KR101770409B1 - UV curing binder and UV curing conductive paste composition comprising it's binder - Google Patents
UV curing binder and UV curing conductive paste composition comprising it's binder Download PDFInfo
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- KR101770409B1 KR101770409B1 KR1020150190226A KR20150190226A KR101770409B1 KR 101770409 B1 KR101770409 B1 KR 101770409B1 KR 1020150190226 A KR1020150190226 A KR 1020150190226A KR 20150190226 A KR20150190226 A KR 20150190226A KR 101770409 B1 KR101770409 B1 KR 101770409B1
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
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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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
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- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- C09D7/1216—
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/02—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of metals or alloys
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Abstract
The present invention provides a conductive paste composition comprising a conductive powder, a photo-curable binder, a solvent, and a photocuring initiator,
Wherein the photo-curable binder is an acrylate compound represented by the following formula (1), wherein the caprolactone substitution ratio of the main chain of the acrylate compound with respect to the hydroxyl group (-OH) is in the range of 5 to 21% Paste composition.
[Chemical Formula 1]
In this formula,
x is 1 to 10, y and z are each independently 0 to 5, R 1 and R 2 are each independently hydrogen, a methyl group, or an ethyl group, and R 3 and R 4 are each independently a hydrogen or a methyl group.
Description
The present invention relates to a conductive paste composition, and more particularly to a binder for a conductive paste used for a conductive paste composition in which a thin film pattern such as an electrode or a wiring for connecting an electrical signal of a semiconductor device is formed and a conductive paste composition .
Recently, with the rapid spread of electronic communication devices, attention has been paid to devices constituting these devices. Conductive pastes are used to form patterns that are formed on a substrate to transmit an electrical signal. Conductive pastes generally include a conductive component (a conductive filler) and a binder component and a solvent that attach the conductive powder to the substrate.
BACKGROUND ART Conductive pastes are used for forming electronic patterns in various battery electronic devices such as circuit boards, RFID antennas, solar cells, and touch panels.
The physical properties of the conductive paste are not only electric conductivity, but also printing properties, hardness, adhesiveness, and the like.
As the conductive powder, metal powders such as Ag, Cu, Ni and the like, metal oxides such as carbon nanotubes, graphene, carbon black, graphite and tin oxide, and indium oxide are used as micro or nano size.
The polymeric conductive paste is classified into an evaporation drying type, a thermosetting type, and a light (UV) curing type depending on the kind of the binder.
The evaporation drying type is basically dried at a temperature of about room temperature, and is forcedly dried at 50 to 130 ° C. depending on the composition of the solvent. It is mainly composed of acrylic resin, copolymerized polyester, polyurethane, vinyl chloride-vinyl acetate copolymer and other thermoplastic resin (Polymer type paste) is mainly used.
The thermosetting type is a method of reacting and curing at about 130 to 150 ° C. A curing agent and a catalyst are mixed with a resin having a functional group such as a hydroxyl group or a carboxyl group. Epoxy resins, phenolic resins, copolymerized polyesters, polyurethanes, vinyl chloride-vinyl acetate copolymers and the like are mainly used as resins for such binders.
The UV curable paste forms a continuous structure of a binder and a conductive powder (filler) through crosslinking of an acrylic group capable of radical reaction by UV, and has a merit that a curing time is short and fine pattern development is possible. The optical (UV) curable paste is obtained through polymerization of acrylate. The acrylate has an excellent hardness, but the substrate adhesiveness is rather poor, and improvement is required.
It is an object of the present invention to provide a photocurable conductive paste composition which is excellent in hardness and adhesive force when forming a pattern (coating film) of an electric and electronic element.
In order to achieve the above object, the present invention provides a conductive paste composition comprising a conductive powder, a photo-curable binder, a solvent, and a photocuring initiator,
Wherein the photo-curable binder is an acrylate compound represented by the following formula (1), wherein the caprolactone substitution ratio of the main chain of the acrylate compound to hydroxy (-OH) is in the range of 5 to 21% Lt; / RTI >
[Chemical Formula 1]
In this formula,
x is 1 to 10,
y and z are each independently 0 to 5, y + z > 1,
R 1 and R 2 are each independently hydrogen, a methyl group or an ethyl group,
R 3 and R 4 are each independently hydrogen or a methyl group.
In the present invention, the photocurable binder preferably has a caprolactone substitution ratio of 7 to 17% with respect to hydroxy (-OH) of the main chain of the acrylate compound.
