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WO2008120839A1 - Nouveau composé semi-conducteur organique et transistor à couches minces organiques utilisant un tel composé - Google Patents

Nouveau composé semi-conducteur organique et transistor à couches minces organiques utilisant un tel composé Download PDF

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WO2008120839A1
WO2008120839A1 PCT/KR2007/003326 KR2007003326W WO2008120839A1 WO 2008120839 A1 WO2008120839 A1 WO 2008120839A1 KR 2007003326 W KR2007003326 W KR 2007003326W WO 2008120839 A1 WO2008120839 A1 WO 2008120839A1
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group
alkyl
aryl
alkoxy
compound
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PCT/KR2007/003326
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Soon-Ki Kwon
Yun-Hi Kim
Jong-Won Park
Dong Min Kang
Sung Ouk Jung
Jang Yeol Baek
Moon-Hak Park
Jin Uk Ju
Tae Hoon Kim
Sang Hun Jang
Sang-Gyeong Lee
Sung Jin Park
Jung-Sik Kim
Jung-Kyu Park
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Gyeongsang National University Industrial And Academic Collaboration Foundation
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Priority claimed from KR1020070031251A external-priority patent/KR100865703B1/ko
Priority claimed from KR1020070031253A external-priority patent/KR100877177B1/ko
Priority claimed from KR1020070035608A external-priority patent/KR100901885B1/ko
Application filed by Gyeongsang National University Industrial And Academic Collaboration Foundation filed Critical Gyeongsang National University Industrial And Academic Collaboration Foundation
Publication of WO2008120839A1 publication Critical patent/WO2008120839A1/fr

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    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
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Definitions

  • the present invention relates to organic thin film transistors (OTFT) . More specifically, it relates to novel organic semiconductor compounds having high ⁇ -electron overlap, and organic thin film transistors which employ the compounds as a semiconductor layer, having improved charge mobility and on/off ratio.
  • OTFT organic thin film transistors
  • OFT organic thin film transistors
  • An OTFT employing an organic semiconductor can be simply produced as compared to a conventional OTFT employing amorphous silicon and polysilicon, with low cost. Further, the OTFT' s have been currently researched since they have advantages in excellent compatibility with plastic substrates for embodiment of flexible displays.
  • An organic thin film transistor generally consists of a substrate, a gate electrode, an insulator, source/drain electrodes and a channel layer.
  • OTFT' s are classified as OTFT' s of bottom contact type (BC type) wherein a channel layer is formed on source and drain electrodes, and those of top contact type (TC type) wherein a metal electrode is formed on a channel layer.
  • BC type bottom contact type
  • TC type top contact type
  • OTFT can be employed as a circuit device in a flexible matrix display having a large area.
  • Fig. 1 is a cross-sectional view showing a general structure of an OTFT comprising a substrate (H)/ a gate electrode (16)/ a gate insulator layer (12) / electrode layers (source, drain) (14 and 15)/ channel material layer (13).
  • a gate electrode is formed on the upper side of the substrate.
  • an insulator is formed, on which channel material layer and source/drain electrodes are formed.
  • the principle of operation of an OTFT having such a structure is described below, by means of an example of p-type semiconductor: First, voltage is applied between the source and the drain to flow the current. Under a low voltage, a current proportional to the voltage flows.
  • the materials employed for an OTFT which is constituted according to the above-described principle include electrodes (source, drain), a substrate and a gate electrode requiring high thermal stability, an insulator having high insulating property and dielectric constant, and a semiconductor material that provides sufficient delivery of the charge.
  • an essential material having various problems to be solved is the organic semiconductor.
  • Organic semiconductors are classified into low molecular, oligomeric and high molecular semiconductors depending on the molecular weight, and into n-type and p-type semiconductors depending on the function of delivery of electrons or holes.
  • a low molecular semiconductor when being used for forming channel material, exhibits excellent charge mobility due to easy purification to remove most of the impurities. Though the purification to high purity is difficult, a high molecular semiconductor shows excellent heat resistance and advantages in preparation, cost and mass production, since it can be spincoated or printed.
  • the charge mobility of high molecular semiconductor is lower than that of low molecular semiconductor, but the former is a substance that can sufficiently overcome the problem from the aspect of the manufacturing process or cost.
  • the high molecular materials should be firstly developed.
