KR101502890B1 - Conductive Inks - Google Patents

Abstract

Conductive material; And at least one benzoxazine-based compound selected from the structures listed in the following general formula (1).
[Formula 1]

Description

Conductive Inks

More particularly, the present invention relates to a conductive ink, wherein the main component is a conductive ink composed of at least one kind of conductive substance and at least one kind of benzoxazine compound, And finally to electroconductive inks that can be directly utilized as various electrode materials in the field of printing electronics.

The printed electronics industry has become a new paradigm in the 21st century as a convergence and eco-friendly industry based on nanotechnology that can greatly change the existing industry framework. In other words, it is based on a printing process that enables a variety of electronic materials and components of a new concept to be manufactured at low temperature, atmospheric pressure, and mass production processes, low cost, flexibility, and large area of products have.

Therefore, the future electronic product market will change according to consumers' emotions, consumption patterns, and various needs, and new markets will be created and new markets will be opened that far exceed the existing market size. Examples of the printed electronic product include an electronic device such as an RFID, a memory, various displays (OLED, EL, electronic paper, flexible display, etc.), a lighting device, a secondary battery, It can be applied to various fields such as substrate (PCB or FPCB), electromagnetic shielding (EMI shielding) and transparent electrode (metal mesh type) film. A rapid market is likely to be formed centering on products. In other words, although the existing process is limited by the type and size of the substrate, the printing process can be used regardless of the type, shape and size of the substrate. Especially, it is easy to apply to a large size or flexible substrate, This is because it is evaluated as an innovative process.

In order to produce such a printed electronic product, an ink compatible with this is indispensable. In particular, the conductive ink is a material for various kinds of electrodes (including transparent electrodes). That is, a material having conductivity in a printing electronic process such as a metal, an alloy, a metal oxide, a carbon nanotube (CNT), a graphene, a graphite, a conductive carbon, a conductive polymer, Conductive inks made of particles, nanowires, or their precursors can be directly printed (or coated) with equipment such as inkjet printers, gravure, flexo, (rotary) screens, offset, gravure-offset, (nano) Drying or firing forms the desired type of metal wiring, which is essential for the printing electronics process.

Until now, the conductive ink required for such a printing electronic process has been researched and developed by many researchers. Particularly, for example, nanoparticle-based inks generally have poor stability over a long period of time or have a problem of blocking nozzles due to agglomeration or precipitation between the particles when printing, so that a polymer material is usually used as a stabilizer If used excessively, it causes another problem such as viscosity increase, surface tension, firing temperature and increase of conductivity.

Conductive inks using metal nanoparticles are described in Nanotechnology, 17, p2424 (2006), J. Mater. Res., 24, p. 1828 (2009), J. Colloid Interface. Sci., 273, p165 (2004), J. Mater. Chem., 19, p3057 (2009), US 2010/0084599 A1, US 2010 / 0009153A1, US 2011 / 0183128A1).

As a means for solving the problem of the metal ink of the nanoparticle type, for example, a metal precursor is most commonly used. Examples thereof include an organic metal salt (Organometallic Salt), an organometallic complex Complex). However, since the organic metal carboxylates including silver are generally sensitive to light, have low solubility and have a high decomposition temperature, they have been limited in applicability to ease of manufacture. As a method for solving such problems, for example, A long carboxylic acid having a carboxylic acid or an alkyl chain may be prepared by using a silver precursor in which an electron donor is coordinated such as an amine compound or a phosphine compound in a salt thereof (Chem. Vapor Deposition, 7, p111 (2001), Organometallics , 15, p2575 (1996), Chem. Mater., 16, p2021 (2004), and J. Chem. Crystallography, 26, p99 (1996)). (US 7691294 B2, US 2011 / 0111138A1, US 8,226,755 B2, and J. Am. Chem. Soc., 134, 1419, 2012), beta-ketocarboxylic acid silver salt containing an organic metal complex or a metal salt 21, p4153 (2006), Chem. Mater., 21, pp. 370-371), inks using a neoalkanoic acid silver salt (Makromol Rapid Commun., 26, p315 P341 (2001), US 2008 / 0003364A1, Adv. Mater., 23, 5524, 2011, WO (2009), US 2011/0008548 A1), as well as silver or copper precursor inks (Organometallics, 2009 / 059273A2, and WO 2010 / 011974A1) have also been developed.

However, these conductive inks have a limitation in various applications to products which require high reliability because of insufficient conductivity or adherence with a substrate when forming metal wiring of a thin film by baking.

Accordingly, the present inventors have made efforts to solve these problems and have come to the present invention.

An object of the present invention is to provide a conductive ink which is easy to form a thin film and has excellent conductivity and adhesion to a substrate.

According to an aspect of the present invention, And at least one benzoxazine-based compound selected from the structures listed in the following general formula (1).

[Formula 1]

R ₁ , R _2, R _3, R ₄ and R ₅ are each independently hydrogen, halogen, amino, nitro, cyano, hydroxy, carboxyl, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₃ ring -C ₃₀ cycloalkyl, substituted or unsubstituted C ₆ -C ₃₀ aryl, substituted or unsubstituted C ₆ -C ₃₀ aralkyl (aralkyl), substituted or unsubstituted C ₁ -C ₃₀ heteroalkyl, substituted or unsubstituted hwandoen C ₂ -C ₃₀ heterocycloalkyl, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl, or substituted or unsubstituted C ₅ -C ₃₀ heteroaralkyl, R ₂ and R ₃ or R ₃ and R ₄ Or R < ₄ & R ₅ may be connected to form a ring, and the ring may be composed of at least one atom selected from the group consisting of C, O and N, L is a chemical bond, a substituted or unsubstituted C ₁ -C ₃₀ alkyl Substituted or unsubstituted C ₁ -C ₃₀ heteroalkylene, substituted or unsubstituted C ₆ -C ₃₀ arylene, substituted or unsubstituted C ₆ -C ₃₀ heteroarylene, -O-, -C O-, -C (CH ₃ ) ₂ -, -C (CF ₃ ) ₂ -, -S-, or -SO ₂ -, R is a substituted or unsubstituted C ₁ -C ₃₀ alkylene, substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene, a substituted or unsubstituted C ₆ -C ₃₀ arylene, a substituted or unsubstituted C ₁ -C ₃₀ hetero alkylene, substituted or unsubstituted Substituted C ₂ -C ₃₀ heterocycloalkylene, substituted or unsubstituted C ₅ -C ₃₀ heteroarylene, and m is an integer of 1 to 1000.

