TW200922935A - Benzodithiophene derivative, and organic thin film transistor and organic thin film light-emitting transistor by using the same - Google Patents

Abstract

Disclosed are: a benzodithiophene derivative having an aromatic hydrocarbon group or an aromatic heterocyclic group in its center; an organic thin film transistor which has, on a substrate, at least three terminals, i.e., a gate electrode, a source electrode and a drain electrode, an insulating layer, and an organic semiconductor layer, and in which the current flowing between the source electrode and the drain electrode is controlled by applying a voltage to the gate electrode, wherein the organic semiconductor layer comprises a specific benzodithiophene having an aromatic hydrocarbon group or an aromatic heterocyclic group in its center; and an organic thin film light-emitting transistor substantially comprising the organic thin film transistor, wherein the emission of light is achieved by utilizing the current flowing between the source electrode and the drain electrode and controlled by applying a voltage to the gate electrode. It becomes possible to provide: an organic compound that exhibits a highly stable field effect mobility even when being exposed to the atmosphere; and an organic thin film transistor and an organic thin film light-emitting transistor each utilizing the organic compound.

Description

200922935 IX. Description of the Invention: [Technical Field] The present invention relates to a novel organic compound benzodiophene derivative which is suitable for use as an organic semiconductor layer of a constituent element of an organic thin film transistor, and has a δ The organic thin film transistor and the organic thin film light-emitting transistor of the organic semiconductor layer are particularly excellent in the stability of the electric field effect mobility even in the state of being exposed to the atmosphere, and the organic thin film using the same Transistors and organic thin luminescence transistors. [Prior Art] A thin film transistor (TFT, Thin Film τ sist〇r) is widely used as a switching element for display such as a liquid crystal display device. A representative tft profile is shown in Figure 3. As shown in the figure, the TFT has a closed electrode, an insulator layer, and an organic semiconductor layer in this order on the substrate, and has a source electrode and a drain electrode formed at a predetermined interval on the organic semiconductor layer. The organic semiconductor layer serves as a channel region, and an on/off operation is performed by controlling a current flowing between the source electrode and the drain electrode by a voltage applied to the gate electrode. Previously, the TFT was fabricated using an amorphous germanium or a polycrystalline germanium, but there was a problem in that a chemical vapor deposition (CVD) device used for fabricating a TFT having such a defect was very expensive, thereby using TFT. The increase in size of display devices and the like has resulted in an increase in manufacturing costs. Further, since the process of forming a film of amorphous germanium or polycrystalline germanium is carried out at a very high temperature, the type of material which can be used as a substrate is limited, and there is a problem that a lightweight resin substrate cannot be used. In order to solve the above problems, it is proposed to use 134113.doc 200922935 organic material in the semiconductor layer instead of the amorphous or polycrystalline silicon TFT (the following machine is used to form a TFT from an organic substance to make == know that there is vacuum evaporation The ore method, the coating method, etc., by such a method of forming a medium, the manufacturing cost is not increased, and the size of the apparatus can be increased, and the process temperature necessary for the time can be made lower. Therefore, (4) The materials used in the materials are less restrictive, and they are urgently needed and put into practical use. The research report is being widely and widely used. /, as an organic semiconductor used in organic TFTs, in (iv) or as a mixture of other compounds. For example, a material of a total (four) polymer or an singular "polymer, a metal phthalocyanine compound, a slightly condensed aromatic W W b n n field effect transistor (fet 'time (10) - Γ) is known, for example. M,5,8-naphthalenetetracarboxylic dianhydride (NTCDA, Naphthalenetetracarboxylic Dianhydride), η,11,12,-tetracyanophthalene-2,6•quinolinedi methane (tcnnqd, lUl,12,12-tetracyanonaphtho- 256-qUinodimethane) M,5,8_Cetyltetraentimide (ntcdi, ene tetracarboxyiic diimide) and fluorinated phthalocyanine. On the other hand, organic electroluminescence (EL, Electr〇) exists as an element that uses conductivity as well. Luminescence. An organic EL device generally applies a strong electric field of 105 V/cm or more in the film thickness direction of an ultra-thin film of 100 nm or less, and forcibly causes a charge to flow 'as opposed to this' in the case of an organic TFT. An electric field of 1 〇 5 V/cm or less causes a charge to flow at a high speed over a distance of more than one. The organic substance constituting the transistor itself must have a high electrical conductivity. However, the above compound in the prior organic TFT is an electric field effect 134113.doc 200922935 The migration rate is small and the response speed is slow, which is problematic in terms of high-speed responsiveness of the transistor, and the on/off ratio is also small. The so-called on/off ratio is when the gate voltage is applied (open circuit). The current flowing between the source and the drain is divided by the value of the current flowing between the source and the pole-no-pole when the gate voltage is not applied. The so-called turn-on current usually increases the closed-pole current. Current value (saturation current) when the current flowing between the source and the drain is saturated. Further, in Patent Documents 1 and 2, a field effect electric power using a condensed aromatic te such as fused pentene for an organic semiconductor layer is produced. A crystal element. Although these elements have a relatively high electric field effect mobility immediately after they are formed, there is a disadvantage that the stability of the pentacene is low in the atmosphere. Patent Document 1: Japanese Patent Laid-Open Publication No. Hei-5-55568 2: Japanese Patent Laid-Open Publication No. Hei No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. 1 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The novel organic compound in the organic semiconductor layer of the constituent elements of the crystal, the organic thin film electromorphic crystal having the organic semiconductor layer, and the organic thin film light-emitting transistor, in particular, provide a state in which the storm is in a state of a large C. An organic compound excellent in stability of electric field effect mobility, an organic thin film transistor using the same, and an organic thin film light-emitting transistor. [Technical means for solving the problem] The present inventors have repeatedly conducted an effort to achieve the above object, 134113.doc 200922935 ==::::=, the electric field effect mobility in the two-state _:::::: The present invention provides a benzodioxin derivative of the present invention, which is represented by the following formula (4): 1_化1 j, in the form of being exposed to the atmosphere.

The aromatic hydrocarbon group or the carbon number of 1 to 60:: / fragrant heterocyclic group ' these groups may also have a substituent; R1 Rio is independently hydrogen for the "Zi Xi 栌 I * 风原千自Atom, cyano, and carbon number are 1 to 30 f [wherein A is a carbon number of 6 to 6 and "" a haloalkyl group having a number of 1 to 3 fluorene and an alkyl group having a carbon number of 1 to 3 fluorene Oxyl, carbon 2, the south of the oxy group, the carbon number is 1, the appearance of the amine group, the carbon number is m ^ - pit-based amine group (the base can also be bonded to each other to form a nitrogen-containing atom) : The carbon number is 1 to 3. (4) 醯 base, carbon number is the secret of the courtyard of the 30th continued: I number is U0 alkylthio group, carbon number is 〇3〇 of haloalkylthio group, carbon = 3~3 ° of the burning base (10), carbon number is "0 aromatic smoke group or carbon shoulder material family heterocyclic group, these groups may also have a substituent, and 1 'and form an aromatic hydrocarbon group having a carbon number of 6 to 60 or a carbon number of Z Fangxianghe heterocyclic group. Further, η is an integer of W0, and in the case of ... or more, plural Α may be the same or different]; 134] 13.d〇c 200922935 (7) - an organic thin film transistor which is provided at least on the substrate The electrode source electrode and the three terminals of the electrode, the insulator layer, and the organic semiconductor layer control the current between the source and the drain by applying a voltage to the gate electrode, and the organic semiconductor layer includes the above (1) a benzodithiophene derivative; (3) an organic thin film light-emitting transistor obtained by using a current flowing between a source and a gate in an organic thin film electric B body as in the above (2) And controlling the light emission by applying a voltage to the gate electrode. [Effects of the Invention] The benzodithiophene derivative represented by the formula (a) of the present invention is difficult to be oxidized and stabilized in the atmosphere, and the benzodithiophene structure itself has high planarity and crystallinity. Therefore, by using it in the organic semiconductor layer of the organic thin film transistor, an organic thin tantalum transistor and an organic thin film light-emitting transistor excellent in stability of electric field effect mobility even in a state of being exposed to the atmosphere can be obtained. [Embodiment] The benzodithiophene derivative of the present invention is a compound represented by the following formula (a): [Chemical 2]

