Nitrogen heterocyclic compound, display panel and display device

A nitrogen heterocyclic compound and display panel technology, applied in organic chemistry, electric solid devices, semiconductor devices, etc., can solve the problems of intermolecular close packing, high refractive index, and luminous efficiency, etc. The effect of short yoke length, improved luminous efficiency, and improved light extraction efficiency

Active Publication Date: 2022-05-20
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the refractive index of the existing CPL materials is generally below 1.9, which cannot meet the requirements of high refractive index; amine derivatives with a specific structure with high refractive index and the use of materials that meet specific parameters improve the light extraction efficiency, but there is no solution. The problem of luminous efficiency (especially for blue light emitting elements)
In order to increase the molecular density and achieve high thermal stability of the materials in the prior art, the molecular structure is designed to be large and loose, and the molecules cannot be tightly packed, resulting in too many holes in the molecular gel during evaporation. Poor coverage

Method used

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  • Nitrogen heterocyclic compound, display panel and display device
  • Nitrogen heterocyclic compound, display panel and display device
  • Nitrogen heterocyclic compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Synthesis of compound CP2

[0075]

[0076] In a 250ml three-necked flask, under nitrogen protection, in 150ml DMF, successively add raw material intermediate M1 (0.012mol), 3-phenanthrolinyl borate (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then Join K 3 PO 4 (0.045mol) aqueous solution, reflux reaction at a temperature of 130°C for 10h. Naturally cool to room temperature, after the reaction, add 100mL deionized water, then drop a few drops of 2M HCl, extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography, and finally purified to obtain the product CP2.

[0077] Compound CP2 elemental analysis result (molecular formula C 40 h 24 N 6 ): theoretical value: C, 81.61; H, 4.11; N, 14.28. Test values: C, 81.63; H, 4...

Embodiment 2

[0079] Synthesis of compound CP4:

[0080]

[0081] In a 250ml three-necked flask, under nitrogen protection, in 150ml DMF, successively add raw material intermediate M1 (0.012mol), 4-quinolyl borate (0.025mol) and palladium acetate (0.0003mol), mix and stir, Then join K 3 PO 4 (0.045mol) aqueous solution, reflux reaction at a temperature of 130°C for 10h. Naturally cool to room temperature, after the reaction, add 100mL deionized water, then drop a few drops of 2M HCl, extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography, and finally purified to obtain the product CP4.

[0082] Compound CP4 element analysis result (molecular formula C 34 h 22 N 4 ): Theoretical values: C, 83.93; H, 4.56; N, 11.51. Test values: C, 83.95; H, 4.54; N, 11.51...

Embodiment 3

[0084] Synthesis of compound CP8:

[0085]

[0086] In a 250ml three-necked flask, under nitrogen protection, in 150ml DMF, successively add raw material intermediate M1 (0.012mol), 4-phenanthrolinyl borate (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then Join K 3 PO 4 (0.045mol) aqueous solution, reflux reaction at a temperature of 130°C for 10h. Naturally cool to room temperature, after the reaction, add 100mL deionized water, then drop a few drops of 2M HCl, extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography, and finally the product CP8 was obtained by purification.

[0087] Compound CP8 (molecular formula C 40 h 24 N 6 ) Elemental analysis results: theoretical value: C, 81.61; H, 4.11; N, 14.28. Test values: C, 81.64;...

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Abstract

The present invention provides a nitrogen heterocyclic compound, which has a structure shown in chemical formula I; wherein, z is 1 or 2, m and n are 1 or 2 respectively, p and q are 0, 1 or 2 respectively; X 1 -X 6 each independently selected from N or C, and at least one is N; R 1 , R 2 and R 3 R 1 and R 2 Can also represent a single bond; Ar 1 and Ar 2 Each is independently selected from any one of substituted or unsubstituted aromatic groups, fused aryl groups, aromatic heterocyclic groups, and fused aromatic heterocyclic groups. The nitrogen heterocyclic compound of the present invention has a higher refractive index, and when it is used as the CPL capping layer of an OLED device, it can improve the light extraction efficiency and luminous efficiency of the top-emitting OLED (especially the most effective for blue light pixels), which can alleviate Angle dependence of light emission from OLED devices (most effective for red / green pixels).

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescence materials, in particular to a nitrogen heterocyclic compound, a display panel and a display device comprising the nitrogen heterocyclic compound. Background technique [0002] After decades of development, OLED has come a long way. Although its internal quantum efficiency is close to 100%, its external quantum efficiency is only about 20%. Most of the light is confined inside the light-emitting device due to factors such as substrate mode loss, surface plasmon loss, and waveguide effect, resulting in a large amount of energy loss. [0003] In top-emitting devices, an organic capping layer (CappingLayer, CPL) is usually evaporated on the semi-transparent metal electrode Al to adjust the optical interference distance, suppress the reflection of external light, and suppress the extinction caused by the movement of surface plasmons, thereby improving the light intensity. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/06C07D239/26C07D251/24C07D401/04C07D401/14C07D471/04C07D519/00H01L51/54
CPCC07D213/06C07D239/26C07D251/24C07D401/04C07D401/14C07D471/04C07D519/00H10K85/615H10K85/626H10K85/654H10K85/6572C07D401/10H10K50/828H10K50/11H10K50/15H10K50/16
Inventor 张磊高威朱晴牛晶华
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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