The conductive material is not particularly limited. That is, a substance showing conductivity or a substance capable of exhibiting conductivity after special treatment corresponds to the present invention. Specifically, for example, the conductive material may include at least one metal selected from the group consisting of Ag, Cu, Ni, Sn, Zn, Au, Co, Al, Fe, Mn, Cr, V, Ti, Zr, Hf, And may include an alloy or an oxide thereof such as Bi, Pb, Cd, Pd, Ru, Rh, Mo, Nb, Ta, W, Re, Os, Ir, Pt, Cs, Sr, Eu, Gd, have.

Also included are metal precursor compounds, for example, where the metal ligand is a carboxylate, an alkoxide, an acetylacetonate, a perchlorate, a nitrate, a sulfate, a phosphate, a carbonate, a halogen, a tetrafluoroborate, , Sulfur compounds and the like.

The metal precursor compound may be a carboxylic acid metal salt, preferably a fatty acid metal salt.

More specifically, for example, the metal precursor compound may be silver oxide, silver nitrate, gold chloride, chloroauric acid, copper sulfate, nickel perchlorate, silver carbonate, The organic acid metal salt may be silver carboxylates, silver complexes or the like. Such metal compounds are disclosed in Korean Patent Application Nos. 10-2012-0149495 and 10-2013-0020270, Chem. Vapor Deposition, 7, p111 (2001), Organometallics, 15, p2575 (1996), Chem. Mater., 16, p2021 (2004), US 7,691,294 B2, US 2011 / 0111138A1, US 8,226,755 B2, and J. Am. Chem. Soc., 134, 1419, (2012), WO 2007 / 004437A1, Makromol Rapid Commun., 26, p315 (2005), J. Mater. Sci., 41, p4153 (2006), Chem. Mater., 21, p343 (2009).

As a more specific example of the metal precursor compound, silver malonates, silver itaconate, silver naphthenate, 2- (hydroxyimino) malonic acid (Silver 2- (hydroxyimino ) malonate, silver diallylmalonate, silver methylmalonate, silver formate, silver acetate, silver acrylate, silver (meth) acrylate, methacrylate, 2,4-pentanedionate, silver cyclopropanecarboxylate, silver cyclopentanecarboxylate, 5-norbornene-2-carboxylic acid Silver 5-norbornene 2-carboxylate, 5-norbornene 2,3-dicarboxylate, silver 1-adamantanecarboxylate, , Silver trifluoroacetate, pentafluoropropionic acid (silver pe natafluoropropionate, silver oxalate, 1,3-acetonedicarboxylate, silver acetoacetate and silver 2-methyl-acetoacetate. acetoacetate, silver oxalate, silver lactate, silver pivalate, silver 2-ethylhexanoate, silver sorbate, malic acid, silver maleate, silver fumarate, silver glyoxylate, silver pyruvate, silver succinate, silver glutalate, and so on. ), Silver gluconate, silver picrate, silver citrate, silver iminodiacetate, silver nitrilotriacetate, ethylenediamine tetraacetic acid, (silver ethylenediaminetetraacetate), silver benzoate (silver benzoate), neodecanoic acid (s ilver neodecanoate, silver stearate, silver oleate, silver linolate, silver abietate, silver alkylammonium carbamates, silver alkylammonium carbonate Compounds (silver alkylammonium carbonates) and the like.

The metal of the metal precursor compound may be gold (Au), copper (Cu), nickel (Ni), tin (Sn), zinc (Zn) or the like in addition to the silver (Ag) The metal precursor compound may be, for example, a carboxylate of various metals as described above.

In addition, the conductive material is not particularly limited as long as it conforms to the present invention, such as carbon nanotube (CNT), graphene, graphite, conductive carbon, and conductive polymer.

In 1-1 to 1-4 of the above general formula [1]

R ₁ , R ₂ , R ₃ , R ₄ And R ₅ are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, epoxy, carboxyl, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl, Substituted or unsubstituted C ₆ -C ₃₀ aryl, substituted or unsubstituted C ₆ -C ₃₀ aralkyl, substituted or unsubstituted C ₁ -C ₃₀ heteroalkyl, substituted or unsubstituted C ₂ -C ₃₀ is a hetero-cycloalkyl, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl, or substituted or unsubstituted C ₅ -C ₃₀ heteroaralkyl. R ₂ and R _{3 ,} or R ₃ and R _{4 ,} or R ₄ and R ₅ may be connected to form a ring. The ring may be composed of at least one atom selected from the group consisting of C, O and N.

In the general formulas 1-2, L represents a chemical bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene, a substituted or unsubstituted C ₁ -C ₃₀ heteroalkylene, a substituted or unsubstituted C ₆ -C ₃₀ arylene , substituted or unsubstituted C ₆ -C ₃₀ hetero arylene group, -O-, -C (O) - , -C (O) O-, -C (CH 3) 2 -, -C (CF 3) 2 -, -S-, or -SO ₂ - a.

In the general formulas 1-3, R is a substituted or unsubstituted C ₁ -C ₃₀ alkylene, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene, a substituted or unsubstituted C ₆ -C ₃₀ arylene, Unsubstituted C ₁ -C ₃₀ heteroalkylene, substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkylene, substituted or unsubstituted C ₅ -C ₃₀ heteroarylene.

On the other hand, in the general formulas 1-4, m is an integer of 1 to 1000.

The term "alkyl" as used herein includes straight, branched, or cyclic hydrocarbon radicals or combinations thereof, and may optionally include one or more double bonds, triple bonds, or combinations thereof in the chain. E., "Alkyl" includes alkenes or alkynes.

The term "heteroalkyl ", by itself or in combination with other terms, unless otherwise indicated, includes one or more carbon atoms and one or more heteroatoms selected from the group consisting of O, N, P, Si and S Means a stable straight-chain or branched or cyclic hydrocarbon radical or combination thereof, wherein the nitrogen, phosphorus and sulfur atoms may optionally be oxidized and the nitrogen heteroatom may optionally be quaternized (ammonium).