In the present invention, the main chain of the acrylate compound is preferably a bisphenol A type (R 1 and R 2 are methyl groups).
The present invention relates to a photocurable resin composition comprising the photocurable binder and comprising 60 to 80% by weight of a conductive powder, 10 to 30% by weight of a photocurable binder, 2 to 15% by weight of a solvent, and 0.5 to 4% By weight, based on the total weight of the composition.
The photo-curable binder is a second component which is selected from the group consisting of 2-hydroxypropyl acrylate (HPA), 4-hydroxybutyl acrylate (4-HBA), polyethylene glycol diacrylate Polyethyleneglycol diacrylate (9EGDA), neopentylglycol hydroxypivalate diacrylate modified caprolactone, bisphenol A diacrylate, trimethylolpropane triacrylate ( Trimethylolpropane triacrylate (TMPTA)), trimethylolpropane triacrylate modified ethylene oxide, dipentaerythritol triacrylate, pentaerythritol tryacrylate (PETA) ), Ditrimethylolpropane tetraacrylate Dipentaerythritol hexaacrylate (DPHA) or dipentaerythritol hexaacrylate modified caprolactone, Hexanedioldiacrylate (HDDA), and the like. , Octyl decyl acrylate (ODA), trimethylo propane trisacrylate (TMPTA), isobonyl acrylate (IBOA), tetraethyleneglycol dicarylate (TTEGDA) , Ethoxylated trimethylopropane triacrylate (TM3EOTA), and the like. The acrylate monomer is preferably 30 to 60% by weight based on the total weight of the photocurable binder.
The photocurable binder is a third component and may further include phenoxy resin. The phenoxy resin is preferably 10% by weight or less based on the total weight of the photocurable binder.
The conductive powder may be selected from the group consisting of silver powder, copper powder, aluminum powder, silver coated metal powder, metal oxide, carbon nanotube, graphene and graphite powder.
The solvent is selected from the group consisting of ethyl citalol acetate (ECA), ethyl carbitol, butyl carbitol, butyl acetate, ethoxyethyl acetate, propylene glycol mono Propylene glycol monomethyl ether acetate, terpineol, N-methylpyrrolidone, ethylene glycol monobutyl ether acetate, ethylene glycol monomethyl ether acetate, glycol monobutyl ether acetate, and methyl ethyl ketone.
The photocuring initiator is a 2-methyl-1- (4-methylthiophenyl) 2-morpholopropane-1-one (Irgacure- 907), phenyl bis (2,4,6-trimethylbenzoyl) phosphine oxide (Irgacure-819), diethoxyacetophenone (DEAP) Phenyl-2-methylpropane-1-one, 1-hydroxycyclohexyl-phenylketone, 1-phenyl- , 2-benzyl-2- (dimethylamino) -4'-morpholinobutyrophenone, alpha -amino acetophenone, Bis (h5-2,4-cyclopentadien-1-yl) bis [2,6-difluoro-3- (1H- -1-yl) bis [2,6-difluoro-3- (1H-pyrrol-1-yl) phenyl] -titanium, 2,3,6-trimethylbenzoylphenyl ethoxyphosphine oxide -Trimethylbenzoyl phenyl ethoxypho sphine oxide, 2,4-diethylthioxthanthone, and the like.
The photocurable conductive paste composition prepared according to the present invention is excellent in physical properties in terms of conductivity, hardness and adhesive force when a pattern (coating film) of an electric / electronic device is formed. Therefore, the photocurable conductive paste composition can be used as a conductive coating material Can be usefully used.
BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is NMR data showing that the hydroxyl group (-OH) of the main chain of the acrylate compound according to the present invention is substituted with caprolactone.
Fig. 2 shows a pencil hardness measurement method of a coating film.
Fig. 3 shows the result of measurement of pencil hardness after coating treatment of a conductive paste prepared according to an embodiment of the present invention.
Fig. 4 shows a method of measuring the adhesion of a coating film.
FIG. 5 shows the result of measuring the adhesive force of a conductive paste prepared according to an embodiment of the present invention after coating treatment.
The present inventors have conducted experiments using phenoxy resin, which is a polymer type paste, as a binder material of a conductive paste. Phenoxy resin has been known to have excellent hardness. However, it has been found that the adhesive strength of the binder is very poor when the conductive paste is manufactured and tested using the paste. To solve this problem, substituting caprolactone in the phenoxy main chain It has been confirmed that the polymer becomes flexible and the adhesion property with the substrate (PET) is greatly improved, thereby developing a photocurable conductive binder.
