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Azacarbazole-based organic photoelectric material and application thereof

An organic optoelectronic material and azacarbazole technology, which is applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of increasing and decreasing the intensity of optical radiation transition constants, unfavorable molecular luminous efficiency, etc., so as to improve the probability of crossover, The effect of improving luminous efficiency and device stability

Inactive Publication Date: 2019-06-07
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although such traditional molecular design has obtained the ideal ΔE ST value, but the complete separation of HOMO and LUMO orbitals and the embedding of barrier units cause the integral of electron exchange between HOMO and LUMO in the molecule to approach 0, that is, the radiative transition rate constant Kr@S1->S in the molecule becomes smaller, Not conducive to the improvement of the luminous efficiency of molecules
In addition, the intermediate barrier unit makes the molecular structure more flexible, thereby reducing the light radiation transition constant of the molecule and the moment intensity during the transition (Kr is proportional to the moment intensity f)

Method used

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  • Azacarbazole-based organic photoelectric material and application thereof
  • Azacarbazole-based organic photoelectric material and application thereof
  • Azacarbazole-based organic photoelectric material and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0055] The specific embodiment of the present invention also provides the above-mentioned preparation method, which is synthesized through the following general synthetic route:

[0056]

[0057] in,

[0058] x 1 、X 2 、X 3 、X 4 each independently selected from C or N, and X 1 , X2, X 3 、X 4 At least one of them is N;

[0059] R 1 , R 2 Each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group;

[0060] R 3 A hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group;

[0061] R 4 , R 5 Each is independently selected from a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C5-C30 heteroaryl group.

[0062] ...

Embodiment 1

[0065] The preparation of embodiment 1:L1

[0066]

[0067] In a three-neck flask equipped with a magnetic stirrer, add a certain amount of A1, sodium hydroxide and 500ml of dry acetone solution under the protection of argon inert gas. Then, a certain amount of B1 was slowly added dropwise, and the stirring reaction was carried out for 8 hours. After the reaction, filter with suction, wash with toluene and ethanol. After xylene recrystallization, L1 powder with a purity of more than 99% was obtained. In order to further improve the purity of L1, a vacuum sublimation apparatus is used to carry out one or more sublimation, and an L1 product with a purity greater than 99.5% can be obtained.

[0068] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0069] 1 H NMR (400MHZ, DMSO-d6):

[0070] 5.7ppm(1H,S), 5.8ppm(2H,S), 6.21ppm(8H,p), 6.37ppm(8H,p), 6.46ppm(4H,d), 6.62ppm(2H,t), 7.00- 7.08ppm(6H,m),7.38-7.4...

Embodiment 2

[0071] The preparation of embodiment 2:L2

[0072]

[0073] In a three-necked flask equipped with a magnetic stirrer, a certain amount of B2, sodium hydroxide and 500ml of dry acetone solution were added under the protection of argon inert gas. Then, a certain amount of A2 was slowly added dropwise, and the stirring reaction was carried out for 8 hours. After the reaction, filter with suction, wash with toluene and ethanol. After xylene recrystallization, L2 powder with a purity of more than 99% was obtained. In order to further improve the purity of L2, a vacuum sublimation apparatus is used to carry out one or more sublimation, and an L2 product with a purity greater than 99.5% can be obtained.

[0074] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0075] 1 H NMR (400MHZ, DMSO-d6):

[0076] 6.21ppm(4H,p),6.37ppm(4H,p),6.46-6.5ppm(4H,d),6.6-6.62ppm(2H,t),7.00-7.08ppm(6H,m),7.38-7.40ppm (4H,t),7.55...

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Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses an azacarbazole-based organic photoelectric material and an application thereof. A energy level difference between a singlet state and triplet state of the azacarbazole-based organic photoelectric material used as an electroluminescent material is less than 300 meV, so the increase the probability of reversegap crossing of triplet state excitons to singlet state excitons is benefited. In addition, the azacarbazole-based organic photoelectric material keeps a low deltaEST, and also has a very matching hole-electron transmission rate, so the increase of the luminous efficiency and the device stability of the material is benefited.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to an azacarbazole-based organic photoelectric material and its application. Background technique [0002] Organic electroluminescent materials are classified into fluorescent electroluminescent materials and phosphorescent electroluminescent materials. Among them, phosphorescent electroluminescent materials can utilize the energy of all excitons through the heavy metal effect, so they have greater advantages. In 2009, thermally activated delayed fluorescence compounds, namely TADF (Thermally activated delayed fluorescence) materials, were proposed and applied in the technical field of organic electroluminescent devices. Under thermal excitation, this kind of fluorescent compound can use the reverse gap crossing of triplet excitons to obtain 100% singlet excitons, which not only avoids the use of expensive heavy metal complexes, but also has device efficiency com...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D471/14C07D519/00C09K11/06H01L51/54
Inventor 谢再锋
Owner AAC TECH NANJING