JP7190484B2 - Inks for manufacturing electronic devices - Google Patents

Description

The present invention relates to an ink for forming wiring and/or electrodes using a printing method in the manufacture of electronic devices. This application claims priority from Japanese Patent Application No. 2018-069677 filed in Japan on March 30, 2018, and the contents thereof are incorporated herein.

Electronic devices manufactured using the printing method include capacitors, inductors, varistors, thermistors, transistors, speakers, actuators, antennas, solid oxide fuel cells, and the like.

For example, a laminated ceramic capacitor is generally manufactured through the following steps.
1. A slurry containing ceramic powder, a binder resin such as polyvinyl acetal resin, and a solvent is formed into a sheet to obtain a green sheet.
2. An ink containing an electrical property-imparting material (e.g. nickel, palladium, etc.), a binder resin (e.g., ethyl cellulose, etc.), and a fluid organic substance (e.g., terpineol, etc.) is applied to the green sheet by a printing method to form a conductive circuit. Wirings, electrodes, etc. (hereinafter sometimes referred to as “wirings, etc.”) are formed (coating step).
3. The applied ink is dried (drying process).
4. A green sheet on which wiring and the like are formed is cut into a predetermined size, and a plurality of sheets are stacked and pressure-bonded.
5. Firing (firing step).

The binder resin contained in the ink has a function of fixing the electrical property-imparting material on the green sheet and a function of imparting an appropriate viscosity to enable formation of a fine print pattern. Conventionally, ethyl cellulose has been mainly used as the binder resin. However, since ethyl cellulose has low thermal decomposition properties, it needs to be baked at high temperatures. Exposing it to high temperatures for a long time may cause the object to be coated to soften or deform, and the carbon component remains as ash after baking. However, the problem was that it caused a decrease in conductivity.

Various attempts have been made to improve the binder resin in order to solve the above problems. For example, Patent Document 1 discloses that the amount of ash generated can be reduced by using a polyvinyl acetal resin instead of ethyl cellulose. However, the use of polyvinyl acetal resins has not provided sufficiently satisfactory results with respect to these problems.

Japanese Patent Application Laid-Open No. 2006-299030

Accordingly, an object of the present invention is an ink for forming wiring and electrodes of an electronic device by a printing method, which has excellent printing accuracy, can be fired at a low temperature, and has an extremely small amount of ash generated after firing. and to provide a method for producing the same.

As a result of intensive studies by the present inventors in order to solve the above problems, the compound represented by the following formula (1) can thicken the fluid organic substance by making it compatible with the fluid organic substance. A compatibilizer in which the composition is uniformly stabilized (prevents sedimentation, local aggregation, or concentration of the composition and stably maintains a homogeneous state) is obtained, represented by the following formula (1). By adjusting the number of carbon atoms in the compound, it is possible to control the viscosity of the resulting compatible material, it can be fired at a lower temperature than binder resins such as ethyl cellulose, and the amount of ash remaining after firing is extremely low. I found less. The present invention has been completed based on these findings.

（式中、Ｒ¹は炭素数１０～２５の１価の直鎖状脂肪族炭化水素基、Ｒ²、Ｒ³は同一又は異なって、炭素数２、４、６、若しくは８の２価の脂肪族炭化水素基、炭素数６の２価の脂環式炭化水素基、又は２価の芳香族炭化水素基を示し、Ｒ⁴は炭素数１～８の２価の脂肪族炭化水素基を示し、Ｒ⁵、Ｒ⁶は同一又は異なって、炭素数１～３の１価の脂肪族炭化水素基、又はヒドロキシアルキルエーテル基を示す。Ｌ¹～Ｌ³はアミド結合を示し、Ｌ¹とＬ³が－ＣＯＮＨ－である場合、Ｌ²は－ＮＨＣＯ－であり、Ｌ¹とＬ³が－ＮＨＣＯ－である場合、Ｌ²は－ＣＯＮＨ－である）
で表される化合物と流動性有機物質との相溶物を含む、電子デバイス製造用インクを提供する。That is, the present invention provides the following formula (1)

(wherein R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms; R ² and R ³ are the same or different and are divalent hydrocarbon groups having 2, 4, 6 or 8 carbon atoms; represents an aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; wherein R ⁵ and R ⁶ are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L ¹ to L ³ represent an amide bond, and L ¹ and When L ³ is -CONH-, L ² is -NHCO-, and when L ¹ and L ³ are -NHCO-, L ² is -CONH-)
Provided is an ink for manufacturing electronic devices, containing a compatible substance of a compound represented by and a fluid organic substance.

The present invention also provides that the fluid organic substance is at least one selected from hydrocarbon oils, ethers, halogenated hydrocarbons, petroleum components, animal and vegetable oils, silicone oils, esters, aromatic carboxylic acids, pyridines, and alcohols. The ink for manufacturing electronic devices is provided.

The present invention further provides the aforementioned ink for manufacturing electronic devices, which further contains an electrical property-imparting material.

（式中、Ｒ¹は炭素数１０～２５の１価の直鎖状脂肪族炭化水素基、Ｒ²、Ｒ³は同一又は異なって、炭素数２、４、６、若しくは８の２価の脂肪族炭化水素基、炭素数６の２価の脂環式炭化水素基、又は２価の芳香族炭化水素基を示し、Ｒ⁴は炭素数１～８の２価の脂肪族炭化水素基を示し、Ｒ⁵、Ｒ⁶は同一又は異なって、炭素数１～３の１価の脂肪族炭化水素基、又はヒドロキシアルキルエーテル基を示す。Ｌ¹～Ｌ³はアミド結合を示し、Ｌ¹とＬ³が－ＣＯＮＨ－である場合、Ｌ²は－ＮＨＣＯ－であり、Ｌ¹とＬ³が－ＮＨＣＯ－である場合、Ｌ²は－ＣＯＮＨ－である）
で表される化合物と流動性有機物質とを相溶させる工程を経て、前記の電子デバイス製造用インクを得る、電子デバイス製造用インクの製造方法を提供する。The present invention also provides the following formula (1)

(wherein R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms; R ² and R ³ are the same or different and are divalent hydrocarbon groups having 2, 4, 6 or 8 carbon atoms; represents an aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; wherein R ⁵ and R ⁶ are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L ¹ to L ³ represent an amide bond, and L ¹ and When L ³ is -CONH-, L ² is -NHCO-, and when L ¹ and L ³ are -NHCO-, L ² is -CONH-)
Provided is a method for producing an ink for producing an electronic device, which obtains the above-mentioned ink for producing an electronic device through a step of making the compound represented by and a fluid organic substance compatible with each other.

