CN107699049A - The organic semiconducting materials composition of inkjet printable - Google Patents

The organic semiconducting materials composition of inkjet printable Download PDF

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Publication number
CN107699049A
CN107699049A CN201710680201.4A CN201710680201A CN107699049A CN 107699049 A CN107699049 A CN 107699049A CN 201710680201 A CN201710680201 A CN 201710680201A CN 107699049 A CN107699049 A CN 107699049A
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China
Prior art keywords
polymer
composition
organic
polymeric additive
semiconducting materials
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CN201710680201.4A
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Chinese (zh)
Inventor
李胜夏
高思敏
蓝河
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Shanghai Mi Fang Electronics Ltd
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Shanghai Mi Fang Electronics Ltd
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Priority to CN201710680201.4A priority Critical patent/CN107699049A/en
Publication of CN107699049A publication Critical patent/CN107699049A/en
Priority to CN201810182681.6A priority patent/CN108485380A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/36—Inkjet printing inks based on non-aqueous solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • 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 a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • 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 a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • 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
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene

Abstract

The present invention relates to semiconductor layer of a kind of organic semiconducting materials composition available for inkjet printing and organic field effect tube and preparation method thereof, the organic semiconducting material composition includes C8 BTBT, polymeric additive and organic solvent；And said composition environmental pollution is small, stable ink-jet can be achieved, the semiconductive thin film continuity prepared using present composition ink-jet is good and crystallinity is strong.

