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Organic photoelectric material based on perylene bisimide derivative and preparation method thereof

A technology of organic photoelectric materials and perylene imides, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as the lack of electroluminescent materials, achieve less harsh reaction conditions, lower requirements for instruments and equipment, and synthesize The effect of a short route

Pending Publication Date: 2022-01-21
YANGZHOU POLYTECHNIC INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently reported luminescent materials are based on blue light emission, while electroluminescent materials that emit red light are relatively lacking.

Method used

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  • Organic photoelectric material based on perylene bisimide derivative and preparation method thereof
  • Organic photoelectric material based on perylene bisimide derivative and preparation method thereof
  • Organic photoelectric material based on perylene bisimide derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] step 1:

[0024]

[0025] Under nitrogen protection, into a 100mL two-necked bottle, add 5.4g (9mmol) of the compound 1,7-dibromoperylenediimide, 3.6g (20mmol) of 2,6-diisopropylaniline, dissolve in 100ml In water propionic acid, react in an oil bath at 120-125°C for 24 hours. The progress of the reaction was detected by thin-layer chromatography. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 80 ml of water, filtered under reduced pressure, and recrystallized from ethanol to obtain compound PDI-Br, 7.8 g, yield: 92%. 1 H NMR (300MHz, CDCl 3 )δ9.21(s,2H),8.82(d,J=6Hz,6H),7.68-7.54(m,J=7.7Hz,6H),5.63(m,2H),1.38(d,J=9.0Hz ,12H).

[0026] step 2

[0027]

[0028] Under the protection of nitrogen, the compound PDI-Br (6g, 7mmol), carbazole (2g, 7mmol), o-phenanthroline (1.2g, 7mmol), potassium carbonate (1g, 7mmol), and catalytic amount of potassium iodide were dissolved in 100ml DMF In the process, nitr...

Embodiment 2

[0033] step 1

[0034]

[0035] The synthesis of PDI-Be, yield 90%, 1 H NMR (300MHz, CDCl 3 ) δ9.16 (s, 2H), 8.78 (d, J=6Hz, 6H), 7.86-7.82 (m, 4H), 7.66-7.52 (m, 6H).

[0036] step 2

[0037]

[0038] The synthesis of PDI-K, yield 85%, 1 H NMR (300MHz, CDCl 3 ) 1 H NMR (300MHz, CDCl 3 )δ9.12(s,2H),8.76(d,J=6Hz,6H),7.86-7.82(m,4H),7.66-7.52(m,6H),7.48-7.36(m,8H),1.28( s, 6H).

[0039] step 3

[0040]

[0041] Synthesis of PDI-BD: Yield 72%, 1 H NMR (300MHz, CDCl 3 ) 1 H NMR (300MHz, CDCl 3 )δ9.14 (s, 2H), 8.78 (d, J=6Hz, 6H), 8.12-7.86 (m, 4H), 7.88-7.84 (m, 4H), 7.68-7.54 (m, 6H), 7.48- 7.36(m,8H), 1.28(s,6H).

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Abstract

The invention relates to an organic photoelectric material based on a perylene bisimide derivative and a preparation method thereof, the material is prepared by taking perylene bisimide as a construction unit through amidation reaction, bromine substitution reaction and coupling reaction, and the material has the following structural formula shown in the description. According to the invention, cheap and easily available bromo-perylene anhydride is used as a raw material, perylene anhydride reacts with an amine compound through an amidation reaction, then bromine on perylene bisimide is monosubstituted to obtain an active intermediate retaining one bromine, target molecules are further prepared through a palladium-catalyzed coupling reaction, the reaction is efficient, the substrate application range is wide, all related reaction raw materials are easy to obtain, the reaction steps are few, and the yield is high.

Description

technical field [0001] The invention relates to the field of organic photoelectric functional materials and organic synthesis, in particular to an organic photoelectric material based on perylene imide derivatives and a preparation method thereof. Background technique [0002] Organic electroluminescent materials are mainly some organic conjugated small molecules or polymers. Organic conjugated small molecules have the characteristics of wide adjustable emission wavelength range and easy modification. The system can be changed by introducing structures such as alkenes, alkynes, and aromatic rings into the molecules. The degree of conjugation can be used to fine-tune the luminous color, push-pull electron pairs, and band structure of the π-conjugated system, thereby changing the photoelectric properties of the compound. Most of the currently reported luminescent materials are based on blue light emission, while red light emitting electroluminescent materials are relatively la...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06H01L51/46H01L51/54
CPCC07D471/06C09K11/06C09K2211/1029C09K2211/1044C09K2211/1007H10K85/6572
Inventor 孔庆磊成焕仁陈娟姜晔苏爽朱晓叶
Owner YANGZHOU POLYTECHNIC INST
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