A perylene thiodiimide N-type photosensitive field-effect transistor material

Abstract

This invention relates to an N-type photosensitive field-effect transistor material based on perylene thiodiimide, with the general structural formula [formula omitted], wherein R is alkyl, benzyl, substituted benzyl, aryl, or substituted aryl. The N-type photosensitive field-effect transistor material of this invention exhibits high mobility and strong light response performance, as well as excellent photosensitivity, providing a material basis for the research and application of photosensitive sensors.

Description

Technical Field

[0001] This invention belongs to the field of transistor material technology, specifically relating to an N-type photosensitive field-effect transistor material of perylene thiodiimide. Background Technology

[0002] Organic field-effect transistors (OFETs) are important organic semiconductor devices, first reported in 1986. They utilize organic semiconductor materials as conductive channels and possess advantages such as ease of fabrication, light weight, low cost, good flexibility / elasticity, and good compatibility with flexible substrates. In recent years, research and development of organic field-effect transistors has been rapid, attracting widespread attention from the scientific and industrial communities and becoming a current research hotspot. Organic field-effect transistors can be applied to logic gates in ring oscillators for RFID cards, active drive circuits for organic flexible displays, organic sensors, memory, electronic paper, and other fields. They have enormous application value in future electronic tags, flexible displays, and sensors. Currently, inorganic field-effect transistors are approaching the natural limit of miniaturization and are still relatively expensive, with many problems remaining in the fabrication of large-surface-area devices. Meanwhile, with the continuous improvement of people's living standards, flexible, foldable, and wearable electronic products have become the main development direction for the future, and low-cost processing has become the most important competitive advantage. This poses a significant challenge to microelectronics based on inorganic semiconductors. Exploring the use of organic semiconductors as active materials for field-effect transistors is an inevitable trend with significant research value and promising prospects. However, research on photosensitive field-effect transistor materials is insufficient, especially on photosensitive N-type field-effect transistors.

[0003] Perylene diimide (PDI) is a classic N-type semiconductor core material used in organic field-effect transistor (OFET) devices, exhibiting high carrier mobility. However, reports on sulfur carbonyl (C=S)-substituted carbonyl (C=O) compounds are scarce. Sulfur, as a group-agent of oxygen, possesses similar chemical and physical properties, and sulfur-containing compounds are an important class of semiconductor materials with excellent optoelectronic properties. Studies on sulfur carbonyl (C=S) perylene diimide (PDI) are limited, and research on the photosensitivity of this material is even less.

[0004] Indigo / semi-indigo is a dye molecule that has long been widely used in the pigment industry. Could this traditional commercial material structure be applied to the emerging semiconductor industry? Semi-indigo molecules can undergo luminescent isomerization under light radiation; the carbon-carbon double bonds in the semi-indigo structure can undergo Z-type and E-type transitions under different light irradiations. (See references: Bull. Chem. Soc. Jpn, 1992, 65, 649-656, Bull. Chem. Soc. Jpn, 1992, 65, 657-663, Chemical Physics Letters 428(2006) 167–173). Its configurational transformations are shown below:

[0005]

[0006] However, there are currently no reports on the design and synthesis of N-type semiconductor materials with high mobility and strong light response performance by combining the good semiconductor properties of the classic N-type semiconductor material structure perylene diimide (PDI), the excellent semiconductor device performance of sulfur-containing compounds, and the configurational transformation of half-thioindole molecules under specific light conditions. Summary of the Invention

[0007] In view of the above-mentioned situation in the prior art, the present invention proposes an N-type photosensitive field-effect transistor material of perylene thiodiimide, the general structural formula of which is as follows:

[0008]

[0009] R can be alkyl, benzyl, substituted benzyl, aryl, or substituted aryl, etc.

[0010] Furthermore, R is preferably C1 to C2. 20 (i.e., alkyl groups having 1 to 20 carbon atoms), more preferably C4 to C5. 12 Alkyl groups (i.e., alkyl groups with 4 to 12 carbon atoms).