134II3.doc 200922935 In the above formula (4), the 'A series carbon number is 6 to 6 (), the divalent group of nicotine groups or the divalent aromatic moieties having a carbon number of 1 to 60; Each group may also have a substituent. Specific examples of the above-mentioned divalent aromatic smoky group of A include benzene, cage, tetraphenyl fused pentacene phenanthrene, fluorene phenanthrene, corannulene, hydrazine, and upper lean, Crown/, bivalent residues such as hexabenzo-e, hexabenz〇c〇r〇nene, and Sumanene. Specific examples of the above-mentioned divalent aromatic heteropolyether group of A include pyridine, well, naphthalene, quince, and lin, and (iv) lin, dian, phenothithiophene, and thienothiophene. - Legacy, ,, a well... B pheno (four) pheno, [1] benzo. Sepheno[3 2-bl thiophene, dibenzofuran, open I, 2 b] dithiazole, dibenzo (tetra), di(tetra)benzodiazepine, dibenzopyrene, etc. A 2 valence residue. In the above formula (4), A is preferably a hexavalent aromatic furnace of 6 to 30. The number of turns of the aromatic furnace is tetraphenyl, pentacene, and phenanthrene. The divalent residue of the carbon number which may have a substituent and the other is preferably a good one. ratio. A divalent aromatic heterocyclic group of 3 〇, more diazepines (tetra), Tsai. Ding, (4) Lin, ", phenanthroline, carbazole, pyridine oxazoline, cultivating quinoxaline, -open thiophene, thienothia _ (1) benzo (tetra) and ... marriage (four) phenotype, _ benzene # Second "open. Cephthophene, bromo, dithiabenzo-r-p-open-furan, benzofuran P, dithia-salt and sulphur, dibenzo phenanthrene, di-p-mono-furan, dithiabenzoindole , Selenium hydrazine I34M3.doc 200922935 Heterobenzoate two-section, two-coded nodular joints, dibenzo-xanthene and other two-valent residues.

In the above formula (4), specific examples of the structure in which a plurality of A represented by _(A)n- are bonded include biphenyl, terphenyl, lignin, lysine, thiophene, phenylthiophene, and thiophene. A structure in which a naphthoquinone, a phenylnaphthalene, a phenylhydrazine, a pyridyl group, or a heterocyclic group is bonded by a single bond. The substituent which may be contained in the above A may be the same as the one below. In the above formula (4), an integer of from 1 to 1 G is preferably an integer of Bu. At η is 1~1〇夕益! When the filling is in the shape of the filling, the substrate is effectively aligned, which contributes to the improvement of the mobility. When η is 2 or more, each of the plurality of octagons may be the same or a thiol group having a carbon number of 1 to 3 Å, and a carbon base of 1 to 3 G. The number of carbon atoms is 2 to 60% of the amine groups (the bases can also be bonded to each other, and the mouth forms a nitrogen atom-containing paper. The carbon number of the paper is (4). The number of soils from 1 to 30 is 1 to 3. The sulfur-burning group has a carbon number of "anthracene, a group, an aromatic hydrocarbon group having a carbon number of 3 or a carbon number of l, and the n-group says "the number is 6," The aromatic heterocyclic group which may have a substituent, and each of the aryl group or the carbon number is (10)^, which forms a aryl group of a aryl group having a carbon number of 6 〜. Further, it is preferred that the alkyl group having a hydrogen number of 1 to 30 or the carbon number of 丨~% in the above-mentioned atom of the general formula, the self-primary atom, the radical, ") is 134113.doc -12-200922935 Burning base. In the above formula (4), the oxime is a hydrogen atom, and at least one of R1, h, R5, R8, R9 and R10 is an alkyl group having a carbon number of 1 to 30 and a carbon number of 1 to 30. Tetraalkyl, i-atomic, cyano.

Further, it is more preferable that R2 and R are in the above formula (4). It is a gas atom, and at least one of Rl and R8 is a 5-carbon [is a hospital base of 1 30, a carbon number of a sputum (10), a dentate atom, a cyano group. Further, it is preferred that in the above formula (4), R], I, I, I, and are hydrogen atoms? 'And 1, R5, mi. At least one of the alkyl groups having a carbon number of 1 to 30, a carbon number of a halo group, a halogen atom, and a cyano group. Specific examples of the respective groups represented by R1 to R]Q of the general formula (a) will be described below.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine atoms. Examples of the alkyl group include a mercapto group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a second butyl group, an isobutyl group 't-butyl group, a n-pentyl group, an n-heptyl group, and an n-octyl group. N-decyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl and the like. Examples of the above-mentioned alkyl group include a chloromethyl group, a fluorene group, a gas group, a 2-chloroethyl group, a 2-chloroisobutyl group, a 1,2-dichloroethyl group, a hydrazine, and a 3-dichloroisopropyl group. 2,3_Dichloro-t-butyl, 1,2,3-trimethylpropyl, bromoindolyl, hydrazine-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2 -dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodonium, i-iodoethyl, 2 - moth ethyl, 2-nonylisobutyl, iota, 2_diethylidene, iota, 3_diisopropyl, 2,3-diiodo-t-butyl, 1,2,3_three Iodopropyl, fluoroindolyl, 1-fluoroindole, 2-fluoroindolyl, 2-fluoroisobutyl, decyl-difluoroethyl, difluoromethyl 134113.doc -13- 200922935 soil, difluoromethyl Base, pentafluoroethyl, perfluoroisopropyl, perfluorobutyl, perfluorocyclohexyl and the like. The alkoxy group is a group represented by -OX], and examples of the oxime may be the same as those described in the above alkyl group, and the alkanoic group is represented by -OX2 as X2. Examples thereof are the same as those already described in the above haloalkyl group. The above alkylamino group is a group represented by -NHX1, and the dialkylamine group is

The bases represented by NX X, χι and χ3, respectively, may be the same as those already explained in the above-mentioned yards. Further, the filaments of the two filaments are bonded to each other to form a ring structure containing a nitrogen atom. Examples of the ring structure include, for example, halazine. The alkanesulfonyl group is represented by the formula -S〇2Xi, which is the same as those described in the above-mentioned alkyl group. The above-mentioned i-burning oxime group is represented by the group of so2x, and as an example of χ2, The same examples as those already described in the above halogen group are mentioned. The sulfur-burning group is a group represented by the first embodiment, and examples of the oxime may be exemplified by the above-mentioned alkyl group. In the case where the above description is the same, the above-mentioned alkanethio group is a group represented by -SX, and 蛊γ2 + ^丨 is taken as an example of X, and examples which are the same as those described above in the above-mentioned group are mentioned. / 烧 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基The group: a base group, a flower base 'slightly tetraphenyl group, a slightly pentaphenyl group, etc.. For the above-mentioned scented heterobasic group, for example, bis-phenanthryl phenyl 'benzene 134113.doc 200922935 open furanyl, cumene thiophene a group, a quinolyl group, a carbazolyl group, a dibenzo group, a benzothiophenyl group, a benzothiadiazolyl group, etc.; and a quinone formula (a) _, which is a mixture of R丨~Rig Examples of the sulfhydryl group and the sulphur-heterocyclic heterocyclic group are the same as those described above for the aromatic hydrocarbon group and the sulphur-heterocyclic heterocyclic group. The earth 1 卞 two-step substitution is shown in the above formula (4). Examples of the substituent of each group: an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkyl group, an alkoxy 'aryloxyindenyl group, an anthracene group, an amine group, a dentate atom, a cyano group, a nitro group, a hydroxyl group And a carboxyl group. However, the specific examples of the compound represented by the general formula (a) in the present invention are not limited thereto: [Chemical 3]