  • the low molecular or oligomeric organic semiconductor materials that have been extensively researched include melocyanine, phthalocyanine, perylene, pentacene, anthracene, C60, thiophene oligomer, and the like. Lucent Technologies and 3M reported high charge mobility of 3.2-5.0 cm 2 /Vs or more by using pentacene monocrystals (Mat. Res. Soc . Symp . Proc . 2003, Vol. 771, L6.5.1-L66.5.11) . Those values are comparable with or superior to that of amorphous silicon.
  • CNRS France
  • France also reported relatively high charge mobility and on/off ratio of 0.01-0.1 cm 2 /Vs by using an oligothiophene derivative.
  • formation of thin film essentially depends on a vacuum process, so that the production cost is high.
  • a high molecular OTFT device was experimentally manufactured by employing F8T2 (a polythiophene substance), having 0.01-0.02 cm 2 /Vs of charge mobility (International Laid-Open No. WO 00/7961, Science, 2000, vol. 290, pp. 2132-2126).
  • F8T2 a polythiophene substance
  • USP 6,107,117 discloses a process for manufacturing an OTFT device having 0.01-0.04 cm 2 /Vs of charge mobility by using a regioregular polythiophene, P3HT.
  • the first object of the present invention is to provide novel organic semiconductor compounds of acene derivatives having a substituent comprising arylacetylene groups.
  • the second object of the present invention is to provide organic semiconductor compounds having excellent charge mobility and high on/off ratio by introducing acetylene derivatives to anthracene having p-type semiconductor property in order to ensure solubility, and an aryl derivative to increase overlap of ⁇ -electrons and intermolecular crystallinity .
  • the third object of the present invention is to provide novel organic semiconductor compounds having high thermal stability, ⁇ - electron overlap and intermolecular crystallinity, and thereby enhanced charge mobility and on/off ratio, by introducing naphthalenes having electron-donor substituents at both terminals .
  • the fourth object of the present invention is to provide an organic thin film transistor having excellent charge mobility and high on/off ratio, by using said organic semiconductor compound having high ⁇ -electron density and ⁇ - electron overlap and intermolecular crystallinity.
  • the present invention relates novel monomolecular organic semiconductor compounds represented by one of Chemical Formulas (1) to (3), and OTFT' s employing the same.
  • the organic semiconductor compounds according to the present invention are characterized by having an anthracene structure substituted with acetylene groups as is represented by Chemical Formula (2) , or characterized by a multi-nuclear aromatic structure which is multi- functionalized at both terminals, comprising naphthalenes having electron-donor substituent (s) , as is represented by Chemical Formula (3).
  • A represents (C 6 -C 30 ) arylene or (C 6 -C 30 ) heteroarylene
  • - Ari and Ar 2 independently represent (C 6 - C 30 ) aryl or (C 4 -C 30 ) heteroaryl
  • m and n independently represent an integer of 1 to 4 ;
  • Ar 1 or Ar 2 may be independently substituted by at least one substituent (s) selected from the group consisting of hydroxyl group, linear, branched or cyclic (Ci-C 30 ) alky1 group, linear, branched or cyclic (Ci-C 30 ) alkoxy group, (C 1 - C 30 ) alkoxy (C 1 -C 30 ) alkyl group, (C 5 -C 30 ) ar (C 1 -C 30 ) alkyl group, (C 5 - C 30 ) aryl group, amino group, mono- or di (C 6 -C 30 ) alkylamino group, mono- or di (C 6 -C 30 ) arylamino group, (C 1 -C 30 ) alkoxycarbonyl group, cyano group or halogen.