[0011] Furthermore, R is preferably phenyl.

[0012] Furthermore, the preferred structural formula for R is... Where n is 5 to 10.

[0013] Furthermore, R is preferably benzyl.

[0014] Furthermore, the preferred structural formula for R is... Where n is 1 to 5.

[0015] Furthermore, the preferred structural formula for R is... Where n is 2 to 10.

[0016] Furthermore, the preferred structural formula for R is... Where n is 1 to 20.

[0017] This invention combines the excellent semiconductor properties of perylene diimide (PDI), a classic N-type semiconductor material, with the superior semiconductor device performance of sulfur-containing compounds, and the configurational transformation of hemisulfide-indole molecules under specific light conditions. Specifically, it designs and synthesizes an N-type photosensitive field-effect transistor material containing a hemisulfide-indole structure and perylene diimide. This material exhibits high mobility, strong light response, and excellent photosensitivity, providing a material basis for the research and application of photosensitive sensors. Detailed Implementation

[0018] To better understand the purpose, technical solution, and advantages of this invention, the following detailed description is provided in conjunction with embodiments.

[0019] This invention proposes an N-type photosensitive field-effect transistor material containing a semi-thiodiimide (PDI) structure and thiodiimide by combining the excellent semiconductor properties of the classic N-type semiconductor material structure, the superior semiconductor device performance of sulfur-containing compounds, and the configurational transformation of semi-thiodiindustrial molecules under specific light conditions. The material of this invention has high mobility and strong light response performance.

[0020] The general formula for synthesizing the material of this invention is as follows:

[0021]

[0022] Step 1: 1-Benzothiophene-3(2H)-one (I in the above general formula) was dissolved in benzene, and an equivalent amount of 4-(BOC-amino)benzaldehyde (II in the above general formula) and a catalytic amount of piperidine were added. The mixture was heated to reflux, and the reaction was monitored by thin-layer chromatography until complete. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined and dried to obtain the intermediate BOC-amino-substituted semithioindigo (III in the above general formula).

[0023] Step 2: The BOC-amino-substituted semithioindole (III) obtained in Step 1 is subjected to trifluoroacetic acid to remove the BOC group, thereby obtaining the intermediate amino-substituted semithioindole (IV in the above general formula).

[0024] Step 3: Tetramethyl 3,4,9,10-perylenetetrathiocarbamate (V in the above general formula) was heated under glacial acetic acid and concentrated hydrochloric acid to give thiomonoacid anhydride compound (VI in the above general formula).

[0025] Step 4: The amino-substituted hemithioindole (IV) obtained in step 2 is reacted with the monoacid anhydride compound (VI) obtained in step 3 to obtain the thioperylene amide derivative (VII in the above general formula);

[0026] Step 5: The thioperylene amide derivative (VII) obtained in step 4 is heated under trifluoroacetic acid conditions to obtain the thioanhydride compound (VIII in the above general formula);

[0027] Step 6: The thioanhydride compound (VIII) obtained in step 5 is reacted with various amine compounds to obtain the target compound, a perylene dithioimide containing a hemithioindole structural unit (T in the above general formula).

[0028] Example 1: Synthesis of representative compound T1

[0029] Compound T1 The synthetic route is shown below:

[0030]

[0031] 30 g (0.2 mol) of 1-benzothiophene-3(2H)-one (I) was dissolved in 300 mL of benzene, and 44.2 g (0.2 mol) of 4-(BOC-amino)benzaldehyde (II) and 1 g of piperidine were added. The mixture was heated under reflux for 5 h, and the reaction was monitored by thin-layer chromatography until it was complete. 300 mL of saturated ammonium chloride aqueous solution was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined and dried to obtain 62.3 g of BOC-amino-substituted semithioindigo (III).

[0032] 1 H NMR (500MHz, CDCl3) δ8.35(s,1H),8.23–8.16(m,2H),7.99–7.89(m,2H),7.84–7.74(m,3H),7.61(td,J=14.9,3.2Hz,1H),7.50(s,1H),1.49(s,9H).

