Novel thermal-activated-delayed-fluorescence luminescent material and application thereof

A technology of thermally activated delay, luminescent materials, applied in luminescent materials, electrical components, circuits, etc., can solve the problems of device efficiency roll-off, low device fluorescence lifetime, lack of red light TADF molecules, etc., to achieve high glass transition temperature, The effect of good luminous properties

Active Publication Date: 2017-07-14
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the device efficiency roll-off of TADF molecules is relatively serious, and the fluorescence lifetime of the device is rela

Method used

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  • Novel thermal-activated-delayed-fluorescence luminescent material and application thereof
  • Novel thermal-activated-delayed-fluorescence luminescent material and application thereof
  • Novel thermal-activated-delayed-fluorescence luminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of intermediate M1

[0035]

[0036] Introduce 4-bromopyridine (15.8g, 0.1mol) and dry tetrahydrofuran (79g) into a 250mL Erlenmeyer flask, stir to dissolve, and set aside.

[0037] Under the condition of nitrogen protection, 5 mL of the above prepared tetrahydrofuran solution of 4-bromopyridine was introduced into a 250 mL three-necked flask. The bath temperature was set at 65°C, the temperature was raised with stirring, and 2 grains of iodine were introduced to initiate the reaction. After initiation, start to drop the remaining 4-bromopyridine in tetrahydrofuran solution, control the dropping speed, and keep the internal temperature below 65°C. After the dropwise addition was completed, the reaction was incubated for 2 hours. After the heat preservation was completed, a solution of 2,5-dibromo-3,6-dimethylterephthalaldehyde (16.0 g, 0.05 mol) in tetrahydrofuran (32 mL) was added dropwise. After the dropwise addition, the stirring w...

Embodiment 2

[0041] Embodiment 2: the preparation of intermediate M2

[0042]

[0043] Using a method similar to Example 1, using an equivalent amount of 2-bromopyridine instead of 4-bromopyridine, and other conditions unchanged, the intermediate M2 was obtained, 7.2 g of white crystals, with a yield of 75.9%.

[0044] Mass spectrum MS (m / e), molecular formula C 20 h 14 Br 2 N 2 o 2 , the theoretical value is 473.9, and the test value is 474.8.

[0045] Elemental analysis (C 20 h 14 Br 2 N 2 o 2 ), theoretical value: C, 50.66%; H, 2.98%; Br, 33.70%; N, 5.91%; O, 6.75%; measured value: C, 50.65%; 5.91%; O, 6.73%.

Embodiment 3

[0046] Embodiment 3: the preparation of intermediate M3

[0047]

[0048] Using a method similar to Example 1, using an equivalent amount of 2,5-dibromo-3,6-diisopropyl terephthalaldehyde to replace 2,5-dibromo-3,6-dimethyl-p-phthalaldehyde Diformaldehyde, other conditions remain unchanged, to obtain intermediate M3, white crystal 8.7g, yield 82%.

[0049] Mass spectrum MS (m / e), molecular formula C 24 h 22 Br 2 N 2 o 2 , the theoretical value is 528.0, and the test value is 529.1.

[0050] Elemental analysis (C 24 h 22 Br 2 N 2 o 2 ), theoretical value C, 54.36%; H, 4.18%; Br, 30.14%; N, 5.28%; O, 6.03%; measured value C, 54.35%; H, 4.20%; ; O, 6.02%.

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Abstract

The invention belongs to the field of organic electroluminescent materials and particularly relates to a novel thermal-activated-delayed-fluorescence luminescent material and an application thereof. The material is characterized by comprising a structure represented by a formula (1) shown in the description, wherein R1 and R2 each is any one independently selected from a group consisting of a hydrogen atom, a C3-C30 substituted or unsubstituted carbazolyl group, a C3-C30 substituted or unsubstituted arylamine group, a C3-C30 substituted or unsubstituted phenothiazine group, a C3-C30 substituted or unsubstituted phenoxazine group, a C3-C30 substituted or unsubstituted phenazine group and a C3-C30 substituted or unsubstituted acridine group, and R1 and R2 are not hydrogen simultaneously; and R3 is any one selected from a group consisting of hydrogen and C1-C10aliphatic straight-chain or branched-chain alkane. The material provided by the invention is stable in property, has good luminescent performance and is applied to organic electroluminescent devices as a luminescent material.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and in particular relates to a novel heat-activated delayed fluorescent luminescent material and its application. Background technique [0002] Thermally activated delayed fluorescence (TADF) is a special fluorescence phenomenon. Its luminescent principle is that the triplet T1 excitons reverse intersystem crossing under thermal activation to generate singlet S1 excitons, and the S1 excitons radiatively transition to generate fluorescence. Due to the low fluorescence efficiency of early TADF molecules, it has not received enough attention. In 2009, Adachi’s research group at Kyushu University in Japan observed TADF in tin complexes for the first time. After unremitting efforts, in 2012, Adachi’s research group with Carbazole was used as the donor, and dicyanobenzene was used as the acceptor. A series of TADF molecules with different colors were designed and synthesized. Among t...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D213/50C07D413/14C07D417/14C07D519/00C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D213/50C07D401/14C07D413/14C07D417/14C07D519/00C09K2211/1088C09K2211/1007C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044H10K85/654H10K85/6572H10K85/657H10K50/11
Inventor 李庆慈振华张成新石宇刘英瑞杨伟
Owner VALIANT CO LTD
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