KR20110079173A - Conductivity polymer hybrid ink composition of low temperature plasticity and ultra low cost for roll to roll printing - Google Patents

Conductivity polymer hybrid ink composition of low temperature plasticity and ultra low cost for roll to roll printing Download PDF

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KR20110079173A
KR20110079173A KR1020090136152A KR20090136152A KR20110079173A KR 20110079173 A KR20110079173 A KR 20110079173A KR 1020090136152 A KR1020090136152 A KR 1020090136152A KR 20090136152 A KR20090136152 A KR 20090136152A KR 20110079173 A KR20110079173 A KR 20110079173A
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conductive polymer
polymer hybrid
roll
hybrid ink
acid
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KR101195036B1 (en
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조규진
박용수
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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
    • C09D11/52—Electrically conductive inks
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/026—Wholly aromatic polyamines
    • C08G73/0266—Polyanilines or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • 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
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • 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
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
    • 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
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C08K2003/0806—Silver
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/001—Conductive additives

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Conductive Materials (AREA)

Abstract

PURPOSE: A conductive polymer hybrid ink composition is provided to improve electroconductivity between metal and conductive polymers and to ensure high sinterability in low temperature cofiring. CONSTITUTION: A conductive polymer hybrid ink comprises a conductive polymer and silver nanoparticles. An organic solvent of the conductive polymer hybrid ink is one solvent selected from NMP(N-Methylpyrrolidone), m-cresol, chloroform, THF(Tetrahydrofuran) and DMF(Dimethylformamide). A method for preparing the conductive polymer hybrid ink comprises a step of doping CSA (Camphorsulfornic acid) into a nanosilver colloid solution to which a mixed aniline monomer is added. The dopant is DBSA (dodecylbenzensulfornic acid) and CSA.

Description

롤투롤 직접 인쇄방식에 적용 가능한 저온 소성용 초저가 전도성 고분자 하이브리드 잉크 {Conductivity polymer hybrid ink composition of low temperature plasticity and ultra low cost for roll to roll printing}Conductivity polymer hybrid ink composition of low temperature plasticity and ultra low cost for roll to roll printing}

본 발명은 롤투롤 직접 인쇄방식에 적용 가능한 저온 소성용 초저가 전도성 고분자 하이브리드 잉크에 관한 것이다.The present invention relates to an ultra-low cost conductive polymer hybrid ink for low temperature firing applicable to a roll-to-roll direct printing method.

본 발명은 전도성 고분자인 폴리아닐린 혼합액(Polyaniline blend)에 나노금속입자를 hybrid 시켜 전기 전도도를 향상 시켜 롤투롤 인쇄방식에 적용하는 것이다. 전도성 고분자가 상업적으로 많이 이용되는 이유는 상용의 고분자처럼 생산 단가가 저렴하고, 에너지 밀도가 높고, 가벼우며, 투명하고, 유연하며 그리고 도핑의 레벨에 따라 전도도를 조절할 수 있는 장점 때문이다. 대표적인 전도성 고분자로는 폴리피롤(Polypyrrole), 폴리아세틸렌(Polyacetylene),폴리티오펜(Polythiophene),폴리아닐린(Poly aniline) 등이 있다. The present invention is to apply a roll-to-roll printing method by hybridizing the nano-metal particles in a polyaniline blend (Polyaniline blend) of the conductive polymer to improve the electrical conductivity. The reason why conductive polymers are widely used commercially is that they are inexpensive, high energy density, light, transparent, flexible, and can control conductivity according to the level of doping. Representative conductive polymers include polypyrrole, polyacetylene, polythiophene, poly aniline, and the like.

그러나 이러한 전도성 고분자의 경우 금속과 비교해서 전도도가 매우 낮다는 단점이 있다. 이를 극복하기 위해서 전도성 고분자와 나노금속입자를 하이브리드 시켜 π-공액구조의 에너지 레벨을 낮추어 훨씬 좋은 전도성 복합체를 제조 할 수 있다.However, such a conductive polymer has a disadvantage in that its conductivity is very low compared to that of metal. In order to overcome this problem, the conductive polymer and the nano metal particles are hybridized to lower the energy level of the π-conjugated structure, thereby making it possible to manufacture a much better conductive composite.

