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

Novel heterocycle-spiro structure compound and application thereof in OLED devices

A technology of heterocyclic spiro compounds, applied in the field of organic electroluminescence display, can solve the problems of low glass transition temperature, easy crystallization of materials, damage to film uniformity, etc.

Active Publication Date: 2019-11-29
北京燕化集联光电技术有限公司
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The organic hole transport materials currently reported are generally small in molecular weight and have a low glass transition temperature. During the use of the material, repeated charging and discharging will easily crystallize the material and destroy the uniformity of the film, thus affecting the service life of the material.

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
  • Novel heterocycle-spiro structure compound and application thereof in OLED devices
  • Novel heterocycle-spiro structure compound and application thereof in OLED devices
  • Novel heterocycle-spiro structure compound and application thereof in OLED devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Synthesis of (Compound 1-5)

[0057] The synthetic route is as follows:

[0058]

[0059] Including the following specific steps:

[0060] A 1-liter three-necked flask equipped with a magnetic stirrer, and potassium tert-butoxide (36.2 g, 0.376 mol), bis(4-tolyl)amine (41.37 g, 0.21 mol, purity 99%) and 100 ml of toluene were added sequentially after argon replacement. After replacing with argon again, 3.4 ml of tri-tert-butylphosphine and 0.5 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. Start to drop a solution consisting of (57.0 g, 0.1 mol, purity 99%) M1 and 100 ml of toluene, and control the temperature at 80-120° C. Cool down to 50°C, add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF, and rotary steam to obtain 68.23g of white solid with a purity of 99.5% and a yield of about 85%.

[0061] Product MS (m / e): 802.30...

Embodiment 2

[0063] Synthesis of (Compound 1-44)

[0064] The synthetic route is as follows:

[0065]

[0066] Including the following specific steps:

[0067] 1 liter three-neck flask, equipped with magnetic stirring, after argon replacement, add potassium tert-butoxide (36.2g, 0.376mol), 4-tolyl-2-naphthylamine (48.93g, 0.21mol, purity 99%) and toluene 100ml . After replacing with argon again, 3.4 ml of tri-tert-butylphosphine and 0.5 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. Start to drop a solution consisting of (63.3g, 0.1mol, purity 99%) M2 and 100ml toluene, and control the temperature at 80-120°C. Cool down to 50°C, add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF, and rotary steam to obtain 78.79g of white solid with a purity of 99.5% and a yield of about 84%.

[0068] Product MS (m / e): 938.22; Elemental analysis (C 63 h 42...

Embodiment 3

[0070] Synthesis of (Compound I-99)

[0071] The synthetic route is as follows:

[0072]

[0073] Including the following specific steps:

[0074] A 1-liter three-neck flask equipped with a magnetic stirrer. After argon replacement, 19.93g (0.188mol) of sodium carbonate, 9,9-dimethyl-2-boronic acid (23.8g, 0.1mol, purity 99%) and 100ml of toluene were added in sequence. After replacing with argon again, 0.23g of Pd132 was added in sequence. After the addition, the temperature was raised to 80°C. Start to drop a solution consisting of (49.1 g, 0.1 mol, purity 99%) M3 and 100 ml of toluene, and control the temperature at 75-80°C. Cool down to room temperature, add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF to obtain 51.34g of white solid with a purity of 99.5% and a yield of about 85%.

[0075] Product MS (m / e): 588.21; Elemental analysis (C 44 h 28 o 2 ): theoretical value C: 89.77%, H: 4.79%...

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

No PUM Login to View More

Abstract

The invention relates to a novel heterocycle-spiro structure compound, which has a structure shown as general formula I, wherien, E1 and E2 independently represent O, S or Se atoms and are different from each other; R1, R2, R3 and R4 independently represent an aromatic group containing n benzene rings and / or aromatic heterocycles and having electron-donating properties or being neutral respectively, or represent H atom; and n represents an integer of 1-7. The compound provided by the invention takes a spiro structure as the main body, the main structure has a rigid structure and an electron-rich structure unit at the same time, can have good thermal stability while providing excellent hole transport performance. The structure has appropriate HOMO and LUMO energy levels and high Eg, can effectively improve the photoelectric performance and the lifetime of OLED devices. An electron-donating group or neutral group is introduced into the structure, so that the compound can be well appliedto OLED devices as a hole transport material.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent display, and in particular relates to a novel organic material with a heterocyclic spiro ring structure and its application. Background technique [0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescent display devices (OLED). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal display devices, OLED does not require a backlig...

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): C07D517/10C07D495/10H01L51/50H01L51/54
CPCC07D517/10C07D495/10H10K85/624H10K85/615H10K85/626H10K85/6576H10K85/6572H10K85/6574H10K85/657H10K50/15
Inventor 范洪涛呼建军梁现丽段陆萌黄春雪杭德余李仲庆曹占广刘阳班全志李继响罗忠林
Owner 北京燕化集联光电技术有限公司
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