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Thermally-activated delayed fluorescence OLED material taking cyclic diketone as core and application of OLED material

A heat-activated delayed, cyclic diketone technology, applied in the direction of luminescent materials, electrical components, circuits, etc., can solve the problems of not being able to meet high-efficiency organic light-emitting diodes, limit the development of efficient delayed fluorescent materials, reduce luminous efficiency, etc., and achieve good applications effect, good performance, and long device life

Active Publication Date: 2017-05-31
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the correlation between the material structure and its photophysical properties and device efficiency is still unclear, which limits the development of high-efficiency delayed fluorescence materials, resulting in a single type of existing TADF materials and low device efficiency, which cannot meet the requirements of high-efficiency organic light-emitting diodes.
[0005] The high-efficiency electroluminescence process usually requires that the wave functions of the molecular frontier orbits overlap to the greatest extent during the transition of electrons to the ground state through excited state radiation. If the overlap is too small, the intersystem crossing process will be accelerated and the luminous efficiency will be reduced.

Method used

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  • Thermally-activated delayed fluorescence OLED material taking cyclic diketone as core and application of OLED material
  • Thermally-activated delayed fluorescence OLED material taking cyclic diketone as core and application of OLED material
  • Thermally-activated delayed fluorescence OLED material taking cyclic diketone as core and application of OLED material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of compound C1

[0040]

[0041] In a 500mL three-necked flask, add 2-(4-bromophenyl)cyclohexane-1,3-dione (2.67g, 0.01mol), 5-phenyl-5,10-dihydrophenazine (2.58g , 0.01mol), sodium tert-butoxide (2.88g, 0.03mol), xylene (300mL), palladium acetate (0.074g), Xantphos (0.348g), under N2 protection, the temperature was raised to reflux, the reaction was kept for 12h, and the At room temperature, add 150mL deionized water to the reaction bottle, stir for 5min, separate the liquid, wash the organic phase twice with 200mL deionized water, collect the organic phase, dry with anhydrous Na2SO4, filter, remove the solvent, and purify the crude product by silica gel column chromatography , the eluent is toluene:petroleum ether=1:2, to obtain compound C1, 2.85 g of light yellow solid, yield 64.2%.

[0042] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 30 h 24 N 2 o 2 , the theoretical value is 444.1838, a...

Embodiment 2

[0043] Embodiment 2: the preparation of compound C4

[0044]

[0045]The preparation method of compound C4 is the same as that of Example 1, except that raw material A1 is used to replace 5-phenyl-5,10-dihydrophenazine in Example 1 to obtain compound C4, 3.23 g of light yellow solid, yield 66.7 %.

[0046] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 33 h 28 N 2 o 2 , the theoretical value is 484.2151, and the test value is 484.2331. Elemental analysis (C 33 h 28 N 2 o 2 ), theoretical value C: 81.79, H: 5.83, N: 5.78, O: 6.60, measured value C: 81.78, H: 5.84, N: 5.77, O: 6.61.

Embodiment 3

[0047] Embodiment 3: the preparation of compound C7

[0048]

[0049] The preparation method of compound C7 is the same as that of Example 1, except that raw material A2 is used to replace 5-phenyl-5,10-dihydrophenazine in Example 1 to obtain compound C7, 3.06 g of light yellow solid, yield 57.3 %.

[0050] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 37 h 27 NO 3 , theoretical value 533.1991, test value 533.1860. Elemental analysis (C 37 h 27 NO 3 ), theoretical value C: 83.28, H: 5.10, N: 2.62, O: 8.99, measured value C: 83.30, H: 5.12, N: 2.61, O: 8.97.

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Abstract

The invention discloses a thermally-activated delayed fluorescence OLED material taking cyclic diketone as a core and application of the OLED material, belonging to the technical field of organic photoelectric materials. The thermally-activated delayed fluorescence OLED material has a structure represented by a formula I (shown in the description). The invention further discloses the application of the OLED material. The OLED material disclosed by the invention is an organic small molecule compound which takes cyclic diketone as a distinguishing feature and is formed by linking an aromatic group with a nitrogen-containing heterocyclic ring. The OLED material has a proper molecular energy level, a relatively high glass-transition temperature and an obvious thermally-activated delayed fluorescence (TADF) characteristic, can be used as a TADF material for preparing a functional layer, particularly a light emitting layer of an organic electroluminescence device, and can be applied to the organic electroluminescence field.

Description

technical field [0001] The invention relates to a thermally activated delayed fluorescent OLED material with a cyclic diketone as the core and an application thereof, belonging to the technical field of organic photoelectric materials. Background technique [0002] At present, products based on OLED display technology have been industrialized. Compared with liquid crystal display technology, OLED display technology has many advantages such as self-luminescence, no radiation, light weight, thin thickness, wide viewing angle, wide color gamut, stable color, fast response speed, strong environmental adaptability, and flexible display. Therefore, OLED display technology is gaining more and more attention and corresponding technical investment. [0003] The basic structural unit of an OLED display is an OLED device, which can be divided into fluorescent devices and phosphorescent devices according to different light-emitting mechanisms. The theoretical internal quantum efficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46C07D498/06C07D513/06C07D471/06C07D487/06C07D491/107C07D221/20C07D471/20C07D491/048C07D221/18C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D221/18C07D221/20C07D241/46C07D471/04C07D471/06C07D471/20C07D487/06C07D491/048C07D491/107C07D498/06C07D513/06C09K2211/1088C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1029H10K85/6572H10K85/657
Inventor 高树坤盛磊张鑫鑫胡葆华陈晓晓矫志
Owner VALIANT CO LTD
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