The ink of the present invention has moderate viscosity and shear thinning properties. Therefore, it is difficult to drip and has good coating properties (or ejection properties). Also, the edge of the drawing portion can be formed sharply, and the printing accuracy can be improved. Furthermore, the ink of the present invention can stably maintain the uniformity of composition. For example, when the ink of the present invention contains an electrical property-imparting agent, it is possible to prevent sedimentation and local aggregation of the electrical property-imparting agent and stably maintain a uniformly highly dispersed state.
Furthermore, compared to the ink obtained by thickening the fluid organic substance with ethyl cellulose, the ink of the present invention can be baked at a low temperature, and the object coated with the ink can be exposed to a high temperature for a long time. can prevent softening and deformation. In addition, the residual amount of ash after baking can be significantly reduced, and various problems caused by residual ash (for example, deterioration of electrical properties when used in conductive ink) can be suppressed. be able to.
Therefore, the ink of the present invention can be suitably used for manufacturing electronic devices. By using the ink of the present invention, it is possible to precisely form wiring having excellent electrical properties by a printing method.

FIG. 2 shows the results of ¹ H-NMR measurement of compound (2-3) obtained in Preparation Example. FIG. 1 shows the results of ¹ H-NMR measurement of compound (1-3) obtained in Preparation Example. FIG. 2 shows the results of ¹ H-NMR measurement of compound (2-4) obtained in Preparation Example. FIG. 1 shows the results of ¹ H-NMR measurement of compound (1-4) obtained in Preparation Example. FIG. 2 shows the results of ¹ H-NMR measurement of compound (2-1) obtained in Preparation Example. 1 is a diagram showing the results of ¹ H-NMR measurement of compound (1-1) obtained in Preparation Example. FIG.

[Inks for manufacturing electronic devices]
The ink of the present invention is an ink that can be suitably used for manufacturing electronic devices, and is an ink that is suitable for forming wiring, electrodes, etc. of electronic devices by applying the ink by a printing method. The ink of the present invention is a composition containing a compatible substance of compound (1) and a fluid organic substance, and the compound (1) thickens the fluid organic substance and stabilizes the composition uniformly. composition.

（式中、Ｒ¹は炭素数１０～２５の１価の直鎖状脂肪族炭化水素基、Ｒ²、Ｒ³は同一又は異なって、炭素数２、４、６、若しくは８の２価の脂肪族炭化水素基、炭素数６の２価の脂環式炭化水素基、又は２価の芳香族炭化水素基を示し、Ｒ⁴は炭素数１～８の２価の脂肪族炭化水素基を示し、Ｒ⁵、Ｒ⁶は同一又は異なって、炭素数１～３の１価の脂肪族炭化水素基、又はヒドロキシアルキルエーテル基を示す。Ｌ¹～Ｌ³はアミド結合を示し、Ｌ¹とＬ³が－ＣＯＮＨ－である場合、Ｌ²は－ＮＨＣＯ－であり、Ｌ¹とＬ³が－ＮＨＣＯ－である場合、Ｌ²は－ＣＯＮＨ－である）(Compound (1))
The compound (1) is represented by the following formula (1).

(wherein R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms; R ² and R ³ are the same or different and are divalent hydrocarbon groups having 2, 4, 6 or 8 carbon atoms; represents an aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; wherein R ⁵ and R ⁶ are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L ¹ to L ³ represent an amide bond, and L ¹ and When L ³ is -CONH-, L ² is -NHCO-, and when L ¹ and L ³ are -NHCO-, L ² is -CONH-)

R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms, such as decyl, lauryl, myristyl, pentadecyl, stearyl, palmityl, nonadecyl, eicosyl and behenyl; straight-chain alkyl groups such as groups; straight-chain alkenyl groups such as decenyl, pentadecenyl, oleyl and eicosenyl groups; and straight-chain alkynyl groups such as pentadecynyl, octadecyl and nonadecynyl groups.

As R ¹ , among others, a monovalent A straight-chain aliphatic hydrocarbon group (particularly preferably an alkyl group having 14 to 25 carbon atoms) is preferred, and a monovalent straight-chain aliphatic hydrocarbon group having 18 to 21 carbon atoms is particularly preferred (particularly preferably , an alkyl group having 18 to 21 carbon atoms).

Examples of divalent aliphatic hydrocarbon groups having 2, 4, 6 or 8 carbon atoms in R ² and R ³ include ethylene group, n-butylene group, n-hexylene group and n-octylene group. .

Examples of the divalent alicyclic hydrocarbon group having 6 carbon atoms for R ² and R ³ include 1,4-cyclohexylene group, 1,3-cyclohexylene group and 1,2-cyclohexylene group. .

Examples of divalent aromatic hydrocarbon groups for R ² and R ³ include arylene groups having 6 to 10 carbon atoms such as 1,4-phenylene group, 1,3-phenylene group and 1,2-phenylene group. mentioned.

As R ² and R ³ , among others, a divalent aliphatic hydrocarbon group having 2, 4, 6 or 8 carbon atoms (particularly preferably a straight-chain alkylene group), more preferably a divalent aliphatic hydrocarbon group having 2, 4, or 6 carbon atoms (especially preferably a linear alkylene group), particularly preferably a divalent having 2 or 4 carbon atoms (particularly preferably a straight-chain alkylene group), most preferably a divalent aliphatic hydrocarbon group having 2 carbon atoms (particularly preferably a straight-chain alkylene group).

R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, and among these, a linear or branched alkylene group is preferred, and particularly preferred, in terms of its excellent thickening effect for fluid organic substances. is a linear alkylene group.

In addition, R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, and more preferably a divalent Aliphatic hydrocarbon groups, particularly preferably divalent aliphatic hydrocarbon groups having 3 to 7 carbon atoms, most preferably divalent aliphatic hydrocarbon groups having 3 to 6 carbon atoms, most preferably 3 to 5 carbon atoms is a divalent aliphatic hydrocarbon group.