  • substituent selected from the group consisting of hydroxyl group, linear, branched or cyclic (Ci-C 30 ) alky1 group, linear, branched or cycl
  • a 1 and A 2 are independently selected from the group consisting of C, Si and Ge; Ri 1 , R 12 , R 13 and R 14 are independently selected from the group consisting of hydrogen; linear, branched or cyclic (Ci-C 30 ) alkyl group; linear, branched or cyclic (C 2 -C 40 ) alkenyl group; linear, branched or cyclic (C 3 -C 40 ) alkynyl group; linear, branched or cyclic (C 1 -C 30 JaIkOXy group; (C 6 -C 40 ) aryl group,- (C 4 - C 30 ) heteroaryl group, (C 6 -C 30 ) ar (C 1 -C 30 ) alkyl group; (C 1 - C 30 ) alkoxy (C 1 -C 30 ) alkyl group; (C 1 -C 30 ) alkoxy (C 2 -C 30 ) alkenyl group; (C 6 -C 40 )
  • Ri5, Ri 6 , RI7A Ri8, RI9 and R 2 O are independently selected from the group consisting of hydrogen; linear, branched or cyclic (Ci-C 30 ) alkyl group; linear, branched or cyclic (C 2 - C 40 )alkenyl group; linear, branched or cyclic (C 3 -C 40 ) alkynyl group; linear, branched or cyclic (Ci-C 30 ) alkoxy group; (C 6 - C 40 ) aryl group; (C 4 -C 30 ) heteroaryl group, (C 5 -C 30 ) ar (Ci-C 30 ) alkyl group; (Ci-C 30 ) alkoxy (C 1 -C 30 ) alkyl group; (Ci-C 30 ) alkoxy (C 2 - C 30 )alkenyl group; (C 6 -C 50 ) heteroaryl (Ci-C 30 ) alkyl group; (Ci-
  • Ar 3 represents (C 6 -C 30 ) arylene or (C 6 -C 30 ) heteroarylene;
  • R 3 1 and R 32 independently represent hydrogen, linear, branched or cyclic (C 1 -C 25 ) alkyl, (C 5 -C 25 ) aryl, (C 4 -C 25 ) heteroaryl, (C 1 -C 25 ) alkoxy (Ci-C 25 ) alkyl , (C 5 -C 25 ) ar (C 1 - C 25 ) alkyl, (C 4 -C 25 ) heteroaryl (C 1 -C 25 ) alkyl, linear, branched or cyclic (C 2 -C 25 ) alkenyl, linear, branched or cyclic (C 2 - C 25 ) alkynyl, mono-, di- or tri (C 1 -C 25 ) alkylsilyl, mono-, di- or tri (C 5 -C 25 ) aryls
  • X 1 and X 2 are independently selected from the group consisting of 0, N, S and (Ci-C 25 ) alkylene; x and y independently represent an integer of 1 or 2; p and r independently represent an integer of 0, 1 or 2 ; q is an integer from 1 to 4 ;
  • Ar 3 may be further substituted by at least one substituent (s) selected from the group consisting of hydroxyl, linear, branched or cyclic (Ci-C 2 s) alkyl, linear, branched or cyclic (C 1 -C 25 ) alkoxy, (Ci-C 25 ) alkoxy (Ci-C 25 ) alkyl, (C 5 -C 25 ) ar (Ci- C 25 ) alkyl, (C 5 -C 25 ) aryl, amino, mono- or di (C 6 -C 25 ) alkylamino, mono- or di (C 6 -C 25 ) arylamino, cyano and halogen; and the alkyl, aryl, heteroaryl, alkoxyalkyl, aralkyl, heteroarylalkyl, alkenyl, alkynyl, alkylsilyl, arylsilyl, heterocycloalkyl or heterocycloalkylalkyl group of
  • the present invention provides an OTFT comprising a first electrode; a second electrode; and an organic semiconductor compound selected from the compounds represented by one of Chemical Formulas (1) to (3) between the first electrode and the second electrode. Further, the present invention provides an OTFT comprising a substrate, a gate electrode, a gate insulator layer, channel material layer and source/drain electrodes, wherein the channel material layer is formed of an organic semiconductor compound selected from the compounds represented by one of Chemical Formulas (1) to (3) .
  • Fig. 1 is a cross-sectional view showing the structure of common OTFT which comprises a substrate/a gate electrode/ a gate insulator layer/ electrode layers (source, drain)/ channel material layer.
  • Fig. 2 illustrates properties of an OTFT employing an organic semiconductor compound (Compound 101) according to the present invention as channel material; (a) transfer curve
  • Fig. 3 illustrates thermal gravity analysis (TGA) curves of the organic semiconductor compounds (Compounds 101, 102, 103 and 104) according to the present invention; (a) Compound (101), (b) Compound (102), (c) Compound (103), (d) Compound (104) .
  • TGA thermal gravity analysis
  • Fig. 4 illustrates differential scanning calorimeter (DSC) curves of the organic semiconductor compounds (Compounds 101 and 102) according to the present invention; (a) Compound (101), (b) Compound (102).
  • DSC differential scanning calorimeter
  • Fig. 5 illustrates DSC curves of the organic semiconductor compounds (Compounds 105, 106, 107 and 108) according to the present invention.
  • Fig. 6 illustrates TGA curves of the organic semiconductor compounds (Compounds 105, 106, 107 and 108) according to the present invention.
