Narrow-emission efficient multi-resonance light-emitting material, preparation method thereof and organic light-emitting diode

A luminescent material and high-efficiency technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as emission peak broadening and spectral red shift, and achieve high color purity, narrow emission spectrum, and excellent photochemical stability Effect

Pending Publication Date: 2022-02-08
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In view of the above deficiencies in the prior art, the purpose of the present invention is to provide a narrow-emission high-efficiency multiple resonance luminescent material and its preparation method and an organic light-emitting diode, aiming at solving the problem of excessive doping concentration of the existing multiple resonance type TADF material. Problems that lead to spectral red shift and emission peak broadening

Method used

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  • Narrow-emission efficient multi-resonance light-emitting material, preparation method thereof and organic light-emitting diode
  • Narrow-emission efficient multi-resonance light-emitting material, preparation method thereof and organic light-emitting diode
  • Narrow-emission efficient multi-resonance light-emitting material, preparation method thereof and organic light-emitting diode

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] This example provides a narrow-emission high-efficiency multiple resonance luminescent material, which is denoted as compound 1. The synthetic route of compound 1 is as follows:

[0084]

[0085] The synthetic method of compound 1 specifically comprises the following steps:

[0086] Add Cz-Br (4.87g, 10mmol), O-Bpin (3.96g, 10mmol), K 2 CO 3 (2.76g, 20mmol), tetrabutylammonium bromide (Bu 4 NBr, 322mg, 1mmol) and Pd(PP 3 ) 4 (578 mg, 0.5 mmol) and degassed. After adding redistilled THF and distilled water by syringe, N 2 Reflux at 80°C for 24h under atmosphere. After the reaction was completed, when the temperature dropped to room temperature, the liquid was separated, the aqueous phase was extracted three times with dichloromethane, and the organic phase was combined, dried with magnesium sulfate, filtered, and the filtrate was concentrated by a rotary evaporator, and separated by column chromatography to obtain compound 1. White solid, 47% yield. 1 H NMR (C...

Embodiment 2

[0088] This example provides a narrow-emission high-efficiency multiple resonance luminescent material, which is denoted as compound 2. The synthetic route of compound 2 is as follows:

[0089]

[0090] The synthetic method of compound 2 specifically comprises the following steps:

[0091] The specific steps are the same as those of compound 1 in Example 1, except that O-Bpin (3.96 g, 10 mmol) in Example 1 is replaced by S-Bpin (4.28 g, 10 mmol).

[0092] Compound 2 was obtained as a white solid with a yield of 49%. 1 H NMR (CDCl 3 ,500MHz)δ(ppm):8.32(2H,dd,J 1 =7.5Hz,J 2 =1.5Hz),7.91-7.90(3H,m),7.46(2H,ddd,J 1 =8.5Hz,J 2 =7.5Hz,J 2 =1.5Hz),7.44(4H,d,J=8.0Hz),7.30(2H,dd,J 1 =8.5Hz,J 2 =7.5Hz),7.28(4H,t,J=7.5Hz),7.10-7.20(4H,m),7.00(4H,t,J=7.5Hz),6.90(2H,dd,J 1 =8.0Hz,J 2 = 2.0 Hz), 6.80 (2H, d, J = 9.0 Hz). Mass (MALDITOF): m / z, calcd for C 48 h 29 BN 2 S 2 + :708.18652; found: 708.18666.

Embodiment 3

[0094] This example provides a narrow-emission high-efficiency multiple resonance luminescent material, which is denoted as compound 3. The synthetic route of compound 3 is as follows:

[0095]

[0096] The synthetic method of compound 3 specifically comprises the following steps:

[0097] The specific steps are the same as those of compound 1 in Example 1, except that O-Bpin (3.96 g, 10 mmol) in Example 1 is replaced by Se-Bpin (5.22 g, 10 mmol).

[0098] Compound 3 was obtained as a white solid with a yield of 35%. 1 H NMR (CDCl 3 ,500MHz)δ(ppm):8.30(2H,dd,J 1 =7.5Hz,J 2 =1.5Hz),7.91-7.90(3H,m),7.40(2H,ddd,J 1 =8.5Hz,J 2 =7.5Hz,J 2 =1.5Hz),7.44(4H,d,J=8.0Hz),7.30(2H,m),7.28(4H,m),7.10-7.20(4H,m),7.00(4H,t,J=7.5Hz ),6.90(2H,dd,J 1 =8.0Hz,J 2 = 2.0 Hz), 6.80 (2H, d, J = 9.0 Hz). Mass (MALDITOF): m / z, calcd for C 48 h 29 BN 2 Se 2 + :804.07542; found: 804.07533.

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Abstract

The invention discloses a narrow-emission efficient multi-resonance light-emitting material, a preparation method thereof and an organic light-emitting diode. The structural general formula of the material is shown in the specification, in the formula, a, b, c and d are respectively and independently selected from aromatic ring groups or aromatic heterocyclic groups with the ring atom number of 5-30; X and Y are each independently selected from nitrogen or oxygen atoms; R1 to R15 are respectively and independently selected from a hydrogen group, a substituted or unsubstituted aromatic ring group or aromatic heterocyclic ring group with the ring atom number of 5 to 50, a straight chain or straight chain alkyl group with the carbon atom number of 1 to 100, and a straight chain or straight chain alkoxy group with the carbon atom number of 1 to 100; R1 to R5 may also be cyano groups; R14 and R15 are each independently present or absent; A and B independently exist or do not exist, and when A and B independently exist, A and B are independently selected from one of an oxygen group atom and an alkyl group; '---' represents that the components can be linked into a bond or can not be linked into a bond. After the material is applied to an organic light emitting diode, the material shows excellent properties of high luminous efficiency, narrow emission spectrum, low sensitivity to doping concentration and the like.

Description

technical field [0001] The invention relates to the field of organic light-emitting materials, in particular to a narrow emission high-efficiency multiple resonance light-emitting material, a preparation method thereof and an organic light-emitting diode. Background technique [0002] According to quantum spin statistics, the electroluminescence process will produce 25% singlet excitons and 75% triplet excitons, due to spin prohibition, they cannot transition to each other in ordinary organic materials, only singlet states Excitons can be used for fluorescence emission, while triplet excitons are usually dissipated in the form of heat and so on. In order to utilize 75% of triplet excitons, heavy metal complexes are introduced, and the spin-orbit coupling between heavy metals and their ligands can convert singlet excitons to triplet states and emit phosphorescence by breaking through the prohibition of electron spin direction. However, phosphorescent devices have disadvantag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1055C09K2211/1059C09K2211/1096H10K85/615H10K85/631H10K85/636H10K85/654H10K85/657H10K85/6572
Inventor 杨楚罗姜鹏程曹啸松
Owner SHENZHEN UNIV
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