Therefore, R ⁴ is preferably a linear or branched alkylene group having 1 to 8 carbon atoms, more preferably a linear alkylene group having 1 to 7 carbon atoms, and most preferably a linear alkylene group having 3 to 7 carbon atoms. A linear alkylene group having 3 to 6 carbon atoms is most preferable, and a linear alkylene group having 3 to 5 carbon atoms is particularly preferable.

Examples of monovalent aliphatic hydrocarbon groups having 1 to 3 carbon atoms for R ⁵ and R ⁶ include linear or branched chain groups having 1 to 3 carbon atoms such as methyl, ethyl, propyl and isopropyl groups. straight-chain or branched-chain alkenyl groups having 2 to 3 carbon atoms such as vinyl group, 1-methylvinyl group and 2-propenyl group; straight chain having 2-3 carbon atoms such as ethynyl group and propynyl group and a branched or branched alkynyl group.

Hydroxyalkyl ether groups for R ⁵ and R ⁶ include mono- or di(hydroxy)C _1-3 alkyl ether groups such as 2-hydroxyethoxy group, 2-hydroxypropoxy group and 2,3-dihydroxypropoxy group. is mentioned.

R ⁵ and R ⁶ are preferably the same or different and are preferably monovalent aliphatic hydrocarbon groups having 1 to 3 carbon atoms, more preferably linear or branched alkyl groups having 1 to 3 carbon atoms. is preferably a straight-chain alkyl group having 1 to 3 carbon atoms, most preferably a methyl group.

Among the compounds represented by the formula (1), the compounds represented by the following formulas (1-1) to (1-9) are preferable because of their excellent solubility in fluid organic substances. In addition, the compound is preferable for the fluid organic substance in that, when the fluid organic substance is transparent, it can be thickened and stabilized while maintaining the transparency.

（式中、Ｒ¹は炭素数１０～２５の１価の直鎖状脂肪族炭化水素基、Ｒ²、Ｒ³は同一又は異なって、炭素数２、４、６、若しくは８の２価の脂肪族炭化水素基、炭素数６の２価の脂環式炭化水素基、又は２価の芳香族炭化水素基を示し、Ｒ⁴は炭素数１～８の２価の脂肪族炭化水素基を示し、Ｒ⁵、Ｒ⁶は同一又は異なって、炭素数１～３の１価の脂肪族炭化水素基、又はヒドロキシアルキルエーテル基を示す。Ｌ¹～Ｌ³はアミド結合を示し、Ｌ¹とＬ³が－ＣＯＮＨ－である場合、Ｌ²は－ＮＨＣＯ－であり、Ｌ¹とＬ³が－ＮＨＣＯ－である場合、Ｌ²は－ＣＯＮＨ－である。Ｒ⁷は水素原子又は炭素数１～３のアルキル基を示す。尚、式（３）において、ＯＲ⁷はＬ²を構成する水素原子と脱水縮合又は脱アルコール縮合して、環を形成していてもよい）(Method for producing compound (1))
Compound (1) is a compound represented by the following formula (3) (hereinafter sometimes referred to as "compound (3)") and a compound represented by the following formula (4) (hereinafter referred to as "compound (4 )”), or a compound represented by the following formula (3′) (hereinafter sometimes referred to as “compound (3′)”) and the following formula (4′) By reacting the compound represented by (hereinafter sometimes referred to as "compound (4')"), the compound represented by the following formula (2) (hereinafter sometimes referred to as "compound (2)" ) and oxidizing the resulting compound (2).

(wherein R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms; R ² and R ³ are the same or different and are divalent hydrocarbon groups having 2, 4, 6 or 8 carbon atoms; represents an aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; wherein R ⁵ and R ⁶ are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L ¹ to L ³ represent an amide bond, and L ¹ and When L ³ is —CONH—, L ² is —NHCO—, and when L ¹ and L ³ are —NHCO—, L ² is —CONH— R ⁷ is a hydrogen atom or has 1 carbon atom represents an alkyl group of 1 to 3. In formula (3), OR ⁷ may undergo dehydration condensation or dealcoholization condensation with a hydrogen atom constituting L ² to form a ring.)

R ¹ to R ⁶ and L ¹ to L ² in the above formula are the same as above.

Examples of the alkyl group having 1 to 3 carbon atoms for R ⁷ in the above formulas (3) and (4') include methyl group, ethyl group, propyl group and isopropyl group.

Examples of the ring formed by dehydration condensation or dealcoholization condensation of OR ⁷ in formula (3) with a hydrogen atom constituting L ² include pyrrolidine-2,5-dione ring and piperidine-2,6-dione. ring and the like.

The amount of compound (4) used should be 1 mol or more per 1 mol of compound (3), and an excess amount can be used.

The amount of compound (4') to be used should be 1 mol or more per 1 mol of compound (3'), and an excess amount can also be used.

The reaction of compound (3) and compound (4) or compound (3') and compound (4') can be carried out by stirring at a temperature of 100 to 120°C for 10 to 20 hours, for example.

The reaction atmosphere is not particularly limited as long as it does not hinder the reaction, and may be, for example, an air atmosphere, a nitrogen atmosphere, an argon atmosphere, or the like. Moreover, the reaction can be carried out by any method such as a batch system, a semi-batch system, or a continuous system.

After completion of the reaction, the resulting reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination thereof.

Compounds (2) thus obtained are preferably compounds represented by the following formulas (2-1) to (2-9).

As the compound (3), for example, a compound represented by the following formula (3-1) can be produced by the following method. R ¹ , R ² , R ³ and R ⁷ in the following formula are the same as above. Also, R ⁷ in formula (3a) and two R ⁷ in formula (3d) may be the same or different. Furthermore, in the compound represented by formula (3d), two COOR ⁷ in the formula may undergo dehydration condensation to form an acid anhydride.

As the compound (3'), for example, a compound represented by the following formula (3'-1) can be produced by the following method. R ¹ , R ² , R ³ and R ⁷ in the following formula are the same as above. Two R ⁷ in formula (3b') may be the same or different. Also, in the compound represented by the formula (3b'), two COOR ⁷ in the formula may be dehydrated and condensed to form an acid anhydride.