Description

The organic semiconducting materials composition of inkjet printable
Technical field
This disclosure relates to organic electronic device, in particular it relates to a kind of organic semiconducting materials composition and organic field effect Answer its preparation method of transistor.
Background technology
Before organic field effect tube (Organic Thin Film Transistor, OTFT) is due to being widely used Scape, cost is low, and it is convenient to prepare, and causes the common interest of people, and OTFT is by electrode (source electrode, drain electrode, grid), insulating barrier and organic Semiconductor group is into OTFT electrode part is prepared by vacuum deposition method more at present, and insulating barrier is prepared by spin coating method more, partly Conductor is then prepared by drop film or spin coating proceeding more.
Inkjet printing, which has, directly to be patterned, non-contact with substrate, material (Drop on Demand) is saved, with flexible base Bottom has extraordinary compatibility, it is easy to accomplish the advantages that large area is processed.Realize the large area system of organic field effect tube One of standby important channel is that (i.e. electrode, the preparation of three parts of insulating barrier and semiconductor layer depend on printing to full printing OFET Technique complete).Ink jettable electrode (conduction) material and insulating layer material all have been realized in commercialization at present, but can spray The semi-conducting material of ink is also rarely reported.
Existing molten liquefied organic semiconducting materials are a lot, and wherein benzothiophenes performance comparision is excellent. WO2012022935A discloses a kind of benzothiophene kind organic semiconductor compound, available for the semiconductor in organic transistor It is prepared by layer.And the liquid composite that the publicly available this kind of chemical combination in solwution method collectively constitutes with polymer and solvent.
But pass through test, there are the following problems for prior art：
Most of existing ink jettable semi-conducting material is using the chlorinated solvents such as chlorine all relatively harmful to human body and environment Benzene or o-dichlorohenzene (Japanese Journal of Applied Physics 2011,50,03CB05, DOI: 10.1143/JJAP.50.03CB05；Nanotechnology 2007,18,345202,8pp,DOI:10.1088/0957- 4484/18/34/345202) the ink jettable ink ductor of document report is although widely used and at present, but viscosity Can be bad, under dedicated for the scene of ink-jet, it is impossible to reach preferable ink-jet effect, cause to prepare the success rate of device compared with It is low.
The content of the invention
In order to solve prior art problem, by repeated screening and experiment, the present invention provides a kind of organic semiconductor combination Material, said composition can be used for the semiconductor layer that organic field effect tube is prepared by ink-jet printing process；Its solvent toxicity It is small, and viscosity index is good, can efficiently be used for inkjet printing.
On the other hand, there is provided the method and use this method of a kind of semiconductor layer for preparing organic field effect tube are made The semiconductor layer of the organic field effect tube of work；Semiconductor layer prepared by a kind of semi-conducting material containing the present invention is also provided Organic field effect tube.
The concrete technical scheme of the present invention is a kind of composition for ink, and said composition contains C8-BTBT (2,7- dioctyls [1] benzothiophene [3,2-b] [1] benzothiophene), polymeric additive and organic solvent；Relative to the described organic molten of 1mL Agent, the content of the C8-BTBT is 1-40mg, and the content of the polymeric additive is 1-40mg；The polymeric additive For insulating polymer and/or semi-conducting polymer；The C8-BTBT has the structure as shown in formula (1)：
Alternatively, the weight average molecular weight of the polymeric additive is 10,000-8,000,000, preferred scope 400, 000-700, between 000.
Alternatively, the insulating polymer is in polystyrene, polymethylstyrene, polymethyl methacrylate It is at least one；The semi-conducting polymer is p-type semiconductor polymer or n-type semiconductor polymer, and the p-type semiconductor polymerize Thing is selected from poly- 3- hexyl thiophenes, contains alkyl-substituted pyrrolo-pyrrole-dione (diketopyrrolopyrrole, DPP) Polymer, the polymer containing diazosulfide unit, the polymer containing 1,4-Dithiapentalene unit, it is poly- (4,4- diphenyl- At least one of (4- methoxyl group -2- methylphenyls) amine) and polymer containing bioxindol unit, the polymerization of described n-type Thing is the copolymer of benzene-naphthalene diimide and di- thiophene.
Alternatively, the polymeric additive is insulating polymer, and the insulating polymer is polystyrene and poly- methyl Methyl acrylate, the weight ratio of the polystyrene and polymethyl methacrylate is 1：(0-5)
Alternatively, the organic solvent is selected from toluene, meta-xylene, paraxylene, ortho-xylene, 1,2,3- front three Benzene, 1,2,4- trimethylbenzene and 1,3,5- trimethylbenzenes, at least one of naphthane and methyl phenyl ethers anisole.
Alternatively, the organic solvent is selected from normal heptane, at least one of naphthane and methyl phenyl ethers anisole.
Alternatively, the viscosity of 20 DEG C of said composition is 0.6-6mPas.
A kind of disclosure second aspect, there is provided method for the semiconductor layer for preparing organic field effect tube；This method bag The organic semiconducting materials composition that disclosure first aspect is provided is included through inkjet printing and post processing, is obtained described organic The semiconductor layer of field-effect transistor.