[0033] 52.9 g of BOC-amino-substituted semithioindigo(III) was dissolved in 200 mL of dichloromethane and 100 mL of trifluoroacetic acid. The mixture was stirred at room temperature for 30 minutes. After removing excess trifluoroacetic acid with a saturated sodium carbonate washing solution, the mixture was concentrated and dried. The crude product was separated by column chromatography to obtain the target product 32.5 g of amino-substituted semithioindigo(IV).

[0034] 1H NMR (500MHz, CDCl3) δ8.35(s,1H),8.00–7.85(m,4H),7.79(dd,J=15.3,3.0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),6.48–6.35(m,2H).

[0035] 109.6 g (0.2 mol) of tetramethyl 3,4,9,10-perylenetetrathiocarbamate (V) was dissolved in 300 mL of glacial acetic acid and 60 mL of concentrated hydrochloric acid. The mixture was heated and stirred at 120 °C for 24 hours. The solution was then concentrated under reduced pressure to remove the residue, yielding 97.5 g of the intermediate compound monothioic anhydride compound (VI).

[0036] 1 H NMR (500MHz, CDCl3) δ9.74 (d, J = 15.0 Hz, 2H), 8.09 (d, J = 15.0 Hz, 4H), 7.46 (d, J = 15.0 Hz, 2H), 3.47 (s, 6H).

[0037] 50.2 g (0.1 mol) of monothioic anhydride compound (VI), 30.4 g (0.12 mol) of amino-substituted hemithioindole (IV), 5.05 g (0.05 mol) of triethylamine, and 6.1 g (0.05 mol) of benzoic acid were dissolved in 500 mL of dry N,N-dimethylformamide. The mixture was heated and stirred at 100 °C for 12 h. The solvent was removed by concentration under reduced pressure, and the residue was separated by column chromatography to obtain 61.5 g of the target intermediate compound, thioperylene amide derivative (VII).

[0038] 1 H NMR(500MHz, CDCl3)δ9.52(d,J=15.0Hz,2H),8.35(s,1H),8.21–8.13(m,2H),8.09(d,J=15.0Hz,4H),8.01–7.86(m,2H ),7.79(dd,J=15.3,3.0Hz,1H),7.68(d,J=15.0Hz,2H),7.61(td,J=14.9,3.2Hz,1H),7.26–7.16(m,2H),3.47(s,6H).

[0039] 59.03 g (0.08 mol) of thioperylene amide derivative (VII) was dissolved in 200 mL of trifluoroacetic acid, heated and stirred at 80 °C for 24 hours, the solution was concentrated under reduced pressure to remove the solution, and 41.5 g of thioanhydride compound (VIII) was obtained by column chromatography.

[0040] 1H NMR (500MHz, CDCl3) δ9.77(d,J=7.5Hz,2H),9.60(d,J=7.5Hz,2H),8.35(s,1H),8.17(d,J=7.5Hz,2H),8.09 (d,J=7.5Hz,4H),7.99–7.89(m,2H),7.82–7.72(m,1H),7.61(td,J=7.5,1.5Hz,1H),7.22(d,J=7.5Hz,2H).

[0041] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 4.38 g (0.06 mol) of n-butylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 27.8 g of the target compound (T1).

[0042] 1 H NMR(500MHz, CDCl3)δ9.73(d,J=15.0Hz,2H),9.57(d,J=15.0Hz,2H),8.35(s ,1H),8.21–8.13(m,2H),8.09(d,J=15.0Hz,4H),7.99–7.88(m,2H),7.79(dd, J=15.3,3.0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),7.28–7.15(m,2H),3.65(t, J=14.7Hz,2H),1.56–1.41(m,2H),1.38–1.21(m,2H),0.90(t,J=12.9Hz,3H).

[0043] Example 2: Synthesis of representative compound T2

[0044] The synthetic route for compound T2 is shown below:

[0045]

[0046] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 6.06 g (0.06 mol) of n-hexylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 22.4 g of the target compound (T2).