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The stupid and dithiophene derivative of the invention is basically bipolar (hole conduction) and n type (electron conduction) bipolar, so that the combination of the source and the drain electrode described below can be used as the p-type element. The n-type element is driven to reduce the lowest unoccupied molecular orbital itaUM0, 0rbital)t from the base of the general formula (a), wherein the base of the accepting material is substituted on the crucible or R, R1°. '^5 (4) The basis of the acceptability of the seed is preferably a chlorine atom, an alkoxy group, a carbon number of ～::1·(tetra), a halogen group having a carbon number of 1 to 3° as a 5"嶒醯基. Moreover, by using the electron-donating-and-substituting bases, the highest λ34Ι I3.doc 200922935 can be used as a P-type semiconductor according to the molecular orbital (HOMO, Highest Occupied Mo丨ecu丨ar 〇rbital) level. Play a role. The electron-donating group is preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having a carbon number of 5%, an alkylamino group having 1 to 30 carbon atoms, and a carbon number of 2 to 6 A dialkylamino group of hydrazine (the amine groups may also be bonded to each other to form a ring structure containing a nitrogen atom). Further, since the purity of the material used in the electronic component such as the transistor is higher, a higher electric field effect mobility and an on/off ratio component can be obtained. Therefore, it is desirable to purify it by column chromatography, recrystallization, distillation, sublimation or the like as needed. It is preferred to increase the purity by repeating such purification methods or by using a plurality of methods in combination. More desirably, the sublimation purification is repeated at least twice or more as a final step of purification as needed. By using such methods, it is preferred to use a material having a purity of 90% or more as measured by a HPLC [High Performance Liquid Chromatography (HPLC), more preferably 95% or more. The material is particularly good to use more than 99% of the material, thereby improving the electric field effect mobility and the on/off ratio of the organic thin germanium transistor and extracting the original properties of the material. Further, the organic thin tantalum crystal system of the present invention is provided with at least a substrate electrode, a source electrode, and a terminal electrode, an insulator layer, and an organic semiconductor layer, at least on the substrate, by 閙炻Φβ Λ rain The above-mentioned organic semiconductor layer contains the above-described benzodioxin derivative of the present invention by applying a voltage to the gate electrode of the Kodak gate to control the current between the source and the drain. The following is clear. The component structure of the organic thin film transistor of the present invention is 134113.doc -22-200922935. The composition of the organic thin film transistor of the present invention is such that at least the idle electrode, the source electrode and the drain electrode 3 are provided on the substrate. The terminal insulator layer and the organic semiconductor layer are thin film transistors that control the source-drain current by applying a voltage to the interpole electrode, and the known semiconductor device layer may be a component other than the component of the semiconductor layer. The constituents - these "as representative of the organic thin film transistor" constitute parts A to D in Figures 1 to 4. > Here, it is known that the organic thin film transistor of the present invention has a structure of a field effect transistor (FET, Fi. ^ W Effeet Translst Gr) depending on the position of the electrode, the order of lamination of the layers, and the like. The organic thin film has an organic semiconductor layer (organic compound layer), a source electrode and a gate electrode formed opposite to each other at intervals, and a distance between the source electrode and the electrode electrode. The gate electrode is formed, and the voltage flowing between the source and drain electrodes is controlled by applying a voltage to the two pad electrodes. Wherein the interval between the source electrode and the drain electrode is determined by the use of the organic thin film transistor of the present invention by the use of the pull & It is...~~, and then 疋5 μπι~1〇〇pm. In the case of A, the details of the element of Fig. 2 are described in more detail. The element = the organic thin film electro-crystal system sequentially has an interlayer electrode and an anode 于 on the substrate, and is formed with a specific interval on the insulator layer. One of the pair of source layers becomes a semiconductor layer. The electric current applied by the organic semi-electrode electrode controls the current flowing between the source electrode and the drain electrode, thereby performing on/off J34II3.doc 23-200922935 The organic thin film transistor, in addition to the components other than the above-mentioned components A to D, also proposes various structures Λ ^ π , the machine film transistor, if applied by the gate electrode Voltage ρ„ ^ . The combination of the current between the source electrode and the drain electrode, which is used to perform the opening/closing operation or the effect of increasing the amplitude, is not limited thereto.仵 constituting 'for example, it may be the top-bottom contact proposed in the 27th issue of the joint lecture of the 49th applied physics relationship by Shishitian, the Industrial Technology Research Institute, 27 Side 3 (March 2002) Type organic thin film transistor (see _ The composition of the vertical organic thin film transistor (see Fig. 6) proposed by the Kudo et al. (10) 8) on page (10) of the University of Science and Technology. (Substrate) The substrate in the organic thin film transistor of the present invention is responsible for supporting the structure of the organic thin film transistor, and as the material, an inorganic compound such as a metal oxide or a nitride may be used in addition to the glass. Plastic film (PET, P〇lyethylene Terephthalate, PES (Polyethersulfone) 'polycarbonate (pc, p〇lycarb〇nate)) or metal substrate or these Complex, laminate, etc. Further, in the case where the structure of the organic thin film transistor can be sufficiently supported by constituent elements other than the substrate, the substrate may not be used. Further, a bismuth (Si) wafer is often used as a material of the substrate. In this case, Si itself can be used as the gate electrode and the substrate. Further, the surface of Si may be oxidized to Si 2 and used as an insulating layer. In this case, a metal layer such as a film may be formed on the Si substrate of the substrate and the gate electrode as the electrode for wire bonding. (Electrode) 134113.doc -24- 200922935 The material of the gate electrode, the source electrode, and the electrode of the organic thin film electro-optic crystal of the present invention is not particularly limited as long as it is a conductive material, and platinum, gold, or the like can be used. Silver, nickel, chromium, copper, iron, tin, antimony, lead, indium, palladium, rhodium, iridium, ruthenium, aluminum, osmium, iridium, molybdenum, tungsten, tin oxide, antimony, indium oxide, tin (I ,Indium Tin 〇xide), push gas oxidation, rhetoric, stone, stone, ink, glass graphite, silver paste and carbon fuel, lining, strontium, sodium, magnesium, calcium, vanadium, titanium, manganese, hammer , gallium, antimony, sodium, sodium-potassium alloy, lock, bell, inscription, town/copper mixture, town/silver mixture, town/sauer mixture, lock/indium mixture, inscription/oxidation mixture H compound.乍 is a method for forming the above electrode, for example, by the following methods: hot money, electron beam evaporation, splashing, atmospheric dust plasma method, ion ore, chemical vapor evaporation, electricity, no electricity , spin coating, printing or inkjet.

