compounds, oled devices and electronic devices

A technology of electronic devices and compounds, applied in the field of OLED, can solve the problems of the efficiency roll-off of phosphorescent materials and the poor stability of phosphorescent devices, and achieve good charge transport performance and electron donating performance, good polarizability, and unique electrical properties. Effect

Active Publication Date: 2021-12-21
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at high current densities, there is a serious efficiency roll-off phenomenon in phosphorescent materials, and the stability of phosphorescent devices is not good.

Method used

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  • compounds, oled devices and electronic devices
  • compounds, oled devices and electronic devices
  • compounds, oled devices and electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Synthesis of compound H01

[0104]

[0105] S1 (2.7mmol), S2 (5.7mmol), (dibenzylideneacetone) dipalladium (0) (0.35mmol), sodium tert-butoxide (10.0mmol), tri-tert-butylphosphine tetrafluoroborate (0.7mmol ) into a 500mL three-necked flask, and while stirring, quickly repeated degassing and nitrogen replacement 3 times, and added 150mL toluene through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain S3 (2.05 mmol, 76%).

[0106]MALDI-TOF MS: Calculated m / z: C 35 h 20 N 2 OS: 516.1; Measured: 516.2.

[0107]

[0108] Under a nitrogen atmosphere, S4 (6.9 mmol) was dissolved in 60 ml of anhydrous THF, and the reaction system was stirred a...

Embodiment 2

[0115] Synthesis of Compound H29

[0116]

[0117] S7 (3.5mmol), S8 (7.4mmol), (dibenzylideneacetone) dipalladium (0) (0.5mmol), sodium tert-butoxide (12.0mmol), tri-tert-butylphosphine tetrafluoroborate (1.0mmol ) into a 500mL three-necked flask, and while stirring, quickly repeated degassing and nitrogen replacement 3 times, and added 180mL toluene through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain S9 (2.56 mmol, 73%).

[0118] MALDI-TOF MS:C 47 h 24 N 2 OS 3 m / z calculated: 728.1; measured: 728.2.

[0119]

[0120] Under a nitrogen atmosphere, S4 (5.5 mmol) was dissolved in 45 ml of anhydrous THF, and the reaction system was stirred...

Embodiment 3

[0127] Synthesis of compound H49

[0128]

[0129] S12 (4.2mmol), S2 (8.5mmol), (dibenzylideneacetone) dipalladium (0) (0.6mmol), sodium tert-butoxide (14.4mmol), tri-tert-butylphosphine tetrafluoroborate (1.2mmol ) into a 500mL three-necked flask, and while stirring, quickly repeated degassing and nitrogen replacement 3 times, and added 160mL toluene through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain S13 (2.9 mmol, 69%).

[0130] MALDI-TOF MS: Calculated m / z: C 33 h 18 N 2 OS 2 : 522.1; measured value: 522.2.

[0131]

[0132] Under a nitrogen atmosphere, S14 (2.8 mmol) was dissolved in 25 ml of anhydrous THF, and the reaction system w...

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Abstract

The invention belongs to the field of OLEDs and provides a thia spiro compound, which has a structure of chemical formula 1, wherein, D 1 and D 2 For electron donating group, a, b are selected from 0, 1 or 2 and a+b≥1; A 1 and A 2 It is an electron-accepting group, c and d are selected from 0, 1, 2, 3 or 4 and c+d≥1; X is a fused aromatic ring or a fused aromatic heterocyclic ring; D 1 and D 2 Respectively selected from carbazole groups, diphenylamine groups, acridine groups; A 1 and A 2 They are respectively selected from nitrogen-containing heterocyclic substituents, arylboron-based substituents, carbonyl-containing substituents, sulfone-based substituents and phosphorus-containing oxygen-based substituents. The spatial configuration of the spiro ring structure in the compound of the present invention is an orthogonal structure, which is beneficial to realize the effective separation of HOMO and LUMO in space. In addition, the spiro ring structure is a non-planar structure. Since the rotation and vibration of the molecule are limited by steric hindrance, the rigidity of the molecule is enhanced, making it more stable, and it also has higher shape stability and prolongs the organic life. lifetime of light emitting devices.

Description

technical field [0001] The invention relates to the technical field of OLEDs, in particular to a thia spiro compound and OLED devices and electronic equipment comprising the compound. Background technique [0002] With the development of electronic display technology, organic light-emitting devices (OLEDs) are widely used in various display devices, and the research and application of OLED light-emitting materials are also increasing. [0003] According to the light-emitting mechanism, the materials used for OLED light-emitting layer mainly include: [0004] (1) fluorescent material; (2) phosphorescent material. [0005] For fluorescent materials, according to spin statistics, the ratio of singlet and triplet excitons in excitons is 1:3, so the maximum internal quantum yield of fluorescent materials does not exceed 25%. According to the Lambertian light emission mode, the light extraction efficiency is about 20%, so the external quantum effect (EQE) of the OLED based on th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C07D417/14C07D487/14C07D519/00C07D413/14C07F5/02C07F9/6558C07F9/6553C07D495/04C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC07D409/14C07D417/14C07D487/14C07D519/00C07D413/14C07F5/027C07F9/65586C07F9/655354C07D495/04C07F9/6561C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1092C09K2211/1051C09K2211/1059C09K2211/1033C09K2211/1096C09K2211/1088H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K50/11
Inventor 高威刘营代文朋张磊牛晶华李侠安平
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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