The step [1] is a step of reacting the compound represented by the formula (3a) with the compound represented by the formula (3b) to obtain the compound represented by the formula (3c). The amount of the compound represented by the formula (3b) to be used should be 1 mol or more per 1 mol of the compound represented by the formula (3a), and an excess amount can also be used. The reaction temperature for this reaction is, for example, 80 to 150° C., and the reaction time is, for example, about 1 to 24 hours.

The step [2] is a step of reacting the compound represented by the formula (3c) with the compound represented by the formula (3d) to obtain the compound represented by the formula (3-1). The amount of the compound represented by formula (3d) to be used may be 1 mol or more, preferably 1 to 3 mol, per 1 mol of the compound represented by formula (3c). The reaction temperature for this reaction is, for example, 80 to 150° C., and the reaction time is, for example, about 0.5 to 10 hours. As this reaction proceeds, water is produced. Therefore, it is preferable to carry out the reaction while removing water using a dehydrating agent (eg, acetic anhydride, etc.) in order to promote the progress of the reaction.

The reaction of [2] is preferably carried out in the presence of a solvent. Examples of the solvent include pentafluorophenol, N,N-dimethylformamide, dimethylacetamide, o-dichlorobenzene and the like. These can be used individually by 1 type or in combination of 2 or more types.

In addition, the reaction of [2] can be carried out in the presence of a base such as triethylamine, pyridine, 4-dimethylaminopyridine, etc., if necessary.

The step [3] is a step of reacting the compound represented by the formula (3a') with the compound represented by the formula (3b') to obtain the compound represented by the formula (3c'). The reaction [3] can be carried out under the same conditions as the reaction [2] above.

The step [4] is a step of reacting the compound represented by the formula (3c') with the compound represented by the formula (3d') to obtain the compound represented by the formula (3'-1). . The reaction [4] can be carried out under the same conditions as the reaction [1] above.

After completion of the reaction in each step, the resulting reaction product is separated by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination of these separation means. can be refined.

As an oxidizing agent used for oxidizing the compound (2) obtained by the above method, for example, hydrogen peroxide can be used. As the hydrogen peroxide, pure hydrogen peroxide may be used, but from the viewpoint of handling, it is usually diluted with an appropriate solvent (eg, water) and used (eg, 5 to 70% by weight excess hydrogen oxide). The amount of hydrogen peroxide to be used is, for example, about 0.1 to 10 mol per 1 mol of compound (2).

The oxidation reaction can be carried out, for example, by stirring at a temperature of 30-70° C. for 3-20 hours.

The oxidation reaction of compound (2) is carried out in the presence or absence of a solvent. Examples of the solvent include alcohol solvents such as methanol, ethanol, 2-propanol and butanol; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, dioxolane, 1,2-dimethoxyethane and cyclopentylmethyl ether. ester solvents such as butyl acetate and ethyl acetate; hydrocarbon solvents such as pentane, hexane, heptane and octane; nitrile solvents such as acetonitrile and benzonitrile. These can be used individually by 1 type or in combination of 2 or more types.

After completion of the reaction, the resulting reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination thereof.

(fluid organic substance)
The fluid organic substance as a raw material is an organic substance having a rheometer viscosity [viscosity (η) at a shear rate of 1 s ⁻¹ at 25° C.] of less than 0.5 Pa·s, for example. Examples of such fluid organic substances include hydrocarbon oils (e.g., hexane, cyclohexane, isododecane, benzene, toluene, poly-α-olefins, liquid paraffin, etc.), ethers (e.g., tetrahydrofuran, etc.), halogenated hydrocarbons, (e.g., carbon tetrachloride, chlorobenzene, etc.), petroleum ingredients (e.g., kerosene, gasoline, light oil, heavy oil, etc.), animal and vegetable oils (e.g., sunflower oil, olive oil, soybean oil, corn oil, castor oil, beef tallow, jojoba oil, squalane, etc.), silicone oils (e.g., dimethylpolysiloxane, methylphenylpolysiloxane, etc.), esters (e.g., octyldodecyl oleate, cetyl octanoate, cetyl ethylhexanoate, glyceryl triisooctanate, neopentyl glycol diiso octanate, etc.), aromatic carboxylic acids, pyridine, alcohols (e.g., α-terpineol, dihydroterpineol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1, 3-butanediol, 1,4-butanediol) and the like. These can be used individually by 1 type or in combination of 2 or more types.

[Method for producing ink for electronic device production]
The ink of the present invention can be produced through a step of making compound (1) and a fluid organic substance compatible. More specifically, it can be produced by mixing the total amount of the fluid organic substance and the compound (1), heating the mixture, and then cooling the mixture to dissolve it. Alternatively, compound (1) is mixed with a portion of the fluid organic substance, heated, and then cooled to produce an ink, which is then mixed with the rest of the fluid organic substance. can be manufactured.

The temperature at which the compound (1) and the fluid organic substance are dissolved is appropriately selected depending on the type of the compound (1) and the fluid organic substance, and is not particularly limited as long as it is a temperature at which the compound (1) and the fluid organic substance are compatible. It is preferable not to exceed 100°C, and if the boiling point of the fluid organic substance is 100°C or less, it is preferably about the boiling point.

Cooling after dissolution may be carried out as long as it can be cooled to room temperature (for example, 25° C.) or lower, and it may be gradually cooled at room temperature, or rapidly cooled by ice cooling or the like.

The amount of compound (1) used depends on the type of the fluid organic substance, but is for example 0.1 to 100 parts by weight, preferably 0.5 to 80 parts by weight, based on 1000 parts by weight of the fluid organic substance. Especially preferably 1 to 60 parts by weight, most preferably 1 to 30 parts by weight. By using the compound (1) within the above range, the fluid organic substance is thickened and a compatible material having a uniformly stabilized composition can be obtained.

The ink of the present invention may contain other components other than the compatible substance of the compound (1) and the fluid organic substance within a range that does not impair the effect of the present invention. The content of the compatible substance (or the total amount of the compound (1) and the fluid organic substance) in the total amount is, for example, 30% by weight or more, preferably 50% by weight or more, particularly preferably 60% by weight or more, and most preferably is 70% by weight or more, particularly preferably 90% by weight or more, and more preferably 97% by weight or more. The upper limit is, for example, 99.9% by weight.