명은 상기의 문제점을 해결하기 위하여 안출된 것으로, 새로운 전도성 고분자 복합체를 제조하는 방법을 제공하는 것이다. The present invention has been made to solve the above problems, to provide a method for producing a new conductive polymer composite.

또한, 상기 방법들에 의해 제조된 전도성 고분자 복합체를 이용하여 롤투롤 직접인쇄가 가능한 전도성 고분자 하이브리드 잉크를 제공하기 위한 것이다.In addition, the present invention provides a conductive polymer hybrid ink capable of directly printing roll-to-roll using the conductive polymer composite prepared by the above methods.

본 발명은 전도성 고분자 복합체를 이용하여 나노금속입자와 전도성 고분자를 포함하는 롤투롤 직접 인쇄방식에 적용 가능한 저온 소성용 초저가 전도성 하이브리드 잉크를 제공한다.The present invention provides an ultra low-cost conductive hybrid ink for low temperature baking which can be applied to a roll-to-roll direct printing method including a nano metal particle and a conductive polymer using a conductive polymer composite.

상기 과제를 달성하기 위하여 본 발명에서는, 유기 용매상에서 안정화된 나노실버입자를 먼저 용해하고, 이 용액에 폴리아닐린 에버랄딘베이스(EB)의 파우더를 첨가한 후 환원제를 첨가하여, 화학 환원중합법(reduce polymerization)으로 전도성 고분자 복합체를 제조하는 방법을 제공한다. 환원제를 첨가하는 이유는 실버 아세테이트의 음이온을 제거하고 실버(Ag)양이온만 남게되면 금속이온을 금속상태가지 환원 시키는 특징이 있기 때문이다. 또한 상기 방법에 의해 제조되는 전기전도성이 우수한 폴리아닐린 복합체를 제공한다.In order to achieve the above object, in the present invention, the nano-silver particles stabilized in an organic solvent are first dissolved, and then a powder of polyaniline aberaldine base (EB) is added to this solution, followed by the addition of a reducing agent, thereby reducing chemical polymerization. polymerization) to provide a method for producing a conductive polymer composite. The reason for the addition of the reducing agent is to remove the anions of the silver acetate and leave only the silver (Ag) cation because the metal ions are characterized by reducing the metal state. Also provided is a polyaniline composite having excellent electrical conductivity prepared by the above method.

상기 과제를 달성하기 위한 본 발명의 또 다른 구성으로는, 유기용매에 폴리아닐린을 용해한 후 나노실버입자를 첨가한 후 환원제를 첨가하여, 화학 환원중합법으로 환원 시킨 후 도판트로 도핑을 시키는 것이다.In still another aspect of the present invention, a polyaniline is dissolved in an organic solvent, followed by addition of nanosilver particles followed by addition of a reducing agent, followed by reduction by chemical reduction polymerization, followed by doping with a dopant.

그러나, 이렇게하여 제조된 전도성 고분자 복합체는 마지막에 침전이 일어나고 저항이 높게 나타나는 단점이 있다.However, the conductive polymer composite thus prepared has a disadvantage in that precipitation occurs at the end and the resistance is high.

이를 해결하기 위해서는 나노실버입자로서 실버아세테이트 대신 질산은을 사용하고, 여기에 아닐린 단량체를 혼합하여 아닐린 착염을 먼저 제조하고, 라디칼을 발생시켜 아닐린 단량체에 안정화된 나노실버 콜로이드 용액을 제조하고, 이 용액에 산화제를 첨가하여, 화학 산화중합법에 의해 폴리아닐린 복합체를 제조하는 방법이 있다.To solve this problem, silver nitrate is used instead of silver acetate as nano silver particles, and aniline complex salts are prepared by first mixing aniline monomers, and a nanosilver colloidal solution stabilized in aniline monomers is generated by generating radicals. There is a method for producing a polyaniline composite by chemical oxidation polymerization by adding an oxidizing agent.

기존의 고가의 금속잉크를 대체할 수 있고, 경제적이고 간편하게 제조하는 방법을 제공하며, 전자파 차폐코팅 및 대전방지용 코팅액으로 유용하게 사용될 수 있다.It is possible to replace the existing expensive metal ink, to provide an economical and simple method of manufacturing, it can be usefully used as electromagnetic shielding coating and antistatic coating liquid.