The photocurable binder of the present invention is obtained by introducing a hydroxyl group (-OH) into an acrylate compound main chain and substituting a part of the hydroxyl group (-OH) with caprolactone as represented by the following formula (1).
[Chemical Formula 1]
(Wherein,
x is 1 to 10,
y and z are each independently 0 to 5, y + z > 1,
R 1 and R 2 are each independently hydrogen, a methyl group or an ethyl group,
R 3 and R 4 are each independently hydrogen or a methyl group.)
In the present invention, the term "caprolactone (CL) substitution ratio" means that the number of substituted caprolactone is calculated as a percentage based on the total number of hydroxyl groups when caprolactone is not bonded to the acrylate compound of
In the present invention, it has been confirmed in the present invention that the adhesiveness is extremely excellent when the hardness is maintained as it is in an acrylate having a CL replacement ratio of 5 to 21% with respect to the total hydroxyl groups. The CL substitution ratio with respect to the total hydroxyl group is more preferably 10 to 15%.
The acrylate compound / composition of Formula 1 may be obtained through the process of
[Reaction Scheme 1]
(Wherein,
x is 1 to 10,
y and z are each independently 0 to 5, y + z > 1,
R 1 and R 2 are each independently hydrogen, a methyl group or an ethyl group,
R 3 and R 4 are each independently hydrogen or a methyl group.)
Bisphenol diacrylate used as a conventional binder does not have a hydroxy group. To solve this problem, glycidol is introduced at both terminals of bisphenol as shown in Formula 3, and acrylate compound of
Then, the caprolactone-substituted bisphenol acrylate compound of
In the formula (1), the CL substitution ratio with respect to the total hydroxyl group preferably ranges from 5 to 21%. When the CL substitution ratio is 5% or less, the adhesive force required as a binder is lowered, and the required hardness is lowered as a binder having 21% or more.
The bisphenol represented by
The photocurable binder according to the present invention may further comprise an acrylate monomer having a polyfunctional group as a second component in addition to the caprolactone-substituted bisphenol acrylate compound of
The acrylate monomer is preferably 30 to 60% by weight based on the total weight of the photocurable binder.
The photocurable binder according to the present invention may further comprise phenoxy resin as a third component in addition to the caprolactone substituted bisphenol acrylate compound of
The present invention provides a photocurable conductive paste composition comprising the photocurable binder of
The photocurable conductive paste composition according to the present invention may contain 60 to 80% by weight of conductive powder, 10 to 30% by weight of a photocurable binder, 2 to 15% by weight of a solvent, and 0.5 to 4% by weight of a photocurable initiator based on the total paste weight have.
The conductive powder may be selected from the group consisting of silver powder, copper powder, aluminum powder, silver coated metal powder, metal oxide, carbon nanotube, graphene and graphite powder. The conductive powder may be spherical or plate-like, and in the case of a plate-like type, it is preferable to use a thickness of 30 to 80 nm and a length of 1 to 5 탆.
The solvent is used for diluting the binder, mixing with the conductive powder, and controlling the paste viscosity. The solvent is selected from the group consisting of ethyl citalol acetate (ECA), ethyl carbitol, butyl carbitol, butyl acetate, ethoxyethyl acetate, propylene glycol mono Propylene glycol monomethyl ether acetate, terpineol, N-methylpyrrolidone, ethylene glycol monobutyl ether acetate, ethylene glycol monomethyl ether acetate, glycol monobutyl ether acetate, methyl ethyl ketone, and the like.
The photocuring initiator is a 2-methyl-1- (4-methylthiophenyl) 2-morpholopropane-1-one (Irgacure- 907), phenyl bis (2,4,6-trimethylbenzoyl) phosphine oxide (Irgacure-819), diethoxyacetophenone (DEAP) Phenyl-2-methylpropane-1-one, 1-hydroxycyclohexyl-phenylketone, 1-phenyl- , 2-benzyl-2- (dimethylamino) -4'-morpholinobutyrophenone, alpha -amino acetophenone, Bis (h5-2,4-cyclopentadien-1-yl) bis [2,6-difluoro-3- (1H- -1-yl) bis [2,6-difluoro-3- (1H-pyrrol-1-yl) phenyl] -titanium, 2,3,6-trimethylbenzoylphenyl ethoxyphosphine oxide -Trimethylbenzoyl phenyl ethoxyph osphine oxide, and 2,4-diethylthioxthanthone. However, the present invention is not limited thereto.
