Organic semiconductor material and preparation method and application thereof
A technology of organic semiconductors and organic solvents, applied in semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve problems such as device instability, achieve high luminous efficiency, excellent thermal stability, and improve transmission performance.
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[0027] The present invention also provides a preparation method of the above-mentioned organic semiconductor material, the steps are as follows:
[0028] Step S1, providing the following compound A, i.e. bromo or iodoalkyltripolyindene, and compound B, i.e. 5-(anthracene-9-yl)selenophen-2-ylboronic acid or 5-(anthracene-9-yl ) Selenophene-2-yl borate;
[0029] Compound A is In the formula, R is C 1 -C 12 The alkyl group, preferably R is C 1 -C 12 straight-chain or branched-chain alkyl; R' is an iodine atom or a bromine atom;
[0030] Compound B is
[0031] Step S2, in an inert gas atmosphere (including nitrogen or argon, etc.), dissolve compounds A and B in the first organic solvent containing a catalyst at a molar ratio of 1:3 to 1:4.5, and perform Suzuki at 60 to 130°C. After 20-40 hours of reaction, the general formula is The compound C; Reaction formula is as follows:
[0032]
[0033]
[0034] Step S3, in an inert gas atmosphere, at a temperature of -78 t...
Embodiment 1
[0041] This embodiment discloses an organic compound containing anthracene, selenophene, and tripolyindene units (that is, organic semiconductor materials, the same below) with the following structure
[0042] 2-(5-(10-cyano-anthracene-9-yl)selenophen-2-yl)-7,12-bis(anthracene-9-yl)selenophen-2-yl)-5,5', 10,10',15,15'-hexaethyltriindene (CNAS3ET):
[0043] CNAS3ET
[0044] The preparation of step 1, tripolyindene:
[0045]
[0046] Add 10 mmol of 1-indanone into a mixed solution containing 8 mL of acetic acid and 4 mL of concentrated hydrochloric acid, heat to 100° C., and stir under reflux for 20 h. After the reaction, the reaction solution was poured into a beaker filled with ice water, and a large amount of solid precipitated immediately. After the precipitate was washed with water, acetone and dichloromethane in sequence, a white solid powder triacinene was obtained with a yield of 91%. EI-MS: m / z 342 (M + ).
[0047] Step 2, the preparation of 5,5', 10,10', 15,15...
Embodiment 2
[0069] This example discloses an organic compound containing anthracene, selenophene, and tripolyindene units with the following structure
[0070] 2,7,12-tris(5-(10-cyano-anthracene-9-yl)selenophen-2-yl)-5,5′,10,10′,15,15′-hexaethyltrimeric Indene (CN3AS3ET):
[0071] CN3AS3ET
[0072] Step one, step two, step four, are identical with embodiment 1;
[0073] Step 3, the preparation of 2,7,12-tribromo-5,5',10,10',15,15'-hexaethyltripolyindene:
[0074]
[0075] Dissolve 5mmol of 5,5', 10, 10', 15,15'-hexaethyltripolyindene in 25mL of dichloromethane, and dissolve 1mL of liquid bromine in 10mL of dichloromethane at 0°C. The dichloromethane solution of liquid bromine was slowly dropped into the reaction system containing 5,5', 10,10', 15,15'-hexa-n-hexyltripolyindene. After the liquid bromine was added dropwise, the system naturally returned to room temperature. Protect from light for 12 hours. After the reaction, the mixture was washed with saturated sodium thiosulfate a...
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