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Organic photoelectric material and application thereof

A technology of organic optoelectronic materials and electroluminescent devices, applied in the fields of luminescent materials, organic chemistry, circuits, etc., can solve the efficiency roll-off, low S1 state radiation transition rate, difficult and high exciton utilization rate and high fluorescence radiation efficiency, etc. problems, to achieve the effect of improved performance, excellent fluorescence emission capability, and wide spectral coverage

Inactive Publication Date: 2018-08-07
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) T of the designed molecule 1 and S 1 states have strong CT features, very small S 1 -T 1 state energy gap, although a high T can be achieved by the TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the T excitation Subconcentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • Organic photoelectric material and application thereof
  • Organic photoelectric material and application thereof
  • Organic photoelectric material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of embodiment 1 compound C01

[0035] (1) Preparation of compound C01-A

[0036]

[0037]Add 1-naphthoic acid 8-sulfonic acid cyclic anhydride (23.4g, 0.1mol), 9,9-dimethyl-2-aminofluorene (25.1g, 0.12mol) and glacial acetic acid (300mL) into a 1L three-necked flask, Raise the temperature to reflux, keep warm for 12 hours under nitrogen atmosphere, then lower to 20-25°C, pour the reaction solution into 1000mL deionized ice water, stir and react for 30min, filter with suction, and use 500mL deionized water to wash and filter Cake, then select 200mL absolute ethanol to reflux for beating, cool down to 20-25°C, filter with suction, collect the filter cake, obtain C01-A as 31.5g, and the calculated yield is 74.10%, mass spectrometry detection (abbreviated as MS) (m / z ): 425.15.

[0038] (2) Preparation of compound C01-B

[0039]

[0040] Add C01-A (21.3g, 0.05mol) and THF (800mL) into a 2L three-necked flask, under a nitrogen atmosphere, control the...

Embodiment 2

[0044] The preparation of embodiment 2 compound C25

[0045] (1) Preparation of compound C25-A

[0046]

[0047] Add 1-naphthoic acid 8-sulfonic acid cyclic anhydride (23.4g, 0.1mol), aniline (10.2g, 0.11mol) and glacial acetic acid (150mL) into a 500mL three-necked flask, heat up to reflux, and keep the reaction under nitrogen atmosphere After 9 hours, lower the temperature to 20-25°C, pour the reaction solution into 1000mL of deionized ice water, stir for 30min, then filter with suction, rinse the filter cake with 150mL of deionized water, and then use 100mL of absolute ethanol to reflux for beating. Cool down to 20-25°C, filter with suction, and collect the filter cake to obtain 23.3 g of C25-A, with a calculated yield of 75.48%. Mass spectrometry (abbreviated as MS) (m / z): 309.06.

[0048] (2) Preparation of compound C25-B

[0049]

[0050] Add C25-A (15.5g, 0.05mol) and THF (400mL) into a 1L three-necked flask. L), keep the reaction for 30 minutes after dropping,...

Embodiment 3

[0054] The preparation of embodiment 3 compound C38

[0055] (1) Preparation of compound C38-A

[0056]

[0057] Add C25-A (12.4g, 0.04mol) and THF (400mL) into a 1L three-necked flask. L), keep the temperature for 1.0 hours after the dropping, control the internal temperature to be less than -78°C, add dibromoethane (9.4g, 0.05mol) dropwise, and keep the temperature for 1.0 hrs after the dropping. Once again, control the internal temperature to less than -70°C, slowly add n-butyllithium n-hexane solution (18mL, 2.5mol / L) dropwise, and keep it warm for 1.0h after the dropping, and control the internal temperature to less than -70°C, add dibromoethane dropwise (9.4g, 0.05mol), after dripping, keep warm for 1.0hrs, slowly heat up to 15-20°C, add 200mL of deionized solution to the reaction solution, stir the reaction for 30min to quench the reaction, remove the solvent under reduced pressure until there is no fraction, Add 300mL of deionized water to stir at room temperature...

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Abstract

The invention belongs to the technical field of photoelectric materials, and particularly relates to an organic photoelectric material and application thereof. The organic photoelectric material has amolecular structure shown as a formula I, wherein, R1 is selected from one of phenyl, alkyl phenyl, biphenyl, naphthyl, phenanthryl, anthryl, fluorenyl and dibenzofuran, R2, R3, R4, R5, R6 and R7 areindependently selected from hydrogen atom, fluorine atom, cyan, isothiocyanate and aromatic heterocyclic radical of 10-50 in carbon atom number and containing at least one of N, S and O. The organicphotoelectric material has high thermostability and high glass transition temperature and can serve as a luminous material to be applied in organic electroluminescence devices, so that maximum currentefficiency of the organic electroluminescence devices is improved, turn-on voltage of the organic electroluminescence devices is lowered, and spectrum covering range of visible light emitted by the organic electroluminescence devices is wide.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to an organic photoelectric material and its application. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the positive and negative ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22C07D417/04C07D417/10C07D417/14C07D487/06C07D498/06C09K11/06H01L51/54
CPCC09K11/06C07D279/22C07D417/04C07D417/10C07D417/14C07D487/06C07D498/06C09K2211/1037H10K85/615H10K85/636H10K85/657H10K85/6572
Inventor 慈振华张梅林存生马永洁石宇胡葆华周银波孟凡民
Owner VALIANT CO LTD
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