  • Fig. 7 illustrates a transfer curve of an OTFT employing Compound (105) as channel material; (a) source-drain voltage; (b) square root current-drain voltage.
  • Fig. 8 illustrates an output curve (current-voltage) of an OTFT employing Compound (105) as channel material.
  • Fig. 9 illustrates TGA curves of the organic semiconductor compounds according to the present invention.
  • (a) Compound (112) (b) Compound (113) , (c) Compound (114) , (d) Compound (116) , (e) Compound (117) and (f) Compound (118) .
  • Fig. 10 illustrates DSC curves of the organic semiconductor compounds according to the present invention.
  • (a) Compound (112) (b) Compound (113) , (c) Compound (114) , (d) Compound (116) , (e) Compound (117) and (f) Compound (118) .
  • Fig. 11 illustrates properties of an OTFT employing Compound 113 as channel material; (a) transfer curve of the OTFT, (b) output curve (current-voltage) of the OTFT.
  • A can be selected from the group consisting of phenylene, naphthylene, anthrylene, phenanthrylene, tetracenylene, pentacenylene, pyrenylene, chrysenylene and fluorenylene.
  • the compound can be exemplified by following arylenes :
  • Ar 1 and Ar 2 are independently- selected from aryl or heteroaryl represented by one of the following chemical formulas (the position of linkage with acetylene group is selected from the aromatic ring carbons of the substituent having one of the structures represented by following formulas) :
  • Ri is independently selected from the group consisting of hydrogen, hydroxyl group, linear, branched or cyclic (Ci-C 30 ) alkyl group, linear, branched or cyclic (Ci- C 30 )alkoxy group, (Ci-C 30 ) alkoxy (Ci-C 30 ) alkyl group, (C 5 - C 30 ) ar (Ci-C 30 ) alkyl group, (C 5 -C 30 ) aryl group, amino group, mono- or di (C 6 -C 30 ) alkylamino group, mono- or di (C 6 -C 30 ) arylamino group, (Ci-C 30 ) alkoxycarbonyl group and cyano group.
  • Ri 5 , Ri 6 , Ri 7 , Ris, R 19 and R 20 are independently selected from the group consisting of (Ci- C 10 ) alkyl group, tri (Ci-Ci 0 ) alkylsilyl group; tri (Ci- C 10 ) alkoxysilyl group and tri (C 6 -Ci 0 ) arylsilyl group.
  • the silyl groups are exemplified by trimethylsilyl, triethylsilyl, tripropylsilyl, dimethylethylsilyl, diethylmethylsilyl, dimethylpropylsilyl , dimethylisopropylsilyl , dipropylmethylsilyl , diisopropylmethylsilyl , dipropylethylsilyl , diisopropylethylsilyl , diethylisopropylsilyl, triisopropylsilyl, trimethoxysilyl, triethoxysilyl and triphenylsilyl .
  • Aryl and heteroaryl selected for Rn to R 14 are exemplified by the substituents represented by one of the following chemical formulas:
  • R 2i , R22, R23 , R24, R25 and R 26 are independently- selected from the group consisting of hydrogen, (Ci-C 30 ) alkyl group, (C 6 -C 30 ) aryl group and (Ci-C 30 ) alkoxy (C 6 -C 30 ) aryl group; and alkyl or aryl of R 21 , R 22 , R23, R24, R25 or R 26 may be substituted by at least one substituent (s) selected from the group consisting of (Ci-C 30 ) alkoxy and halogen; and the position of linkage where the substituent is bonded is selected from the carbons in the substituent ring.
  • Ar 3 is exemplified by arylene or heteroarylene having the structure represented by one of the following chemical formulas:
  • R 4x to R 47 are independently selected from the group consisting of hydrogen, (C 1 -C 25 ) alkyl, (C 5 -C 2S ) aryl and (C 5 -C 25 ) ar(Ci-C 2 5) alkyl, and the alkyl and aryl of said R 41 to R 47 may be further substituted by at least one substituent (s) selected from the group consisting of (Ci-C 25 ) alkoxy and halogen.