The terms "cycloalkyl" and "heterocycloalkyl ", by themselves or in conjunction with another term, refer to a cyclic version of" alkyl "and" heteroalkyl ", respectively,

The term "aryl" means a polyunsaturated, aromatic, hydrocarbon substituent which may be a single ring or multiple rings (one to three rings) fused or covalently bonded together unless otherwise specified. The term "heteroaryl" means an aryl group (or ring) comprising 1 to 4 heteroatoms selected from N, O, P and S (in each case on a separate ring in the case of multiple rings) The atoms are optionally oxidized and the nitrogen atom (s) are optionally quaternized. Heteroaryl groups can be attached to the remainder of the molecule through carbon or heteroatoms.

The term "aralkyl" refers to an alkyl group substituted with aryl and aryl, wherein the alkyl and aryl moieties are independently optionally substituted.

The term "heteroaralkyl" refers to an alkyl group substituted with aryl and heteroaryl, respectively, wherein the alkyl and heteroaryl moieties are independently optionally substituted.

In the expression "substituted or unsubstituted" described herein, "substituted" means that one or more hydrogen atoms in the hydrocarbon are each independently replaced with the same or different substituents. Useful substituents include, but are not limited to:

Such substituents include, but are not limited to, -F; -Cl; -Br; -CN; -NO ₂ -OH; A C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted by -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C ₁ -C ₂₀ alkoxy group unsubstituted or substituted with -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C ₆ -C ₃₀ aryl group which is unsubstituted or substituted by a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C ₆ -C ₃₀ heteroaryl group which is unsubstituted or substituted by a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH; C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or substituted by -OH or unsubstituted C ₅ -C ₂₀ cycloalkyl group; C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or substituted by -OH or unsubstituted C ₅ -C ₃₀ heterocycloalkyl group; And a group represented by -N (G ₁ ) (G ₂ ). Wherein G ₁ and G ₂ are each independently selected from the group consisting of hydrogen; A C ₁ -C ₁₀ alkyl group; Or a C ₆ -C ₃₀ aryl group substituted or unsubstituted with a C ₁ -C ₁₀ alkyl group.

More specifically, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, And examples thereof include methyl, ethyl, propyl, isopropyl, n-butyl, ethylhexyl, n-heptyl, octyl, isoheptyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, docodecyl, cyclopropyl, cyclopentyl, cyclohexyl, , Methoxyethyl, 2-hydroxypropyl, methoxypropyl, aminoethyl, cyanoethyl, mercaptoethyl, chloroethyl, methoxy, ethoxy, butoxy, hexyloxy, phenoxy, methoxyethoxyethyl , Methoxyethoxyethoxyethyl, imidazolyl, carboxymethyl, trimethoxysilylpropyl, triethoxysilylpropyl, phenyl, methoxyphenyl, cyanophenyl, tolyl, benzyl And the like, but the present invention is not limited thereto.

Preferably, in order to accelerate the curing reaction by radical polymerization, R ₂ , R ₃ , R ₄ And R < ₅ > may be a hydrocarbon group containing at least one double bond.

The compound represented by the general formula (1) can be specifically selected from the following structures (the half-salt formulas 2-1 to 2-13).

[Formula 2]

Wherein R ₁ , R ₂ , R ₃ , and R ₅ are the same as defined in the general formula (1).

Rc is cardanol-based alkyl, mainly a hydrocarbon chain having 15 (C ₁₅ ) carbon atoms and containing 0 to 3 double bonds.

,

,

,

등이 주성분으로 이루어진 혼합물로 이루어져 있다.
That is, Rc is generally

,

,

,

And the like.

Also, Ru is a urushiol-based alkyl, usually a carbon chain having 15 carbon atoms (C ₁₅ ) and containing 0 to 3 double bonds.

,

,

,

,

,

,

,

등이 주성분으로 이루어진 혼합물로 이루어져 있다.
That is, Ru is generally

,

,

,

,

,

,

,

And the like.

The above general formulas 2-1 and 2-2 were prepared based on a raw material obtained by vacuum distillation from a cashew nut shell liquid (CNSL) extracted from a fruit of a cashew tree as a cardanol-based benzo-phosgene compound Cardanol, cardol, 2-methylcardol, and anacardic acid.

On the other hand, the general formula 2-3 and the general formula 2-4 are cardol-based benz photo compounds, and the general formulas 2-5 and 2-6 are anacardic acid-based benz photo compounds Where Rc in the above formulas may be a mixture of long hydrocarbon compounds having double bonds as described above.

In the formulas 2-7 and 2-8, Urushiol extracted and purified from raw urushi (lacquer) was used as a urushiol-based benzopyrazole compound. In the above formulas, It can be a mixture of hydrocarbon compounds and only representative components are shown here.

On the other hand, in the above general formula, the kind of the benzo photochemical compound and the production method thereof are not particularly limited. For example, starting materials for making such compounds may be prepared according to the preparation methods described in the literature or by a more suitable modification, and can be prepared and used directly when the substance is not in the literature or in the absence of a manufacturing process have. Representative examples thereof are shown for example in [Reaction Scheme 1] and [Reaction Scheme 2].

[Reaction Scheme 1]

[Reaction Scheme 2]

The starting materials shown in the reaction schemes may be commercially prepared and commercially available, or they can be generally prepared and used according to methods known in the literature. In order to prepare a benzoimide, there may be a difference in the production method such as production of a solvent-free solid or a solvent-free solid depending on the type and nature of the amine. However, The method is not limited. Specific examples of the amine used herein include ammonia, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, t-butylamine, isoamylamine, n- Amines, amylamines, 2-ethylhexylamines, cyclohexylamines, allylamines, propargylamines, ethylenediamines, hexamethylenediamines, phenylenediamines, monoethanolamines, 2-methyl-1-propanol, 2-amino-2-ethyl-1,3-propanediol, methoxyethylamine, benzylamine, phenethylamine, 3- Amines such as 3-aminopropyltriethoxy silane, polyetheramines or JEFFAMINE, polyallylamine and the like. Of these, amine compounds having a carbon number of 30 (C ₃₀ ) or less are preferable, But is not limited thereto.

