WO2017212882A1 - 有機半導体デバイス製造用組成物 - Google Patents
有機半導体デバイス製造用組成物 Download PDFInfo
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- WO2017212882A1 WO2017212882A1 PCT/JP2017/018473 JP2017018473W WO2017212882A1 WO 2017212882 A1 WO2017212882 A1 WO 2017212882A1 JP 2017018473 W JP2017018473 W JP 2017018473W WO 2017212882 A1 WO2017212882 A1 WO 2017212882A1
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- organic semiconductor
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 151
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 239000000463 material Substances 0.000 claims abstract description 73
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000002904 solvent Substances 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000002541 furyl group Chemical group 0.000 claims abstract description 21
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 21
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 19
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- -1 n-decyl group Chemical group 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 150000001787 chalcogens Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
Definitions
- the present invention relates to a composition containing a condensed pi-conjugated molecule, which is an organic semiconductor material, in a state dissolved in a solvent, and relates to a composition used for manufacturing an organic semiconductor device by a printing method.
- Transistors are important semiconductor devices included in displays and computer equipment, and are currently manufactured using inorganic semiconductor materials such as polysilicon and amorphous silicon.
- Thin film transistors using inorganic semiconductor materials are manufactured by plasma enhanced chemical vapor deposition (PECVD), sputtering, and the like.
- PECVD plasma enhanced chemical vapor deposition
- the manufacturing process temperature is high, the manufacturing equipment is expensive and expensive, and the large area thin film transistor.
- the problem is that the characteristics tend to be non-uniform when the film is formed.
- substrates that can be used are limited by the manufacturing process temperature, and glass substrates have been mainly used.
- a glass substrate has high heat resistance, but is weak against impact and difficult to reduce in weight and lacks flexibility. Therefore, when a glass substrate is used, it is difficult to form a light and flexible transistor.
- an organic semiconductor device can be manufactured at a low manufacturing process temperature by a simple method such as a coating method. Therefore, a plastic substrate having low heat resistance can be used, and a display or the like. This is because it is possible to reduce the weight, flexibility, and cost of the electronic device.
- Patent Document 1 describes an N-shaped condensed pi-conjugated molecule as an organic semiconductor material having excellent carrier mobility. It is described that o-dichlorobenzene, 1,2-dimethoxybenzene or the like is used as a solvent for dissolving the organic semiconductor material.
- an object of the present invention is to provide a composition for producing an organic semiconductor device capable of forming an organic semiconductor device having a stable and high carrier mobility.
- an organic semiconductor device having a stable and high carrier mobility can be obtained by using a specific solvent having a moisture content of a specific value or less and a specific organic semiconductor material. It was found that it can be formed.
- the present invention has been completed based on these findings.
- the present invention provides a composition for producing an organic semiconductor device, which contains 2,3-dihydrobenzofuran as a solvent and the following organic semiconductor material, and the water content of the solvent is 0.25% by weight or less.
- Organic semiconductor material compound represented by the following formula (1-1), compound represented by the following formula (1-2), compound represented by the following formula (1-3), formula (1-4) At least one compound selected from the group consisting of a compound represented by formula (1-5) below and a compound represented by formula (1-6) below Wherein X 1 and X 2 are the same or different and are an oxygen atom, a sulfur atom or a selenium atom.
- M is 0 or 1.
- n 1 and n 2 are the same or different and 0
- R 1 and R 2 are the same or different and each represents a fluorine atom, a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group, a furyl group, a thienyl group, or a thiazolyl group
- One or more of the hydrogen atoms contained in the alkyl group may be substituted with fluorine atoms
- one or more of the hydrogen atoms contained in the aryl group, pyridyl group, furyl group, thienyl group, and thiazolyl group are (It may be substituted with a fluorine atom or an alkyl group having 1 to 10 carbon atoms)
- the organic semiconductor material includes a compound represented by the following formula (1-7), a compound represented by the following formula (1-8), a compound represented by the following formula (1-9), and the following formula (1- It is preferably at least one compound selected from the group consisting of compounds represented by 10).
- R 3 and R 4 are the same or different and are a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group, a furyl group, a thienyl group, or a thiazolyl group)
- the content of the solvent in the total amount of the composition for manufacturing an organic semiconductor device is preferably 99.999% by weight or less.
- the content of the organic semiconductor material in the composition for manufacturing an organic semiconductor device is preferably 0.005 parts by weight or more with respect to 100 parts by weight of the solvent.
- the content of 2,3-dihydrobenzofuran in the total amount of the solvent contained in the composition for producing an organic semiconductor device is preferably 50% by weight or more.
- the content of at least one compound is preferably 50% by weight or more.
- a composition for producing an organic semiconductor device comprising 2,3-dihydrobenzofuran as a solvent and the following organic semiconductor material, wherein the water content of the solvent is 0.25% by weight or less.
