Small organic molecule electron transport materials based on naphthalimide units and their applications

An electron transport material, the technology of naphthalene diimide, which is 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., to achieve Improve electroluminescent efficiency, improve stability, and facilitate processing

Active Publication Date: 2022-06-07
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Small organic molecule electron transport materials based on naphthalimide units and their applications
  • Small organic molecule electron transport materials based on naphthalimide units and their applications
  • Small organic molecule electron transport materials based on naphthalimide units and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0048]

[0049] The preparation method is as follows: take 1,4,5,8-naphthalenetetracarboxylic anhydride (2.68g, 10mmol); 25mL of concentrated sulfuric acid in a 100mL single-neck flask, stir for 1h until the system is clear, add brominated reagent 1,3 in batches, 5-Tribromo-1,3,5-thiazinane-2,4,6-trione (1.83g, 5mmol), react 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 give white crystals of brominated naphthalene tetracarboxylic anhydride (Br-NDA). Yield 2.42 g, 70% yield.

[0050] NMR analysis of the prepared monomers, the results are 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....

Embodiment 2

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

[0060]

[0061] The preparation method is as follows: take 1,4,5,8-naphthalenetetracarboxylic anhydride (2.68g, 10mmol); 25mL of concentrated sulfuric acid in a 100mL single-neck flask, stir for 1h until the system is clear, add brominated reagent 1,3 in batches, 5-Tribromo-1,3,5-thiazinane-2,4,6-trione (1.83g, 5mmol), react 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 give white crystals of brominated naphthalene tetracarboxylic anhydride (Br-NDA). Yield 2.42 g, 70% yield.

[0062] NMR analysis of the prepared monomers, the results are 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 ): δ16...

Embodiment 3

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

[0072]

[0073] The preparation method is as follows: take 1,4,5,8-naphthalenetetracarboxylic anhydride (2.68g, 10mmol); 25mL of concentrated sulfuric acid in a 100mL single-neck flask, stir for 1h until the system is clear, add brominated reagent 1,3 in batches, 5-Tribromo-1,3,5-thiazinane-2,4,6-trione (1.83g, 5mmol), react 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 give white crystals of brominated naphthalene tetracarboxylic anhydride (Br-NDA). Yield 2.42 g, 70% yield.

[0074] NMR analysis of the prepared monomers, the results are 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 ): δ16...

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Abstract

The invention provides an organic small molecule electron transport material based on a naphthalene diimide unit and an application thereof, belonging to the field of organic photoelectric materials. The invention solves the problems of less selection of electron transport materials and poor device stability in the quantum dot light-emitting diode device in the prior art. The chemical structure of the organic small molecule electron transport material of the present invention contains naphthalene diimide units, and its advantages are: 1) The energy level of the lowest unoccupied molecular orbital is low, which is beneficial to the injection and transmission of electrons in QLED devices, and the highest occupied molecular orbital The energy level is low, which can block the injection of holes in the QLED device. The above two aspects are conducive to improving the electroluminescence efficiency of the QLED device; There is no absorption; 3) It has a rigid configuration, which can inhibit the crystallization of the material, which is beneficial to the processing in QLEDs and improves the stability of QLED devices.

Description

technical field [0001] The invention belongs to the field of organic optoelectronic materials, in particular to an organic small molecule electron transport material based on a naphthalene diimide unit and an application thereof. Background technique [0002] Quantum dots light-emitting diodes (QLEDs) is a color display technology, which can not only 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. It has bright application prospects in the display. 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 light-emitting devices can achieve high luminous efficiency and meet the needs of commercial applications, but their device stability is poor. The hole transport layer generally used in QLEDs is an organic polymer material, ...

Claims

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Application Information

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Patent Type & Authority Patents(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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