The benzo photochemicals prepared as described above can be polymerized while the rings are opened at a temperature of 200 to 250 ^° C. For promoting the polymerization reaction, organic acids such as formic acid, para-toluenesulfonic acid, dodecylbenzenic acid and polystyrenesulfonic acid, inorganic acids such as sulfuric acid, hydrochloric acid, nitric acid and phosphoric acid, and Lewis acids such as AlCl ₃ , PCl ₅ and BF ₃ Can be used. When the conductive ink containing the benzo photographic compound is applied to a substrate, the polymerization reaction of the benzo photographic compound occurs at the temperature, so that the conductive thin film may include the polymer of the benzo photographic compound. As a result, the resulting coating film exhibits excellent heat resistance and chemical resistance as well as excellent adhesion to a substrate.

An example of the polymer structure formed by the polymerization reaction in the following Reaction Scheme 3 is shown.

[Reaction Scheme 3]

On the other hand, in the compounds having a large number of unsaturated double bonds in the side chain such as the above-mentioned cardanol and urushiol, in addition to the ring-opening polymerization of the above-mentioned benzophenone rings, the double bonds of the side chains undergo radical polymerization, . ≪ / RTI > As an additive for accelerating this curing reaction, which is referred to as autoxidation, there is a fatty acid metal salt, for example, neodecanoic acid, naphthenic acid, or 2-ethylhexanoic acid metal salt, Fe, Co, Ce, V, Pb, Zr, Bi, Al, Sr, (Ca), zinc (Zn), lithium (Li), potassium (K), and the like are used as driers. These are mainly formed by the formation of active oxygen radicals and the catalysis of autoxidation Or to accelerate the crosslinking reaction. Of course, any compound of the benzo-phthalate system of the present invention, such as a hydroquinone system, a bisphenol system, and a polyvinyl phenol system, is also applicable when there is a radical polymerizable derivative in the side chain. Therefore, the above-mentioned drying agents can be both a main core material of the conductive ink of the present invention and simultaneously serve as a desiccant. The radicals generated by the autoxidation reaction also contribute to the reduction reaction of the metal precursors, thereby easily forming nanoparticles and contributing to the conductivity by firing.

On the other hand, although the use amount of these benzo photographic compounds is not limited, it is generally in the range of 0.1 to 99.9%, preferably 0.3 to 50%, more preferably 0.5 to 25% by weight based on the solid content of the conductive ink. Too little or too much use can result in problems with adhesion or too much resistance and problems with conductivity. These cross-linking polymers, which undergo ring-opening crosslinking reaction, are suitable for various printing electronic applications such as electric and electronic parts which are required to have reliability because of excellent chemical resistance such as acid resistance and basicity as well as adhesion.

Meanwhile, various compounds such as a solvent and an additive may be required to produce the conductive ink according to the present invention.

For example, when a metal precursor is used as a conductive material, a complexing agent or a ligand is generally required to easily dissolve in a commonly used solvent and to dissolve in a high concentration. The compounds well known as such substances are mainly electron donors such as amine compounds having a nitrogen atom, mercaptan compounds having a sulfur element, phosphine compounds containing phosphorus, or mixtures thereof . They are all known to be involved in complex formation as sigma electron donors.

The amine compounds include, for example, primary, secondary, or tertiary amines and / or quaternary ammomium salts, wherein the amine is alkyl, aryl , Aralkyl, and the like. In particular, alkyl may be linear, branched, or cyclic, and may be a multi-amine or a functional group such as hydroxy, alkoxy, ester, amide, or urethane. And the like. Specific examples thereof include ammonia, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, t-butylamine, isoamylamine, n-hexylamine, diethylamine, Amino-2-propanol, 3-amino-1-propanol, 2-ethylhexylamine, Amino-2-ethyl-1,3-propanediol, N, N-diethylhydroxyamine, methoxyethylamine, N, N-diethylethylenediamine , N, N, N, N-tetramethylethylenediamine, pyridine, morpholine, imidazole, benzylamine, phenethylamine, ammonium carbamate, ammonium carbonate, tetraethylammonium bicarbonate, Ethyl ammonium bromide, tetrabutyl ammonium hydroxide, polyethyleneimine, polybis Amine, 3-amino propyltriethoxysilane, and the like may silane (3-aminopropyltriethoxy silane) such as amines and derivatives thereof and the amine compound having a carbon number of usually less than ₂₀ (C 20) is preferable is not particularly limited thereto. Examples of the phosphine-based compound include trimethylphosphine, tributylphosphine, triphenylphosphine, and the like. As the sulfur compound, ethane thiol, dodecylthiol, dimethyl sulfide, tetrahydrothiophene, For example, tetrahydrothiophene, bismuthiol, mercaptopropyltrimethoxy silane, and the like. In addition, the metal precursor and the phi electron donor may form complexes, and some compounds may be weakly bonded. Examples of the organic solvent include cyclooctadiene, butadiene, norbornadiene, allyl alcohol, vinyltriethylsilane, propargyl alcohol, 1-ethynyl Butyne-2-ol, 2-methyl-3-butyne-2-ol, 3-ol, 3-methyl-1-pentyne-3-ol and 3,5-dimethyl- -3-ol, surfinol 61). The amount of the electron donors to be used is not limited, but is generally in the range of 0.5 to 95% by weight, preferably 0.5 to 50% by weight relative to the metal precursor, Is in the range of 0.5 to 25%.

