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Bipolar organic photoelectric material based on N-C=O resonance structure, and preparation method and application thereof

A technology of organic optoelectronic materials and resonance structures, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of triplet energy level reduction, conjugated system extension, molecular band gap narrowing, etc., and achieve high triplet state Energy level, easy availability of raw materials, favorable effects on injection and transport

Inactive Publication Date: 2020-06-02
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in such a Donor-Acceptor structure, there is usually a strong intramolecular interaction between the donor and the acceptor unit, and the conjugation system is extended, so that the molecule has a narrow band gap and a red-shifted luminescence, as well as a triplet energy level. reduce

Method used

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  • Bipolar organic photoelectric material based on N-C=O resonance structure, and preparation method and application thereof
  • Bipolar organic photoelectric material based on N-C=O resonance structure, and preparation method and application thereof
  • Bipolar organic photoelectric material based on N-C=O resonance structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the preparation method of organic optoelectronic material 1

[0026] Take two reaction flasks, add 0.50g carbazole and 0.24g N,N-carbonyldiimidazole, vacuumize, blow argon three times, and under the protection of nitrogen, add 10mL ultra-dry dimethyl sulfoxide to dissolve the substrate. Heat and stir at 100-120°C for 6 hours. After the reaction, cool to room temperature, add deionized water to precipitate a white precipitate, filter with suction, collect the white solid and dissolve it in dichloromethane, dry it with anhydrous sodium sulfate, filter, and concentrate the filtrate , purified by column chromatography to give a white solid. Yield: 44%. 1 HNMR (DMSO-d 6 ,400MHz)δ(ppm):8.30(d,J=8Hz,4H),7.44-7.37(m,8H),7.43(d,J=8Hz,4H). 13 C NMR (CDCl 3 ,100MHz)δ(ppm):149.53,137.95,127.24,125.91,123.57120.20,114.58.HRMS(EI):m / zcalcdforC 25 h 16 N 2 O[M] + :361.1347; found: 361.1341..

[0027] The structure is as follows:

[0028]

Embodiment 2

[0029] Example 2: Performance characterization of phosphorescent organic electroluminescent devices (PhOLEDs)

[0030] In this embodiment, the device using the complex as the light-emitting layer may include: 1. a conductive glass layer (ITO); 2. a hole injection layer PEDOT:PSS; 3. a hole transport layer (TAPC); 4. an exciton blocking layer ( mCP); 5. Light emitting layer; 6. Electron transport layer (TmPyPB); 7. Electron injection layer (LiF); 8. Cathode Al.

[0031] The fabrication method of PhOLEDs is as follows: first spin-coat PEDOT:PSS hole injection layer on the cleaned glass substrate (ITO), and then sequentially vapor-deposit. ITO / PEDOT:PSS(30nm) / 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6-tetrachloride(TAPC)(20nm) / N,N′- dicarbazolyl-3,5-benzene(mCP)(8nm) / host:18wt%FIrpic(22nm) / 1,3,5-tri(m-pyrid-3-yl-phenyl)benzene(TmPyPB)(35nm) / LiF (1nm) / Al(100nm). The host material in the light-emitting layer is the material 1 prepared in the above examples. The current densi...

Embodiment 3

[0032] Example 3: Performance characterization of thermally activated delayed fluorescence organic electroluminescent devices (TADF OLEDs)

[0033] In this embodiment, the device using small organic molecules as the light-emitting layer may include: 1. Conductive glass layer (ITO); 2. Hole injection layer PEDOT:PSS; 3. Light-emitting layer; 4. Exciton blocking layer (TSPO1); 5. . Electron transport layer (TPBi); 6. Electron injection layer (Liq); 7. Cathode Al.

[0034] The fabrication method of TADFOLEDs is as follows: first spin-coat the PEDOT:PSS hole injection layer on the cleaned ITO, and then vapor-deposit sequentially. ITO / PEDOT:PSS(30nm) / TAPC(20nm) / mCP(8nm) / host:30wt%bis-[4-(9,9-dimethyl-9,10-dihydroacridine)-phenyl]-sulfone(DMAC-DPS )(20nm) / diphenylphosphineoxide-4-(triphenylsilyl)phenyl(TSPO1)(5nm) / 1,3,5-tris(N-phenylbenzmidazol-2-yl)benzene(TPBi)(35nm) / LiF(1nm) / Al (100nm). The host material in the light-emitting layer is the material 1 prepared in the above examp...

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Abstract

The invention discloses a bipolar organic photoelectric material based on an N-C=O resonance structure, and a preparation method and an application thereof. The general molecular structural formula ofthe material is represented by formula I. The material has good solubility and thermal stability, high triplet state energy level and very balanced carrier transport capacity, so injection and transport of holes and electrons are facilitated.

Description

technical field [0001] The invention relates to a bipolar organic photoelectric material and its preparation method and use, in particular to a bipolar organic photoelectric material based on an N-C=O resonance structure, its preparation method and its use. Background technique [0002] Organic optoelectronic materials are a class of organic materials with photoelectric activity, which are widely used in organic light-emitting diodes, organic solar cells, organic thin-film transistors, organic memories and sensors, etc. field. Among them, organic optoelectronic materials with bipolar transport properties can efficiently transport electrons and holes simultaneously, which plays an important role in the preparation of high-performance organic optoelectronic devices. At present, the types of bipolar organic photoelectric materials constructed are relatively single, and most of them are based on the donor (Donor)-acceptor (Acceptor) structure or the Donor-bridging unit (π bridg...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D209/88C09K11/06H01L51/54
CPCC07D209/86C07D209/88C09K11/06C09K2211/1029H10K85/6572
Inventor 陈润锋姜贺靳继彪黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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