[실시예 1]Example 1

본 발명에 따른 전도성 폴리아닐린 제조Preparation of conductive polyaniline according to the present invention

1M 염산 200ml에 아닐린 단량체 6.5g 과 o-anisidine 3.7g 을 혼합하여 약 30분동안 교반을 시켜준다. 시간이 지나면 암모늄퍼설페이트(ammoniumpersulphate) (1M, 100ml)를 교반하여 약 1시간동안 적하한다. 적하가 종료되면 24시간 동안 반응을 진행한다. 시간이 지나고 반응이 종료되면 감압필터를 이용하여 필터를 한다.이 때, 불순물을 완전히 제거하기 위해서 de-ionized water 를 이용하여 세척(washing)을 3회 반복한다. 필터를 통해 얻어진 파우더는 60℃ 진공오븐(vacuum oven)에서 약 24시간 동안 건조를 시킨다. 건조를 통해 얻어진 파우더는 10% 암모 니아수(ammoniumchloride)를 de-ionized water(10%, 200ml)에 혼합한 용액에 첨가한 후 약 24시간 교반한다. 반응이 종료되면 감압필터를 이용하여 필터를 하고 남아있는 암모니아수를 완전히 제거하기 위해 de-ionized water 로 세척(washing)을 해주면서 3회 반복한다. 필터가 끝나면 얻어진 파우더는 완전히 건조가 될 때가지 60℃ 진공오븐(vacuum oven)에서 건조를 시켜준다. 최종으로 dark green 색의 폴리아닐린 파우더가 얻어진다. In 200 ml of 1M hydrochloric acid, 6.5g of aniline monomer and 3.7g of o-anisidine are mixed and stirred for about 30 minutes. After some time, ammoniumpersulphate (1M, 100ml) was stirred and added dropwise for about 1 hour. When the dropping is finished, the reaction proceeds for 24 hours. When the reaction is over and the reaction is completed, filter using a vacuum filter. At this time, washing is repeated three times using de-ionized water to completely remove impurities. The powder obtained through the filter is dried for about 24 hours in a 60 ℃ vacuum oven (vacuum oven). The powder obtained by drying is added to a solution of 10% ammonium chloride in de-ionized water (10%, 200ml) and stirred for about 24 hours. After the reaction is completed, the filter is filtered using a reduced pressure filter and washed three times with washing with de-ionized water to completely remove the remaining ammonia water. When the filter is finished, the powder obtained is dried in a 60 ° C. vacuum oven until completely dry. Finally, a dark green polyaniline powder is obtained.

[실시예 2][Example 2]

본 발명에 따른 전도성 폴리아닐린 복합체 제조Preparation of Conductive Polyaniline Composites According to the Present Invention

유기용매로 m-cresol 20g 에 폴리아닐린 파우더를 4 중량%로 분산을 시키고,실버아세테이트를 10중량%로 첨가한다. 롤투롤 인쇄가 가능하기 위해서는 50~300cp 정도의 점도가 있어야 인쇄 패턴이 좋아진다. 그래서 폴리아닐린의 파우더의 중량%를 높여준다. 이를 30분 동안 혼합시키고, 시간이 지나면 환원제인 페닐하이드라이진(Phenyl-hydrazine)을 유기용매인 m-cresol과 혼합시켜 약 5분동안 적하한다. 적하하는 동안 갈색으로 색이 변한다. 적하가 끝나면 도판트인 CSA(Camphorsulfornic acid)로 도핑을 시켜준다. 제조된 전도성 폴리아닐린 복합체는 UV 분광 분석법에 위해 450nm 부근에서 양자점이 형성되는 걸 확인함으로써 나노실버콜로이드가 제조됨을 확인 하였다. 제조된 전도성 폴리아닐린 복합체는 TEM 과 EDX 분석으로 균일한 크기의 입자를 확인하였다. 전도성은 4-probe station 측정장비로 3000 S/cm 를 확인하였다. The organic solvent is dispersed in 4% by weight of polyaniline powder in 20 g of m-cresol, and 10% by weight of silver acetate is added. In order to enable roll-to-roll printing, the viscosity should be about 50 ~ 300cp to improve the printing pattern. This increases the weight percent of polyaniline powder. This is mixed for 30 minutes, and after a while, phenyl hydrazine, a reducing agent, is mixed with m-cresol, an organic solvent, and added dropwise for about 5 minutes. Changes color to brown during dripping After dropping, dopant is doped with CSA (Camphorsulfornic acid). The prepared conductive polyaniline composite was confirmed that nanosilver colloid was prepared by confirming that quantum dots were formed at around 450 nm for UV spectroscopy. The prepared conductive polyaniline composite confirmed particles of uniform size by TEM and EDX analysis. The conductivity was 3000 S / cm by 4-probe station measuring equipment.

