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Organic micromolecule material based on 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application

An acceptor unit and small molecule technology, applied in the field of organic small molecule materials, to achieve the effect of easy purification, good reproducibility and low sublimation temperature

Active Publication Date: 2018-09-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] So far, there are few reports on organic small molecule optoelectronic functional materials based on 2,6-dimethyl-4-benzonitrile acceptor unit and phenyl aromatic amine heterocycle or phenyl aromatic amine donor unit.

Method used

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  • Organic micromolecule material based on 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application
  • Organic micromolecule material based on 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application
  • Organic micromolecule material based on 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Preparation of organic small molecule materials based on 2,6-dimethyl-4-benzonitrile acceptor unit with structural formula 1:

[0030] (1) Synthesis of intermediate product 1: under a nitrogen atmosphere, 183 mg of phenoxazine and 10 ml of bromobenzene were added to a 250 ml wide-mouth three-necked round-bottomed reaction flask, and dissolved in 70 ml of toluene solution. Add 5 grams of potassium carbonate subsequently, stir and ventilate for 15 minutes. Subsequently, a solution of 44.6 mg of palladium acetate and 0.73 mg of tri-tert-butylphosphine was added, stirred with aeration for 30 minutes, and then heated to 110 degrees Celsius. Reflux for 24 hours. After cooling down to stop the reaction, the liquid in the reaction system was removed by rotary evaporation to obtain the intermediate product 10-phenyl-10H-phenoxazine. Product Molecular Formula: C 18 h 13 NO; molecular weight: 259.31; elemental analysis results: C, 83.37; H, 5.05; N, 5.40; O, 6.17. The reactio...

Embodiment 2

[0039] Preparation of organic small molecule materials based on 2,6-dimethyl-4-benzonitrile acceptor unit with structural formula 2:

[0040] Compared with Example 1, the difference is that phenoxazine is replaced by an equivalent amount of 9,9-dimethyl-9,10-dihydroacridine, and other raw materials and steps are the same as in Example 1.

[0041] (1) Molecular formula of intermediate product 1: C 21 h 19 N; molecular weight: 285.39; elemental analysis results: C, 88.38; H, 6.71; N, 4.91. The reaction formula is as follows:

[0042]

[0043] (2) Molecular formula of intermediate product 2: C 21 h 18 BrN; molecular weight: 364.29; elemental analysis results: C, 69.24; H, 4.98; Br, 21.93; N, 3.85. The reaction formula is as follows:

[0044]

[0045] (3) Molecular formula of intermediate product 3: C 27 h 30 BNO 2 ; Molecular weight: 411.35; Elemental analysis results: C, 78.84; H, 7.35; B, 2.63; N, 3.41; The reaction formula is as follows:

[0046]

[0047] (...

Embodiment 3

[0050] Preparation of organic small molecule materials based on 2,6-dimethyl-4-benzonitrile acceptor unit with structural formula 3:

[0051] Compared with Example 1, the difference is that the phenoxazine is replaced by an equivalent amount of 10,10-dimethyl-5,10-dihydrodibenzo[b,e][1,4]aniline, Other raw materials and steps are all with embodiment 1.

[0052] (1) Molecular formula of intermediate product 1: C 20 h 19 NSi; molecular weight: 301.46; elemental analysis results: C, 79.68; H, 6.35; N, 4.65; Si, 9.32. The reaction formula is as follows:

[0053]

[0054] (2) Molecular formula of intermediate product 2: C 20 h 18 BrNSi; molecular weight: 380.36; elemental analysis results: C, 63.16; H, 4.77; Br, 21.01; N, 3.68; Si, 7.38. The reaction formula is as follows:

[0055]

[0056] (3) Molecular formula of intermediate product 3: C 26 h 30 BNO 2 Si; Molecular weight: 427.21; Elemental analysis results: C, 73.06; H, 7.07; B, 2.53; N, 3.28; O, 7.49; Si, 6.57....

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses an organic micromolecule material based on a 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application. The organic micromolecule material has a structural formula as shown in formula (I), and Ar in the formula shows a phenyl aromatic amine heterocycle or phenyl aromatic amine donor unit. Thematerial has a weak intramolecular charge transfer state, and thus, fluorescence emission of a zone from dark blue to ultraviolet can be realized. Meanwhile, because the molecules have quite short effective conjugated length, the material has high triplet state energy level. In the application of an organic electroluminescent device, the problem of unbalanced charge carriers of a unipolar organicphotoelectric material can be solved effectively, therefore, the structure of the device is simplified, and the performance of the device is improved.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to an organic small molecule material based on a 2,6-dimethyl-4-benzonitrile acceptor unit and its preparation and application. Background technique [0002] Thermally activated delayed fluorescent materials have become an international research and development hotspot because of their comprehensive performance comparable to phosphorescent materials containing heavy metals. Due to the small single triplet splitting energy of this type of pure organic compound material, when applied to a device, it can effectively capture triplet excitons, thereby realizing 100% internal quantum efficiency of an organic electroluminescent device. In this critical period of the industrialization of organic light-emitting diodes, the efficiency, lifetime and stability of pure organic thermally activated delayed fluorescent light-emitting devices still need to be impro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/38C07D279/22C07D241/46C07D219/02C07F7/08C07F7/10C07C253/30C07C255/58C07C255/50C07D209/86C07D209/88C09K11/06H01L51/54
CPCC09K11/06C07C255/50C07C255/58C07D209/86C07D209/88C07D219/02C07D241/46C07D265/38C07D279/22C07F7/0816C07F7/083C09K2211/1037C09K2211/1033C09K2211/104C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1029H10K85/633H10K85/615H10K85/657H10K85/6572H10K2102/00H10K2102/301
Inventor 苏仕健蔡欣佚邱伟栋乔振洋
Owner SOUTH CHINA UNIV OF TECH
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