- Organic semiconductor material compound represented by the following formula (1-1), compound represented by the following formula (1-2), compound represented by the following formula (1-3), formula (1-4) At least one compound selected from the group consisting of a compound represented by formula (1-5) below and a compound represented by formula (1-6) below Wherein X 1 and X 2 are the same or different and are an oxygen atom, a sulfur atom or a selenium atom.
- M is 0 or 1.
- n 1 and n 2 are the same or different and 0
- R 1 and R 2 are the same or different and each represents a fluorine atom, a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group, a furyl group, a thienyl group, or a thiazolyl group
- One or more of the hydrogen atoms contained in the alkyl group may be substituted with fluorine atoms
- one or more of the hydrogen atoms contained in the aryl group, pyridyl group, furyl group, thienyl group, and thiazolyl group are (It may be substituted with a fluorine atom or an alkyl group having 1 to 10 carbon atoms)
- the organic semiconductor material includes a compound represented by the formula (1-1), a compound represented by the formula (1-4), and a compound represented by the formula (1-6).
- [3] The composition for manufacturing an organic semiconductor device according to [1] or [2], wherein X 1 and X 2 are the same or different and are an oxygen atom or a sulfur atom.
- [4] The composition for manufacturing an organic semiconductor device according to any one of [1] to [3], wherein m is 0.
- [5] The composition for producing an organic semiconductor device according to any one of [1] to [4], wherein n 1 and n 2 are 1.
- R 1 and R 2 are the same or different and are each a C 1-20 alkyl group (preferably a C 4-15 alkyl group, more preferably a C 6-12 alkyl group, still more preferably a C 6-10 alkyl group).
- R 1 and R 2 may be the same or different and are each a C 1-20 alkyl group (preferably a C 4-15 alkyl group, more preferably a C 6-12 alkyl group, still more preferably a C 6-10 alkyl group). Group) (provided that one or more hydrogen atoms contained in the alkyl group may be substituted with a fluorine atom), for producing an organic semiconductor device according to any one of [1] to [5] Composition.
- the composition for manufacturing an organic semiconductor device according to [1] which is at least one compound selected from the group consisting of compounds represented by (1-10).
- R 3 and R 4 are the same or different and are a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group, a furyl group, a thienyl group, or a thiazolyl group
- R 3 and R 4 may be the same or different and are each a C 1-20 alkyl group (preferably a C 4-15 alkyl group, more preferably a C 6-12 alkyl group, still more preferably a C 6-10 alkyl group). Group), a phenyl group, a furyl group, or a thienyl group.
- R 3 and R 4 may be the same or different and are each a C 1-20 alkyl group (preferably a C 4-15 alkyl group, more preferably a C 6-12 alkyl group, still more preferably a C 6-10 alkyl group).
- composition for manufacturing an organic semiconductor device according to any one of [8] to [10], which is more preferably 90% by weight or more, and still more preferably 95% by weight or more.
- any one of [1] to [11], wherein the content of the solvent (preferably 2,3-dihydrobenzofuran) in the total amount of the composition for manufacturing an organic semiconductor device is 99.999% by weight or less.
- the content of the solvent (preferably 2,3-dihydrobenzofuran) in the total amount of the composition for manufacturing an organic semiconductor device is 90.000% by weight or more (preferably 93.000% by weight or more, more preferably 95.% by weight).
- Organic semiconductor material in the composition for manufacturing an organic semiconductor device preferably a compound represented by the formula (1-1), a compound represented by the formula (1-2), the formula (1 -3), a compound represented by the formula (1-4), a compound represented by the formula (1-5), and a compound represented by the formula (1-6)
- the content of at least one compound selected from the group is 0.005 parts by weight or more (preferably 0.008 parts by weight or more, more preferably 0.01 parts by weight or more) with respect to 100 parts by weight of the solvent.
- the composition for manufacturing an organic semiconductor device according to any one of [1] to [13].
- An organic semiconductor material in the composition for producing an organic semiconductor device preferably a compound represented by the formula (1-1), a compound represented by the formula (1-2), the formula (1) -3), a compound represented by the formula (1-4), a compound represented by the formula (1-5), and a compound represented by the formula (1-6)
- the content of at least one compound selected from the group is 1 part by weight or less (preferably 0.5 parts by weight or less, more preferably 0.2 parts by weight or less) with respect to 100 parts by weight of the solvent.
- the content of 2,3-dihydrobenzofuran in the total amount of the solvent contained in the composition for producing an organic semiconductor device is 50% by weight or more (preferably 80% by weight or more, more preferably 90% by weight or more, The composition for producing an organic semiconductor device according to any one of [1] to [15], which is preferably 95% by weight or more.