V, as a method of patterning as needed, there is a method of forming an electrode by using the above-described method to form a conductive 'special film' using a known photolithography method or lift-off method, by means of aluminum or A method of (4) is carried out by forming a photoresist layer on a metal foil such as copper to form a photoresist layer. The film thickness of the electrode formed by the hunting is not particularly limited as long as the current can be conducted: =.2 nm~10 _, = 4 nm to 300 _, and the right range is the above preferred range. Inside, the thickness is thinner and the resistance is higher: no voltage drop occurs. Further, when it is not too thick and does not require the formation of a film B' and other layers such as a protective layer or an organic semiconductor layer, the a laminated film can be made smooth without causing a difference. In the organic thin film transistor of the present invention, as the other source electrode, the electrode and the electrode gate electrode, and the method for forming the same, it is preferred to use a solution, a slurry or an ink containing the above-mentioned 134113.doc •25-200922935 conductive material. It is especially preferable to contain a conductive polymer or a fluid electrode material containing metal particles containing gold, silver and copper. Further, in order to suppress damage to the organic semiconductor, it is preferable to make water = 60 wt%. Among them, preferred is a solvent or dispersion medium containing more than 9% by weight of water. As the dispersion containing the metal fine particles, for example, a well-known guide material of the thief can be used, and a dispersion containing metal fine particles having a particle diameter of usually 〇5 =0 nm and i nm to 1 〇 nm is preferable. As the material of the metal fine particles, for example, starting, gold, silver, nickel, chromium, copper, iron, tin, antimony, button, indium, palladium, iridium, chain, iridium, aluminum, lanthanum, cerium, indium, or crane can be used. , zinc, etc. It is preferred to form an electrode using a dispersion which uses a dispersion stabilizer mainly comprising an organic material, and disperses the metal microparticles in a dispersion of water or a dispersion medium of any organic solvent. Examples of the method for producing the dispersion of the metal fine particles include a physical production method such as a vapor phase evaporation method, a mineralization method, a metal vapor phase synthesis method, a colloid method, a co-precipitation method, and the like, and a metal ion reduction method is used. The chemical formation method of the metal micro-zizi is produced, and it is preferable to use the Japanese Patent Laid-Open Publication No. Hei No. 1-76800, the Japanese Patent Laid-Open Publication No. U_8〇647, and the Japanese Patent Laid-Open No. 1-3 19538. No. 2, pp. Manufactured by a vapor phase evaporation method disclosed in Japanese Laid-Open Patent Publication No. 2001-35255, Japanese Patent Application Laid-Open No. Hei. No. Hei. a dispersion of metal particles. 134113.doc -26- 200922935 can be formed by direct ink jet method using these metal fine particle dispersions, or can be formed by a lithography method, a laser lift-off method, or the like from a coating film. It is also possible to use a method of patterning by printing such as letterpress, gravure, lithography or screen printing. After the electrode is formed and the solvent is dried, it is considered to be: 2 =: the metal microparticles are thermally fused to form a target shape, and further used as another gate electrode, a source electrode, and a non-polar material, and the use is improved by doping or the like. Conductivity is not good, for example, A conductive polymer is also a car: if it is also suitable to use conductive polyaniline, conductive, conductive poly olefin (polyethylene: dimer... Oxygen-two C Hr B The complex of acid, etc., by which the material can be ==, the contact resistance between the drain electrode and the organic semiconductor layer. The special method can also be stripped by lithography or laser by inkjet method. The law is similar to: Form, also, the second edition: the second edition, screen printing and other printing methods for patterning. / The secret of the f pole and the _ electrode (four) is in contact with the organic semiconductor layer τ: Good Ρ ^ ^ is called the military resistance is less. At this time, the lightning control element corresponds to the electric field effect mobility, which is the work of the pole material...t may be small. It is generally determined by electricity. The size relationship of the energy level is determined by setting the work function (W) of the electrode material to a, The free electricity of the semiconductor layer 134113.doc •27· 200922935 (Ip) is set to b, and the electron affinity of the organic semiconductor layer (A η machine inflammation is better to satisfy the following 阙 (also c, bearing type. Where, a, b, and c: & amp, / ancient position is the positive value of the benchmark. And C is vacuum in the P-type organic thin film electro-optic crystal wm, the shape of the hip, preferably b-a<; i 5 eV (formula (1))' is better in b. In the system, if the above-mentioned Guan Wei Guan Beibei has been able to maintain the performance of the device, the work function of the electrode material is better. Preferably, the work function is 4.0 eV or more, and more preferably the work function is above. The value of the work function of the metal, for example, from the basics of the chemical handbook U-page 493 (revised the third edition of the Japanese Chemical Society The above list of effective metals with a work function of 4.0... or higher disclosed in the publication of the company's (4) year can be selected. The high work function metals are mainly Ag (426, 4.52, 4.64, 4.74 eV), Al ( 4.06, 4.24, 4.41 eV), Au (5.1, 5.37, 5.47 eV), Be (4.98 eV), Bi (4.34 eV), Cd (4.08 eV), Co (5.0 eV), Cu (4.65 eV), Fe ( 4.5, 4.6 7, 4.81 eV), Ga (4.3 eV),

Hg (4.4 eV), Ir (5.42, 5.76 eV), Mn (4.1 ev), Mo (4.53, 4.55, 4.95 eV), Nb (4.02, 4.36, 4.87 eV), Ni (5.04, 5.22 > 5.35 eV) , Os (5.93 eV), Pb (4.25 eV), Pt (5.64 eV), Pd (5.55 eV), Re (4.72 eV), Ru (4.71 eV), Sb (4.55, 4.7 eV), Sn (4.42 eV) , Ta (4.0, 4.15, 4.8 eV), Ti (4.33 eV), V (4.3 eV), W (4.47, 4.63, 5.25 eV), Zr (4. 〇 5 eV). Preferred among these are noble metals (Ag, Au, Cu, Pt), Ni, Co, Os, Fe, Ga, Ir, Mn, Mo, Pd, Re, Ru, V, W. In addition to metal, indium tin oxide (ITO, Indium Tin Oxide), polyaniline, polyethylene dioxythiophene doped polystyrene sulfonate 134113.doc -28- 200922935 (PEDOT: PSS - Polyethylene Dioxy Thiophene doped Conductive polymer such as with Polystyrene Sulf〇nic acid) and carbon. As the electrode material, if one or a plurality of such high work function substances are contained, the work function satisfies the above formula (I), and is not particularly limited. In the case of an n-type organic thin film transistor, it is preferable that .5 eV (formula) is more preferably 3 «1 〇 eV, and in the relationship with the organic semiconductor layer, if the above relationship is satisfied It is preferable to obtain a high-performance device, in particular, it is preferable to select a work function of the electrode material as small as possible, preferably a work function of 4.3 eV or less, and more preferably a work function of 3 7 eV or less. As a specific example of the low work function metal, it is disclosed in, for example, the basics of the chemical handbook - page 493 (revised the third edition of the Chemical Society of Japan, Maruzen Co., Ltd., issued 1983), which has a work of 4.3 eV or less. The above list of effective metals of the function can be selected, including Ag (4.26 eV), Al (4.06, 4.28 eV), Ba (2.52 eV), Ca (2.9 eV), Ce (2.9 eV), Cs (1.95 eV). ), Er (2.97 eV), Eu (2.5 eV), Gd (3.1 eV), Hf (3.9 eV), In (4.09 eV), K (2.28 eV), La (3.5 eV), Li (2.93 eV), Mg(3.66 eV) » Na(2.36 eV) » Nd(3.2 eV), Rb(4.25 eV), Sc(3.5 eV), Sm(2.7 eV), Ta(4.〇> 4.15 eV), Y(3.1 eV),

Yb (2.0 eV), Zn (3.63 eV), and the like. Preferred among these are Ba, Ca, Cs, Er, Eu, Gd, Hf, K, La, Li, Mg, Na, Nd, Rb, Y, Yb, Zn. As the electrode material, if one or a plurality of such low work functions are contained, the work function satisfies the above formula (II) without particular limitation. However, 'low work function metals are prone to deterioration if they come into contact with moisture or oxygen in the atmosphere. </ RTI> It is desirable to coat, for example, or Au in the air, 134113.doc •29· 200922935 Stable metal. The film thickness necessary for coating must be ι 〇 (10) or more. The thicker it is, the more it can be protected by oxygen or water. However, it is preferable to use 1 μm or less for reasons such as thickness and thickness. Further, in the organic thin film transistor of the present embodiment, for example, in order to improve the implantation efficiency, a buffer layer may be provided between the organic semiconductor layer and the source electrode and the electrodeless electrode. As the buffer layer, a material having a high work function such as sub 3 or V 2 〇 6, In-Sm oxide, in_Ce oxide, oxidized chin, or nickel oxide is preferable in the p-type organic thin tantalum transistor. The organic thin tantalum transistor is preferably used in the cathode of the organic EL, m Li2〇, CsF,