  • the aryl or heteroaryl selected for the substituent R 31 or R 32 is exemplified by the substituents represented by one of the following chemical formulas: wherein, R 51 , R 52 , R 53 , R 54 , R 55 and R 56 are independently selected from the group consisting of hydrogen, amino, linear, branched or cyclic (C 1 -C 25 ) alkyl, linear, branched or cyclic (C 1 -C 25 ) alkoxy, (C 1 -C 25 ) alkoxy (C 1 -C 25 ) alkyl, (C 5 -C 25 ) ar (C 1 - C 25 )alkyl, (C 5 -C 25 ) aryl, mono- or di (C 6 -C 25 ) alkylamino, mono- or di (C 6 -C 25 ) arylamino group; and the position of linkage where the substituent is bonded is selected from the carbons in the substituent ring.
  • the organic semiconductor compounds represented by Chemical Formula (1) according to the present invention are organic semiconductor compounds of acene derivative type, which have arylacetylene substituents at both terminal, with high ⁇ -electron density and ⁇ -electron overlap and intermolecular crystallinity .
  • the organic semiconductor compounds according to the present invention represented by Chemical Formula (2) are organic semiconductor compounds modified by acetyl group at 9- and/or 10 -position of anthracene. Those compounds facilitate formation of intermolecular packing and ⁇ -stacking, and provide excellent crystallinity. Further, aliphatic groups enhance solubility and flowability of these molecules, helping to give crystallinity to the molecules.
  • the organic semiconductor compounds according to the present invention represented by Chemical Formula (3) are multi-nuclear aromatic derivatives functionalized by naphthalenes having electron-donor substituent (s) . These compounds are very linear, having naphthalenes as electron- rich multi-nuclear aromatics at both terminals, thereby facilitating intermolecular packing and ⁇ -stacking and providing excellent crystallinity. Aliphatic groups are also helpful to provide the molecules with crystallinity by increasing the solubility and flowability of these molecules. As can be seen from the differential scanning calorimeter (DSC) curves, these compounds have different phase transition temperatures; which indirectly shows that the organic semiconductor compounds according to the present invention represented by Chemical Formula (3) have liquid crystallinity . The liquid crystallinity is a major cause of excellent crystallinity of these molecules.
  • DSC differential scanning calorimeter
  • organic semiconductor compounds represented by one of Chemical Formulas (1) to (3) according to the present invention can be exemplified by following compounds, but they are not restricted thereto.
  • the organic semiconductor compound having arylacetylene structure represented by Chemical Formula (1) wherein Ari and Ar 2 are identical so that the compound has symmetrical structure, can be prepared by coupling 2 equivalents of arylacetylene compound with dihaloaryl compound, as shown in Reaction Formula (1) .
  • the coupling reaction is proceeded by using Cul/Pd (PPh 3 ) 2 Cl 2 as a coupling agent in the presence of triethylamine and organic solvent.
  • Ar 1 X-A-X Ar 1 -A- -Ar 1
  • the asymmetric compounds can be prepared by separately reacting arylacetylene compound and dihaloaryl compound in discrete steps :
  • Ar 1 - + X-A-X ⁇ Ar 1 zzz A-X
  • the process for preparing the organic semiconductor compounds having arylacetylene structure represented by Chemical Formula (1) according to the present invention is not restricted by above-described process for preparation.
  • the compounds may be prepared according to conventional organic chemical reactions other than the processes described above.
  • the arylacetylene compound and halodiaryl compound, employed as intermediates can be easily prepared via conventional organic chemical reactions by a person having ordinary skill in the art .
  • the final organic semiconductor compounds represented by Chemical Formula (3) according to the present invention can be prepared via alkylation, Grignard coupling reaction, Suzuki coupling reaction, or the like.
  • the process for preparing the organic semiconductor compounds represented by one of Chemical Formulas (1) to (3) according to the present invention is not restricted by above- described processes for preparation.
  • the compounds may be prepared according to conventional organic chemical reactions other than the processes described above.
  • the organic semiconductor compounds according to the present invention can be employed as channel material in an OTFT.
  • the OTFT according to the present invention comprises a first electrode; a second electrode; and an organic semiconductor compound represented by one of Chemical Formulas (1) to (3) between the first electrode and the second electrode. More specifically, the present invention provides an OTFT comprising a substrate (11) , a gate electrode (16) , a gate insulator (12) , channel material (13) and source/drain electrodes (14 and 15) , wherein the channel material is made of an organic semiconductor compound selected from the compounds represented by one of Chemical Formulas (1) to (3) .