- the compound represented by the formula (1-1), the compound represented by the formula (1-4), and the formula (1) in the total amount of the organic semiconductor material contained in the composition for producing an organic semiconductor device The content of at least one compound selected from the group consisting of compounds represented by 1-6) is 50% by weight or more (preferably 80% by weight or more, more preferably 90% by weight or more, more preferably 95% by weight).
- Any one of [1] to [18], wherein the water content of the solvent is 0.19% by weight or less (preferably 0.08% by weight or less, more preferably 0.05% by weight or less).
- the composition for organic-semiconductor device manufacture of description The content of at least one compound selected from the group consisting of compounds represented by 1-6) is 50% by weight or more (preferably 80% by weight or more, more preferably 90% by weight or more, more preferably 95% by weight).
- composition for producing an organic semiconductor device of the present invention can stably form an organic semiconductor device having high carrier mobility.
- composition for producing organic semiconductor devices contains 2,3-dihydrobenzofuran as a solvent and the following organic semiconductor material, and is a solvent.
- the water content is 0.25% by weight or less.
- compounds represented by the following formulas (1-1) to (1-6) may be collectively referred to as “specific organic semiconductor materials”.
- Organic semiconductor material compound represented by the following formula (1-1), compound represented by the following formula (1-2), compound represented by the following formula (1-3), formula (1-4) At least one compound selected from the group consisting of a compound represented by formula (1-5) below and a compound represented by formula (1-6) below
- solvent 23-dihydrobenzofuran is a compound represented by the following formula (2).
- the composition of the present invention uses 2,3-dihydrobenzofuran as a solvent.
- 2,3-dihydrobenzofuran exhibits good solubility in the above specific organic semiconductor materials, especially at high concentrations, and has the characteristics of drying suitable for the process temperature and the ability to easily crystallize the organic semiconductor material into a thin film. Therefore, the organic semiconductor device formed from the composition of the present invention exhibits high carrier mobility when used in combination with the specific organic semiconductor material.
- the content of 2,3-dihydrobenzofuran in the total amount (100% by weight) of the solvent contained in the composition of the present invention is not particularly limited, but is preferably 50% by weight or more (eg, 50 to 100% by weight), more Preferably it is 80 weight% or more, More preferably, it is 90 weight% or more, Most preferably, it is 95 weight% or more.
- the content is 50% by weight or more, there is a tendency that the solubility of the specific organic semiconductor material is further improved, and single crystallization of the organic semiconductor material in a thin film can easily occur.
- composition of the present invention may contain a solvent (other solvent) other than 2,3-dihydrobenzofuran.
- solvents other solvents
- examples of the other solvents include solvents that are generally used for electronic materials and are compatible with 2,3-dihydrobenzofuran. You may contain 1 type (s) or 2 or more types of said other solvent.
- the water content of the solvent used in the composition of the present invention is 0.25% by weight or less as described above.
- the carrier mobility tends to decrease.
- the water content is preferably 0.19% by weight or less, more preferably 0.08% by weight or less, and still more preferably 0.05% by weight or less.
- the water content of 2,3-dihydrobenzofuran is preferably within the above range. The water content can be measured by the Karl Fischer method.
- the composition of the present invention comprises, as an organic semiconductor material, a compound represented by the above formula (1-1), a compound represented by the above formula (1-2), a compound represented by the above formula (1-3) , At least one selected from the group consisting of a compound represented by the above formula (1-4), a compound represented by the above formula (1-5), and a compound represented by the above formula (1-6) Is used.
- the above specific organic semiconductor materials are characterized by forming a herringbone structure of organic semiconductors and having a two-dimensional overlap of ⁇ electrons, exhibiting high carrier mobility and high transistor characteristics as organic semiconductors To do.
- X 1 and X 2 are the same or different and are an oxygen atom, a sulfur atom, or a selenium atom.
- an oxygen atom or a sulfur atom is preferable in view of high carrier mobility, and a sulfur atom is particularly preferable.
- M is 0 or 1. From the viewpoint of excellent solubility in 2,3-dihydrobenzofuran and high carrier mobility, it is preferably 0.
- n 1 and n 2 are the same or different and are 0 or 1. From the viewpoint of excellent solubility in 2,3-dihydrobenzofuran and high carrier mobility, 1 is preferable.
- R 1 and R 2 are the same or different and are a fluorine atom, a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group, a furyl group, a thienyl group, or a thiazolyl group.
- Examples of the C 1-20 alkyl group in R 1 and R 2 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, Examples thereof include linear or branched alkyl groups such as n-heptyl group, n-decyl group, n-undecyl group and n-tetradecyl group. Among them, a C 4-15 alkyl group is preferable, a C 6-12 alkyl group is more preferable, and a C 6-10 alkyl group is more preferable. In the C 1-20 alkyl, one or more of the hydrogen atoms contained in the alkyl group may be substituted with a fluorine atom.