The ink of the present invention preferably contains an electrical property-imparting material (eg, at least one selected from conductive metal materials, semiconductor materials, magnetic materials, dielectric materials, and insulating materials) as another component. .

As the conductive metal material and magnetic material, well-known and commonly used materials can be used. Examples include iron/chromium oxide, ferrite, and alloys thereof. Well-known and commonly used semiconductor materials can be used, for example, pentacene, fullerene derivatives, polythiophene derivatives, metals (copper, indium, gallium, selenium, arsenic, cadmium, tellurium, and alloys thereof), silicon fine particles, and the like. can be mentioned. As the dielectric material and insulating material, well-known and commonly used materials can be used, such as cycloolefin polymer, fluororesin, butyral resin, glass, paper, Teflon (registered trademark), and the like.

The content of the electrical property-imparting material (the total amount when two or more are contained) is, for example, about 0.1 to 30% by weight, preferably 0.1 to 20%, based on the total amount (100% by weight) of the ink for manufacturing electronic devices. % by weight, particularly preferably 0.1 to 10% by weight, most preferably 0.1 to 5% by weight, especially preferably 0.1 to 3% by weight.

The viscosity of the ink of the present invention measured by a rheometer [viscosity (η) at a shear rate of 0.3 s ⁻¹ at 25° C.] is in the range of 10 Pa s or more (for example, 10 to 100 Pa s). It is preferable in that the applied composition can be prevented from sagging or flowing, and the application accuracy can be improved. In addition, the uniformity of the composition can be stably maintained, and when the ink for manufacturing an electronic device of the present invention contains an electrical property-imparting agent, sedimentation and local aggregation of the electrical property-imparting agent can be prevented. , is preferable in that a uniformly highly dispersed state can be stably maintained.

In addition, the viscosity of the ink of the present invention measured by a rheometer [viscosity (η) at a shear rate of 0.1 s ⁻¹ at 25° C.] is in the range of 10 Pa s or more (for example, 10 to 100 Pa s). It is preferable in that the applied composition can be prevented from sagging or flowing, and the application accuracy can be improved. In addition, the uniformity of the composition can be stably maintained, and when the ink for manufacturing an electronic device of the present invention contains an electrical property-imparting agent, sedimentation and local aggregation of the electrical property-imparting agent can be prevented. , is preferable in that a uniformly highly dispersed state can be stably maintained.

The ink of the present invention has a shear-thinning property, and the viscosity ratio [viscosity at 25° C. and a shear rate of 1 s ⁻¹ measured by a rheometer/viscosity ratio at a shear rate of 10 s ⁻¹ measured by a rheometer] is, for example, It is greater than 1.5, preferably 2 or more, particularly preferably 3 or more. The upper limit is, for example, 10, preferably 8. Therefore, the viscosity can be lowered during application, and, for example, when the application is performed using a printing machine or the like, the ejection property is excellent. Moreover, by rapidly increasing the viscosity after application, the applied composition can be prevented from sagging and the application accuracy can be improved.

Since the ink of the present invention has appropriate viscosity and shear thinning properties as described above, a binder resin (for example, a polymer compound having a molecular weight of 10,000 or more such as ethyl cellulose resin, alkyl cellulose resin, polyvinyl acetal resin, acrylic resin, etc.) is used. It is not necessary to add, and even if it is added, the amount added is, for example, 10% by weight or less, preferably 5% by weight or less, of the total amount of ink (100% by weight). If the amount of the binder resin added exceeds the above range, the ash derived from the binder resin generated by firing causes deterioration in electrical properties, which is not preferable.

Furthermore, the above-mentioned compatible substance contained in the ink of the present invention has excellent thermal decomposability and is easily reduced in molecular weight. Therefore, the ink of the present invention can be fired at a lower temperature (for example, 100 to 350° C., preferably 150 to 300° C., particularly preferably 150 to 250° C.) compared to the ink to which viscosity is imparted by a binder resin such as ethyl cellulose. It is possible to prevent softening and deformation of the object to be coated in the baking process.

Since the ink of the present invention has the above properties, it can be discharged satisfactorily onto the surface of a base material (for example, a ceramic substrate, a green sheet, etc.) by, for example, screen printing, and the edge of the drawing portion can be made sharper. Printing accuracy can be improved. In addition, when the ink of the present invention contains an electrical property-imparting material, the sedimentation and local aggregation of the electrical property-imparting material are prevented, and a uniformly highly dispersed state is stably maintained for ejection and printing. By drying and baking the ejected ink, it is possible to accurately form wiring having excellent electrical properties (for example, conductivity or insulation).

Therefore, the ink of the present invention can be used, for example, as an ink for manufacturing wiring and/or electrodes of capacitors, inductors, varistors, thermistors, speakers, actuators, antennas, solid oxide fuel cells (SOFC), etc. (especially multilayer ceramic capacitors). Especially useful.

When the ink of the present invention contains an electrical property-imparting material, it is selectively discharged, for example, by screen printing or the like to desired positions on the substrate surface provided with electrodes, circuits, etc., and then electronic parts or the like are attached. By sintering them together, the substrate and electronic components can be electrically connected. In addition, since it can be fired at a low temperature, it can be mounted at a lower temperature than solder mounting, and can be used for mounting electronic components having poor heat resistance.

Therefore, the ink of the present invention can be used as an adhesive ( For example, it is particularly useful as a conductive adhesive).

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples.

Preparation Example 1 <Production of compound (1-3)>
Methyl docosanoate (20.0 g, 56.4 mmol) and ethylenediamine (16.9 g, 281 mmol) were stirred at 110° C. for 18 hours and the reaction was washed with methanol before filtering. The solvent was distilled off from the filtrate, and the resulting residue was purified by recrystallization using hexane. N-docosanoylethylenediamine was obtained as white crystals (yield 65%, 14.0 g, 36.7 mmol).

To a solution of N-dimethylformamide (40 ml) was added N-docosanoylethylenediamine (12.0 g, 31.4 mmol) and triethylamine (6.35 g, 62.8 mmol) to succinic anhydride (3.45 g, 34.5 mmol). was added in minutes and stirred at 100° C. for 15 minutes. After dissolving the succinic anhydride, acetic anhydride (4.81 g, 47.1 mmol) was added dropwise to the reaction crude liquid over 10 minutes, and the mixture was stirred at 100°C for 1 hour. The reaction mixture was poured into water (200ml) and the precipitate was filtered and washed with water. The precipitate was purified and purified by recrystallization with 2-propanol. N-docosanoylaminoethylsuccinimide was obtained as a white crystalline powder (92% yield, 13.4 g, 28.9 mmol).