  • the constitution of the OTFT of the present invention includes a top-contact type which comprises a substrate/a gate electrode/ a gate insulator layer/ channel material layer/ source / drain electrode in the order (not shown) , as well as a bottom-contact type which comprises a substrate (H)/ a gate electrode (16)/ a gate insulator layer (12)/ source and drain electrodes (14 and 15)/ channel material layer (13) in the order as shown in Fig. 1.
  • the organic semiconductor compounds according to the present invention are low-molecular semiconductor compounds having typical properties of p-type semiconductors.
  • the acene derivatives comprising arylacetylene group, represented by Chemical Formula (1) contain acetylene groups to increase intermolecular linearity.
  • When these compounds are applied to an OTFT excellent charge mobility and high on/off ratio can be effected due to high ⁇ -electron overlap of the compounds.
  • the compounds having anthracene structure substituted with acetylenes, represented by Chemical Formula (2) have enhanced ⁇ -electron overlap and intermolecular crystallinity, so that an OTFT having excellent charge mobility and high on/off ratio can be obtained therefrom.
  • the multi-nuclear aromatic derivatives functionalized with naphthalenes having electron-donor substituents at both terminals, as represented by Chemical Formula (3) are very linear.
  • the compounds are thermally stable, facilitate intermolecular packing and ⁇ - stacking, and provide excellent crystallinity.
  • the effects of excellent hole and electron mobility, low threshold voltage, large current change per unit voltage and high on/off ratio can be obtained.
  • n-type silicon used for conventional OTFT is preferably used.
  • the substrate comprises the function of a gate electrode. Otherwise, a glass substrate or a clear plastic substrate having excellent surface smoothness, easiness in handling and water resistance may be also used. In this case, a gate electrode should be added on the substrate.
  • the material usable as a substrate is exemplified by glass, polyethylenenaphthalate (PEN) , polyethyleneterephthalate (PET) , polycarbonate (PC) , polyvinylalcohol (PVP) , polyacrylate, polyimide, polynorbornene and polyethersulfone (PES) , but not limited thereto.
  • the gate insulator (12) any conventionally used insulator having high dielectric constant may be employed.
  • the insulator may be a strongly dielectric insulator selected from the group consisting of Ba 0.33 Sr 0.66 1 TiO 3 (BST) , Al 2 O 3 , Ta 2 O 5 , La 2 O 5 , Y 2 O 3 and TiO 2 ; an inorganic insulator selected from the group consisting of PdZr 0 .
  • the gate electrode (16) and the source/drain electrodes (14 and 15) can be made of any conductive substance, the substance can be preferably selected from the group consisting of gold (Au) , silver (Ag) , aluminum (Al) , nickel (Ni) , chromium (Cr) and indium tin oxide (ITO) .
  • the surface may be treated by coating with HMDS (1, 1, 1, 3 , 3 , 3-hexamethyldisilazane) , OTS
  • OTDS octadecyltrichlorosilane
  • the channel material layer employing the organic semiconductor compound according to the present invention may be coated via a coating process conventionally known in the art, including vacuum vapor-deposition, screen printing, printing process, spin casting process, spin coating process, dipping process or ink-jet process, to form a thin film.
  • Vapor-deposition of the channel material layer can be carried out by using a hot solution at a temperature of 40 ° C or higher, to make the thickness of about 500 A.
  • reaction mixture was extracted with dichloromethane, dried over MgSO 4 and evaporated by using a rotary evaporator to remove the solvent .
  • reaction was continued at 100 ° C for 24 hours, and then quenched by pouring the mixture to 2N-HC1.
  • the reaction mixture was extracted with chloroform, dried over MgSO 4 and evaporated by using a rotary evaporator to remove the solvent.
  • Desired compound (111) was obtained according to the same procedure as described in Example 10, but using 2-bromo-5- (5- bromothiophen-2-yl) thiophene (Compound 16) (0.015 mol) obtained from Preparation Example 12, and 6-methoxynaphthalen- 2-yl-2-boronic acid (Compound 18) (0.033 mol) obtained from Preparation Example 13. Yield: 51%.
  • Desired compound (112) was obtained according to the same procedure as described in Example 10, but using 2-bromo-5- (5- bromothiophen-2-yl) thiophene (Compound 16) (0.015 mol) obtained from Preparation Example 12, and 6- (hexyloxy) naphthalen-2-yl-2-boronic acid (Compound 20) 0.033 mol) obtained from Preparation Example 14. Yield: 45%.