- Examples of the C 6-13 aryl group in R 1 and R 2 include phenyl, naphthyl, fluorenyl, biphenylyl group and the like. Of these, a phenyl group is preferred.
- Examples of the pyridyl group include 2-pyridyl, 3-pyridyl, and 4-pyridyl groups.
- Examples of the furyl group include 2-furyl and 3-furyl groups.
- Examples of the thienyl group include 2-thienyl and 3-thienyl groups.
- Examples of the thiazolyl group include 2-thiazolyl group.
- One or more hydrogen atoms contained in the aryl group, pyridyl group, furyl group, thienyl group, and thiazolyl group may be substituted with a fluorine atom or an alkyl group having 1 to 10 carbon atoms.
- alkyl group having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, n-pentyl, n-hexyl, and n-heptyl.
- linear or branched alkyl groups such as an n-decyl group.
- an alkyl group having 1 to 6 carbon atoms is preferable, and an alkyl group having 1 to 3 carbon atoms is particularly preferable.
- examples of the group in which at least one hydrogen atom contained in the aryl group is substituted with an alkyl group having 1 to 10 carbon atoms include a tolyl group and a xylyl group.
- examples of the group in which at least one hydrogen atom contained in the aryl group is substituted with a fluorine atom include a p-fluorophenyl group and a pentafluorophenyl group.
- R 1 and R 2 are the same or different from each other in that they have solubility in 2,3-dihydrobenzofuran and high carrier mobility, and they are a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group.
- Group, furyl group, thienyl group or thiazolyl group is preferable, and a C 1-20 alkyl group is more preferable.
- a compound represented by the above formula (1-1), a compound represented by the above formula (1-4), a compound represented by the above formula (1-6) It is preferable in that it can maintain a crystal state even in a high temperature environment exceeding 120 ° C., and can easily obtain a thin film crystal having excellent thermal stability.
- R 3 and R 4 are the same or different and are a C 1-20 alkyl group, a C 6-13 aryl group, a pyridyl group, a furyl group, a thienyl group, or a thiazolyl group, and the above R 1 , R 2 Examples thereof are the same as those of C 1-20 alkyl group, C 6-13 aryl group, pyridyl group, furyl group, thienyl group, and thiazolyl group.
- R 3 and R 4 are preferably the same group from the viewpoints of solubility in 2,3-dihydrobenzofuran and high carrier mobility, and are preferably a C 1-20 alkyl group, a phenyl group, a furyl group. Or a thienyl group is more preferred, and a C 1-20 alkyl group (a C 4-15 alkyl group is preferred, a C 6-12 alkyl group is more preferred, and a C 6-10 alkyl group is more preferred) is even more preferred. .
- the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2) can be produced by the production method described in International Publication No. 2014/136827.
- the specific organic semiconductor material includes, for example, trade names “C 10 -DNBDT-NW”, “C 6 -DNBDT-NW”, “C 8 -DNBDT”, “C6-DNT-VW” (hereinafter referred to as “Pi”).
- Ci trade names
- Commercially available products such as “C 10 -DNTT” (manufactured by Daicel Corporation), “C 8 -BTBT” (manufactured by Sigma Aldrich), and the like can also be used.
- the above-mentioned specific organic semiconductor material has a structure in which a benzene ring is connected to both wings with a cross-linked portion by a chalcogen atom as a bending point, and substituents are introduced into the benzene rings at both ends. Therefore, it has higher solubility in 2,3-dihydrobenzofuran than a linear molecule having the same number of rings, and hardly precipitates even in a low temperature environment.
- the composition of the present invention may contain an organic semiconductor material other than the specific organic semiconductor material, but the specific organic semiconductor in the total amount (100% by weight) of the organic semiconductor material contained in the composition of the present invention.
- the content of the material is not particularly limited, but is preferably 50% by weight or more (for example, 50 to 100% by weight), more preferably 80% by weight or more, further preferably 90% by weight or more, and particularly preferably 95% by weight or more. It is.
- the said content is content of the sum total of 2 or more types of the said specific organic-semiconductor material.
- composition of the present invention (a composition for producing an organic semiconductor device) comprises 2,3-dihydrobenzofuran as a solvent, a compound represented by the formula (1-1) as an organic semiconductor material, and a compound represented by the formula (1-2).
- a compound represented by formula (1-3), a compound represented by formula (1-4), a compound represented by formula (1-5), and a compound represented by formula (1-6) At least one compound selected from the following compounds.