Alternatively, the temperature of the post processing is 50-150 DEG C.
Alternatively, this method also includes：Before the inkjet printing steps, make what disclosure first aspect provided to have It is stirred successively after the mixing of machine semiconductor material combinations thing, ultrasonic and filtering.
The disclosure third aspect, there is provided the organic effect made by a kind of method that disclosure second aspect is provided is brilliant The semiconductor layer of body pipe.
Disclosure fourth aspect, there is provided a kind of organic field effect tube, including substrate, insulating barrier and electrode, it is described to have Field effect transistors also include the semiconductor layer that the disclosure third aspect is provided.
Alternatively, the substrate is flexible substrates, and the flexible substrates are selected from PEN, gathered to benzene At least one of naphthalate, polyimides and dimethyl silicone polymer.
Alternatively the insulating barrier and electrode are prepared by solwution method；The solwution method is selected from drop coating, inkjet printing, silk screen At least one of printing, spin coating and blade coating.
Alternatively, the insulating barrier and electrode are prepared by ink-jet printing process.
The disclosure is by allocating the composition of organic semiconducting materials composition, there is provided for preparing organic effect crystal The organic semiconducting materials composition of pipe semiconductor layer, said composition have suitable viscosity and surface tension, can use spray The method of ink printing prepares semiconductor layer, can realize that whole soln method, even full impact system prepare p-type organic effect crystalline substance Body pipe, the disclosure use all to endanger less non-chlorine solvent to environment and operating personnel, use the disclosure provide ink Formula can prepare OTFT with large area；Said composition property stable in the air is high, and semiconductor prepared therefrom Layer has preferable crystal property, it is possible to increase the performance of transistor device；Meanwhile the last handling process of inkjet printing is easy, The application of semiconductor layer on a flexible substrate can be realized.
Brief description of the drawings
Fig. 1 is OTFT structure charts prepared by the present invention；
Fig. 2 is the OTFT transfer curve figures that this is prepared clearly.
Embodiment
Below, technical scheme will be described in detail in conjunction with specific embodiments, it is necessary to explanation, specific implementation Example is only several specific embodiments of the present invention, is not intended as the restriction for technical solution of the present invention.
Composition for ink preparation example
In flask, 1L naphthanes (purchase manufacturer is taken：Sigma-Aldrich；The trade mark：522651), with 9g 2,7- bis- Octyl group [1] benzothiophene [3,2-b] [1] benzothiophene (purchase manufacturer：Sigma-Aldrich；Article No.：, and 1g 747092) Polystyrene (purchase manufacturer：Sigma-Aldrich；The trade mark：81413；Weight average molecular weight 300,000) mixing, in ultrasound condition Lower stirring 1 hour, the ultrasonic time is minute 5, supersonic frequency 20-40kHz；Ink product is filtrated to get, filtering Precision is 0.1-0.5 microns.
Through measurement, the viscosity of ink is：2.77mPas, the surface tension of ink are：26.4mN/m.
OTFT preparation examples
First on polyimide substrate grid is printed successively with ink jet printing device (Dimatix-2831), insulating barrier, Source electrode and drain electrode, prepare OTFT polycrystalline substances.
Ink prepared by preparation example is fitted into the print cartridge of ink jet printing device and carries out inkjet printing：Shower nozzle voltage is 23V, Nozzle temperature is 45 DEG C, and base reservoir temperature is 45 DEG C, puts 15 microns of spacing, the printing-filming on polycrystalline substance；By partly leading for printing Body film is put on warm table heats 30min with 90 DEG C, obtains OTFT as shown in Figure 1.
The transfer curve for preparing the OTFT devices completed is as shown in Figure 2.
For verification the verifying results, prepare experiment by a large amount of repetitions and be prepared for 100 devices wherein, the device for having 92% is sexual Can, the device performance average value such as following table of the device of statistics is shown.
Mobility average value/cm2(V*s)-1 On-off ratio average value Threshold voltage average value/V
9.6*10-4 3.1*103 2.4
Embodiment 2-9
According to the method for preparation example, adjust constituent content therein and be prepared for one group of embodiment, its composition is as shown in the table：
It is as follows to survey above-described embodiment relevant parameter：
Embodiment Viscosity (mPas) Surface tension (mN/m) Ink-jet situation
Embodiment 2 2.358 25.5 Ink-jet can be stablized
Embodiment 3 2.771 26.5 Ink-jet can be stablized
Embodiment 4 3.347 26.8 Ink-jet can be stablized
Embodiment 5 4.690 26.2 Ink-jet can be stablized
Embodiment 6 1.225 26.6 Cannot
Embodiment 7 1.733 26.2 Ink-jet can be stablized
Embodiment 8 0.413 20.5 Cannot
Embodiment 9 0.613 20.3 Cannot
Understood with reference to preparation example of the present invention and parameter, present invention employs the relatively large solvent of viscosity, on inkjet printing Work well, with the addition of the viscosity that polymer significantly increases ink in the present composition in addition, improve the stabilization of ink-jet Property, is mixed into the crystallinity that polymer improves semiconductive thin film in addition, the defects of reducing OTFT semiconductor/interfacial dielectric layer Interface state density (Nss).