[0047] 1H NMR(500MHz, CDCl3)δ9.53(d,J=15.0Hz,2H),9.08(d,J=15.0Hz,2H),8.35( s,1H),8.23–8.12(m,4H),8.09(d,J=15.0Hz,2H),8.02–7.88(m,2H),7.79(d d,J=15.3,3.0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),7.31–7.11(m,2H),3.14 (t,J=15.2Hz,2H),1.82–1.51(m,2H),1.41–1.08(m,6H),1.03–0.75(m,3H).

[0048] Example 3: Synthesis of representative compound T3

[0049] The synthetic route for compound T3 is shown below:

[0050]

[0051] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 7.75 g (0.06 mol) of n-octylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 26.7 g of the target compound (T3).

[0052] 1 H NMR(500MHz, CDCl3)δ9.73(s,2H),9.57(s,2H),8.34(s,1H),8.21–8.12(m,2H),8.08(d,J=15.0Hz,4H),8.00–7.87(m,2H),7 .83–7.74(m,1H),7.60(td,J=14.9,3.1Hz,1H),7.30–7.12(m,2H),3.65(s,2H),1.61(s,2H),1.39–1.12(m,9H),0.89(s,3H).

[0053] Example 4: Synthesis of representative compound T4

[0054] The synthetic route for compound T4 is shown below:

[0055]

[0056] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 10.86 g (0.06 mol) of n-dodecaneamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 17.5 g of the target compound (T4).

[0057] 1 H NMR (500MHz, CDCl3) δ9.82(d,J=15.0Hz,2H),9.58(d,J=15.0Hz,2H),8.35(s,1H),8.20–8.13(m,2H),8.09(d,J=15.0H z,4H),7.99–7.88(m,2H),7.79(dd,J=15.3,3.0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),7.29–7.11(m,2H),3.52(s,3H).

[0058] Example 5: Synthesis of representative compound T5

[0059] The synthetic route for compound T5 is shown below:

[0060]

[0061] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 5.58 g (0.06 mol) of aniline, 2.53 g (0.025 mol) of triethylamine, and 3.0 g (0.025 mol) of benzoic acid were dissolved in 200 mL of dry N,N-dimethylformamide. The mixture was heated and stirred at 100 °C for 12 h. The solvent was removed by concentration under reduced pressure, and the residue was separated by column chromatography to obtain 19.1 g of the target compound (T5).

[0062] 1 H NMR (500MHz, CDCl3) δ9.68(d,J=14.8Hz,2H),9.58(d,J=15.0Hz,2H),8.35(s,1H),8.21–8.13(m,2H),8.09(d,J=15. 0Hz,4H),8.00–7.87(m,2H),7.79(dd,J=15.3,3.0Hz,1H),7.67–7.47(m,4H),7.38–7.26(m,2H),7.25–7.17(m,2H).

[0063] Example 6: Synthesis of representative compound T6

[0064] The synthetic route for compound T6 is shown below:

[0065]

[0066] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 10.6 g (0.06 mol) of 4-hexylaniline, 2.53 g (0.025 mol) of triethylamine, and 3.0 g (0.025 mol) of benzoic acid were dissolved in 200 mL of dry N,N-dimethylformamide. The mixture was heated and stirred at 100 °C for 12 h. The solvent was removed by concentration under reduced pressure, and the residue was separated by column chromatography to obtain 21.7 g of the target compound (T6).

[0067] 1 H NMR(500MHz, CDCl3)δ9.64(d,J=15.0Hz,4H),8.35(s,1H),8.21–8.12(m,2H),8.09(d,J=15.0Hz,4H),7.99–7.87(m,2H),7.82–7.68(m, 1H),7.61(td,J=14.9,3.2Hz,1H),7.28–6.94(m,6H),2.52(t,J=15.3Hz,2H),1.74–1.47(m,2H),1.44–1.17(m,4H),1.00–0.77(m,3H).

