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Branching structure functional material based on minami carbazole and preparation method and application thereof

A technology for arylation of trioxacarbazole and trioxacarbazole, which is applied in the field of six-arm or three-arm branched structural functional materials and their preparation, and achieves the effect of wide application value and excellent thermal stability

Inactive Publication Date: 2007-10-31
FUDAN UNIV
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  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no reports of related literature or published patents on the application of conjugated functional materials containing tricarbazole structural units in the field of organic electronics, especially in the fields of organic electroluminescence.

Method used

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  • Branching structure functional material based on minami carbazole and preparation method and application thereof
  • Branching structure functional material based on minami carbazole and preparation method and application thereof
  • Branching structure functional material based on minami carbazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0188] Embodiment 1: the synthesis of compound a-1

[0189] (1) Synthesis of Tricarbazole Precursor

[0190] Synthesis of Hexabromotricarbazole

[0191] Br 2 (22.44g, d=3.12g / ml, 7.19ml, 140.2mmol) was dissolved in acetocyanide (30ml), and added dropwise to the solution of indole (5.44g, 46.6mmol) in acetocyanide (100ml) for about 10min. Finish. The mixture was stirred overnight, and the obtained dark green precipitate was filtered, washed with a large amount of acetocyanide solution, and recrystallized in a DMSO / acetone mixed solution to obtain an off-white solid (3.21 g, 25.2%). 1 H NMR (400MHz, DMSO, δ, ppm): 12.13(3H, s), 8.88(3H, s), 7.87(3H, s).IR(KBr disc) / cm -1 : 3419.8, 2358.9, 1633, 1600, 1469, 1431, 1399, 1361, 1296, 1264, 1225, 1074, 1025, 949, 920, 866, 850, 701, 636, 529. Elemental analysis (%): Experimental determination: C 35.12, H 1.12, N 5.16; Theoretical: C 35.21, H 1.11, N 5.13.

[0192] Synthesis of Hexabromobutyl Tricarbazole

[0193] Hexabromotric...

Embodiment 2

[0203] The synthesis of embodiment 2 compound a-2

[0204] (1) Synthesis of hexabromohexyl tricarbazole

[0205] Synthesized according to the method in compound a-1, wherein the alkyl bromide can be 1-bromohexane, and the yield is 66%. 1 H NMR (400Hz, CDCl 3 , ppm, δ): 8.02 (s, 3H), 7.55 (s, 3H), 4.08 (m, 6H), 1.74 (brs, 6H), 1.33-1.26 (m, 18H), 0.87-0.84 (m, 9H ). 13 C NMR (100MHz, CDCl 3 , ppm, δ): 140.31, 138.93, 125.19, 123.13, 118.72, 115.43, 114.76, 101.53, 47.17, 31.70, 30.41, 26.41, 22.86, 14.24. MS (MALDI-TOF): Calcd for C 42 h 45 Br 6 N 3 : 1064.87; Found: 1069.0(M + ), 991.0 ([M-Br] + ), 913.1 ([M-2Br] + ), 833.2 ([M-3Br] + , 100%), 753.3 ([M-4Br] + ), 675.3 ([M-5Br] + ), 597.5 ([M-6Br] + ). Elemental analysis (%): experimental determination: C47.19 H 4.20, N, 3.89; theoretical value: C 47.09 H 4.23, N, 3.92.

[0206] (2) Synthesis of 9,9-dihexylfluorene monoboronic acid

[0207] Same as the synthesis of 9,9-dihexylfluorene monoboronic acid in compou...

Embodiment 3

[0211] The synthesis of embodiment 3 compound a-5

[0212] (1) Synthesis of hexabromophenylated tricarbazole

[0213] Hexabromotricarbazole (2.45g, 3mmol), 1-iodobenzene (2.75g, 13.5mmol), 1,10-phenanthroline (0.162g, 0.9mmol), CuI (98.5mg, 0.9mmol) and KOH (1.4g, 25mmol) was heated to reflux in a p-xylene (100ml) solution for 24h, and the obtained crude product was recrystallized in n-hexane and ethanol in turn to obtain a white crystal product (2.35g, 75%). 1 H NMR (400Hz, CDCl 3 , ppm, δ): 8.40(s, 3H), 7.71(s, 3H), 7.35-7.18(m, 15H). 13 CNMR (100MHz, CDCl 3 , ppm, δ): 141.2, 138.2, 129.4, 127.7, 125.6, 123.5, 121.6, 117.3, 116.9, 116.8, 114.8, 112.6. MS (MALDI-TOF): Calcd for C 42 h 21 Br 6N 3 : 1040.68; Found: 1047.0(M + ), 969.1 ([M-Br] + ), 891.3 ([M-2Br] + ), 813.4 ([M-3Br] + , 100%), 735.6 ([M-4Br] + ), 657.8 ([M-5Br] + ), 579.9 ([M-6Br] + ).

[0214] (2) Synthesis of 9,9-dihexylfluorene monoboronic acid

[0215] Same as the synthesis of 9,9-dihexylfluo...

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Abstract

The invention disclose a preparing method of functional material based on branched structure of three carbazole and application in organic electronic material technique domain, which is characterized by the following: choosing three carbazole derivant as skeleton of branched structure molecular; choosing fluorescent light chromogen as functional group; grafting to the surrounding of the skeleton; getting the functional molecular compound with three arms or six arms structure; adopting microwave auxiliary method to prepare this material. This material possesses precise structure and good heat endurance, which can be used to solar battery and organic fieldistor.

Description

technical field [0001] The invention belongs to the technical field of organic electronic materials, and specifically relates to a class of functional materials with six-arm or three-arm branched structures with tricarbazole as the core and fluorescent chromophore oligomers as branches, as well as its preparation method and its application in organic electrophoresis. Applications in luminescence, solar cells, organic field effect transistors and other fields. technical background [0002] In the past ten years, compared with inorganic semiconductor materials, organic semiconductor materials are easy to design, simple to prepare, easy to cut, easy to process (such as low-cost spin coating and inkjet printing technology for solution method, etc.) To achieve many characteristics and advantages such as flexible devices, many famous multinational companies and world-class universities are competing to participate in research and development, making the emerging discipline of orga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14C09K11/06H01L51/00H01L51/30H01L51/46H01L51/54H10K99/00
CPCY02E10/549
Inventor 黄维赖文勇
Owner FUDAN UNIV
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