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Porphyrin copolymer containing diketopyrrolopyrrole unit, preparation method and application thereof

A technology of diketopyrrolopyrrole and copolymer, which is applied in the field of preparation of porphyrin copolymer containing diketopyrrolopyrrole units, can solve the problems of narrow material spectral response, low hole mobility, poor stability, etc., and achieve High quantum efficiency, reduced process flow, and increased density

Inactive Publication Date: 2011-12-28
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Description
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Problems solved by technology

[0004] The purpose of the embodiments of the present invention is to provide a porphyrin copolymer containing diketopyrrolopyrrole units, which aims to solve the technical problems of narrow spectral response, low hole mobility and poor stability of materials in organic photoelectric devices in the prior art

Method used

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  • Porphyrin copolymer containing diketopyrrolopyrrole unit, preparation method and application thereof
  • Porphyrin copolymer containing diketopyrrolopyrrole unit, preparation method and application thereof
  • Porphyrin copolymer containing diketopyrrolopyrrole unit, preparation method and application thereof

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preparation example Construction

[0033] see figure 2 , the preparation method of the above-mentioned porphyrin copolymer containing diketopyrrolopyrrole units comprises the following steps:

[0034] S01: respectively provide compounds A, B, C, and D represented by the following structural formulas,

[0035]

[0036] Among them, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 from C 1 -C 32 the alkyl group;

[0037] S02: In an organic solvent system containing a catalyst and an oxidizing agent, the compounds A, B, and C are subjected to a polycondensation oxidation reaction to generate 5,15-bis(9,9-dialkylfluorene)porphyrin;

[0038] S03: In an organic solvent system containing a catalyst, 5,15-bis(9,9-dialkylfluorene)porphyrin is subjected to a bromination substitution reaction to generate 5,15-dibromo-10,20-bis(9 , 9-dialkylfluorene) porphyrin;

[0039] S04: Under an inert gas environment and in an organic solvent system containing a catalyst, 5,15-dibromo-10,20-bis(9,9-dialkylfluorene)porphyrin and compoun...

Embodiment 1

[0087] In the copolymer (I-1) of this embodiment, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 Same as C 8 h 17 , its structural formula is as follows:

[0088]

[0089] It can be seen from the structural formula that the porphyrin copolymer containing diketopyrrolopyrrole units in the first embodiment has a symmetrical bifluorenyl structure. Through this uniform and symmetrical structure, the porphyrin copolymer containing diketopyrrolopyrrole units can be copolymerized The material has better light-absorbing properties and photoelectric properties. due to R 1 , R 2 , R 3 , R 4 Both use C 8 h 17 , so compounds A and B are both 9,9-dioctyl-2-aldehyde fluorene, so only one kind of raw material is needed, which simplifies the preparation process and reduces the cost, and the yield is high. If it is not such a symmetrical structure, then compounds A and B have different structures, different raw materials need to be obtained, and there are relatively more by-products.

[009...

Embodiment 2

[0113] In the copolymer (I-2) of the present embodiment, R 1 for CH 3 , R 2 for C 8 h 17 , R 3 for C 10 h 21 , R 4 for C 16 h 33 , R 5 for C 8 h 17 , R 6 for C 16 h 33 , its structural formula is as follows:

[0114]

[0115] The preparation process is described in detail below.

[0116] Step 1, the preparation of 10-(9-methyl-9-octylfluorene)-20-(9-decyl-9-hexadecylfluorene) porphyrin, the reaction formula is as follows:

[0117]

[0118] The specific process is as follows: Prepare an anhydrous and oxygen-free device, weigh 0.320g 9-methyl-9-octylfluorene, 0.56g 9-decyl-9-hexadecylfluorene, 0.30g di Pyrromethane was dissolved in dichloromethane, nitrogen gas was introduced for 30 minutes, 2 mL of trifluoroacetic acid was added with a syringe, stirred at room temperature for 3 hours, then 1.82 g was added into DDQ, stirred at room temperature for 30 minutes, and finally 2 mL of triethylamine was added to quench After the reaction, the solvent was concen...

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Abstract

The invention relates to the technical field of organic materials, and provides pyrrole-pyrrole-dione unit-containing porphyrin copolymer. The copolymer is shown by a structural formula (I), wherein R1, R2, R3, R4, R5 and R6 are the same or different C1-C32 alkyl groups; and n is an integer of 1-100. The invention also provides a preparation method and application of the pyrrole-pyrrole-dione unit-containing porphyrin copolymer. Since the pyrrole-pyrrole-dione unit-containing porphyrin copolymer has a fluorenyl porphyrin structure and a pyrrole-pyrrole-dione unit, so that the copolymer has superior light and heat stability and filming property; and pyrrole-pyrrole-dione and porphyrin groups are introduced into the polymer, so that the spectral response range of the polymer is widened.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and in particular relates to a porphyrin copolymer containing a diketopyrrolopyrrole unit, a preparation method and application thereof. Background technique [0002] Compared with inorganic semiconductor materials, organic semiconductor materials have the advantages of adjustable molecular and energy level structures through chemical modification, fast response, easy processing into large-area flexible devices, and low cost. Therefore, they are widely used in solar cells, transistors, and new flat panel displays. It has broad application prospects in many fields such as lighting devices, high-density storage, and biosensing. Conjugated polymers, as a special polymer material, have attracted widespread attention. They not only have the electrical and optical properties of metals and semiconductors, but also have good processing and mechanical properties unique to polymers. [0003] The...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46H01L51/54
CPCY02E10/50Y02E10/549
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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