- the composition of the present invention uses a combination of 2,3-dihydrobenzofuran and the above-mentioned specific organic semiconductor material, so that after applying and drying the composition of the present invention, a thin film single crystal having a herringbone structure in the plane direction of the substrate Thus, a crystal structure suitable for exhibiting high carrier mobility and high transistor characteristics as an organic semiconductor can be obtained.
- the water content of the solvent is 0.25% by weight or less.
- the composition of this invention shows the stably high carrier mobility compared with the case where a moisture content exceeds 0.25 weight%.
- an organic semiconductor material can be used individually by 1 type or in combination of 2 or more types.
- the content of the solvent in the total amount (100% by weight) of the composition of the present invention is, for example, 99.999% by weight or less.
- the lower limit is, for example, 90.000% by weight, preferably 93.000% by weight, particularly preferably 95.000% by weight, and the upper limit is preferably 98.990% by weight.
- the content of 2,3-dihydrobenzofuran is preferably within the above range.
- content of the organic-semiconductor material in the composition of this invention is not specifically limited, For example, 0.005 weight part or more with respect to 100 weight part of solvents, Preferably it is 0.008 weight part or more, More preferably, it is 0.00. 01 parts by weight or more.
- the upper limit of the content of the organic semiconductor material is, for example, 1 part by weight, preferably 0.5 part by weight, more preferably 0.2 part by weight.
- the content of the specific organic semiconductor material is preferably within the above range.
- the composition of the present invention generally requires components (eg, epoxy resin, acrylic resin, cellulose resin, butyral resin, etc.) contained in the composition for manufacturing an organic semiconductor device. It can mix
- components eg, epoxy resin, acrylic resin, cellulose resin, butyral resin, etc.
- the heat resistance is lower than that of a glass substrate, but an organic semiconductor device can be directly formed on a plastic substrate that is resistant to impact and lightweight and flexible, and is resistant to impact, lightweight and flexible. Display and computer equipment can be formed.
- the specific organic semiconductor material contained in the composition is crystallized by a self-organizing action, and high carrier mobility (for example, 0.0005 cm 2 / Vs or more, preferably 0.001 cm 2 / Vs or more, more preferably 0.05 cm 2 / Vs or more, more preferably 0.1 cm 2 / Vs or more, particularly preferably obtained organic semiconductor devices having a 1.0 cm 2 / Vs or higher) It is done.
- the composition of the present invention can dissolve the specific organic semiconductor material at a high concentration, the specific organic semiconductor material can be dissolved at a relatively low temperature (for example, 20 to 100 ° C., preferably 20 to 80 ° C.). Can be dissolved in concentration. Therefore, although it has lower heat resistance than glass substrates, it can withstand impacts and can directly form organic EL elements on lightweight and flexible plastic substrates, forming impact-resistant, lightweight and flexible displays and computer equipment. can do.
- the composition of the present invention contains 2,3-dihydrobenzofuran as a solvent, when applied on a substrate, the specific organic semiconductor material is crystallized by a self-organizing action, and an organic semiconductor crystal thin film having high crystallinity (for example, an organic EL element) is obtained. Furthermore, the organic semiconductor crystal thin film can be easily formed by a simple coating method such as a printing method or a spin coating method, and the cost can be greatly reduced.
- composition of the present invention is, for example, a mixture of 2,3-dihydrobenzofuran and the above-mentioned specific organic semiconductor material, 0.1% at a temperature of about 70 to 150 ° C. in an air atmosphere, a nitrogen atmosphere or an argon atmosphere. It can be prepared by heating for about 5 hours.
- the water content of 2,3-dihydrobenzofuran was measured by a trade name “Karl Fischer Moisture Meter AQ-6, AQUA® COUNTER” (manufactured by Hiranuma Sangyo Co., Ltd.).
- Example 1 “C 10 -DNTT” as an organic semiconductor material in a solvent 2,3-dihydrobenzofuran having a water content of 0.04% by weight in a 25 ° C. environment so that the concentration of the organic semiconductor material becomes 0.03% by weight.
- the mixture was mixed and heated at 100 ° C. for 3 hours under a nitrogen atmosphere and light shielding conditions to obtain a composition (1) for manufacturing an organic semiconductor device.
- melt dissolution of the organic-semiconductor material was confirmed visually.
- a silicon substrate (SiO 2 , thickness of 100 ⁇ m) was ultrasonically cleaned with acetone and isopropanol, and then subjected to UV ozone treatment at room temperature for 30 minutes. SAM coating with ⁇ -phenethyltrichlorosilane was performed at 120 ° C. for 30 minutes. Thereafter, ultrasonic cleaning was performed with toluene and isopropanol.
- the composition (1) for manufacturing an organic semiconductor device was applied on a silicon substrate by using an edge casting method described in International Publication No. 2013/125599. Then, it dried at 100 degreeC under vacuum for 10 hours, gold
- a bottom gate-top contact type organic FET (channel length: 100 ⁇ m, channel width: 2 mm) was produced.
