Novel organic polymer and method for producing same

A technology of organic polymers and organic semiconductors, which is applied in the fields of final product manufacturing, sustainable manufacturing/processing, semiconductor/solid-state device manufacturing, etc. It can solve the problems of insufficient carrier mobility and low film strength, and achieve a large overlapping range, Effect of improving solubility and high carrier mobility

Inactive Publication Date: 2018-12-21
THE UNIV OF TOKYO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] In these compounds, although the carrier mobility in the direction of the long axis of the molecule can be ensured, since they are low-molecular compounds, not only the strength of the film is low, but also the carrier mobility is insufficient.

Method used

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  • Novel organic polymer and method for producing same
  • Novel organic polymer and method for producing same
  • Novel organic polymer and method for producing same

Examples

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Embodiment

[0199] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

Synthetic example 1

[0201]

[0202] An orange suspension of 2,6-dibromonaphthalene-1,5-diol (1) (100 g, 315 mmol) / dichloromethane (700 mL) / pyridine (101 mL, 126 mmol) was cooled to 0 °C under argon atmosphere . While stirring, trifluoromethanesulfonic anhydride (2) (134 mL, 818 mmol) / dichloromethane (100 mL) solution was added dropwise, and the dark red suspension was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the organic layer was extracted with chloroform. After the extract was filtered through silica gel, the filtrate was concentrated under reduced pressure, and the resulting crude product was washed with acetone to obtain the target compound (3) (2,6-dibromonaphthalene-1,5-bis Triflate) as a white solid (110 g, 60% yield).

[0203] NMR: 1H-NMR (400MHZ, CDCl3): δ (PPm) 7.88 (d, 2H, J = 8.8HZ, ARH), 8.02 (d, 2H, J = 8.8HZ, ARH).

Synthetic example 2

[0205]

[0206]Under argon atmosphere, argon was bubbled into a brown solution of compound (3) (1 g, 1.7 mmol) / N,N-dimethylformamide (7 mL) / diisopropylamine (8.6 mL) for 15 minutes. Thereafter, while stirring at room temperature, copper(I) iodide (32.7 mg, 0.17 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) After methyl chloride complex (70.2 mg, 0.086 mmol), trimethylsilylacetylene (TMS-≡) (4) (0.5 mL, 3.6 mmol), the black suspension was stirred at room temperature for 12 hours. After diluting the reaction mixture with chloroform, it filtered through silica gel. The filtrate was concentrated under reduced pressure, and the resulting crude product was recrystallized in hexane to obtain the target compound (5) (2,6-dibromo-1,5-bis(2-trimethylsilane ethynyl)naphthalene) as a pale yellow solid (0.79 g, 86% yield).

[0207] NMR: 1H-NMR (400MHZ, CDCl3): δ (PPm) 0.35 (S, 18H, Si (CH3) 3), 7.71 (d, 2H, J = 8.8HZ, ARH), 8.14 (d, 2H, J = 8.8HZ, ARH).

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Abstract

Provided are: a novel organic polymer which is useful for the formation of an organic semiconductor; and a use of the novel organic polymer. This organic polymer is obtained by subjecting a compound represented by formula (Ia) to a coupling reaction. In the formula, each of ring A and ring B represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring; n represents 0 or an integer of 1-6; each of R<1> to R<2+n> represents a substituent (such as an alkyl group); each of a1 to a(2+n) represents an integer of 0-2; the ring C represents benzene rings which are sequentially ortho-condensed to an adjacent benzene ring non-linearly in accordance with the number of n; and X represents a hydrogen atom, a halogen atom, a lithium atom or -MgX1 (with X1 representing a halogen atom).

Description

technical field [0001] The present invention relates to a novel organic polymer (semiconductor polymer) that can be used in semiconductor elements such as field effect transistors and photoelectric conversion elements, and is useful for forming organic semiconductors, its manufacturing method, an organic semiconductor containing the polymer, and a semiconductor device (or electronic equipment). Background technique [0002] As organic compounds having semiconductor properties, polyacene compounds such as metallophthalocyanines, pentacenes, and butylenes are known. However, these compounds have low solubility in organic solvents, so it is difficult to form a film by coating, printing, etc., and a thin film must be formed by a vapor deposition process. Furthermore, in the vapor-deposited film of the above-mentioned compound, the phase of the HOMO orbital of the above-mentioned compound changes periodically with respect to the long-axis direction of the molecule. Therefore, i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L29/786H01L51/05H01L51/30H01L51/46
CPCH01L29/786C08G61/126H01B1/127C09D5/24C09D11/52C08G2261/412C08G2261/3243C08G2261/1412C08G2261/91C08G2261/92C08G2261/95C08G2261/51C09D165/00Y02P70/50H10K85/113H10K10/00H10K30/00C08G61/10C08G61/12Y02E10/549H10K85/6576H10K10/20H10K10/462C08G2261/314
Inventor 冈本敏宏竹谷纯一池田大次岩谷真男
Owner THE UNIV OF TOKYO
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