N-docosanoylaminoethylsuccinimide (4.00 g, 8.60 mmol) and N,N-dimethyl-1,3-propanediamine (2.63 g, 25.8 mmol) were stirred at 120° C. for 18 hours. The reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. The obtained solid was purified by recrystallization using acetone and methanol. N-(docosanoylaminoethylaminosuccinamoylaminopropyl)-N,N-dimethylamine (compound (2-3)) represented by the following formula (2-3) was obtained as a white crystalline powder ( Yield 94%, 4.58 g, 8.08 mmol). ¹ H-NMR (CDCl ₃ ) measurement results of the obtained compound are shown in FIG.

N-(docosanoylaminoethylaminosuccinamoylaminopropyl)-N,N-dimethylamine (4.00 g, 7.06 mmol), 35% hydrogen peroxide solution (2.06 ml) and 2-propanol (10 ml) was stirred at 60° C. for 5 hours. Palladium carbon (about 10 mg) was added to the reaction solution and stirred at room temperature for 18 hours. The reaction mixture was filtered, the solvent was distilled off, and the residue was purified by column chromatography (silica gel, 2-propanol/methanol). N-(docosanoylaminoethylaminosuccinamoylaminopropyl)-N,N-dimethylamine oxide (compound (1-3)) represented by the following formula (1-3) was obtained as a white solid (yield: yield 69%, 2.84 g, 4.87 mmol). ¹ H-NMR (CDCl ₃ ) measurement results of the obtained compound are shown in FIG.

Preparation Example 2 <Production of compound (1-4)>
N-docosanoylaminoethylsuccinimide was obtained in the same manner as in Preparation Example 1.

The resulting N-docosanoylaminoethylsuccinimide (8.00 g, 17.2 mmol) and hexamethylenediamine (10.0 g, 86.1 mmol) were stirred at 120° C. for 18 hours. The reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. The obtained solid was purified by recrystallization using acetonitrile and methanol. N-(docosanoylaminoethyl)aminosuccinamoylaminohexylamine was obtained as a white crystalline powder (69% yield, 6.91 g, 11.9 mmol).

N-(docosanoylaminoethyl)aminosuccinamoylaminohexylamine (3.25 g, 5.59 mmol), 37% aqueous formaldehyde (2.73 ml) and formic acid (1.55 g, 33.7 mmol) were treated with 2-propanol ( 15 ml) and stirred at 100° C. for 4 hours. The reaction mixture was poured into 1M aqueous sodium hydroxide solution (20 ml) and crystals were filtered. The obtained crystals are recrystallized with methanol and acetone to give N-(docosanoylaminoethylaminosuccinamoylaminohexyl)-N,N-dimethylamine (compound (2 -4)) was obtained as a white solid (89% yield, 3.03 g, 4.98 mmol). ¹ H-NMR (CDCl ₃ ) measurement results of the obtained compound are shown in FIG.

N-(docosanoylaminoethylaminosuccinamoylaminohexyl)-N,N-dimethylamine (2.80 g, 4.60 mmol), 35% hydrogen peroxide solution (1.30 ml) and 2-propanol (10 ml) was stirred at 60° C. for 5 hours. Palladium carbon (about 10 mg) was added to the reaction solution and stirred at room temperature for 18 hours. The reaction mixture was filtered, the solvent was distilled off, and the residue was purified by column chromatography (silica gel, 2-propanol/methanol). N-(docosanoylaminoethylaminosuccinamoylaminohexyl)-N,N-dimethylamine oxide (compound (1-4)) represented by the following formula (1-4) was obtained as a white solid (yield: yield 74%, 2.13 g, 3.40 mmol). ¹ H-NMR (CDCl ₃ ) measurement results of the obtained compound are shown in FIG.

Preparation Example 3 <Production of compound (1-1)>
Methyl eicosanoate (18.0 g, 55.1 mmol) and ethylenediamine (16.5 g, 276 mmol) were stirred at 110° C. for 18 hours and the reaction was washed with methanol before filtering. The solvent was distilled off from the filtrate, and the resulting residue was purified by recrystallization using hexane. N-eicosanoylethylenediamine was obtained as white crystals (yield 68%, 13.3 g, 37.5 mmol).

To a solution of N-dimethylformamide (30 ml) was added N-eicosanoylethylenediamine (10.0 g, 28.2 mmol) and triethylamine (5.71 g, 56.4 mmol) to succinic anhydride (3.10 g, 31.0 mmol). Add over 10 minutes and stir at 100° C. for 15 minutes. After dissolving the succinic anhydride, acetic anhydride (4.32 g, 42.3 mmol) was added dropwise to the reaction crude liquid over 10 minutes, and the mixture was stirred at 100°C for 1 hour. The reaction mixture was poured into water (150ml) and the precipitate was filtered and washed with water. The precipitate was purified and purified by recrystallization with 2-propanol. Yield (11.2 g, 25.7 mmol) of N-eicosanoylaminoethylsuccinimide was obtained as a 91% white crystalline powder.

N-Eicosanoylaminoethylsuccinimide (4.00 g, 9.16 mmol) and N,N-dimethyl-1,3-propanediamine (2.81 g, 27.5 mmol) were stirred at 120° C. for 18 hours. The reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. The obtained solid was purified by recrystallization using acetone and methanol. N-(Eicosanoylaminoethylaminosuccinamoylaminopropyl)-N,N-dimethylamine (compound (2-1)) represented by the following formula (2-1) was obtained as a white crystalline powder. (91% yield, 4.49 g, 8.34 mmol). ¹ H-NMR (CDCl ₃ ) measurement results of the obtained compound are shown in FIG.