NaC〇3, κα, MgF2, CaC〇3 and the like have metal-tested, soil-measured metal ion-bonded compounds. For the P-type organic thin film transistor, FeCl3, tetracyanoquinodimethane (TCNQ 'TetraCyan〇quinodimethane), 2 3 5 6 tetrafluoro-7,7,8,8-tetracyanoquinone pair II are preferred. Cyanide compounds such as methane (F4_tcnq, 2,3,5,6_tetrafluoro-7,7,8,8-tetracyanoquinodimethane), hexa-nitrotriphenylene (HAT, Hexaazatriphenylene); CFx or Ge02, SiO2, Mo03, V2〇5 , V〇2, v2〇3, Mn〇, Mn3〇4,

Zr02, W03, Ti02, ln203, ZnO, NiO, Hf02, Ta205,

Reactive metals such as Re〇3, Pb〇2, In-Sm oxide, In-Ce oxide, and other metal oxides other than alkaline earth metals; inorganic compounds such as ZnS and ZnSe, which cause oxygen in many cases. Vacancies, which are suitable for tunneling. Further, 'may be triphenyl diamine (TPD' Triphenyl Diamine) or N, N' bis (1-naphthyl) hydrazine, hydrazine, _diphenyl-1,1,-diphenyl-4,4 An amine compound such as NPD (Naphthylphenylbiphenyl Diamine) or CuPc 134113.doc -30-200922935 is equivalent to a compound used as a hole-laying layer and a hole transport layer in an organic EL device. Further, it is preferred to contain two or more of the above compounds. It is known that the buffer layer has the effect of lowering the reading voltage by lowering the implantation barrier of the carrier and driving the transistor at a low voltage, but the inventors have found that not only the low voltage effect is exhibited for the compound of the present invention. Moreover, there is an effect of improving the mobility. The reason for this is that there is a carrier trap in the interface between the organic semiconductor and the insulator layer. If the carrier voltage is applied by applying a gate voltage, the carrier that is initially implanted is used to fill the trap. By inserting a buffer layer, the voltage can be filled with a low voltage to increase the mobility. The buffer layer may be present between the electrode and the organic semiconductor layer in a thin manner, and has a thickness of 〇ι η.3〇 nm ′ preferably 0.3 nm to 20 nm. (Insulator layer) / The material of the insulator layer in the organic thin film transistor of the present invention is not particularly limited as long as it is insulating and can be formed into a film, and a metal oxide (including an oxide of Shi Xi) can be used. ), metal nitrides (including nitrides of Shi Xi), polymers, and organic low molecules are equivalent to materials having a resistivity of 1 〇 or more at room temperature, and particularly preferred are inorganic oxides having a relatively high dielectric constant as inorganic The oxides may, for example, be cerium oxide, aluminum oxide, oxidized knob, titanium oxide, emulsified tin, oxidized sulphur, sulphuric acid, sulphuric acid, yttrium acid, strontium titanate, barium titanate, titanic acid Pot, barium magnesium fluoride, barium oxide, oxyfluoride, magnesium oxide, barium oxide, barium titanate, barium oxide 'barium titanate, barium strontium citrate, bismuth pentoxide, bismuth citrate The ruthenium, the antimony trioxide and the combination thereof are preferably ruthenium oxide, aluminum oxide, 134113.doc -31 · 200922935 ruthenium oxide, titanium oxide. It is also suitable to use nitriding wheat (Si3N4, SixNy (X, Xinghuaming, etc. inorganic nitride. Μ 11 Further, the insulator layer may also be formed of a precursor material containing a metal alkoxide, and the solution of the precursor substance is packaged. The insulating layer is formed on the substrate by, for example, a chemical solution treatment including heat treatment. The metal in the metal alkoxide may be selected, for example, from a transition metal, a lanthanoid element or a main group element, and specific examples thereof Ba (Ba), Sr (Sr), Titanium (T〇, Syria (B!), (Ta), Wr (Zr), Iron (Fe), Record (10), Manganese (Mn), Ship (Pb), 镧 ( La), chain (Li), sodium (Na), potassium (K), repair (Rb), hammer (Cs), strontium (Fr), bismuth (Be), town (10)), per (called, sharp (Nb) , 铊 (T1), mercury (Hg), copper (Cu), cobalt (c), ruthenium (Rh), ruthenium, osmium (Y), etc. Further, as the alkoxide in the above metal alkoxide, for example, Derived from the following compounds: alcohols including methanol, ethanol, propanol, isopropylbutanol, isobutanol, etc.; including nonoxylethanol, ethoxyethanol, propoxyethanol, butoxyethanol Alkoxy alcohol, heptoxyethanol, methoxypropanol, ethoxypropanol, propoxypropanol, butoxypropanol, pentoxypropanol, heptoxypropanol alkoxy alcohol In the present month, if the insulator layer is formed of the material as described above, the polarization tends to occur in the insulator layer, thereby reducing the threshold voltage of the transistor operation. In addition, in the above materials, especially When an insulator layer is formed of tantalum nitride such as Si3N4, SixNy, SiONx (x, y&gt; 〇), a depletion layer is more likely to be generated, and the threshold voltage of the transistor operation can be further reduced. As an insulator layer using an organic compound, a (four) sub-layer can also be used. Amine, 134113.doc •32- 200922935 Polyamide, polyester, polyacrylate, photoradical polymerization, photo-cationic polymerization, photo-curing resin, copolymer containing acrylonitrile, polyethylene, polyvinyl alcohol , novolak resin and cyanoethyl pullulan. In addition, 'can also use wax, polyethylene, gas enthalpy, polyethylene terephthalate, polyoxymethylene, polyvinyl chloride, polyvinylidene fluoride, poly Methyl methacrylate, poly , polycarbonate, polyethylenimine cyanoethyl pullulan, poly(vinylphenol) (PVP 'p〇iy (vinyi phenol)), poly(methyl methacrylate) (PMMA, P〇ly (methyl methacrylate) )), polycarbonate (PC,

Polycarbonate), polystyrene (ps, P〇iystyrene), polyolefin, polyacrylamide, poly(acrylic acid), novolak resin, resol resin, quinone imine, polybenzazole, epoxy resin, In addition to this, a polymer material having a relatively high dielectric constant such as pullulan can also be used. As the organic compound material or polymer material used in the insulator layer, a material having water repellency is particularly preferable. By having water repellency, the interaction between the insulator layer and the organic semiconductor layer can be suppressed, and the crystallinity of the organic semiconductor layer can be improved by the cohesiveness inherently possessed by the organic semiconductor to improve the device performance. As an example as described above, Yasuda et al JpnjAppl can be cited.

