours under nitrogen protection, cooled, and the solvent was removed, crude The product was subjected to silica gel column chromatography to obtain intermediate compound A-1-1 as a solid, 92.6 mg, with a yield of 93%.

[0121] In the reaction flask, add compound A-1-1 (63mg, 0.2mmol), N,N-bis(4-biphenyl)-N-(4-bromophenyl)amine [CAS: 499128-71-1 ] (119g, 0.25mmol), tetrahydrofuran (5ml), tetrakis(triphenylphosphine) palladium (20mg), potassium carbonate aqueous solution (2mol / l, 2mL), heated under reflux overnight under nitrogen protection. Stop the reaction, extract three times with dichloromethane, combine the organic phases, and...

Synthetic example 2

[0128] Synthesis of compound B-1

[0129] In a reaction flask, add bromobenzene (54.5mg, 0.35mmol), hydroxy-substituted iminodibenzyl (143mg, 0.68mmol), potassium tert-butoxide (112mg, 1mmol), palladium acetate (10mg), 2-(bicyclic Hexylphosphine)-biphenyl (30mg) and 10ml of toluene were added to 80°C for 4 hours under nitrogen protection and reacted for 4 hours, cooled to obtain compound B-1-1; then added hot HBr to replace, remove the solvent, and the crude product was used on a silica gel column The intermediate compound B-1-2 was obtained by chromatography as a solid 97 mg, with a yield of 80%.

[0130] Referring to the synthesis process of compounds A-1-1 and A-1 in Synthesis Example 1, under the same conditions, the reactants were replaced to obtain compound B-1, 92 mg, with a yield of 45%.

[0131] Structure Characterization:

[0132] Mass Spectrum m / z: 590.27;

[0133] Element content (%): C 44 h 34 N 2 . C, 89.46%; H, 5.80%; N, 4.74%;

[0134] 1 H NMR: δ2.92 (...

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Abstract

The invention discloses a dibenzazepine compound used in an organic layer of an OLED device. A nitrogen-containing seven-membered ring in the compound and two benzene rings form a conjugated pi bond, electrons in a molecule have delocalization, and the molecule has rigidity and stability and is an electron-rich unit with rigidity. When the compound is used as a hole transport material, the compound has good hole mobility, stable performance, long service life and low working voltage. Meanwhile, the molecule has a special torsion structure and a three-dimensional space structure, a thin film formed by deposition has larger transverse resistance, transverse diffusion of charges among pixels of different colors is effectively blocked, the problem of color crosstalk is greatly weakened, and the color developing effect of a display panel is improved. Therefore, the dibenzazepine compound disclosed by the invention has good application potential in the aspect of preparing organic electroluminescent devices and related display devices.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials. More specifically, it relates to a dibenzoazepine compound and an organic electroluminescent device. Background technique [0002] At present, an organic electroluminescent device (OLED device) basically consists of an anode, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and a cathode. [0003] At present, OLED devices generally use HT material and P-type dopant to co-evaporate to obtain the hole transport layer (HIL). Color>Green>Red relationship, which leads to the fact that when the blue light device is lit, the charge will flow laterally to the red and green sub-pixels through the P-type doped HTL layer, so the red and green pixels are lit, or work in the green pixel , the charge flows laterally to the red pixel, and red is lit, causing color crosstalk. Therefore, with the in...

Claims

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Application Information

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IPC IPC(8): C07D223/28C07D223/14C07D267/18C09K11/06H01L51/54
CPCC07D223/28C07D223/14C07D267/18C09K11/06C09K2211/1033C09K2211/1029C09K2211/1011H10K85/657H10K85/6572
Inventor 孙玉倩张东旭邱丽霞
Owner BOE TECH GRP CO LTD
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