A solvent, a resin, a stabilizer, a dispersing agent, a reducing agent, a coupling agent, a leveling agent, a surfactant, a wetting agent, a thickener, and a sizing agent for controlling viscosity of an ink or forming a smooth thin film. Specific examples of the solvent include water, methanol, ethanol, isopropanol, butanol, benzyl alcohol, diacetone alcohol, methoxyethanol, ethoxyethanol, butoxyethanol, ethylene glycol, diethylene glycol, propylene glycol mono But are not limited to, methyl ether, monoglyme, diglyme, butyl carbitol, alpha-terpineol, glycerine, ethyl acetate, butyl acetate, ethyl lactate, carbitol acetate, acetone, methyl ethyl ketone, cyclohexane A solvent such as methanol, ethanol, propanol, isopropanol, butanol, isopropanol, butanol, isopropanol, butanol, isopropanol, , Terpin, white spirit, petrol, ligroin and the like, or mixed solvents thereof. Examples of the resin include acrylic, polyvinyl, polyolefin, polyester, polyamide, and polyurethane. Various resins such as water-soluble, thermoplastic, thermosetting, or ultraviolet-curable resins such as polysulfone, epoxy, phenol, maleate, phenoxy, alkyd, melamine, urea, silicone, fluorine and cellulose resins and latex and natural resins . A reducing agent may be required if necessary, for example, sodium hypophosphite, sodium sulfite, sodium borohydride, dimethylamine borane, diethylamine But are not limited to, diethylamine borane, carbohydrazide, hydrazine, Rochelle salt, erythobate, diethylhydroxylamine, methylethylketoxime, hydroquinone, hydroquinone, formic acid, formaldehyde, ammonium formate, triethylammonium formate, tetramethylammonium formate, glucose, citric acid, ascorbic acid, phenidone, quinhydrone quinhydrone, dopamine, p-methylaminophenol sulfate, 1,2,3-trihydroxybenzene, para-ami Aminophenol, diaminophenol, 2 - [(4-amino-3-methylphenyl) ethylamino] ethyl sulfate, (4-amino-3-methylphenyl) ethylamino] ethyl] methanesulfonamide) and 4- (N- (2- (N-ethyl-N-2-hydroxyethyl) -2-methylphenylenediamine sulfate) is selected from the group consisting of Can be used. The surfactant generally includes a nonionic surfactant, an anion, a cation, or an amphoteric surfactant, and examples of the wetting agent include ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, polyethylene glycol, And Surfynol and Dynol series of Air Product products. Examples of the thickening agent include hydroxypropyl cellulose and benton, and the leveling agent may be a BYK series or the like. However, the use amount of such additives is not particularly limited as long as it matches the ink characteristics of the present invention.

The viscosity of the conductive ink of the present invention is not particularly limited. That is, the coating and printing method may be free from problems in the manufacture of the thin film and the pattern, but is usually in the range of 0.1 to 1,000,000 cPs, more preferably in the range of 1 to 100,000 cPs. The conductive ink of the present invention preferably has a viscosity ranging from 0.1 to 50 cPs when measured at room temperature of 20 ° C so as to be suitable for inkjet printing, Can be adjusted to a range of 1 to 20 cPs, more preferably 3 to 15 cPs. If it is lower than the above range, the thickness of the thin film after firing or firing tends to be insufficient and the conductivity tends to be lowered. When the firing temperature is higher than the above range, the ink is difficult to be smoothly discharged through the nozzle.

In the meantime, the method for producing the conductive ink of the present invention is not particularly limited as long as it meets the object of the present invention. For example, the solvent, the reaction temperature, the concentration, the pressure, and the use of the catalyst are not particularly limited.

In addition, the conductive ink of the present invention may contain, in addition to the above components, 1 (one) selected from the group consisting of metal powder, metal oxide, metal nanoparticle, metal wire, carbon nanotube, graphene, conductive carbon, graphite, conductive polymer, Or in the form of a hybrid ink obtained by mixing or reacting with a species or more.

According to another aspect of the present invention, there is provided a conductive thin film obtained by applying the above-described conductive ink.

The coating or printing method for forming the conductive thin film by depositing the conductive ink may include spin coating, pipetting, blade coating, bar or rod coating, But are not limited to, a roll coating, a spray coating, a curtain coating, a dip coating, a flow coating, a comma coating, a slot die coating, a dispensing, (Eg, casting, stamping, imprinting, pad printing, inkjet printing, offset, screen, gravure, flexography printing, lithography, It is possible.

The coating thin film or pattern film thus obtained can be chemically treated with a liquid or a vaporous acid or a basic compound with a chemical substance such as an oxidizing agent or a reducing agent or can be chemically treated with heat, plasma, infrared (IR), ultraviolet (UV) The present invention can also be used to form a faster and better conductive film through a physical treatment process such as laser, microwave, electrical, magnetic treatment, or a combination thereof.

The above-mentioned post-treatment step may be heat-treated under a normal inert atmosphere, but it can be treated in air, nitrogen, carbon monoxide or hydrogen and air or various mixed gases as necessary. The post-treatment is preferably carried out at a temperature of 500 ° C or less, preferably 300 ° C or less, and may be lower or higher depending on the substrate. The post-treatment time is not particularly limited, but it is better if the batch or the continuous process is not a big problem, as soon as possible. A surface treatment process for adding a metal plating process (electrolytic or electroless) after the heat treatment or reduction treatment or for protecting the metal electrode, if necessary, may be added, and the present invention is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited by these examples.

According to the present invention, there is provided a conductive ink which is easy to form a thin film, has excellent conductivity after firing, and has excellent adhesion to various substrates. In addition, a metallic thin film on a mirror having excellent reflectance can be easily produced.

Fig. 1 shows the reflection curve of the sample prepared in Example 14. Fig.
2 shows an optical image of the sample prepared in Example 14. Fig.
3 is a SEM photograph of the sample prepared in Example 14. Fig.
4 shows an atomic force microscope (AFM) photograph of the sample prepared in Example 14. Fig.

Hereinafter, various embodiments of the present invention will be described in detail.

<Synthesis of benzo photographic compound>

Example 1.

Synthesis of cardanol-based methyl benzoxazine [General Formula 2-1, R ₁ = CH ₃ ]

A solution of 68.6 grams (0.8 mole) of formaldehyde aqueous solution (35%) in 150 milliliters of dioxane was added to a 1000 ml three-necked flask equipped with a stirrer. The solution was cooled to 5 ^° C and 31.5 grams (0.4 mole) Of a methylamine aqueous solution (40%) dissolved in 100 milliliters of dioxane was slowly dropped over 30 minutes. After the reaction was completed, a solution of 120 grams (0.4 mole) of cardanol dissolved in 100 milliliters of dioxane was slowly added. The reaction was further continued for 30 minutes while stirring at room temperature, and then the temperature was raised to 90 ^° C and reacted for 5 hours. After the completion of the reaction, the reaction product was vacuumed to remove all of the solvent. The solution was diluted with 500 ml of ethyl acetate and washed successively with 3N aqueous sodium hydroxide solution and brine three times. The organic solution was separated, dried over anhydrous sodium sulfate The solvent was blown off in vacuo to give 135.5 grams (yield: 95.2%) of a viscous pale red liquid.

Example 2.

Synthesis of cardanol-based allyl benzoxazine [General Formula 2-1, R ₁ = Allyl]

In the same manner as in Example 1 except that 22.8 g (0.4 mol) of allylamine was used instead of methylamine, 142.3 g (yield: 93.1%) of a red liquid was obtained.

