Red-green-blue heat-activated delayed fluorescent material, and synthetic method and application thereof

A technology of thermally activated delayed, fluorescent materials, applied in the fields of luminescent materials, chemical instruments and methods, preparation of organic compounds, etc. Effects of inverse intersystem crossing constant, high synthesis efficiency, and high photoluminescence quantum yield

Active Publication Date: 2019-09-24
WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As the first generation of fluorescent materials, although they have a long lifetime, their luminous efficiency is low. In OLEDs, the ratio of excitons in singlet and triplet states is 1:3, and the theoretical upper limit of internal quantum efficiency is only 25%, which greatly limits fluorescence. Applications of Electroluminescent Devices
As a second-generation transition metal complex phosphorescent material, the singlet state can be transferred to the triplet state by intersystem crossing (ISC), and the internal quantum efficiency is almost 100%. However, the phosphorescent material needs to be doped with precious and rare metals such as Ir and Pt, and the material cost is high and the service life is short.

Method used

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  • Red-green-blue heat-activated delayed fluorescent material, and synthetic method and application thereof
  • Red-green-blue heat-activated delayed fluorescent material, and synthetic method and application thereof
  • Red-green-blue heat-activated delayed fluorescent material, and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of red, green and blue thermally activated delayed fluorescent materials

[0032] The synthetic route is as follows:

[0033]

[0034] Add raw material 1 (1.47g, 5mmol), carbazole (1.00g, 6mmol), palladium acetate (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol) in 100mL two-necked flask ), then NaOt-Bu (0.58g, 6mmol) was added into the glove box, and 40mL of toluene that had been dehydrated and deoxygenated was injected into the glove box under an argon atmosphere, and reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL of ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 2:1), to obtain Blue-white powder 1.6g, yield 84%.

[0035] The obtained product, that is, the proton NMR spectrum data of compound 1 is: 1H NMR (300MHz, CD2Cl2, δ): 8.55(...

Embodiment 2

[0036] Example 2: Synthesis of red, green and blue thermally activated delayed fluorescent materials

[0037] The synthetic route is as follows:

[0038]

[0039] Add raw material 1 (1.47g, 5mmol), phenoxazine (1.01g, 6mmol), palladium acetate (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6 mmol), then NaOt-Bu (0.58 g, 6 mmol) was added into the glove box, and 40 mL of toluene previously dehydrated and deoxygenated was poured into the glove box under an argon atmosphere, and reacted at 120° C. for 24 hours. Cool to room temperature, pour the reaction solution into 200mL of ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 2:1), to obtain Green powder 1.5g, yield 76%.

[0040] The obtained product, that is, the proton NMR spectrum data of compound 2 is: 1H NMR (300MHz, CD2Cl2, δ): 7.14(d, J=6.3Hz, 2H), 7.05-6.96(m, ...

Embodiment 3

[0041] Example 3: Synthesis of red, green and blue thermally activated delayed fluorescent materials

[0042] The synthetic route is as follows:

[0043]

[0044]Add raw material 1 (1.47g, 5mmol) in 100mL two-necked flask, dimethyl diphenylamine (1.10g, 6 mmol), palladium acetate (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17 g, 0.6mmol), and then NaOt-Bu (0.58g, 6mmol) was added into the glove box, and 40mL of toluene, which had been dehydrated and deoxygenated beforehand, was injected under an argon atmosphere, and reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 2:1), to obtain Red powder 1.6g, yield 76%.

[0045] The obtained product, that is, the proton nuclear magnetic spectrum data of compound 3 is: 1H NMR (300MHz, CD2Cl2,...

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PUM

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Abstract

The invention relates to the technical field of organic light-emitting materials, specifically to a red-green-blue heat-activated delayed fluorescent material, and a synthetic method and an application thereof. The red-green-blue heat-activated delayed fluorescent material has a general formula which is described in the specification. The blue-green-blue heat-activated delayed fluorescent material has novel structure, low singlet and triplet state energy level difference, fast reverse intersystem crossing constant (kRISC) and high photoluminescence quantum yield (PLQY). The heat-activated delayed fluorescent material has significant characteristics and long service life, and can be applied to mass-produced electroluminescence-based display and light-emitting device structures.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a red, green and blue thermally activated delayed fluorescent material, its synthesis method and application. Background technique [0002] Organic Light Emitting Diode (OLED) is a sandwich-type device composed of electrode / light-emitting layer / electrode structure invented by Chinese-American professor Deng Qingyun and others. When a current passes through it, a strong electric field will drive the organic light-emitting layer in the middle of the device electrodes to emit light. Based on the electroluminescence phenomenon of OLEDs, OLEDs are widely used in information display and solid-state lighting and other fields. [0003] The continuous renewal of organic light-emitting materials has greatly promoted the development of OLED technology. Generally speaking, fluorescent materials belong to the first generation, and transition metal complex phosphorescen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D265/38C07C225/22C07C221/00C09K11/06H01L51/50H01L51/54
CPCC07D209/86C07D265/38C07C225/22C07C221/00C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1033H10K85/631H10K85/657H10K85/6572H10K50/11H10K2101/20C09K2211/1018H10K2101/10H10K2101/30
Inventor 罗佳佳李先杰黄金昌顾宇杨林白亚梅
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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