Phys. Vol. 42 (2003) PP. 6614-6618 discloses a parylene derivative or Janos Veres et al., Chem. Mater. Vol. 16 (2004) ρρ. 4543-4555. Further, when the top gate structure shown in FIGS. 1 and 4 is used, if the organic compound as described above is used as the material of the insulator layer, damage to the organic semiconductor layer can be reduced and film formation can be achieved. Therefore, it is an effective method. The above-mentioned insulator layer may be a mixed layer using a plurality of inorganic or organic 134113.doc -33.200922935 compound materials as described above, and may also be a laminated structure of + i '. In this case, the material is mixed, and the material having a higher dielectric constant and the material having water repellency are incorporated into the entangled layer, thereby controlling the performance of the attack. Further, the insulator layer may be formed of an anodized film. Preferably, the anode oxide gas film or the anode oxide film is contained, and the oxide film can be sealed. Yangyang &amp; hydrogen a, σ anode deuterated metal is formed by a known method of &amp; polar oxidation. You &amp; π π Β ± yarn, the metal for the cation treatment, the method of oxidizing treatment is not particularly limited, and a known method can be used. An oxide film is formed by performing an anode on m. As the electrolyte used in the (four) minimization treatment, any one of the membranes may be used, and the use of guaiac acid, phosphoric acid, oxalic acid, acid, acid, fluorescein, phenyl acid, etc. may be used. Alternatively, two or more kinds of mixed acids or (4) salts may be combined. The anodizing treatment strip dissolves and produces various changes, so it is not possible to use the electric 曰, j 夂, generally the concentration of the 疋 electrolyte is 重量 重量 wt%, the electrolyte temperature is 5 〜 (4), current The density is 0.5~60 AW, the voltage is bu (10) volt, the electrolysis is clear, and the range is ~5. A preferred anodizing treatment uses an aqueous solution of sulfuric acid, scalylic acid or boric acid as an electrolytic solution, and a method of treating with a direct current can also use an alternating current. The concentration of these acids is preferably Μ% by weight, preferably 20 to 250 seconds of electrolytic treatment at a temperature of the electrolyte of 2 〇 to 5 (rc, current density = 0.5 to 20 A/cm 2 ). The thickness of the insulator layer, if the thickness of the layer is thin, the effective voltage applied to the organic semiconductor becomes large, so that the driving voltage and the threshold voltage of the device itself can be reduced, and the leakage current between the source and the gate will become larger. Since I34ll3.doc •34· 200922935, it is necessary to select an appropriate film thickness, usually g10nm~5μιη, preferably π nm~2 μπι 'more preferably 1〇〇nm~1 μηι. Also, in the above insulator layer Between the organic semiconductor layer and the organic semiconductor layer, the alignment treatment can be carried out. As a preferred example, the surface of the insulator layer is subjected to a water repellent treatment to reduce the interaction between the insulator layer and the organic semiconductor layer, thereby making the organic semiconductor a method for improving the crystallinity of a layer, specifically 5, a decane coupling agent, for example, hexamethylene diazoxide, octadecyl trigasket, trichlorosulfanyl sulphate, sulphate, and sulphur Automatic combination of acid-renewing, hospital-based acid retardation, etc. After the film material is brought into contact with the surface of the insulating film in the liquid phase or the gas phase to form an automatic combined film, the drying process is appropriately performed. Further, for the liquid crystal alignment, it is preferably on the surface of the insulating film. A method comprising rubbing a surface of a polyimide or the like and rubbing the surface thereof is provided. The method for forming the insulator layer includes a vacuum evaporation method, a molecular beam crystal method, an ion beam method, and a low energy ion. Beam method, ion plating method, chemical vapor deposition (CVD) method, antimony ore method, Japanese Patent Laid-Open No. W06, Japanese Patent Unexamined Gazette, Japanese Patent No. 2_-12 Chest No., Japanese Patent The special dry process such as the atmospheric differential plasma method disclosed in Japanese Patent Laid-Open Publication No. 2000-1 85362, spray coating method, spin coating method, coating method, dip coating method, and roll coating method are disclosed. A wet process such as a coating method such as a bar coating method or a die coating method, a method of printing wet ink I, or a patterning method such as ink can be used depending on the material. For the second method, the T method may be used: a method of dispersing the interface active agent or the like as needed, 1; 134113.doc 35 200922935 precursors such as alkoxide Wei., cross, 3⁄4, 么+ I body, combined with liquid coating, drying, the so-called sol-gel method. The film thickness of the organic semiconductor layer in the organic thin tantalum transistor of the present invention is not particularly limited 'usually 〇 5 nm 〜 】, preferably 2 (four) 〜 25 〇 coffee. Further, the method for forming the organic semiconductor layer is not particularly limited, and a square can be used, for example, by molecular beam evaporation (MBE method, Molecular Epitaxy), vacuum evaporation method, chemical distillation, and solvent. Dipping method, spin coating method, Tao prayer method, bar coating method, light f method printing, coating method, drying, electropolymerization, molecular beam evaporation, self in the liquid The combination, and combinations of these, are formed from the material of the organic semiconductor layer as described above. If the crystallinity of the organic semiconductor layer is increased, the electric field effect mobility is improved. Therefore, when it is used in the film formation in the gas phase (evaporation, antimony ore, etc.), it is preferable to form the substrate temperature in the film formation. Keep at high temperatures. The temperature is preferably ς Λ &gt; The film m is more preferably 70 to 15 ° C. Further, no matter whether it is formed, or not, if it is annealed after being formed, a high-performance device can be obtained. The annealing temperature is preferably 50 to 200 ° C, and more preferably the time is preferably 1 丨 min ~ 丨 2 hours, more preferably 丨 ~ ^ 〇 hours. In the present invention, the organic semiconductor layer may be selected from the group consisting of the materials of the formula (4). Alternatively, a plurality of types of semiconductors may be used in combination, or a semiconductor obtained by using a (tetra)pentaphenyl or a phenanthrene oligomer may be used in a plurality of mixed films or laminated layers. A method for forming the organic thin film transistor of the present invention is not particularly limited to the use of a known method, and if it is in accordance with the required element structure, it is completely I34I13.doc-36-200922935^ The formation of the electrode, the formation of the insulator layer/the formation of the source electrode, the formation of the source electrode, and the formation of the step of the electrode of the drain electrode prevent the contact with the atmosphere and prevent the performance of the element due to phase-to-phase: oxygen or the like. Therefore, when it is necessary to contact the atmosphere, it is preferable to set the step of the organic half to be completely out of contact with the atmosphere, and to laminate the surface of the organic semiconductor layer before the film formation (for example) Second, in the case of partial layering of the source electrode and the = electric surface on the insulating layer, the organic semiconductor layer is laminated after being cleaned and activated by the material line irradiation, ultraviolet/ozone irradiation, oxygen: flying power. In addition, the ρ-type FT material is also used to make the performance of the 提 者 ― ― ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” ” The oxygen or water is organically formed on the entire surface of the peripheral surface of the organic transistor or a gas barrier layer. As a material for forming the gas barrier layer, the domain Φ 01γ ^ ^ $ Medium: Commonly used, for example, Polyethylene, Ethyl, Alcohol Copolyvinyl Ethylene, Polyvinylidene Chloride, Polyfluorotrifluoroethylene, etc. may be used. Further, it may be used as an insulating property exemplified in the above-mentioned insulator layer. The organic thin film transistor of the present invention can also be used as a light-emitting element by using a charge implanted from a source electrode and a pole electrode, and can be controlled by a liquid that flows between a source and a pole electrode by a closed-electrode controller. light intensity. That is, a = 骐 transistor is used as a light-emitting element (organic EL). It is possible to integrate the illuminating transistor and the illuminating element' so that the opening of the display can be improved; = 134113.doc • 37· 200922935; used as = facilitating and reducing the cost' gives a practical advantage. ΓOrganic luminescent electric crystal material, (4) The above-mentioned I is sufficient for the above-mentioned materials, but in order to make the organic thin enamel electro-optical crystal of the present invention operate, it must be self-sourced and the poles are implanted in the hole: Second:! Planting electrons 'In order to improve the luminescence performance, it is better to meet the following conditions. (Source, immersion): To improve the implantability of the hole, it is better to at least - the hole is implanted The electrode electrode includes an electrode having a work function of 42 ev or more. In order to improve the implantability of the electron, it is preferable to implant at least the electrode. The electron-interposer electrode includes an electrode having a work function of at least the substance e. It is more preferable to have an organic film in which one is a hole implant: 'and the other is an electron-carrying electrode. Light-emitting electro-crystal (component composition) The embedding property of the hole is preferably inserted into the hole-laying layer between at least one electrode and the ::: body layer. As a hole-laying layer, it can be listed as: The amine used as the hole-laying material and the hole-transporting material in the core piece ^In order to improve the embedding property of the electrons At least one electrode...: The implant layer. Like the hole, the electron implant layer can be used for electronic implant materials used in organic components. It is better to have a hole implant layer under one electrode. And an organic thin film light-emitting transistor having an electron-distributing layer under the electrode of the other 134JJ3.doc -38-200922935. In the organic thin film light-emitting transistor of the present embodiment, for example, the organic semiconductor layer and the source electrode and And a buffer layer is provided between the electrode electrodes to explain the planting efficiency. w EXAMPLES Next, the present invention will be described in more detail using the examples. Synthesis Example 1 (Synthesis of Compound (48)) A compound (48) was synthesized in the following manner. ), the synthetic path is as follows: [Chem. 11]