Example 3.

Synthesis of cardanol-based benzoxazine [General Formula 2-2, R ₁ = Cardanol]

A solution of 51.4 grams (0.6 mol) of formaldehyde aqueous solution (35%) in 150 milliliters of dioxane was added to a 1000 mL three-necked flask equipped with a stirrer, and the resulting solution was cooled to 5 ^° C and 11.4 grams (0.2 mol) Of an aqueous ammonia solution (30%) dissolved in 100 milliliters of dioxane was slowly dropped over 30 minutes. After the reaction was completed, a solution of 120 grams (0.4 mole) of cardanol dissolved in 100 milliliters of dioxane was slowly added. The reaction was continued for 30 minutes while stirring at room temperature, and then the temperature was raised to 80 ^° C and the reaction was carried out for 6 hours. After completion of the reaction, the reaction product was vacuumed to remove all the solvent. The solution was diluted with 300 ml of chloroform and washed with 300 ml of distilled water three times. The organic solution was separated, dried over anhydrous sodium sulfate, 123.1 grams (yield: 94.2%) of a viscous dark reddish brown liquid was obtained.

Example 4.

Synthesis of urushiol-based methyl benzoxazine [General Formula 2-7, R ₁ = CH ₃ ]

In the same manner as in Example 1 except that 143.5 grams (0.4 mol) of urushiol (prepared by extracting green lacquer with ethanol) was used in place of cardanol, 158.4 grams (yield: 95.7%) of a viscous I got a reddish brown liquid.

Example 5.

Synthesis of urushiol-based allyl benzoxazine [Formula 2-7, R ₁ = Allyl]

In the same manner as in Example 2 except that 143.5 grams (0.4 mole) of uriciol was used instead of cardanol, 167.1 grams (yield: 94.8%) of a viscous brown liquid were obtained.

Example 6.

Synthesis of urushiol-based benzoxazine [General Formula 2-8, R ₁ = urushiol]

In the same manner as in Example 3 except that 143.5 grams (0.4 mole) of uriciol was used instead of cardanol, 148.7 grams (yield: 96.5%) of viscous reddish brown liquid was obtained.

Example 7.

Synthesis of Hydroquinone-based 2-ethylhexyl benzoxazine [General Formula 2-9 and / or 2-10, R ₁ = 2-ethylhexyl, R ₂ = H, R ₃ = H]

A solution of 68.4 grams (0.8 mole) of formaldehyde aqueous solution (35%) in 150 milliliters of dioxane was added to a 1000 ml three-necked flask equipped with a stirrer and the solution was cooled to 5 ^° C and 51.7 grams (0.4 mole) Of 2-ethylhexylamine dissolved in 100 milliliters of dioxane was slowly dropped over 30 minutes. After the reaction was completed, a solution in which 22.0 grams (0.2 mole) of hydroquinone was dispersed was added to 100 milliliters of dioxane. The reaction was further continued for 30 minutes while stirring at room temperature, and then the temperature was slowly raised to react for 12 hours under reflux conditions. After completion of the reaction, the reaction solution was completely dried in vacuo, and the remaining liquid was diluted with 500 ml of ethyl acetate, washed successively with 3N aqueous sodium hydroxide solution and brine three times, and then the organic solution was separated and dried with anhydrous sodium sulfate And the solvent was blown off in vacuo to give 78.5 grams (yield: 87.9%) of a viscous brown liquid.

Example 8.

Synthesis of bisphenol A-based 2-ethylhexyl benzoxazine [General Formula 2-11, R ₁ = 2-ethylhexyl, R ₂ = H, X═C (CH ₃ ) ₂ ]

A viscous liquid of 97.1 grams (yield: 85.9%) was obtained in the same manner as in Example 7, except that 45.6 grams (0.2 mole) of bisphenol A was used instead of hydroquinone.

Example 9.

Synthesis of hydroquinone-based benzoxazine polymer [General Formula 2-12, R = (CH ₂ ) ₆ , R ₂ = H, R ₃ = H]

24.0 grams (0.8 mole) of paraformaldehyde and 23.2 grams (0.2 mole) of hexamethylenediamine were mixed in 300 milliliters of chloroform and dissolved with heating. To this was slowly added 22.0 grams (0.2 mole) of hydroquinone, mixed well with stirring and allowed to react for 6 hours under reflux conditions. After completion of the reaction, the solvent was blown off in vacuo, and the viscous reaction product was diluted with 500 ml of chloroform, and washed successively with 3N aqueous sodium hydroxide solution and brine three times. The organic solution was separated, dried over anhydrous sodium sulfate, I got a big liquid with all the blowing viscous. This was diluted with 100 milliliters of chloroform, and then gradually dropped into 2 liters of a methanol solution to obtain a solid. It was filtered and then completely dried in vacuo to give 53.4 grams of a pale red solid.

Example 10.

Synthesis of polyvinylphenol-based benzoxazine [General Formula 2-13, R ₁ = 2-ethylhexyl]

24.0 grams (0.8 mole) of paraformaldehyde, 51.7 grams (0.4 mole) of ethylhexylamine and 48.0 grams of poly (4-vinylphenol) were mixed well at room temperature with stirring, Was ^heated to 130 ^° C and reacted for 1 hour. After completion of the reaction, the reaction product was diluted with 200 milliliters of chloroform, and then gradually dropped into 2 liters of an aqueous methanol solution to form a solid. The product was filtered and dried under vacuum to obtain 102.1 grams of a pale yellow solid.

&Lt; Metal ink production and evaluation >

Example 11.

2.0 g of neodecanoic acid was dissolved in a silver neodecanoate solution (xylene at a weight ratio of 3: 5 with xylene in a weight ratio of 1: 1 by weight) Dissolved solution) and mixed well for 10 minutes. This solution was filtered using a 0.45 micron Teflon filter to produce a yellow transparent silver silver precursor ink. The silver ink composition thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C for 30 minutes. As a result, a mirror image was formed well. The adhesive strength was 5 B and the measured surface resistance value was 0.30 Ω / □.

Example 12.