- carrier mobility was measured using the semiconductor parameter analyzer (model number "keithley 4200", Keithley Instruments Co., Ltd. product).
- Examples 2-8 A composition for producing an organic semiconductor device was prepared in the same manner as in Example 1 except that the organic semiconductor material shown in Table 1 was used and the contents of the solvent and the organic semiconductor material were changed as shown in Table 1. An FET was fabricated and the carrier mobility was evaluated.
- Comparative Examples 1 to 4 The organic semiconductor material and water content solvent 2,3-dihydrobenzofuran shown in Table 1 were used, and the organic content was changed in the same manner as in Example 1 except that the contents of the solvent and organic semiconductor material were changed as shown in Table 1.
- a composition for manufacturing a semiconductor device was prepared, an organic FET was prepared, and carrier mobility was evaluated.
- C 10 -DNTT Compound represented by the following formula (1-11), trade name “C 10 -DNTT”, manufactured by Daicel Corporation
- C 8 -DNBDT a compound represented by the following formula (1-12), trade name “C 8 -DNBDT”, manufactured by Pi Crystal Co., Ltd.
- C 6 -DNT-VW a compound represented by the following formula (1-13), trade name “C 6 -DNT-VW”, manufactured by Pi Crystal Co., Ltd.
- C 8 -BTBT Compound represented by the following formula (1-14), trade name “C 8 -BTBT”, manufactured by Sigma Aldrich ⁇ Solvent> DHBF: 2,3-dihydrobenzofuran, manufactured by Daicel Corporation
- composition of the present invention can be used for the purpose of producing an organic semiconductor device by a printing method.
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Abstract
Description
有機半導体材料:下記式(1-1)で表される化合物、下記式(1-2)で表される化合物、下記式(1-3)で表される化合物、下記式(1-4)で表される化合物、下記式(1-5)で表される化合物、及び下記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物
[1]溶剤としての2,3-ジヒドロベンゾフラン及び下記有機半導体材料を含有し、溶剤の含水率が0.25重量%以下である有機半導体デバイス製造用組成物。
有機半導体材料:下記式(1-1)で表される化合物、下記式(1-2)で表される化合物、下記式(1-3)で表される化合物、下記式(1-4)で表される化合物、下記式(1-5)で表される化合物、及び下記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物
[2]前記有機半導体材料が、前記式(1-1)で表される化合物、前記式(1-4)で表される化合物、及び前記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物である、[1]に記載の有機半導体デバイス製造用組成物。
[3]前記X1、X2が、同一又は異なって、酸素原子又は硫黄原子である、[1]又は[2]に記載の有機半導体デバイス製造用組成物。
[4]前記mが0である[1]~[3]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[5]前記n1、n2が1である[1]~[4]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[6]前記R1、R2が、同一又は異なって、C1-20アルキル基(好ましくはC4-15アルキル基、より好ましくはC6-12アルキル基、さらに好ましくはC6-10アルキル基)、C6-13アリール基(好ましくはフェニル基)、ピリジル基、フリル基、チエニル基、又はチアゾリル基(但し、前記アルキル基が含有する水素原子の1以上はフッ素原子で置換されていてもよく、前記アリール基、ピリジル基、フリル基、チエニル基、及びチアゾリル基が含有する水素原子の1以上はフッ素原子又は炭素数1~10のアルキル基で置換されていてもよい)である、[1]~[5]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[7]前記R1、R2が、同一又は異なって、C1-20アルキル基(好ましくはC4-15アルキル基、より好ましくはC6-12アルキル基、さらに好ましくはC6-10アルキル基)(但し、前記アルキル基が含有する水素原子の1以上はフッ素原子で置換されていてもよい)である、[1]~[5]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[8]有機半導体材料が、下記式(1-7)で表される化合物、下記式(1-8)で表される化合物、下記式(1-9)で表される化合物、及び下記式(1-10)で表される化合物からなる群より選択される少なくとも1種の化合物である[1]に記載の有機半導体デバイス製造用組成物。