Hereinafter, the present invention will be described in detail with reference to examples. The following examples are only exemplary embodiments of the present invention, but the scope of the present invention is not limited thereto.
Example 1: Preparation of caprolactone substituted photocurable binder
(y and z are each independently 0 to 5 and y + z > 1)
(a) 1 mole of bisphenol A diglycidyl ether (3 ') and 2 moles of acrylic acid were reacted at room temperature for 4 hours under benzyltriethylammonium chloride catalyst to obtain bisphenol A acrylate compound (2') .
(b) 2 mol of? -caprolactone was added to 1 mol of the bisphenol A compound and reacted under Sn (Oct) 2 catalyst to obtain caprolactone grafted bisphenol A acrylate (1 ').
(c) the molar ratio of the bisphenol A acrylate compound (2 ') prepared in (a) to the caprolactone substituted bisphenol A acrylate compound (1') prepared in (b) was 1: 0.01, 1: 0.03, Bisphenol A acrylate / (caprolactone substituted) bisphenol A acrylate (1: 0.06, 1: 0.10, 1: 0.15, 1: 0.20, 1: 0.25, 1: 0.30, Lt; / RTI >
(d) In order to confirm the caprolactone substitution ratio after the curing of the bisphenol A acrylate mixture, a small amount of photocuring initiator (Irgacure-907: Irgacure-819) was added to each sample of the bisphenol A acrylate mixture of (c) After the reaction, the caprolactone replacement ratio of the main chain of the acrylate compound to the hydroxyl group (-OH) was calculated through 1 H NMR data.
The calculation method of the caprolactone substitution ratio with respect to the hydroxyl group (-OH) of the acrylate compound is shown in Fig. As shown in FIG. 1, the 1 H NMR peak of the hydroxyl group (-OH) of the acrylate compound appears at 5.4 ppm, and the -OH peak decreases (changes) as the -OH is substituted with caprolactone (CL) , And the peak reduction amount is calculated through the difference between the peak of bisphenol and the integral ratio.
(d) caprolactone prepared according to the present embodiment, a substituted bisphenol A acrylate binder CL substitution rate of each sample was 1 H NMR measurement results of 1%, 2%, 5%, 9%, 15%, 17%, 21 %, 26%, 32% and 43%, respectively.
Example 2: Preparation of conductive paste
The caprolactone-substituted bisphenol A acrylate composition prepared in Example 1 was blended with the components and contents shown in Table 1 below as binders to prepare each photocurable conductive paste composition according to CL replacement ratio.
bookbinder
* HDDA: 1,6-Hexanediol diacrylate
* ECA: Diethylene Glycol Monoethyl Ether Acetate (Ethyl Carbitol Acetate)
* Irgacure-907 TM : 2-methyl-1- (4-methylthiophenyl) 2-morpholopropan-1-one
* Irgacure-819 TM : Phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide
Experimental Example 1: Measurement of hardness of photocurable conductive paste
The hardness test after the formation of the coating film of the conductive paste composition prepared in Example 2 was conducted. The hardness test was carried out at a light intensity of 1500 (mj / ㎠) after forming the coating film, and the coating was cured at 130 ° C for 2 minutes and dried.
The test method was pencil hardness method and measured according to
As shown in Table 2 and FIG. 3, excellent results were obtained with 4H hardness until the substitution ratio of caprolactone-substituted bisphenol A acrylate compound and caprolactone (CL) was 21%, and when CL replacement ratio was 26% or more It can be seen that the hardness is rapidly lowered. It can be confirmed that the more the hydroxyl group (-OH) of the bisphenol A acrylate compound is substituted with caprolactone, the bad influence is given to the hardness.
Experimental Example 2: Adhesion test of photocurable conductive paste
The adhesive force test of the conductive paste composition prepared in Example 2 was carried out after the formation of the coating film. The adhesion test was carried out at 130 ° C for 2 minutes under a light intensity of 1500 (mJ / cm 2) after drying.
The test method was measured according to
The criteria for determining the adhesive strength of the coating film are shown in Fig. 4, and the results of the adhesion test are shown in Table 3 and Fig.
As shown in Table 3 and FIG. 5, the bisphenol A acrylate compound not substituted with caprolactone had very poor coating adhesion due to the 80% of the pattern cells being damaged. As the caprolactone (CL) replacement ratio was increased, It can be confirmed that it is improved.