0.2 g of the solution of the cardanol allyl benzoate prepared in Example 2 in a 1: 1 ratio by weight with toluene was mixed with 2.0 g of a neodecanoate solution (in a ratio of 3: 5 in toluene to toluene in a weight ratio ) And mixed well for 10 minutes. This solution was filtered using a 0.45 micron Teflon filter to prepare a brown silver precursor ink. The silver ink composition thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C for 30 minutes. As a result, a mirror image was formed well. The adhesion was 5 B, the measured surface resistance value was 0.25 Ω / □.

Example 13.

0.05 g of neodecanoic acid was added to the ink prepared in Example 11 to prepare an ink, followed by coating and baking at the same temperature. As a result, the mirror image was formed well and the adhesive force was 5B. 0.31? / ?.

Example 14.

An ink was prepared and coated in the same manner as in Example 11 except that the Kadanol-based benzo photograph prepared in Example 3 was used. When the ink was baked at the same temperature, a mirror image was formed well. At this time, The average reflectance measured in the 780nm range was 92.3%, the adhesive strength was 5B, and the measured surface resistance value was 0.24? / ?.

Example 15.

As a result of firing the ink prepared in Example 11 at 250 ° C for 30 minutes, a mirror image was formed and the adhesive strength was 5 B and the measured surface resistance value was 0.15 Ω / □.

Example 16.

As a result of firing the ink prepared in Example 11 at 210 ° C for 30 minutes, an enamel film was formed, and the adhesion was 5B and the measured surface resistance value was 1.54 Ω / □.

Example 17.

The ink prepared in Example 11 was coated on a glass substrate instead of a polyimide (PI) film and fired under the same conditions. As a result, the silver film was well formed, the adhesion was 5B, and the measured surface resistance value was 0.8? / ?.

Example 18.

0.15 grams of the solution of urushiol methylbenzoate prepared in Example 4 in a 1: 1 ratio by weight with xylene, 2.0 grams of neodecanoate solution in a ratio of 3: 5 with xylene in a weight ratio Dissolved solution) and mixed well for 10 minutes. The resulting reddish brown solution was filtered using a 0.45 micron Teflon filter to prepare a brown ink. The silver ink thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C for 30 minutes. As a result, a mirror image was formed well. The adhesive strength was 5 B and the measured surface resistance value was 0.25 Ω / .

Example 19.

The ink was prepared and coated in the same manner as in Example 18 except that the urushiol allyl benzoate prepared in Example 5 was used. When the ink was baked at the same temperature, the mirror image was well formed and the adhesive strength was 5B, The resistance value was 0.21? / ?.

Example 20.

The ink was prepared and coated in the same manner as in Example 18 except that the urushiol benzoquinone prepared in Example 6 was used. When the ink was baked at the same temperature, the mirror image was formed well and the adhesive strength was 5B, the measured surface resistance The value was 0.20? / ?.

Example 21.

0.2 g of the hydroquinone ethylhexylbenzoate prepared in Example 7 dissolved in a 1: 1 ratio by weight with xylene was dissolved in 2.0 g of a silver naphthenate solution (mixed with xylene at a weight ratio of 1: 2 Dissolved solution) and mixed well for 10 minutes. The obtained solution was filtered using a 0.45 micron Teflon filter to prepare a reddish brown ink. The silver ink thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C for 30 minutes. As a result, the mirror image was formed well. The adhesive strength was 5 B and the measured surface resistance value was 0.35 Ω / □ .

Example 22.

0.2 g of the bisphenol-based ethylhexylbenzoate prepared in Example 8 dissolved in a 1: 1 ratio by weight with xylene was mixed with 2.0 g of a neodecanoate solution of silver neodecanoate in a weight ratio of 3: 5 Solution) and mixed well for 10 minutes. The resulting reddish brown solution was filtered using a 0.45 micron Teflon filter to produce a clear transparent ink. The silver ink thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C for 30 minutes. As a result, a mirror image was formed well. The adhesion was 5 B and the measured surface resistance value was 0.45 Ω / □ .

Example 23.

0.1 g of the solution dissolved in a 1: 1 ratio by weight of xylenes of the urushiol benzo prepared in Example 6 was dissolved in 2.0 g of a silver sorbate solution (1: 2 ratio by weight with n-butylamine) Dissolved solution) and mixed well for 10 minutes. This solution was filtered using a 0.45 micron Teflon filter to produce a reddish brown silver precursor ink. The silver ink composition thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C for 30 minutes to form a silver film. The adhesive strength was 5 B and the measured surface resistance value was 0.25 Ω / □ .

Example 24.

The ink was prepared and coated in the same manner as in Example 11, except that the hydroquinone-based benzo photopolymer obtained in Example 9 was used. As a result of firing at the same temperature, the silver film was well formed and the adhesion was 5B, The value was 0.38? / ?.

Example 25.

The ink was prepared and coated in the same manner as in Example 11 except that the polyvinylphenol-based benzo photopolymer obtained in Example 10 was used, and as a result of firing at the same temperature, the silver film was well formed and the adhesive strength was measured as 5B The surface resistance value was 0.56? / ?.

Example 26.

0.1 g of the solution dissolved in a 1: 1 ratio by weight of xylenes of urushiol benzoquinone prepared in Example 6 was dissolved in 2.0 g of gold oxide hydrate (HAuCl ₄ xH2O, chloroauric acid) solution (dissolve in 4: 6 by weight with isopropyl alcohol) and mixed well for 10 minutes. This solution was filtered using a 0.45 micron Teflon filter to produce a reddish brown gold precursor ink. The gold ink composition thus prepared was coated on a polyimide (PI) film using a spin coater and then fired at 230 ° C for 30 minutes. As a result, a gold thin film was well formed on the mirror. The adhesion was 5 B and the measured surface resistance value was 3.2 Ω / □.

Comparative Example 1

In Example 11, ink was prepared and coated in the same manner using only neodecanoic acid without using a cardanol-based methylbenzo photographic compound, and as a result of firing at the same temperature, uneven silver film was formed, and the adhesive strength was measured as 4B The average surface resistance value was 13.2 Ω / □.

Comparative Example 2

An ink was prepared and coated in the same manner as in Example 11 except that a phenoxy resin was used instead of a benzoxazine-based compound. The ink was fired at the same temperature to form a dark film. The adhesive strength was 5 B and the measured surface resistance value was 58.5 kΩ / □.

Example 27.