[9]前記R3、R4が、同一又は異なって、C1-20アルキル基(好ましくはC4-15アルキル基、より好ましくはC6-12アルキル基、さらに好ましくはC6-10アルキル基)、フェニル基、フリル基、又はチエニル基である、[8]に記載の有機半導体デバイス製造用組成物。
[10]前記R3、R4が、同一又は異なって、C1-20アルキル基(好ましくはC4-15アルキル基、より好ましくはC6-12アルキル基、さらに好ましくはC6-10アルキル基)である、[8]に記載の有機半導体デバイス製造用組成物。
[11]前記有機半導体デバイス製造用組成物に含まれる有機半導体材料全量における、前記式(1-7)で表される化合物、前記式(1-8)で表される化合物、前記式(1-9)で表される化合物、及び前記式(1-10)で表される化合物からなる群より選択される少なくとも1種の化合物の含有量が、50重量%以上(好ましくは80重量%以上、より好ましくは90重量%以上、さらに好ましくは95重量%以上)である、[8]~[10]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[12]前記有機半導体デバイス製造用組成物全量における溶剤(好ましくは2,3-ジヒドロベンゾフラン)の含有量が、99.999重量%以下である、[1]~[11]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[13]前記有機半導体デバイス製造用組成物全量における溶剤(好ましくは2,3-ジヒドロベンゾフラン)の含有量が、90.000重量%以上(好ましくは93.000重量%以上、より好ましくは95.000重量%以上、さらに好ましくは98.990重量%以上)である、[1]~[12]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[14]前記有機半導体デバイス製造用組成物中の有機半導体材料(好ましくは、前記式(1-1)で表される化合物、前記式(1-2)で表される化合物、前記式(1-3)で表される化合物、前記式(1-4)で表される化合物、前記式(1-5)で表される化合物、及び前記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物)の含有量が、前記溶剤100重量部に対して、0.005重量部以上(好ましくは0.008重量部以上、より好ましくは0.01重量部以上)である、[1]~[13]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[15]前記有機半導体デバイス製造用組成物中の有機半導体材料(好ましくは、前記式(1-1)で表される化合物、前記式(1-2)で表される化合物、前記式(1-3)で表される化合物、前記式(1-4)で表される化合物、前記式(1-5)で表される化合物、及び前記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物)の含有量が、前記溶剤100重量部に対して、1重量部以下(好ましくは0.5重量部以下、より好ましくは0.2重量部以下)である、[1]~[14]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[16]前記有機半導体デバイス製造用組成物に含まれる溶剤全量に占める2,3-ジヒドロベンゾフランの含有量が、50重量%以上(好ましくは80重量%以上、より好ましくは90重量%以上、さらに好ましくは95重量%以上)である、[1]~[15]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[17]前記有機半導体デバイス製造用組成物に含まれる有機半導体材料全量における、前記式(1-1)で表される化合物、前記式(1-2)で表される化合物、前記式(1-3)で表される化合物、前記式(1-4)で表される化合物、前記式(1-5)で表される化合物、及び前記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物の含有量が、50重量%以上(好ましくは80重量%以上、より好ましくは90重量%以上、さらに好ましくは95重量%以上)である、[1]~[16]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[18]前記有機半導体デバイス製造用組成物に含まれる有機半導体材料全量における、前記式(1-1)で表される化合物、前記式(1-4)で表される化合物、及び前記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物の含有量が、50重量%以上(好ましくは80重量%以上、より好ましくは90重量%以上、さらに好ましくは95重量%以上)である、[17]に記載の有機半導体デバイス製造用組成物。
[19]前記溶剤の含水率が0.19重量%以下(好ましくは0.08重量%以下、より好ましくは0.05重量%以下)である、[1]~[18]のいずれか1つに記載の有機半導体デバイス製造用組成物。
[20]0.0005cm2/V以上(好ましくは0.001cm2/Vs以上、より好ましくは0.05cm2/Vs以上、さらに好ましくは0.1cm2/Vs以上、特に好ましくは1.0cm2/Vs以上)のキャリア移動度を有する有機半導体デバイスを形成可能である[1]~[19]のいずれか1つに記載の有機半導体デバイス製造用組成物。
本発明の有機半導体デバイス製造用組成物(以下、単に「本発明の組成物」と称する場合がある)は、溶剤としての2,3-ジヒドロベンゾフラン及び下記有機半導体材料を含有し、且つ、溶剤の含水率が0.25重量%以下である。なお、本明細書において、下記式(1-1)~(1-6)で表される化合物を総称して、「特定の有機半導体材料」と称する場合がある。