When the CL substitution ratio is 5% or more, the adhesive strength is 5B.
From the above results, it can be seen that the photocurable conductive paste of the present invention satisfies the physical properties required for hardness and adhesion when the substitution ratio of caprolactone (CL) is within the range of 5 to 21%.
Claims (13)
Wherein the photo-curable binder is an acrylate compound represented by the following formula (1), wherein the caprolactone substitution ratio with respect to the hydroxyl group (-OH) of the main chain of the acrylate compound ranges from 5 to 21%
Photocurable conductive paste composition.
[Chemical Formula 1]
In this formula,
x is 1 to 10,
y and z are each independently 0 to 5, y + z > 1,
R 1 and R 2 are each independently hydrogen, a methyl group or an ethyl group,
R 3 and R 4 are each independently hydrogen or a methyl group.
Wherein the photocurable binder is characterized in that the substitution ratio of caprolactone with respect to the hydroxyl group (-OH) of the main chain of the acrylate compound is 7 to 17%.
Wherein the main chain of the acrylate compound is a bisphenol A type (R 1 , R 2 is a methyl group).
Wherein x of the acrylate compound is 1. The photocurable conductive paste composition according to claim 1,
Wherein the photocurable conductive paste composition comprises 60 to 80 wt% of conductive powder, 10 to 30 wt% of a photocurable binder, 2 to 15 wt% of a solvent, and 0.5 to 4 wt% of a photocuring initiator based on the total paste weight.
The photocurable binder may be selected from the group consisting of Dipentaerythritol hexaacrylate (DPHA), Dipentaerythritol triacrylate, Trimethylolpropane triacrylate (TMPTA)), hexanediol diacrylate (2-hydroxypropyl acrylate (HPA)), 4-hydroxybutyl acrylate (4-HBA)), polyethylene glycol diacrylate (Polyethyleneglycol diacrylate, 9EGDA), neopentylglycol hydroxypivalate diacrylate modified caprolactone, bisphenol A diacrylate, trimethylolpropane triacrylate-modified ethylene Oxide (Trimethylolpropane triacrylate modified ethylene oxide), pentaerythritol triacryl (Pentaerythritol tryacrylate (PETA)), ditrimethylolpropane tetraacrylate (DTMPTA), octyl decyl acrylate (ODA), trimethylo propane trisacrylate (TMPTA) Further comprises an acrylate monomer selected from the group consisting of isobonyl acrylate (IBOA), tetraethyleneglycol dicarylate (TTEGDA), ethoxylated trimethylopropane triacrylate (TM3EOTA) Wherein the photocurable conductive paste composition is a photocurable conductive paste composition.
Wherein the acrylate monomer is 30 to 60% by weight based on the total weight of the photocurable binder.
Wherein the photo-curable binder further comprises phenoxy resin.
Wherein the phenoxy resin is 10% by weight or less based on the total weight of the photocurable binder.
Wherein the conductive powder is selected from the group consisting of silver powder, copper powder, aluminum powder, silver coated metal powder, metal oxide, carbon nanotube, graphene, and graphite powder.
The solvent is selected from the group consisting of ethyl citalol acetate (ECA), ethyl carbitol, butyl carbitol, butyl acetate, ethoxyethyl acetate, propylene glycol mono Propylene glycol monomethyl ether acetate, terpineol, N-methylpyrrolidone, ethylene glycol monobutyl ether acetate, ethylene glycol monomethyl ether acetate, glycol monobutyl ether acetate, methyl ethyl ketone, and the like.
The photocuring initiator is a 2-methyl-1- (4-methylthiophenyl) 2-morpholopropane-1-one (Irgacure- 907), phenyl bis (2,4,6-trimethylbenzoyl) phosphine oxide (Irgacure-819), diethoxyacetophenone (DEAP) Phenyl-2-methylpropane-1-one, 1-hydroxycyclohexyl-phenylketone, 1-phenyl- , 2-benzyl-2- (dimethylamino) -4'-morpholinobutyrophenone, alpha -amino acetophenone, Bis (h5-2,4-cyclopentadien-1-yl) bis [2,6-difluoro-3- (1H- -1-yl) bis [2,6-difluoro-3- (1H-pyrrol-1-yl) phenyl] -titanium, 2,3,6-trimethylbenzoylphenyl ethoxyphosphine oxide -Trimethylbenzoyl phenyl ethoxypho sphine oxide, and 2,4-diethylthioxthanthone. The photocurable conductive paste composition of claim 1,
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