[0068] Example 7: Synthesis of representative compound T7

[0069] The synthetic route for compound T7 is shown below:

[0070]

[0071] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 12.3 g (0.06 mol) of 4-octylaniline, 2.53 g (0.025 mol) of triethylamine, and 3.0 g (0.025 mol) of benzoic acid were dissolved in 200 mL of dry N,N-dimethylformamide. The mixture was heated and stirred at 100 °C for 12 h. The solvent was removed by concentration under reduced pressure, and the residue was separated by column chromatography to obtain 24.1 g of the target compound (T7).

[0072] 1H NMR(500MHz, CDCl3)δ9.63(d,J=15.0Hz,4H),8.35(s,1H),8.23–8.13(m,2H),8.09(d,J=15.0Hz,4H),7.99–7.85(m,2H),7.79(dd,J=15.3,3 .0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),7.28–7.05(m,6H),2.52(t,J=12.1Hz,2H),1.79–1.46(m,2H),1.37–1.08(m,9H),1.07–0.67(m,3H).

[0073] Example 8: Synthesis of the representative compound T8

[0074] The synthetic route for compound T8 is shown below:

[0075]

[0076] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 13.98 g (0.06 mol) of p-decylaniline, 2.53 g (0.025 mol) of triethylamine, and 3.0 g (0.025 mol) of benzoic acid were dissolved in 200 mL of dry N,N-dimethylformamide. The mixture was heated and stirred at 100 °C for 12 h. The solvent was removed by concentration under reduced pressure, and the residue was separated by column chromatography to obtain 22.7 g of the target compound (T8).

[0077] 1 H NMR(500MHz, CDCl3)δ9.63(d,J=15.0Hz,1H),8.35(s,1H),8.21–8.13(m,1H),8.09(d,J=14.8Hz,1H),7.99–7.87(m,1H),7.79(dd,J=15.4,3.1Hz,1H) ,7.61(td,J=14.9,3.2Hz,1H),7.26–7.16(m,1H),7.17–7.08(m,1H),2.52( t,J=15.6Hz,1H),1.78–1.46(m,1H),1.38–1.10(m,4H),0.98–0.72(m,1H).

[0078] Example 9: Synthesis of representative compound T9

[0079] The synthetic route for compound T9 is shown below:

[0080]

[0081] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 6.42 g (0.06 mol) of benzylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 27.5 g of the target compound (T9).

[0082] 1 H NMR (500MHz, CDCl3) δ9.68(d,J=15.0Hz,2H),9.57(d,J=15.0Hz,2H),8.35(s,1H),8.20–8.13(m,2H),8.09(d,J =15.0Hz,4H),8.02–7.85(m,2H),7.79(dd,J=15.3,3.0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),7.40–7.15(m,7H).

[0083] Example 10: Synthesis of representative compound T10

[0084] The synthetic route for compound T10 is shown below:

[0085]

[0086] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 8.1 g (0.06 mol) of 4-ethylbenzylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 19.4 g of the target compound (T10).

[0087] 1 H NMR (500MHz, CDCl3) δ9.67(d,J=15.0Hz,2H),9.57(d,J=15.0Hz,2H),8.35(s,1H),8.22–8.14(m,2H),8.09(d,J=15.0Hz, 4H),7.99–7.86(m,2H),7.79(dd,J=15.3,3.0Hz,1H),7.61(td,J=14.9,3.2Hz,1H),7.32–7.16(m,4H),7.14–6.99(m,2H).

[0088] Example 11: Synthesis of representative compound T11

[0089] The synthetic route for compound T11 is shown below:

[0090]

[0091] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 12.3 g (0.06 mol) of 4-heptylbenzylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 17.3 g of the target compound (T11).

