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A kind of fluorescent material and its synthesis method

A fluorescent material and synthesis method technology, applied in the field of organic light-emitting materials, can solve the problems of difficult carrier injection, limited application, poor carrier mobility, etc., to avoid the use of rare metals, strong fluorescent characteristics, and improve The effect of quantum efficiency

Active Publication Date: 2021-12-24
WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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Problems solved by technology

The early OLED light-emitting materials are traditional fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, but traditional fluorescent materials can only use singlet excitons to emit light, so the OLDE theory of traditional fluorescent materials The internal quantum efficiency is 25%. Although in terms of theoretical research, organic fluorescent materials have made great progress. For example, Professor Adachi developed a thermally induced delayed fluorescent material (TADF), which realizes the intersystem transition from triplet to singlet state of excitons. Leaping, theoretically the internal quantum efficiency can reach 100% (Adv.Mater., 2009, 21, 4802), but the actual situation is not, it depends on the number of electrons transitioning from singlet state to ground state per unit time and triplet state crossing The ratio of the number of electrons to the singlet state, if the electrons in the triplet state do not quickly cross to the singlet state, it will gradually return to the ground state in the form of heat, resulting in energy loss
And because the spectrum is too wide, the emitted light color is impure, the luminous efficiency of blue light materials is low, and the life is short, so the application of TADF materials in the display field is limited
[0003] OLED is composed of red, green and blue organic light-emitting molecules to produce three primary colors and then display various colors. Among them, blue light-emitting materials are difficult to inject carriers due to their short light-emitting wavelength and wide energy band gap; and blue light-emitting materials are difficult to inject due to their special Molecular structure, carrier mobility is also relatively poor, coupled with the visual function, the luminous efficiency and lifetime of blue light materials are much lower than those of red light and green light
Blue light performance has become an unavoidable short board affecting OLED display
At present, fluorescent materials with TTA (triple-triple annihilation) effect, due to the annihilation effect of electrons in the triplet state, increase the total amount of singlet electrons, and the theoretical internal quantum efficiency can reach 62.5%, which has also been obtained in the field of display. Extensive attention, the demand for blue light-emitting materials with excellent performance in the OLED display field provides opportunities and challenges for the development and design of fluorescent materials with TTA properties

Method used

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  • A kind of fluorescent material and its synthesis method
  • A kind of fluorescent material and its synthesis method
  • A kind of fluorescent material and its synthesis method

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Experimental program
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Effect test

Embodiment 1

[0057] This embodiment provides a deep blue fluorescent material (target compound 1), its structural formula is shown in formula (1-a):

[0058]

[0059] The synthetic route of target compound 1 is as follows:

[0060]

[0061] The synthesis method comprises the following steps: adding the reactant (6.99g, 10mmol) having the structural formula (2-a), 5mL concentrated hydrochloric acid and 15mL glacial acetic acid into a 50mL reaction vessel, and then reacting at 120°C for 24h. After cooling, pour into ice water, add 1mol / L sodium bicarbonate aqueous solution to neutralize the acid, then extract with dichloromethane (DCM) three times, wash with water three times, dry over anhydrous sodium sulfate, filter and concentrate. Using 200-300 mesh silica gel column chromatography with petroleum ether / DCM (4:1, V / V) as the eluent, 5.43 g of the target compound 1 was obtained as a white solid with a yield of 82%. 1HRMS[M+H]+calcd.for C50H34N2: 662.2722; found: 662.2734.

[0062] ...

Embodiment 2

[0064] This embodiment provides a deep blue fluorescent material (target compound 2), its structural formula is shown in formula (1-b):

[0065]

[0066] The synthetic route of target compound 2 is as follows:

[0067]

[0068] The reactant (6.99g, 10mmol), 5mL of concentrated hydrochloric acid and 15mL of glacial acetic acid were added into a 50mL reaction vessel, and reacted at 120°C for 24h. After cooling, pour into ice water, add 1mol / L sodium bicarbonate aqueous solution to neutralize the acid, then extract with dichloromethane (DCM) three times, wash with water three times, dry over anhydrous sodium sulfate, filter and concentrate. Using 200-300 mesh silica gel column chromatography with petroleum ether / DCM (4:1, V / V) as the eluent, 5.43 g of the target compound 2 was obtained as a white solid with a yield of 82%. 1HRMS[M+H]+calcd. for C50H34BN: 659.2784; found: 659.2798.

Embodiment 3

[0070] The target compound 1 and 2 and the traditional fluorescent material (Ref) shown in the formula (3) are subjected to photophysical test analysis, and the fluorescence emission spectrum is as follows figure 1 Shown; Parameters such as the electrochemical energy level of target compound 1 and 2 and Ref are measured, the lowest singlet state (S1) and the lowest triplet state energy level (T1) of target compound 1 and 2 and Ref and their energy level difference, And the test results of photoluminescence quantum efficiency PLQY are shown in Table 1 below.

[0071]

[0072] S1 is determined by room temperature fluorescence spectroscopy, T1 is determined by low temperature (77K) phosphorescence spectroscopy, and HOMO and LUMO are determined by electrochemical redox. Photoluminescence spectrum (photoluminescence, referred to as PL spectrum), PL peak refers to the strongest emission peak of the photoluminescence spectrum; PLQY was measured with the help of the Absolute PLQuan...

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Abstract

The present application discloses a fluorescent material and a synthesis method thereof. The fluorescent material has the following structural formula: wherein, Y is an N atom or a B atom; X 1 and x 2 same or different and selected from C atom or Si atom; R 1 , R 2 , R 3 , R 4 The same or different, selected from hydrogen atom, alkyl, hydrocarbon aryl or heteroaryl; R 5 , R 6 , R 7 , R 8 same or different, selected from alkyl, hydrocarbon aryl or heteroaryl; or R 5 and R 6 form a cyclic group; or R 7 and R 8 form a cyclic group. The material has good fluorescence characteristics and high quantum efficiency, and can be used in the light-emitting layer of organic electroluminescent devices. The synthesis method of the fluorescent material is simple, avoiding the use of rare metals, and has huge applications in the field of OLEDs. prospect.

Description

technical field [0001] The application belongs to the field of organic luminescent materials, and in particular relates to a fluorescent material and a synthesis method thereof. Background technique [0002] With the continuous development of OLED technology in the fields of display and lighting, people will pay more attention to the research on its core materials, especially organic electroluminescent materials. The early OLED light-emitting materials are traditional fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, but traditional fluorescent materials can only use singlet excitons to emit light, so the OLDE theory of traditional fluorescent materials The internal quantum efficiency is 25%. Although in terms of theoretical research, organic fluorescent materials have made great progress. For example, Professor Adachi developed a thermally induced delayed fluorescent material (TADF), which realizes the intersystem transition from triple...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22C07F5/02C07C211/61C09K11/06H01L51/50H01L51/54
CPCC07D471/22C07F5/02C07C211/61C09K11/06C09K2211/1044C09K2211/104C09K2211/1007C09K2211/1011C09K2211/1014H10K85/622H10K85/633H10K85/657H10K85/6572H10K50/11H10K50/12H10K85/658C09B57/00H10K85/322C09K2211/1018
Inventor 王煦王彦杰
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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