有機半導体材料:下記式(1-1)で表される化合物、下記式(1-2)で表される化合物、下記式(1-3)で表される化合物、下記式(1-4)で表される化合物、下記式(1-5)で表される化合物、及び下記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物
2,3-ジヒドロベンゾフランは、下記式(2)で表される化合物である。本発明の組成物は、溶剤として2,3-ジヒドロベンゾフランを用いる。2,3-ジヒドロベンゾフランは、上記特定の有機半導体材料に対して特に高濃度で良好な溶解性を示し、またプロセス温度に適した乾燥性、有機半導体材料を薄膜で単結晶化させやすい特性を有するため、上記特定の有機半導体材料と組み合わせて用いることで、本発明の組成物から形成された有機半導体デバイスは高いキャリア移動度を示す。
本発明の組成物は、有機半導体材料として、上記式(1-1)で表される化合物、上記式(1-2)で表される化合物、上記式(1-3)で表される化合物、上記式(1-4)で表される化合物、上記式(1-5)で表される化合物、及び上記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物を用いる。上記特定の有機半導体材料は、有機半導体のヘリングボーン構造を形成し、π電子の二次元的な重なりを有することが特徴であり、高いキャリア移動度を発現し、有機半導体として高いトランジスタ特性を発現する。
本発明の組成物(有機半導体デバイス製造用組成物)は、溶剤として2,3-ジヒドロベンゾフランと、有機半導体材料として式(1-1)で表される化合物、式(1-2)で表される化合物、式(1-3)で表される化合物、式(1-4)で表される化合物、式(1-5)で表される化合物、及び式(1-6)で表される化合物から選択される少なくとも1種の化合物を含有する。本発明の組成物は、2,3-ジヒドロベンゾフランと上記特定の有機半導体材料を組み合わせて用いることにより、本発明の組成物を塗布・乾燥後、基板の平面方向にヘリングボーン構造の薄膜単結晶を容易に作製でき、高いキャリア移動度を発現し、有機半導体として高いトランジスタ特性を発現するのに適した結晶構造が得られる。また、溶剤の含水率は0.25重量%以下である。これにより、本発明の組成物は、含水率が0.25重量%超の場合に比べて、安定して高いキャリア移動度を示す。なお、有機半導体材料は、1種を単独で、又は2種以上を組み合わせて使用することができる。
25℃環境下、含水率0.04重量%の溶剤2,3-ジヒドロベンゾフラン中に、有機半導体材料としての「C10-DNTT」を、有機半導体材料濃度が0.03重量%となるように混合し、窒素雰囲気、遮光条件下、100℃で3時間加熱して、有機半導体デバイス製造用組成物(1)を得た。得られた有機半導体デバイス製造用組成物(1)について、有機半導体材料の溶解を目視で確認した。
表1に示した有機半導体材料を使用し、表1に示すように溶剤及び有機半導体材料の含有量を変更した以外は実施例1と同様にして有機半導体デバイス製造用組成物を調製し、有機FETを作製しキャリア移動度を評価した。
表1に示した有機半導体材料及び含水率の溶剤2,3-ジヒドロベンゾフランを使用し、表1に示すように溶剤及び有機半導体材料の含有量を変更した以外は実施例1と同様にして有機半導体デバイス製造用組成物を調製し、有機FETを作製しキャリア移動度を評価した。
Claims (6)
- 溶剤としての2,3-ジヒドロベンゾフラン及び下記有機半導体材料を含有し、溶剤の含水率が0.25重量%以下である有機半導体デバイス製造用組成物。
有機半導体材料:下記式(1-1)で表される化合物、下記式(1-2)で表される化合物、下記式(1-3)で表される化合物、下記式(1-4)で表される化合物、下記式(1-5)で表される化合物、及び下記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物
- 前記有機半導体デバイス製造用組成物全量における溶剤の含有量が、99.999重量%以下である、請求項1又は2に記載の有機半導体デバイス製造用組成物。
- 前記有機半導体デバイス製造用組成物中の有機半導体材料の含有量が、前記溶剤100重量部に対して、0.005重量部以上である、請求項1~3のいずれか1項に記載の有機半導体デバイス製造用組成物。
- 前記有機半導体デバイス製造用組成物に含まれる溶剤全量に占める2,3-ジヒドロベンゾフランの含有量が、50重量%以上である、請求項1~4のいずれか1項に記載の有機半導体デバイス製造用組成物。
- 前記有機半導体デバイス製造用組成物に含まれる有機半導体材料全量における、前記式(1-1)で表される化合物、前記式(1-2)で表される化合物、前記式(1-3)で表される化合物、前記式(1-4)で表される化合物、前記式(1-5)で表される化合物、及び前記式(1-6)で表される化合物からなる群より選択される少なくとも1種の化合物の含有量が、50重量%以上である、請求項1~5のいずれか1項に記載の有機半導体デバイス製造用組成物。
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EP17810063.2A EP3471160B1 (en) | 2016-06-09 | 2017-05-17 | Composition for manufacturing organic semiconductor devices |
US16/308,352 US10892424B2 (en) | 2016-06-09 | 2017-05-17 | Composition for manufacturing organic semiconductor device |
CN201780034357.3A CN109314186A (zh) | 2016-06-09 | 2017-05-17 | 有机半导体器件制造用组合物 |
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EP3471160A1 (en) | 2019-04-17 |
CN109314186A (zh) | 2019-02-05 |
KR20190016964A (ko) | 2019-02-19 |
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JP6979402B2 (ja) | 2021-12-15 |
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