  • a cleansed glass substrate (11) aluminum was vacuum deposited as a gate electrode (16) with a thickness of 65 ⁇ A and then PVP as a gate insulator (12) was coated by spin coating with a thickness of 5500 A Gold (Au) as source-drain electrodes (14 and 15) was then vacuum deposited thereto with a thickeness of 450A The length of the channel was 30 ⁇ m, and the width 150 ⁇ m.
  • Compound (101) obtained from Example 1 was vacuum deposited at 80 ° Cof substrate temperature at a rate of 0.3 Asec with a thickness of 500 A to prepare an OTFT device of bottom-contact mode as shown in Fig. 1. By using the device, the current transmission property was measured, and the current transmission curves are shown in Fig. 2.
  • I SD is source-drain current
  • ⁇ or ⁇ FE ⁇ is charge mobility
  • C 0 electrostatic capacity of insulating film
  • W is channel width
  • L is channel length
  • V G is gate voltage
  • V ⁇ is threshold voltage
  • Interrupting leakage current is the current flowing under off-state, that is obtained as minimum value under off- state from the current ratio.
  • Subthreshold slope shows the extent of change in drain current versus change in gate voltage before reaching the threshold voltage. It is obtained as the amount of change in gate voltage required for 10 -fold increase of drain current.
  • Threshold voltage V th is minimum voltage required to drive an OTFT device, and obtained as the point of intersection of the slope of the linear portion of the I D -V G graph and the value under off-state.
  • An OTFT device was manufactured according to the same procedure described in Example 19, but using pentacene, of which the chemical structure is shown below, as a substance for creating channel material.
  • the current transmission property of the device was measured, and several measured physical properties are shown in Table 1. [Table 1]
  • Example 19 As can be seen from Table 1, the device of Example 19 employing Compound (101) according to the present invention exhibited higher charge mobility and current on/off ratio, and much lower interrupting leakage current, threshold voltage and subthreshold slope, as compared to the device of Comparative Example 1. Thus it is confirmed that the compounds according to the present invention provide excellent performance when being employed in an organic thin film transistor.
  • chromium was vapor- deposited by sputtering process as a gate electrode (16) with a thickness of IOOOA and then SiO 2 as a gate insulator (12) was vapor-deposited by CVD process with a thickness of 1000 A ITO as source-drain electrodes (14 and 15) was then vapor- deposited thereon by sputtering process with a thickness of 1200 A Before vapor-depositing the organic semiconductor material, the substrate was washed with isopropyl alcohol over 10 minutes.
  • the sample was soaked in a solution of octadecyltrichlorosilane diluted in hexane to 10 mM of concentration over 30 seconds, washed with acetone, and dried. Then, the oligoanthracene derivative (Compound 105) obtained from Example 5 was dissolved and spin-coated thereto with a thickness of 7O ⁇ A to provide an OTFT device of bottom-contact mode .
  • I SD is source-drain current
  • ⁇ or ⁇ FET charge mobility
  • C 0 electrostatic capacity of insulating film
  • W is channel width
  • L is channel length
  • V G is gate voltage
  • V ⁇ is threshold voltage
  • Interrupting leakage current (I Off ) is the current flowing under off-state, that is obtained as minimum value under off- state from the current ratio.
  • n-type silicon was employed, and the substrate comprises the fuction of a gate electrode.
  • titanium (10 nm) and gold (80 nm) were vapor- deposited to form a source and a drain electrode.
  • the gap between the source and drain had 25 ⁇ m to 500 ⁇ m of width (W) , and 5 ⁇ m to 50 ⁇ m of length (L) .
  • the organic semiconductor compounds prepared from Example 12-14 and 16-18 (Compounds 112, 113, 114, 116, 117 and 118) were spin-cast to form channel material having 5O ⁇ A of thickness, and an organic thin film transistor of bottom-contact mode (as shown in Fig. 1) was manufactured therefrom.
  • Example 24 Evaluation of thermal properties of organic semiconductor compounds Thermal properties of organic semiconductor compounds prepared from Example 12-14 and 16-18 (Compounds 112, 113, 114, 116, 117 and 118) were examined by means of thermal gravity analysis (TGA) and differential scanning calorimeter (DSC) with heating them from 40 ° Cto 700 ° Cat a rate of 10 ° (7min under nitrogen atmosphere. The results are shown in Figs. 9 and 10.
  • a novel organic semiconductor compound according to the present invention being a mono- molecular organic semiconductor having inherent structure, is stable at ambient temperature, and can be easily synthesized by means of various processes.
