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Organic small molecule electron transport material based on naphthalimide unit and application thereof

An electron transport material, a technology of naphthalene diimide, applied in the field of organic small molecule electron transport materials, can solve the problems of insufficient device efficiency and stability, high LUMO energy level, unfavorable electron injection and transport in devices, etc. Improve electroluminescence efficiency, improve stability, and facilitate processing

Active Publication Date: 2021-07-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are also QLED devices using small organic molecules as the electron transport layer reported in the literature, but the LUMO energy level of these organic small molecule electron transport materials is high, which is not conducive to the injection and transport of electrons in the device, resulting in the efficiency and stability of the device. not good enough

Method used

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  • Organic small molecule electron transport material based on naphthalimide unit and application thereof
  • Organic small molecule electron transport material based on naphthalimide unit and application thereof
  • Organic small molecule electron transport material based on naphthalimide unit and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: DNDI (4-b-C8) small organic molecule, structural formula is as follows:

[0048]

[0049] The preparation method is: weigh 1,4,5,8-naphthalene tetracarboxylic anhydride (2.68g, 10mmol); put 25mL concentrated sulfuric acid in a 100mL single-necked bottle, stir for 1h until the system is clear, add brominated reagent 1,3, 5-Tribromo-1,3,5-thiazinane-2,4,6-trione (1.83g, 5mmol) was reacted at room temperature for 8h. After the reaction, the system was poured into ice water, stirred for 3 h, filtered with suction, washed with methanol and dried to obtain the crude product as light yellow powder. The product was recrystallized from N,N-dimethylformamide to obtain white crystals of bromonaphthalic anhydride (Br-NDA). Yield 2.42g, 70% yield.

[0050] Carry out nuclear magnetic analysis to the monomer of preparation, the result is as follows:1 H NMR (400MHz, DMSO-d 6 ):δ8.71(s,1H),8.57(d,1H),8.21(d,1H); 13 C NMR (100MHz, DMSO-d 6 ): δ168.1, 160.0, 159.4, 1...

Embodiment 2

[0059] Embodiment 2: DNDI (4-d-C5) small organic molecule, structural formula is as follows:

[0060]

[0061] The preparation method is: weigh 1,4,5,8-naphthalene tetracarboxylic anhydride (2.68g, 10mmol); put 25mL concentrated sulfuric acid in a 100mL single-necked bottle, stir for 1h until the system is clear, add brominated reagent 1,3, 5-Tribromo-1,3,5-thiazinane-2,4,6-trione (1.83g, 5mmol) was reacted at room temperature for 8h. After the reaction, the system was poured into ice water, stirred for 3 h, filtered with suction, washed with methanol and dried to obtain the crude product as light yellow powder. The product was recrystallized from N,N-dimethylformamide to obtain white crystals of bromonaphthalic anhydride (Br-NDA). Yield 2.42g, 70% yield.

[0062] Carry out nuclear magnetic analysis to the monomer of preparation, the result is as follows: 1 H NMR (400MHz, DMSO-d 6 ):δ8.71(s,1H),8.57(d,1H),8.21(d,1H); 13 C NMR (100MHz, DMSO-d 6 ): δ168.1, 160.0, 159.4,...

Embodiment 3

[0071] Embodiment 3: DNDI (4-n-C6) small organic molecule, structural formula is as follows:

[0072]

[0073] The preparation method is: weigh 1,4,5,8-naphthalene tetracarboxylic anhydride (2.68g, 10mmol); put 25mL concentrated sulfuric acid in a 100mL single-necked bottle, stir for 1h until the system is clear, add brominated reagent 1,3, 5-Tribromo-1,3,5-thiazinane-2,4,6-trione (1.83g, 5mmol) was reacted at room temperature for 8h. After the reaction, the system was poured into ice water, stirred for 3 h, filtered with suction, washed with methanol and dried to obtain the crude product as light yellow powder. The product was recrystallized from N,N-dimethylformamide to obtain white crystals of bromonaphthalic anhydride (Br-NDA). Yield 2.42g, 70% yield.

[0074] Carry out nuclear magnetic analysis to the monomer of preparation, the result is as follows: 1 H NMR (400MHz, DMSO-d 6 ):δ8.71(s,1H),8.57(d,1H),8.21(d,1H); 13 C NMR (100MHz, DMSO-d 6 ): δ168.1, 160.0, 159.4,...

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Abstract

The invention provides an organic small molecule electron transport material based on a naphthalimide unit and application thereof, belongs to the field of organic photoelectric materials, and solves the problems that in the prior art, the quantum dot light-emitting diode device is few in electron transport material selection and poor in device stability. The chemical structure of the organic small molecule electron transport material contains a naphthalimide unit, and the organic small molecule electron transport material has the advantages that 1) the lowest unoccupied molecular orbital energy level is low, electron injection and transport in a QLED device are facilitated, the highest occupied molecular orbital energy level is low, hole injection in the QLED device can be blocked, and the above two aspects are beneficial for improving the electroluminescent efficiency of the QLED device; (2) the absorption spectrum is mainly not located in a visible light region and does not absorb light emitted by the light-emitting layer in the QLED device; and 3) the material has a rigid configuration, can inhibit crystallization of the material, is beneficial to processing in a QLED, and is beneficial to improving the stability of a QLED device.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to an organic small molecule electron transport material based on a naphthalene diimide unit and an application thereof. Background technique [0002] Quantum dot light-emitting diodes (quantum dots light-emitting diodes, QLEDs) is a color display technology, not only can be printed and processed to achieve low cost and large area, but also has the outstanding advantages of high color purity and good color saturation. In high-definition color Display has a bright application prospect. The basic device structure of QLED is transparent electrode / hole transport layer / quantum dot light-emitting layer / electron transport layer / metal electrode. After years of research, QLED's red, green, and blue three-color light-emitting devices can achieve high luminous efficiency, which can meet the needs of commercial applications, but their device stability is poor. The ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C07D519/00C07F7/10H01L51/50H01L51/54
CPCC07F7/0838C07D471/06C07D519/00H10K85/621H10K85/615H10K85/655H10K85/40H10K85/6572H10K50/115H10K50/16Y02E10/549
Inventor 刘俊高鱼越王利祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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