Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Azacyclo-compound, display panel and display device

A technology of nitrogen heterocyclic compounds and compounds, applied in the field of organic electroluminescent materials, can solve the problems of poor coverage, luminous efficiency, and high refractive index, so as to alleviate angle dependence and improve light extraction efficiency , Improve the effect of luminous efficiency

Inactive Publication Date: 2018-12-14
WUHAN TIANMA MICRO ELECTRONICS CO LTD
View PDF5 Cites 6 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Azacyclo-compound, display panel and display device
  • Azacyclo-compound, display panel and display device
  • Azacyclo-compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Synthesis of Compound CP01

[0085]

[0086] In a 250ml three-neck flask, under nitrogen protection, in 150ml DMF, sequentially add raw material intermediate M1 (0.012mol), intermediate M12 (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then add 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 is over, 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 CP01.

[0087] The elemental analysis result of compound CP01 (molecular formula C 42 h 28 N 6 ): Theoretical values: C, 81.80; H, 4.58; N, 13.63. Test values: C, 81.8...

Embodiment 2

[0089] Synthesis of Compound CP03

[0090]

[0091] In a 250ml three-necked flask, under the protection of nitrogen, in 150ml DMF, sequentially add raw material intermediate M2 (0.012mol), intermediate M12 (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then add 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 is over, 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 the product CP03 was obtained.

[0092] The elemental analysis result of compound CP03 (molecular formula C 45 h 32 N 6 ): Theoretical values: C, 82.29; H, 4.91; N, 12.80. Test values: C, 82...

Embodiment 3

[0094] Synthesis of Compound CP05

[0095]

[0096] In a 250ml three-necked flask, under nitrogen protection, in 150ml DMF, sequentially add raw material intermediate M3 (0.012mol), intermediate M12 (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then add 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 is over, 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 the product CP05 was obtained.

[0097] The elemental analysis result of compound CP05 (molecular formula C 41 h 27 N 7 ): Theoretical values: C, 79.72; H, 4.41; N, 15.87. Test values: C, 79.74; H,...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
glass transition temperatureaaaaaaaaaa
thicknessaaaaaaaaaa
Login to View More

Abstract

The invention provides an azacyclo-compound having the structure shown in the chemical formula 1. In the formula 1, X1 to X6 independently represent N or C atoms, at least one of X1 to X6 is an N atom, m and n independently represent 0, 1 or 2, m+n is greater than 1, R1 represents a hydrogen atom, a C1-C10 linear or branched alkyl group, a substituted or unsubstituted phenyl group, a diphenyl group, a terphenyl group, a pyridyl group, a naphthyl group or an anthracenyl group, Ar is selected from a dimethyl fluorene group, a phenyl group and a carbazolyl group, and Ar1 and Ar2 independently represent a substituted or unsubstituted benzimidazole group. The azacyclo-compound has a high refractive index, when the azacyclo-compound is used as a CPL cap layer of an organic light-emitting and display device (such as an OLED), light extraction efficiency and luminous efficiency of the top emission organic photoelectric device can be improved, and the angular dependence of OLED device illumination is reduced. The azacyclo-compound has a small extinction coefficient in the blue region and almost no absorption of blue light and improves luminous efficiency.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescent 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. E...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C09K11/06H01L51/50H01L51/54H01L27/32
CPCC09K11/06C07D401/14C07D403/14C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1044H10K59/00H10K85/626H10K85/654H10K85/6572H10K50/11H10K50/16
Inventor 张磊高威朱晴牛晶华卢艳范昌煊
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com