Claims (4)

전도성 고분자, 실버나노입자를 포함하는 전도성 고분자 하이브리드 잉크.A conductive polymer hybrid ink containing a conductive polymer and silver nanoparticles. 유기용매로서 NMP(N-Methylpyrrolidone),m-cresol, 클로로포름(Chloroform), THF(Tetrahydrofuran), DMF(Dimethylformamide) 로부터 선택되어지는 하나의 용매인 것을 특징으로 하는 전도성 고분자 하이브리드 잉크 제조방법.A method for producing a conductive polymer hybrid ink, wherein the organic solvent is one solvent selected from NMP (N-Methylpyrrolidone), m-cresol, chloroform (Chloroform), THF (Tetrahydrofuran), and DMF (Dimethylformamide). 상기 혼합 아닐린 단량체가 첨가된 나노실버콜로이드 용액에 CSA(Camphorsulfornic acid)로 도핑하는 단계;Doping the nanosilver colloidal solution to which the mixed aniline monomer is added with CSA (Camphorsulfornic acid); 도판트(dopant)로 DBSA(dodecylbenzensulfornic acid),CSA(Camphorsulfornic acid) 로부터 선택되어지는 하나의 도판트(dopant)인 것을 특징으로 하는 전도성 고분자 하이브리드 잉크 제조방법.A dopant is a dopant selected from dodecylbenzensulfornic acid (DBSA) and camphorsulfornic acid (CSA) as a dopant. 폴리아닐린(Polyaniline) 과 PSS(Poly styrene sulfornic acid) 블렌드(blend)하여 전도성 고분자 제조하는 단계Manufacturing a conductive polymer by blending polyaniline and poly styrene sulfornic acid (PSS) 도면 1. 전도성 고분자 하이브리드 잉크.Figure 1. Conductive polymer hybrid ink.
Figure 112009082214101-PAT00001
Figure 112009082214101-PAT00001
 도면 2. 아닐린 단량체에 안정화된 나노실버입자의 UV 흡수스펙트럼.Figure 2. UV absorption spectrum of nanosilver particles stabilized in aniline monomers.
Figure 112009082214101-PAT00002
Figure 112009082214101-PAT00002
 도면 3. 전도성 고분자 하이브리드 잉크의 TEM 및 EDX 분석도.Figure 3. TEM and EDX analysis of conductive polymer hybrid inks.
Figure 112009082214101-PAT00003
Figure 112009082214101-PAT00003
 도면 4. 전도성 고분자 하이브리드 잉크를 사용하여 롤투롤 직접인쇄 방식에 적용하여 인쇄된 안테나 패턴.Figure 4. Antenna pattern printed by applying to roll-to-roll direct printing using conductive polymer hybrid ink.
Figure 112009082214101-PAT00004
Figure 112009082214101-PAT00004
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KR101280119B1 (en) * 2011-09-26 2013-06-28 서울대학교산학협력단 Micropatterning of graphene sheets by inkjet printing and its wideband dipole-antenna application
CN115954136A (en) * 2023-02-28 2023-04-11 浙江视讯玻显科技有限公司 Transparent high-temperature sintered silver paste and preparation method, use method and application thereof

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KR100663695B1 (en) 2004-02-11 2007-01-02 (주) 파루 Preparation Conductive Inkject Ink Using Conducting Polymer
KR100568164B1 (en) 2004-11-03 2006-04-05 삼성정밀화학 주식회사 Preparation method of conducting polyaniline composites and its conducting polyaniline composites

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KR101280119B1 (en) * 2011-09-26 2013-06-28 서울대학교산학협력단 Micropatterning of graphene sheets by inkjet printing and its wideband dipole-antenna application
CN115954136A (en) * 2023-02-28 2023-04-11 浙江视讯玻显科技有限公司 Transparent high-temperature sintered silver paste and preparation method, use method and application thereof

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