[0092] 1 H NMR(500MHz, CDCl3)δ9.68(d,J=15.0Hz,2H),9.57(d,J=15.0Hz,2H),8.35(s,1H),8 .22–8.12(m,2H),8.09(d,J=15.0Hz,4H),8.00–7.86(m,2H),7.79(dd,J=15.3,3.0Hz ,1H),7.61(td,J=14.9,3.1Hz,1H),7.29–7.16(m,4H),7.12–7.02(m,2H),4.45(s,2 H), 2.59 (t, J = 14.6Hz, 2H), 1.74–1.49 (m, 2H), 1.39–1.13 (m, 8H), 1.03–0.66 (m, 3H).

[0093] Example 12: Synthesis of the representative compound T12

[0094] The synthetic route for compound T12 is shown below:

[0095]

[0096] 34.6 g (0.05 mol) of thioanhydride compound (VIII), 14.82 g (0.06 mol) of 4-decylbenzylamine, and 7.74 g (0.06 mol) of N,N-diisopropylethylamine were dissolved in 200 mL of 1,4-dioxane and heated under reflux for 2 hours. The solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain 25.1 g of the target compound (T12).

[0097] 1H NMR(500MHz, CDCl3) δ9.67(d,J=14.8Hz,2H),9.57(d,J=15.0Hz,2H),8.35(s,1H),8. 22–8.12(m,2H),8.09(d,J=15.0Hz,4H),7.99–7.89(m,2H),7.84–7.74(m,1H),7.61( td,J=14.8,3.1Hz,1H),7.28–7.17(m,4H),7.14–7.02(m,2H),4.45(s,2H),2.59(t,J =15.6Hz,2H),1.64(tt,J=30.4,15.0Hz,2H),1.38–1.10(m,13H),1.06–0.80(m,3H).

[0098] Fabrication of organic field-effect transistors

[0099] Cleaning and finishing of silicon wafers

[0100] The Si / SiO2 substrate was purchased directly from the market, with a SiO2 thickness of 250 nm. The silicon wafer was ultrasonically cleaned for 10 min each with pure water, acetone, and isopropanol. After drying with nitrogen, it was irradiated with UV for 10 min to obtain a clean silicon wafer. Then, it was immersed in a 0.1 mol / L toluene solution at 65 °C for 20 min. After that, it was cleaned with toluene to remove surface residues, dried with nitrogen, and OTS-modified silicon wafers were obtained for later use.

[0101] Device fabrication and performance testing

[0102] A semiconductor mask is used to mask the silicon wafer, and a suitable substrate temperature is selected. The thin film is then fabricated under high vacuum. The vacuum level is approximately 2.0 × 10⁻⁶. -4 Pa, the evaporation rate of the semiconductor material (the semiconductor material obtained according to Examples 1-12 of the present invention) is controlled at... After thin film preparation, electrodes are deposited using an electrode mask, with Au as the electrode material. The Au electrode deposition rate is controlled at [value missing]. The fabricated devices had channel aspect ratios of 380μm / 38μm, 580μm / 58μm, 780μm / 78μm, and 980μm / 98μm. Semiconductor performance was tested using a Keithly 4200 semiconductor analyzer. Id-Vg and Id-Vd curves were measured under normal conditions and under UV illumination. Mobility was calculated using the formula below.

[0103] I d =(W / 2L)μ TFT C i (V g -Vth ) 2

[0104] The switching ratio of the device is obtained based on the current ratio at 0V and -60V.

[0105] Device performance of representative materials obtained according to the above embodiments 1-12 of the present invention:

[0106] Data for compound DPh-BTBF devices:

[0107]

[0108] According to the table above, it can be seen from the mobility data under normal conditions and light radiation that the representative semiconductor materials obtained according to the above embodiments 1-12 of the present invention exhibit excellent photosensitivity.

Claims

1. A perylene thiodiimide N-type photosensitive field-effect transistor material, the general structural formula of which is as follows: in, R is an alkyl, phenyl, benzyl, substituted benzyl, or substituted aryl group having 1 to 20 carbon atoms; The structural formula of the substituted aryl group is Where n is 5 to 10; or , where n is 1 to 5; The structural formula of the substituted benzyl group is Where n is 2 to 10; or , where n is 1 to 20.

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