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Organic small-molecular semiconductor material

A technology of small molecules and semiconductors, applied in the field of organic semiconductor materials, can solve the problems of reducing the spectral bandwidth of materials and reducing the effective conjugate length of molecules, and achieve the effects of long spectral absorption wavelength, extended effective conjugate length and good planarity

Active Publication Date: 2015-10-14
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, when multiple aromatic conjugated units are introduced into the center of the linear oligothiophene, due to the steric hindrance between the aromatic units, the aromatic units are often twisted, resulting in a non-coplanar structure, thereby reducing the effective conjugated length of the molecule. , which in turn leads to a further reduction in the spectral bandwidth of the material, preventing further red shift of the material absorption spectrum

Method used

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  • Organic small-molecular semiconductor material
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  • Organic small-molecular semiconductor material

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Experimental program
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Effect test

Embodiment 1

[0104] Embodiment 1 refers to image 3 , the synthesis and preparation process of the organic small molecule semiconductor material can be:

[0105] A (0.80g, 1.03mmol), tetrakis(triphenylphosphine) palladium (0.12g, 0.104mmol), B (0.95g, 2.28mmol), DMF (8mL), The reaction was carried out at 80°C for 20 hours. After the reaction was completed, the solid was collected by precipitation with methanol and purified by column chromatography to obtain the final product C (0.96g), with a yield of 83%. Wherein the characterization result of product is as follows:

[0106] MS (MALDI-TOF): Calcd, 1114.37; Found, 1114.58.

[0107] 1 H NMR (CDCl 3 ,400MHz):δ=9.85(s,2H),δ=7.64(s,2H),δ=7.58(s,2H),δ=4.46(s,8H),δ=4.19(d,4H),δ =2.86(t,4H),δ=1.87~1.79(m,2H),δ=1.75~1.68(m,8H),δ=1.56~1.43(m,16H)δ=1.36~1.30(m,8H) , δ=1.06(t,6H), δ=0.97(t,6H), δ=0.91(t,6H).

Embodiment 2

[0108] Embodiment 2: see Figure 4 , the synthesis and preparation process of the organic small molecule semiconductor material can be:

[0109] Add C (0.22g, 0.20mmol), 3-ethyl-2-thio-4-thiazolidinedione (71mg, 0.44mmol), 5 drops of piperidine, 10mL dry chloroform, reflux for 4h, water Interextract with chloroform, dry the organic phase, filter, spin dry the solvent, and recrystallize with ethanol to obtain the final product D (0.21g), with a yield of 74%. The characterization result of this product D is as follows:

[0110] MS (MALDI-TOF): Calcd, 1402.36; Found, 1402.62.

[0111] 1 H NMR (CDCl 3 ,400MHz):δ=8.00~7.70(s,2H),δ=7.70~7.40(s,2H),δ=7.40~7.10(s,2H),δ=4.60~4.30(s,8H),δ= 4.30~4.10(m,8H),δ=2.90~2.70(t,4H),δ=1.90~1.75(m,2H),δ=1.75~1.60(m,8H),δ=1.60~1.40(m, 16H) δ=1.40~1.20(m,8H), δ=1.10~0.90(m,24H).

Embodiment 3

[0112] Embodiment 3: see Figure 5 , the synthesis and preparation process of the organic small molecule semiconductor material can be:

[0113] Add A (0.11g, 0.14mmol), tetrakis(triphenylphosphine)palladium (17mg, 14.2μmol), E (0.24g, 0.31mmol), DMF (3mL) into a 25mL single-necked bottle under anhydrous and oxygen-free conditions, in The reaction was carried out at 80°C for 20 hours. After the reaction was completed, the solid was collected by precipitation with methanol and purified by column chromatography to obtain the final product F (0.21 g), with a yield of 84%.

[0114] The characterization result of this product F is as follows:

[0115] MS (MALDI-TOF): Calcd, 1804.80; Found, 1804.43.

[0116] 1 H NMR (CDCl 3 ,400MHz):δ=8.20(s,2H),δ=7.62(s,2H),δ=7.57(s,2H),δ=7.19(s,2H),δ=4.46(m,8H),δ =4.29(t,4H),δ=4.19(d,4H),δ=2.83(t,8H),δ=1.84~1.83(m,2H),δ=1.73~1.67(m,16H),δ= 1.44~1.25(m,56H), δ=1.06(t,6H), δ=0.98(t,6H), δ=0.89(t,18H).

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Abstract

An organic small-molecular semiconductor material includes a benzo-diheterocyclic ring derivative [pi] conjugated unit and a composite structure, which is composed of an aromatic ring unit or an aromatic diheterocyclic ring derivative unit, being connected directly to the benzo-diheterocyclic ring derivative [pi] conjugate unit. The organic small-molecular semiconductor material has a structure formula as follows, wherein X and X1 includes S or O, Y includes a structural unit which can form a five-membered aromatic ring unit or a six-membered aromatic ring unit with an adjacent butadiene unit, R includes hydrogen, a substituted or non-substituted C1-C20 alkyl group or hetero alkyl group or a substituted or non-substituted modified aromatic or hetero-aromatic [pi]-conjugated unit derivative, R1 includes a substituted or non-substituted C1-C20 alkyl group or hetero alkyl group, which is connected to the X, R2 is substituted groups which are distributed on selected positions of the five-membered aromatic ring unit or the six-membered aromatic ring unit, and the T includes an electron acceptor group unit which is directly connected to a position 1 and an oligothiophene short-chain unit which is mainly formed by combining 1-12 modified or non-modified thiophenes. The organic small-molecular semiconductor material, compared with a linear oligothiophene material, is lower in spectral bandwidth and is longer in spectral absorption wavelength.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to a class of linear oligothiophene organic semi-small molecule semiconductor material, which can be applied to organic semiconductor devices. Background technique [0002] Organic semiconductor materials have the advantages of light weight, good flexibility, low production cost and easy large-scale production. product. [0003] Organic semiconductor materials mainly include high molecular organic materials and small molecular organic materials. Since the polymer material is a mixture, its structure is uncertain, the dispersion is large, it is not easy to purify, and it is easy to cause differences between material batches. However, organic small molecule semiconductor materials have a single and definite structure, are easy to purify, and have many advantages such as good reproducibility in practical applications. [0004] Organic semiconductor materials have a wide range of ...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D495/04
CPCC07D495/04C07D519/00
Inventor 王立磊马昌期
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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