(4 8) Add toluene (1 〇 ml) and distilled water (2 〇 ml) to a single-mouth flask, and add sodium carbonate (0.42 g), then remove the solvent under argon at 9 °C. Gas for 2.5 hours. Thereafter, 'cooling to room temperature, adding 5,5,_dibromo-2,2'-biphenone (〇·37 g, 1.14 mmol), (benzo[i,2-b:4,3-b ,]dithiophen-2-yl)-4,4,5,5-tetradecyl-1,3,5-dioxaborane (0.79 g, 2.51 mmol) and 0.08 g (〇.〇7 mmol) Tetrakis(triphenylphosphine)palladium was stirred at 85 ° C for 3 days under an argon atmosphere. After completion of the reaction, after cooling to room temperature, the reaction solution was added to methanol (300 ml), and subjected to suction filtration and collection of a precipitate, which was washed with dilute hydrochloric acid, water and methanol to recover a color solid. The recovered solid was subjected to Soxhlet extraction with decyl alcohol (300 ml), and the recovered solid was dried and purified by sublimation (280: (:)) to obtain 0.17 g (0.32 mmol, yield 28%) of an orange solid compound. (48) The measurement results were confirmed by the measurement of 400 MHz 134113.doc -39-200922935 iH-NMR and LIM-TOF MS. The measurement results are as follows: &lt;'h-nmr&gt; Device: JNM-ECA 400 (manufactured by JEOL Ltd.)] H-NMR (DMSO-d6) d : 7.39 (d J = 3 9 tr

, ., 2H), 7.45 (d, J = 3.9 Hz, 2H), 7.83 (d, J = 5.5 Hz, 2H) 7 〇., 46 (d, J = 8.9 Hz, 2H), 7.93 (d, J = 8.9 Hz, 2H), 7.94 (d J = ς c , 5-5 Hz, 2H), 8.12 (s, 2H) &lt;LDI-TOF MS&gt;

Device: AXIMA-CFR (manufactured by Shimadzu Corporation) was calibrated and tested. Conditions: Angiotensin® was used as a standard substance. MS (LDI-TOF), calcd for C48H30S2 = 541.94 found m/z 541.66 (M+, 100) Synthesis Example 2 (Synthesis of Compound (49)) Compound (49) was synthesized in the following manner, and the synthetic route is as follows: 12]

Toluene (5.0 ml) and steamed water (1·1 ml) were added to a one-necked flask, and sodium carbonate (0.21 g) was added thereto, and then degassed for 2.5 hours in a argon atmosphere under a argon atmosphere. Then 'cool down to room temperature, add 5,5'-*^ 134113.doc • 40· 200922935

Bromo-2,2'-linked 0-cetin (0.37 g, 1 · 14 mmol), (7-methylbenzo-2_b:4,3-b']: D-secen-2-yl)-4, 4,5,5-tetradecyl-1,3,5-dioxole (0.35 g' 1.05 mmol) and 35 mg (0.030 mmol) of tetrakis(triphenylscale)palladium in an argon atmosphere Stir at 95 °C for 3 days. After completion of the reaction, after cooling to room temperature, the reaction solution was added to methanol (300 ml), suction filtered, and the precipitate was collected, and washed with dilute hydrochloric acid, water, and methanol to recover a color solid. The recovered solid was subjected to Soxhlet extraction with methanol (300 ml), and the recovered solid was purified by sublimation purification (31 〇t) to obtain a compound of 〇1 〇g (0.18 mmol, yield 36%) of an orange solid. (Μ). The target was confirmed by measurement of 400 MHz W-NMR and LDI-TOF MS. The measurement results are shown below. Ή-NMR (DMSO-d6) d : 2.65 (s, 6H), 7.38 (d, J = 3.7 Hz, 2H), 7.43 (d, J = 3.7 Hz, 2H), 7.61 (s, 2H), 7.76 ( d, J = 8.7 Hz, 2H), 7.79 (d, J = 8.7 Hz, 2H), 8.01 (s, 2H) MS (LDI-TOF), calcd for C48H3〇S2 = 569.97, found, m/z = 569.74 (M+, 100) Example 1 (Production of Organic Thin Film Transistor) An organic thin film transistor was produced by the following procedure. First, a Si 2 film having a thickness of 300 (10) was formed by thermal oxidation on the surface of a substrate having a diameter of _ _ and a resistivity of 0.02 Qcm or less. The germanium substrate also serves as a gate electrode, and the Si〇2 film serves as a gate insulating film. Then, the Shixi substrate is cut into a size i i i 3 and ultrasonic cleaning is performed for about 5 minutes. The stone substrate is placed in a vacuum evaporation apparatus for organic thinning, and the air is immersed in a vacuum of about 134113.doc -41 - 200922935 and the thickness is 30 nm. The compound (48) film is used as an organic semiconductor layer of a field effect transistor (FET). At this time, the heating temperature of the organic unit to which the compound (48) is added is adjusted to about 270 ° C, and the vapor deposition rate is adjusted to about 〇.〇i nm/s. The substrate is heated without steaming the substrate. After the completion of the vapor deposition, the test material and the material were taken out from the vacuum vapor deposition apparatus for the organic film, and the test was carried out in the vacuum vapor deposition apparatus for the metal thin film after passing through the atmosphere. After the material is exhausted to a vacuum of about 2×10·3 Pa, a metal film having a thickness of 30-50 nmi is formed through a metal mask formed with an electrode pattern having a channel length of 20 μm and a channel width of 2 mm, and a source is formed. Electrode and drain electrodes (see Figure 7). The P-type FET characteristics were obtained by measuring the gate current and the drain voltage characteristic of the FET of the compound (48) prepared above, and the carrier mobility was calculated from the gate voltage dependence of the drain current of the self-saturation region. It is 3 cm2/Vs. As the measuring device, a semiconductor parameter analyzer (trade name: 4145B, manufactured by HP Corporation) was used. Further, in the measurement, the sample was placed in a vacuum of 〇.lPa & right vacuum in a state of being shielded. Further, in order to investigate the atmospheric stability of the characteristics of the FET obtained in the present invention, after the device was fabricated, it was stored in the atmosphere for 9 days, and then the zeta current and the gate voltage characteristics were measured again to calculate the carrier migration. As a result, the value of 1.7x10-3 Cm2/Vs was obtained, and it was found that the carrier mobility was hardly deteriorated. Example 2 (Manufacturing of Organic Thin Twisted Oxide) In Example 1, after treating the surface of the gate insulating film with hexamethylene diazide (HMDS, Hexmethyldisilane), with 1341I3.doc • 42-200922935 In the same manner as in the first embodiment, the p-type FET characteristics were obtained when the FET was formed by vacuum-decomposing the film of the compound (48), and the carrier mobility was 26 χΐ〇·3 cm/Vs. After the FET was stored in the air for 9 days, the carrier mobility was 2 ΗΓ 3 em 2 /Vs '. No deterioration was observed. Example 3 (manufacture of an organic thin film transistor); In Example 2, when a film of the compound (48) was vapor-deposited, heating was performed using a heater to make the substrate temperature loot. As a result, what is the characteristic of the obtained F曰ET? The type&apos; and the carrier mobility is somewhat lower than that of the room temperature steaming apparatus'&gt;&lt;1〇-3^%. After 9 days of storage in the atmosphere, the carrier mobility was 4.9 x 1 (r3em2/Vs, and the characteristics were hardly deteriorated. Example 4 (manufacture of organic thin film transistor) before vapor deposition of the compound (48) film, An element was produced in the same manner as in Example except that a 1 wt% polystyrene gas imitation solution (6000 rpm, 60 sec) was spin-coated and a polystyrene layer having a thickness of 7 Å (10) was inserted as an insulator layer. As a result, the obtained FET has a characteristic type and a carrier mobility of 1.9XUT2 Cm2/Vs. After the FET is stored in the atmosphere for 9 days, the carrier mobility is 2.0x1 〇·2 cm2/Vs. Example 5 (Manufacturing of Organic Thin Film Transistor) M0O3 was used instead of the buffer layer for steaming 'vacuum distillation 8~9 run for the source-drain electrode alone, and the compound (48) was inserted. An element was produced in the same manner as in Example 4 except that the film was formed between the films. As a result, the characteristics of the obtained FET were _, and the carrier mobility was 6·6 χ 1 〇·2 cmVVs. After 9 days of storage, the carrier mobility was 5'0xl (T2 cm2/Vs, and the characteristics were hardly deteriorated). 134113.doc •43· 200922935 Comparative Example 1 (Manufacture of organic thin tantalum crystal) In Example 2, pentacene was used instead of compound (48), and the resulting FET was characterized by 卩 type and carrier migration. The rate is shown as Μ·] (10) 2... high mobility, but after 9 days of storage in the atmosphere, the carrier mobility is 1·3χ1〇_3 cm2/vs 'reduced by even 2 digits. The results are shown in The first table. [Table 1] Example of the compound type of the organic semiconductor layer, the type of electric solar body ~ ------- P type - P type η penalty table electric field effect mobility - (em2 / Vs, ν ϊχϊΟ ^ ] Field effect mobility after 9 days (cm2/Vs) Example 1 (48) Example 2 (48) 1.7x10'3 Example 3 (48) &quot; 2.6x10^1 2.7x10'3 Example 4 ( 48) _6.6x10'3 4.9x10" Example 5 C48) UxTo^ 2.0χ10'ζ Comparative Example 1 Thick five stupid---- Ρ--^--1 θ.βχϊο5 ^ΓΛ ------ ---- 5.0χ10'2 ____^8x1 Ο·1 1.3xl0'j [Industrial use possibility] The crystal system uses a material having a benzene layer, thereby obtaining the above-mentioned detailed description of the organic thin film of the present invention. °The structure of the plug-in skeleton As an organic semiconductor, an element having high stability in the atmosphere is obtained. [Brief Description of the Drawing] FIG. 2 is a view showing an example of the composition of the organic thin film of the present invention. FIG. 2 is a view showing the organic thin film transistor of the present invention. Fig. 3 is a view showing an example of the element configuration of the organic thin film transistor of the present invention. 134113.doc • 44-200922935 Fig. 4 is a view showing an example of the element configuration of the organic thin film transistor of the present invention. Fig. 5 is a view showing an example of the element configuration of the organic thin film transistor of the present invention. Fig. 6 is a view showing an example of the element configuration of the organic thin film transistor of the present invention. Fig. 7 is a view showing an example of the constitution of the organic thin film transistor in the embodiment of the present invention. 134113.doc -45-