N-(Eicosanoylaminoethylaminosuccinamoylaminopropyl)-N,N-dimethylamine (4.00 g, 7.42 mmol), 35% hydrogen peroxide solution (2.16 ml) and 2-propanol (10 ml) ) was stirred at 60° C. for 5 hours. Palladium carbon (about 10 mg) was added to the reaction solution and stirred at room temperature for 18 hours. The reaction mixture was filtered, the solvent was distilled off, and the residue was purified by column chromatography (silica gel, 2-propanol/methanol). N-(Eicosanoylaminoethylaminosuccinamoylaminopropyl)-N,N-dimethylamine oxide (compound (1-1)) represented by the following formula (1-1) was obtained as a white solid ( Yield 58%, 2.39 g, 4.30 mmol). ¹ H-NMR (CDCl ₃ ) measurement results of the obtained compound are shown in FIG.

Preparation Example 4 <Production of compound (1-5)>
A compound represented by the following formula (2-5) was obtained in the same manner as in Preparation Example 2 except that methyl octadecanoate was used instead of methyl docosanoate, and a compound represented by the following formula (1-5) was obtained. Obtained.

Preparation Example 5 <Production of compound (1-6)>
A compound represented by the following formula (2-6) was obtained in the same manner as in Preparation Example 1 except that methyl octadecanoate was used instead of methyl docosanoate, and a compound represented by the following formula (1-6) was obtained. Obtained.

Preparation Example 6 <Production of compound (1-7)>
A compound represented by the following formula (2-7) was obtained in the same manner as in Preparation Example 2 except that methyl palmitate was used instead of methyl docosanoate, and a compound represented by the following formula (1-7) was obtained. Obtained.

Preparation Example 7 <Production of compound (1-8)>
A compound represented by the following formula (2-8) was obtained in the same manner as in Preparation Example 1 except that methyl palmitate was used instead of methyl docosanoate, and a compound represented by the following formula (1-8) was obtained. Obtained.

Preparation Example 8 <Production of compound (1-9)>
A compound represented by the following formula (2-9) was obtained in the same manner as in Preparation Example 2 except that methyl myristate was used instead of methyl docosanoate, and a compound represented by the following formula (1-9) was obtained. Obtained.

Examples 1-8, Comparative Examples 1-2 <Production of ink>
Various flowable organic substances (1,3-butanediol (1,3-BG), α-terpineol (TPO)) shown in Table 1 were weighed into test tubes by 1 cm ³ . 10 mg of each of the obtained compounds was added and mixed, heated and stirred at 100° C. to make the fluid organic substance and the compound compatible, and cooled to 25° C. to obtain an ink. In Comparative Examples, ethyl cellulose (EC: trade name “Ethocel STD200”, manufactured by Nisshin Kasei Co., Ltd.) was used in place of the compounds obtained in Preparation Examples, and dissolved by heating at a liquid temperature of 80°C for 24 hours. The ink was obtained by cooling to 25°C.

The viscosity of the resulting ink was measured using a cone-plate sensor (using a cone angle of 1° for a diameter of 60 mm and a cone angle of 1°, 2°, and 4° for a diameter of 35 mm) and a viscosity and viscoelasticity measuring device (rheometer) equipped with a Peltier temperature controller. ) (trade name “RheoStress600”, manufactured by HAAKE), under conditions of 25 ° C., the viscosity is measured by changing the shear rate in logarithmic increments from 0.1 to 100 s ⁻¹ in a steady flow viscosity measurement mode. Viscosity effects (shear thinning properties and thickening properties) were evaluated.

<Shear thinning property evaluation>
The shear thinning properties of the obtained ink were evaluated according to the following criteria from [viscosity at a shear rate of 1 s ^-1 /viscosity at a shear rate of 10 s ^-1 ].
1: 1.5 or less 2: over 1.5 and 3.0 or less 3: over 3.0 and 4.5 or less 4: over 4.5

<Thickening evaluation>
Based on the viscosity of the obtained ink at a shear rate of 0.1 s ^-1 , the thickening property was evaluated according to the following criteria.
1: 5 Pa s or less 2: More than 5 Pa s and 10 Pa s or less 3: More than 10 Pa s and 50 Pa s or less 4: More than 50 Pa s

In addition, the residual ash content at 250° C. of the inks obtained in Examples and Comparative Examples was measured by the following method.
Using TG-DTA, 20 mg of each ink is heated from 20 ° C. to 400 ° C. at 10 ° C./min, and the residual ash content at 250 ° C. is measured, and the ratio of the residual ash content to the total amount of ink (= ash residual rate). was calculated.

The above results are summarized in the table below.

From Table 1 above, it was confirmed that the ink of the present invention has moderate viscosity and shear-thinning properties, and has a very low residual ash ratio. On the other hand, the inks of Comparative Examples had low viscosity, poor shear-thinning properties, and high residual ash ratio.