Claims (9)

1. a kind of organic semiconducting materials composition, said composition contains the C8-BTBT (2,7- with the structure as shown in formula (1) Dioctyl [1] benzothiophene [3,2-b] [1] benzothiophene), polymeric additive and organic solvent；Have relative to described in 1mL Solvent, the C8-BTBT contents are 1-40mg, and the content of the polymeric additive is 1-40mg；It is characterized in that, described Polymeric additive is insulating polymer and/or semi-conducting polymer；The organic solvent is selected from meta-xylene, to diformazan Benzene, ortho-xylene, 1,2,3- trimethylbenzene, 1,2,4- trimethylbenzene, 1,3,5- trimethylbenzene, normal heptane, in naphthane and methyl phenyl ethers anisole One or more of
2. composition according to claim 1, it is characterised in that the weight average molecular weight of the polymeric additive is 10, 000-8,000,000。
3. composition according to claim 1 or 2, it is characterised in that the insulating polymer is selected from polystyrene, gathered At least one of methyl styrene, polymethyl methacrylate；The semi-conducting polymer is p-type semiconductor polymer or n Type semi-conducting polymer, the p-type semiconductor polymer are selected from poly- 3- hexyl thiophenes, contain alkyl-substituted pyrrolo- pyrrole Cough up diketone (diketopyrrolopyrrole, DPP) polymer, the polymer containing diazosulfide unit, containing and two It is the polymer of thiophene unit, poly- (4,4- diphenyl-(4- methoxyl group -2- methylphenyls) amine) and poly- containing bioxindol unit At least one of compound, described n-type polymer are the copolymer of benzene-naphthalene diimide and di- thiophene.
4. composition according to claim 1,
Characterized in that, the polymeric additive is insulating polymer, the insulating polymer is polystyrene and poly- methyl Methyl acrylate, the weight ratio of the polystyrene and polymethyl methacrylate is 1：(0-5).
5. composition according to claim 1, it is characterised in that the viscosity that 20 DEG C of said composition is 0.6-6mPas.
A kind of 6. method for the semiconductor layer for preparing organic field effect tube, it is characterised in that this method includes making right will The organic semiconducting materials composition in 1-5 described in any one is asked to obtain the organic field effect through inkjet printing and post processing Answer the semiconductor layer of transistor.
7. according to the method for claim 7, it is characterised in that the temperature of the post processing is 50-150 DEG C.
8. according to the method for claim 8, it is characterised in that this method also includes：Before the inkjet printing steps, Make in the organic semiconducting materials composition in claim 1-5 described in any one to be stirred successively after each component mixing, Ultrasound and filtering.
9. the semiconductor for the organic field effect tube that the method according to any one in claim 6-8 is prepared Layer.
CN201710680201.4A 2017-11-10 2017-11-10 The organic semiconducting materials composition of inkjet printable Withdrawn CN107699049A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
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CN108715710A (en) * 2018-05-07 2018-10-30 天津大学 A kind of ink-jet printing ink and preparation method thereof
CN113087720A (en) * 2021-03-03 2021-07-09 北京大学深圳研究生院 N-type organic semiconductor material based on benzothieno [3,2-b ] benzothiophene and preparation method and application thereof
CN114729920A (en) * 2019-10-29 2022-07-08 P.E.S.科技有限公司 Analysis system for volatile organic compounds in soil

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CN112210249B (en) * 2019-10-31 2021-12-17 天津大学 Method for preparing organic semiconductor single crystal film
CN112210246A (en) * 2019-10-31 2021-01-12 天津大学 Ink-jet printing ink and its application in preparing organic semiconductor single crystal film

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
DE10135640A1 (en) * 2001-07-21 2003-02-06 Covion Organic Semiconductors Organic semiconductor solution used for organic integrated switches, organic field effect transistors, organic thin film transistors, organic solar cells and organic laser diodes contains one or more additives
WO2005055248A2 (en) * 2003-11-28 2005-06-16 Merck Patent Gmbh Organic semiconducting layer formulations comprising polyacenes and organic binder polymers
JP5722884B2 (en) * 2009-05-29 2015-05-27 スリーエム イノベイティブ プロパティズ カンパニー Fluorinated silylethynylpentacene compounds and compositions, and methods of making and using the same
WO2011076324A1 (en) * 2009-12-23 2011-06-30 Merck Patent Gmbh Compositions comprising organic semiconducting compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108715710A (en) * 2018-05-07 2018-10-30 天津大学 A kind of ink-jet printing ink and preparation method thereof
CN114729920A (en) * 2019-10-29 2022-07-08 P.E.S.科技有限公司 Analysis system for volatile organic compounds in soil
CN113087720A (en) * 2021-03-03 2021-07-09 北京大学深圳研究生院 N-type organic semiconductor material based on benzothieno [3,2-b ] benzothiophene and preparation method and application thereof
CN113087720B (en) * 2021-03-03 2022-09-27 北京大学深圳研究生院 N-type organic semiconductor material based on benzothieno [3,2-b ] benzothiophene and preparation method and application thereof

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Application publication date: 20180213