Claims (1)

200922935 X. Patent application scope · 1. A benzo-pheno-* organism, which is represented by the following formula (4) f: where ', the carbon number is 6 to 6. The divalent aromatic nicotyl group or the carbon number of the divalent aromatic heterocyclic ring/ample may also have a substitution: di I. Each is independently a hydrogen atom, a _ atom, a cyano group, a carbon number: V, an alkyl group, a sterane* having a carbon number of 1 to 30, and a halogen having a carbon number of 30 and an alkoxygen number of 1 to 30. An alkoxy group, an alkylamine having a carbon number of 1 to 3 Å, and a bis. The second base of the amine group (the base can also be bonded to each other to form: nitrogen, ^ structure), the carbon number is (four) of the dazzle sulfhydryl group, the carbon number is (four) of the halocarbon g fluorenyl group, the carbon number is 1~ 30 alkane furnace beauty, f $ stone 1 坑 坑 硫 ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' The carbon number is · two = there is a m to find each group can also have a smoke base or a carbon number of 6 to 60 aromatic number ~::: two square: family heterocyclic group; and 'one whole...项心: A plurality of Α may be the same or different]. A bacterium having a divalent aromatic hydrocarbon group having a slave number of 6 to 30 in the above formula (4). I34113.doc 200922935 3. The stupidity of claim 1 In __, A is a (four) A derivative, which is a divalent aromatic heterocyclic group which is read as 1 to 3 Å in the above formula (4). 4. In the case of a request, R, R An imaginary derivative, wherein the above formula (4) is a halogen atom, a cyano group, a halo group having a carbon number of 1 to 30. 5. If the request is a 婪 _ _ thiophene derivative Wherein t, R2, r D "" in the above formula (a) 3, R6 and R7 are argon atoms And U; W, 1 K5 ' Rg ' Rg 乂 - one is carbon number is ~ 3 decane A, A main pit base, the number of turns is 〜 ~ 3 0 of the tooth alkyl, the south atom or cyanide base. 6. In the benzophenanthrene derivative of the claim, Rm, R5, R, R- in the above 4 formula (4) RR φ 6 R7, R9 &amp; Rl 〇 is a hydrogen atom, and Λ y is The carbon number is an alkyl group of 1 to 30, a carbon number, a crypto group, or a cyano group. Read as 1 to 30 in the benzodiazepine of claim 1, the RR lane "Ding Bio' S in the above formula (4) and the ruler, R3, R6, R7 and 1 are hydrogen atoms, and R4, R5, R9 Broad base - material carbon number is 1 ~ (10) silk, Wei is 丨 ~ 30 of the decyl, south atom or cyano. 30 from 8. 9. as requested 1 $ poor j £ _ &amp; a porphin derivative, wherein η is an integer of 丨~5. ΜIn the above formula (4), an organic thin film transistor having a pole, a source, and an occupant, is provided with a free electrode, an electrode, and 〉And 3 terminals of the electrode, 纟g绫I* #半导体》n #丄心在绝缘层层和有机(三), and the difference between the voltage applied to the gate electrode, where 卜,th 彳市彳原- The immersed, L organic semiconductor layer comprises, as claimed, an ip m-opened dithiophene derivative. pp. 134U3.doc 200922935 10. The organic thin film transistor of claim 9 has a buffer layer between the organic semiconductor layer and The source and the electrode a 2 = 骐 light-emitting transistor 'which is used in the organic thin film electrode according to claim 9 'utilizes the source _ The light is generated by the current flowing between the electrodes, and the light is controlled by applying a voltage to the gate electrode. 12. The organic thin film light-emitting transistor of claim 11, wherein at least one of the source and the drain includes a work function. A substance of 4.2 eV or more, and/or at least one of which contains a material having a work function of 4.3 eV or less. 13. The organic thin film light-emitting transistor of claim 11, wherein between the source and the organic semiconductor layer, and The electrode between the pole and the organic semiconductor layer has a buffer layer. 1341l3.doc