As a summary of the above, the configuration of the present invention and its variations will be added below.
[1] An ink containing a compatible substance of the compound represented by formula (1) and a fluid organic substance.
[2] The ink according to [1], wherein R ² and R ³ in formula (1) are the same or different and are a divalent aliphatic hydrocarbon group having 2, 4, 6 or 8 carbon atoms.
[3] The ink according to [1], wherein R ² and R ³ in formula (1) are the same or different and are a linear alkylene group having 2, 4, 6 or 8 carbon atoms.
[4] The ink according to [1], wherein R ² and R ³ in formula (1) are the same or different and are a divalent aliphatic hydrocarbon group having 2 or 4 carbon atoms.
[5] The ink according to [1], wherein R ² and R ³ in formula (1) are the same or different and are a linear alkylene group having 2 or 4 carbon atoms.
[6] The ink according to [1], wherein R ² and R ³ in formula (1) are the same or different and are a divalent aliphatic hydrocarbon group having 2 carbon atoms.
[7] The ink according to [1], wherein R ² and R ³ in formula (1) are the same linear alkylene group having 2 carbon atoms.
[8] The ink according to any one of [1] to [7], wherein R ⁴ in formula (1) is a linear or branched alkylene group having 1 to 8 carbon atoms.
[9] The ink according to any one of [1] to [7], wherein R ⁴ in formula (1) is a linear alkylene group having 1 to 7 carbon atoms.
[10] The ink according to any one of [1] to [7], wherein R ⁴ in formula (1) is a linear alkylene group having 3 to 7 carbon atoms.
[11] The ink according to any one of [1] to [7], wherein R ⁴ in formula (1) is a linear alkylene group having 3 to 6 carbon atoms.
[12] The ink according to any one of [1] to [7], wherein R ⁴ in formula (1) is a linear alkylene group having 3 to 5 carbon atoms.
[13] any one of [1] to [12], wherein R ⁵ and R ⁶ in formula (1) are the same or different and are a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms; Ink as described.
[14] Any one of [1] to [12], wherein R ⁵ and R ⁶ in formula (1) are the same or different and represent a linear or branched alkyl group having 1 to 3 carbon atoms; Ink described in .
[15] The ink according to any one of [1] to [12], wherein R ⁵ and R ⁶ in formula (1) are the same or different and represent a linear alkyl group having 1 to 3 carbon atoms. .
[16] The ink according to any one of [1] to [12], wherein R ⁵ and R ⁶ in formula (1) are both methyl groups.
[17] The ink of [1], wherein the compound represented by formula (1) is at least one compound selected from compounds represented by formulas (1-1) to (1-9). .
[18] Any one of [1] to [17], wherein the fluid organic substance has a viscosity (η) of less than 0.5 Pa·s at 25°C and a shear rate of 1 s ^-1 measured by a rheometer. Ink described in one.
[19] The fluid organic substance is at least one selected from hydrocarbon oils, ethers, halogenated hydrocarbons, petroleum components, animal and vegetable oils, silicone oils, esters, aromatic carboxylic acids, pyridines, and alcohols. The ink according to any one of [1] to [18].
[20] The ink according to any one of [1] to [19], containing 0.1 to 100 parts by weight of the compound represented by formula (1) with respect to 1000 parts by weight of the fluid organic substance.
[21] The ink according to any one of [1] to [20], further comprising an electrical property-imparting agent.
[22] The compatible material according to [21], wherein the content of the electrical property imparting material is 0.1 to 30% by weight of the total amount of the compatible material.
[23] The ink according to any one of [1] to [22], which has a viscosity of 10 Pa·s or more at 25° C. and a shear rate of 0.3 s ⁻¹ as measured by a rheometer.
[24] The ink according to any one of [1] to [23], which has a viscosity of 10 Pa·s or more at 25° C. and a shear rate of 0.1 s ⁻¹ as measured by a rheometer.
[25] The viscosity ratio [viscosity at a shear rate of 1 s ⁻¹ at 25° C. measured by a rheometer/viscosity at a shear rate of 10 s ⁻¹ measured by a rheometer] is greater than 1.5, [1] to [24] The ink according to any one of .
[26] The content of at least one high-molecular-weight compound selected from ethyl cellulose resin, alkyl cellulose resin, polyvinyl acetal resin, and acrylic resin is 10% by weight or less of the total amount of the compatible material, [1]- The ink according to any one of [25].
[27] The ink of [26], wherein the polymer compound has a molecular weight of 10,000 or more.
[28] The ink according to any one of [1] to [25], wherein the content of the polymer compound with a molecular weight of 10,000 or more is 10% by weight or less of the total amount of the compatible material.
[29] The ink according to any one of [1] to [28], which is an ink for manufacturing electronic devices.
[30] The ink according to any one of [1] to [28], which is an ink for manufacturing wiring or electrodes.
[31] The ink according to any one of [1] to [28], which is an adhesive for manufacturing laminated ceramic capacitors.
[32] Use of the ink according to any one of [1] to [28] as an ink for manufacturing electronic devices.
[33] Use of the ink according to any one of [1] to [28] as an ink for manufacturing wiring and/or electrodes.
[34] Use of the ink according to any one of [1] to [28] as an adhesive for manufacturing a multilayer ceramic capacitor.
[35] A method for manufacturing an electronic device, using the ink according to any one of [1] to [28].
[36] A method for manufacturing wiring and/or electrodes of an electronic device, using the ink according to any one of [1] to [28].
[37] A method for manufacturing a multilayer ceramic capacitor, using the ink according to any one of [1] to [28].
[38] A method for producing an ink, wherein the ink according to any one of [1] to [28] is obtained through a step of making the compound represented by Formula (1) compatible with a fluid organic substance.
[36] The method for producing an ink according to [38], wherein the ink is an ink for electronic device production.
[40] The method for producing an ink according to [38], wherein the ink is an ink for producing wiring and/or electrodes of an electronic device.
[41] The method for producing an ink according to [38], wherein the ink is an adhesive for manufacturing a laminated ceramic capacitor.

The ink of the present invention has moderate viscosity and shear thinning properties. Therefore, it has good coatability. Also, printing accuracy can be improved. Furthermore, it can be fired at a low temperature, and the residual amount of ash after firing can be remarkably reduced. Therefore, the ink of the present invention can be suitably used for manufacturing electronic devices.

Claims (4)

Formula (1) below

(wherein R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms; R ² and R ³ are the same or different and are divalent hydrocarbon groups having 2, 4, 6 or 8 carbon atoms; represents an aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; wherein R ⁵ and R ⁶ are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L ¹ to L ³ represent an amide bond, and L ¹ and When L ³ is -CONH-, L ² is -NHCO-, and when L ¹ and L ³ are -NHCO-, L ² is -CONH-)
An ink for manufacturing electronic devices, containing a compatible substance of a compound represented by and a fluid organic substance. Claim 1, wherein the fluid organic substance is at least one selected from hydrocarbon oils, ethers, halogenated hydrocarbons, petroleum components, animal and vegetable oils, silicone oils, esters, aromatic carboxylic acids, pyridines, and alcohols. The ink for manufacturing electronic devices according to . 3. The ink for manufacturing electronic devices according to claim 1, further comprising an electrical property-imparting material. Formula (1) below

(wherein R ¹ is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms; R ² and R ³ are the same or different and are divalent hydrocarbon groups having 2, 4, 6 or 8 carbon atoms; represents an aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R ⁴ represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; wherein R ⁵ and R ⁶ are the same or different and represent a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl ether group, L ¹ to L ³ represent an amide bond, and L ¹ and When L ³ is -CONH-, L ² is -NHCO-, and when L ¹ and L ³ are -NHCO-, L ² is -CONH-)
A method for producing an electronic device manufacturing ink, wherein the electronic device manufacturing ink according to any one of claims 1 to 3 is obtained through a step of compatibilizing the compound represented by and a fluid organic substance.

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