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Difluoro-bithiophene polymer as well as preparation method and application thereof to FET (field effect transistor)

A technology of polymers and dibromo compounds, applied in the fields of electric solid devices, semiconductor devices, semiconductor/solid-state devices, etc., can solve the problems of high LUMO energy level of polymers, unfavorable electron injection into the transport layer, and weak electron withdrawing ability. , to achieve the effect of easy electron injection, high yield and improved planarity

Active Publication Date: 2017-04-26
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the vast majority of polymer semiconductor materials are p-type materials. This is because electron-withdrawing acceptors in polymers such as diketopyrrolopyrrole (that is, diketopyrrolopyrrole, DPP for short, Z.Yi.; S.Wang.; Y.Liu .Adv.Mater.2015,27,3589.), isoindigo, etc. have weak electron-absorbing ability, and the corresponding polymer LUMO energy level is relatively high, which is not conducive to electron injection in the transport layer

Method used

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  • Difluoro-bithiophene polymer as well as preparation method and application thereof to FET (field effect transistor)
  • Difluoro-bithiophene polymer as well as preparation method and application thereof to FET (field effect transistor)
  • Difluoro-bithiophene polymer as well as preparation method and application thereof to FET (field effect transistor)

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Embodiment 1, polymer P1FIID-2FBT (formula I-1)

[0081] The reaction equation is as Figure 6 shown.

[0082] 1) 6-Bromo-1-(4-decyltetradecyl)indole-2,3-dione

[0083] Add 6-bromoisatin (2.00g, 8.85mmol), potassium carbonate (2.93g, 21.24mmol), 1-iodo-4-decyltetradecane (4.93g, 10.62mmol) into a 100mL two-necked flask, 20mL Anhydrous N,N-dimethylformamide, 20mL anhydrous tetrahydrofuran, protected by argon. Reaction at 70°C for 12h. Extract with water and dichloromethane, dry. The solution was spin-dried and passed through a column (eluent: petroleum ether: dichloromethane = 2:1) to obtain 4.09 g of an orange solid. Yield: 82.1%.

[0084] The structural characterization data are as follows:

[0085] Mass Spectrum: HR-MALDI-TOF:[M+Na] + calcd for C32H 52 BrNNaO 2 :584.30794,found:584.30746.

[0086] H NMR and C NMR: 1 H NMR (400MHz, CDCl 3 )δ7.46(d,J=8.0Hz,1H),7.28(dd,J 1 =8.0Hz,J 2 =1.2Hz, 1H), 7.06(d, J=1.2Hz, 1H), 3.67(t, J=7.6Hz, 2H), 1.66(m, 2H), 1.4...

Embodiment 2

[0109] Embodiment 2, polymer P2FIID-2FBT (formula I-2)

[0110] The reaction equation is as Figure 6 shown.

[0111] 1) 6,6'-dibromo-7,7'-difluoro-1,1'-bis(4-decyltetradecyl)isoindigo (Formula 2)

[0112] Add 6-bromo-7-fluoro-1-(4-decyltetradecyl)indole-2,3-dione (0.61g, 1.06mmol) to a 100mL two-necked flask, 6-bromo-7- Fluoro-1-(4-decyltetradecyl)indol-2-one (0.60g, 1.06mmol), p-toluenesulfonic acid (20.2mg, 0.106mmol), 20mL acetic acid, protected by argon. React at 120°C for 12h. Extract with water and dichloromethane, dry. The solution was spin-dried and passed through a column (eluent: petroleum ether: dichloromethane = 6:1) to obtain 0.70 g of a red solid. Yield: 58.7%.

[0113] The structural characterization data are as follows:

[0114] Mass Spectrum: HR-MALDI-TOF:[M+Na] + calcd for C 64 h 102 Br 2 f 2 N 2 NaO 2 :1151.61537,found:1151.61487.

[0115] H NMR and C NMR: 1 H NMR (400MHz, CDCl 3 )δ8.89(d, J=8.4Hz, 2H), 7.19(m, 2H), 3.90(t, J=7.2Hz, 4H), 1....

Embodiment 3

[0123] Embodiment 3, the spectral performance of polymer P1FIID-2FBT and P2FIID-2FBT, electrochemical performance and field effect transistor performance

[0124] 1) Spectral and electrochemical properties of polymers P1FIID-2FBT and P2FIID-2FBT

[0125] figure 1 For the polymer P1FIID-2FBT ( figure 1 (A)) and P2FIID-2FBT ( figure 1 (B) UV-Vis absorption spectra in solution and film.

[0126] Depend on figure 1 It can be seen that the optical bandgaps of the polymer films P1FIID-2FBT and P2FIID-2FBT are 1.59eV and 1.40eV respectively (the optical bandgaps are based on the formula E g =1240 / λ calculation, where E g is the optical band gap, and λ is the boundary value of the UV absorption curve). Depend on figure 1 It can be seen that both polymers have relatively strong intramolecular charge transfer peaks, indicating that the intermolecular forces of the polymers are relatively strong.

[0127] figure 2 For the polymer P1FIID-2FBT ( figure 2 (A)) and P2FIID-2FBT ( ...

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Abstract

The invention discloses a difluoro-bithiophene polymer as well as a preparation method and application thereof to an FET (field effect transistor). The structural formula of the difluoro-bithiophene polymer is as shown in formula I, wherein n is a natural number ranging from 5 to 100. According to the invention, a fluorine atom is introduced to a thiophene ring to obtain difluoro-bithiophene (2FBT); the fluorine atom has a strong electron-withdrawing property, the atomic radius is small, and the interaction with other atoms such as a hydrogen atom or a sulphur atom is relatively strong, so that the introduction of the fluorine atom can improve the molecular planarity and promote molecular stacking. A polymer taking 2FBT as a donor has relatively low LUMO energy level, and the electron injection of a transport layer is relatively easy, so that the bipolar transfer characteristic can be expressed. The difluoro-bithiophene polymer provided by the invention can be used as a semiconducting material to prepare an OFET (organic field effect transistor). The OFET prepared by taking the difluoro-bithiophene polymer as a semiconducting layer has relatively high migration rate (mu), thereby having a good application prospect in bipolar OFETs.

Description

technical field [0001] The invention relates to a difluorodithiophene polymer, its preparation method and its application in field effect transistors. Background technique [0002] Organic field-effect transistors (OFETs for short) are voltage-controlled devices that regulate the current between the source and drain electrodes through the gate voltage. The organic semiconductor active layer is the core part of the device. Compared with non-field-effect transistors, organic field-effect transistors can be processed by solution method, and can be printed in a large area to prepare flexible devices. The semiconductor layer of the organic field effect transistor can be selected from organic conjugated small molecules or conjugated polymers. Due to the better film-forming properties of polymers, there are more types of polymers. Using polymers as semiconductor layers to construct OFETs is currently a research hotspot in this field. [0003] Semiconductor layer materials can be ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D209/34H01L51/05H01L51/30
CPCC07D209/34C08G61/124C08G61/126C08G2261/414C08G2261/92C08G2261/146C08G2261/1412C08G2261/124C08G2261/3241C08G2261/3223H10K85/151H10K85/113H10K10/46
Inventor 刘云圻杨杰赵志远陈金佯施龙献郭云龙王帅
Owner INST OF CHEM CHINESE ACAD OF SCI
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