  • it When being used as an active layer in an OTFT, it is able to form a thin film via vacuum deposition process and is coatable via wet process at ambient temperature.
  • an OTFT having both sufficiently high electron mobility and low interrupting leakage current can be manufactured.
  • the excellent liquid crystallinity of the compounds facilitates intermolecular arrangement and provides remarkable crystallinity.
  • the organic thin film transistor manufactured by applying the novel organic semiconductor compound according to the present invention facilitates intramolecular or intermolecular charge mobility due to the introduction of various substituent (s) and substituent group (s) .
  • the OTFT exhibits improved hole and electron mobility, excellent on/off ratio, as well as very low interrupting leakage current, threshold voltage and subthreshold slope, as measured.
  • the compounds according to the present invention can be utilized as an active layer for organic thin film transistor devices.
  • an electronic device having excellent efficiency and performance can be manufactured by utilizing an OTFT employing the novel organic semiconductor compound according to the present invention.
  • the OTFT can be also manufactured by means of vacuum deposition, or solution process such as spin coating and printing, so that the production cost of an electronic device employing an OTFT can be lowered.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)

Abstract

Cette invention concerne des nouveaux composés semi-conducteurs organiques mono-moléculaires ainsi que des transistors à couches minces organiques comprenant de tels composés. Les composés semi-conducteurs organiques décrits dans cette invention se caractérisent par une structure constituée d'un dérivé d'acène substitué par des groupes acétylène aux deux extrémités, une structure constituée d'un dérivé d'anthracène substitué par des groupes acétylène, ou une structure d'un dérivé aromatique multi-nucléaire fonctionnalisé par le naphtalène présentant un substitutif donneur d'électrons aux deux extrémités.
PCT/KR2007/003326 2007-03-30 2007-07-09 Nouveau composé semi-conducteur organique et transistor à couches minces organiques utilisant un tel composé WO2008120839A1 (fr)

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KR10-2007-0031251 2007-03-30
KR1020070031251A KR100865703B1 (ko) 2007-03-30 2007-03-30 아릴아세틸렌 구조의 유기반도체 화합물 및 이를 이용한유기박막트랜지스터
KR1020070031253A KR100877177B1 (ko) 2007-03-30 2007-03-30 아세틸렌기가 치환된 안트라센 구조의 유기반도체 화합물및 이를 이용한 유기박막트랜지스터
KR10-2007-0031253 2007-03-30
KR1020070035608A KR100901885B1 (ko) 2007-04-11 2007-04-11 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터
KR10-2007-0035608 2007-04-11

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WO2009112854A1 (fr) * 2008-03-11 2009-09-17 Merck Patent Gmbh Composés présentant des propriétés électroluminescentes ou de transport des électrons
WO2009154877A1 (fr) * 2008-06-19 2009-12-23 3M Innovative Properties Company Semi-conducteurs organiques pouvant être traités en solution
US8178873B2 (en) 2007-12-17 2012-05-15 3M Innovative Properties Company Solution processable organic semiconductors
CN103641806A (zh) * 2013-11-19 2014-03-19 常州市天华制药有限公司 一种4-苯乙炔苯酐的制备方法
CN111599548A (zh) * 2020-05-28 2020-08-28 天津大学 特高压直流gil用柔性界面功能梯度盆式绝缘子制造方法

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US8178873B2 (en) 2007-12-17 2012-05-15 3M Innovative Properties Company Solution processable organic semiconductors
WO2009112854A1 (fr) * 2008-03-11 2009-09-17 Merck Patent Gmbh Composés présentant des propriétés électroluminescentes ou de transport des électrons
US8507896B2 (en) 2008-03-11 2013-08-13 Merck Patent Gmbh Compounds having electroluminescent or electron transport properties
WO2009154877A1 (fr) * 2008-06-19 2009-12-23 3M Innovative Properties Company Semi-conducteurs organiques pouvant être traités en solution
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CN103641806A (zh) * 2013-11-19 2014-03-19 常州市天华制药有限公司 一种4-苯乙炔苯酐的制备方法
CN111599548A (zh) * 2020-05-28 2020-08-28 天津大学 特高压直流gil用柔性界面功能梯度盆式绝缘子制造方法
CN111599548B (zh) * 2020-05-28 2021-10-22 天津大学 特高压交流gil用柔性界面功能梯度盆式绝缘子制造方法

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