1.0 gram of Cadenol allylbenzoate prepared in Example 2, 5.0 grams of neodecanoic acid, 5.0 grams of silver oxide and 3.0 grams of alpha-terpineol were mixed well using a hybrid mixer to obtain a uniform paste Ink was obtained. The film was coated on a polyimide (PI) film using a bar coater and then fired at 230 ° C for 30 minutes. The film was well formed and its adhesion was 5B and the measured surface resistance was 0.08 Ω / □.

Example 28.

In the same manner as in Example 27 except that 5.0 g silver nanoparticles having an average particle size of 80 nm were used in place of silver oxide, ink was prepared and coated in the same manner, The adhesive strength was 5B and the measured surface resistance value was 0.10 Ω / □.

Example 29.

60.0 grams of silver particles with an average particle size of 3 microns, 15.0 grams of alpha-terpineol, 20.0 grams of butyl carbitol acetate, and 3-roll mill were used in 5.0 grams of the urushiol benzoquinone prepared in Example 6 Followed by mixing well to obtain a uniform paste ink. It was printed on ITO - coated glass using a screen printer and then fired at 230 ℃ for 30 min. The result showed that the silver film was well formed. The adhesion was 5B and the measured surface resistance value was 0.15 Ω / □.

Example 30.

2.0 g of neodecanoate was dissolved in a mixture of 0.15 g of the solution dissolved in 1: 1 ratio by weight of xylenes and 0.05 g of iron neodecanoate prepared in Example 6, Solution (solution dissolved in xylene at a ratio of 3: 5 by weight) slowly for 10 minutes while slowly dropping. The obtained reddish-brown solution was filtered using a 0.45 micron Teflon filter to prepare a reddish-brown ink. The silver ink thus prepared was coated on a polyimide (PI) film using a spin coater and fired at 230 ° C. for 30 minutes. As a result, a mirror image was formed well. The adhesion was 5 B and the measured surface resistance value was 0.18 Ω / □ .

Example 31.

The procedure of Example 30 was repeated, except that the cardanol-based benzo photograph prepared in Example 3 was used in the form of a mixture solution of 0.15 gram of the solution dissolved with xylene at a weight ratio of 1: 1 and 0.05 gram of stannous neodecanoate , And dark enamel film was formed. The adhesive strength was 5B and the measured surface resistance value was 0.51 Ω / □.

Measurement and evaluation

1) Conductivity evaluation: After making a rectangular sample with a pattern of 1 cm x 3 cm, it is subjected to surface resistance measurement (4 probes) with an AIT model CMT-SR1000N,

2) Adhesion evaluation: Measured by cross-cut tape test (ASTM D3359).

3) Reflectance measurement: Measured using a Varian Cary 5000 in the wavelength range of 380 to 780 nm

Claims (14)

Metal particles or metal precursors; And
1. A conductive ink comprising at least one benzoxazine-based compound selected from the structures listed in the following general formula (1):
[Formula 1]

R ₁ , R _2, R _3, R ₄ and R ₅ are each independently hydrogen, halogen, amino, nitro, cyano, hydroxy, carboxyl, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₆ ring -C ₃₀ aryl, substituted or unsubstituted C ₁ -C ₃₀ heteroalkyl, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl;
R ₂ and R ₃ or R ₃ and R ₄ or R ₄ and R ₅ is connected to form a ring, said ring being composed of one or more atoms selected from the group consisting of C, O and N;
L is a chemical bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene, a substituted or unsubstituted C ₁ -C ₃₀ heteroalkylene, a substituted or unsubstituted C ₆ -C ₃₀ arylene, a substituted or unsubstituted C ₆ -C ₃₀ hetero arylene group, -O-, -C (O) - , -C (O) O-, -C (CH 3) 2 -, -C (CF 3) 2 -, -S-, or -SO ₂ - and;
R is a substituted or unsubstituted C ₁ -C ₃₀ alkylene, a substituted or unsubstituted C ₆ -C ₃₀ arylene, a substituted or unsubstituted C ₁ -C ₃₀ heteroalkylene, or a substituted or unsubstituted C ₅ -C ₃₀ arylene, -C ₃₀ heteroarylene, and;
m is an integer of 1 to 1000; The method according to claim 1,
R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, And examples thereof include methyl, ethyl, propyl, isopropyl, n-butyl, ethylhexyl, n-heptyl, octyl, isoheptyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, docodecyl, cyclopropyl, cyclopentyl, cyclohexyl, , Methoxyethyl, 2-hydroxypropyl, methoxypropyl, aminoethyl, cyanoethyl, mercaptoethyl, chloroethyl, methoxy, ethoxy, butoxy, hexyloxy, phenoxy, methoxyethoxyethyl , One selected from the group consisting of methoxyethoxyethoxyethyl, imidazolyl, carboxymethyl, trimethoxysilylpropyl, triethoxysilylpropyl, phenyl, methoxyphenyl, cyanophenyl, tolyl, Conductive ink. The method according to claim 1,
The compound represented by the general formula (1) is a conductive ink selected from the following general formula (2)
[Formula 2]

In the above formula, Rc is a cadanol-based alkyl and Ru is a uriciol-based alkyl. The method according to claim 1,
R ₂ , And at least one of R ₃ , R ₄ and R ₅ is a hydrocarbon group containing at least one double bond. delete The method according to claim 1,
Wherein the metal precursor compound is a carboxylic acid metal salt. The method according to claim 1,
Wherein the metal precursor compound is a fatty acid metal salt. The method of claim 6,
Wherein the metal of the carboxylic acid metal salt is silver (Ag) or gold (Au). The method according to claim 1,
The conductive ink further comprises at least one additive selected from the group consisting of a solvent, a complexing agent, a resin, a stabilizer, a dispersing agent, a reducing agent, a coupling agent, a leveling agent, a surfactant, a wetting agent, a thickener and a shaving agent. The method according to claim 1,
A conductive ink having a viscosity range of 0.1 to 50 cPs when measured at room temperature of 20 ° C to be suitable for inkjet printing. delete The method according to claim 1,
And a viscosity range of 1 to 100,000 cPs when measured at a room temperature of 20 캜. A conductive thin film obtained by applying the conductive ink according to any one of claims 1 to 4, 6 to 10, and 12. 14. The method of claim 13,
Wherein the conductive thin film comprises a polymer of the benzofosane compound contained in the conductive ink.

Images