JP2003313271A - Active energy ray-curable resin composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an active energy ray-curable resin composition which gives a cured product having excellent memory after change in shape in spite of its low elastic modulus and excellent adhesion to a substrate having poor wettability such as an ITO deposited film as well, and furthermore has good curability at a low viscosity capable of being used in gravure printing, or the like. <P>SOLUTION: The active energy ray-curable resin composition comprises 1-20 pts. bisepoxy resin (component A) having a molecular weight of <2,000, 30-99 pts. oxetane compound (component B), and a small amount of a photocation polymerization initiator. <P>COPYRIGHT: (C)2004,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a curable resin having a low viscosity and excellent in coating property and leveling property, which can be used for manufacturing an electronic device member or an optical member, and can also be used for gravure printing or the like. The present invention relates to a good active energy ray-curable resin composition. Further, the present invention has a very low elastic modulus at room temperature, which is obtained by curing the active energy ray-curable composition, and is excellent in resilience after shape change, and I
The present invention relates to a cured product having excellent adhesion to a substrate having poor wettability such as a TO (tin-doped indium oxide) vapor deposition film. further,
The present invention relates to a coating material for coating an ITO vapor-deposited film of a transparent touch panel or a wiring formed thereon, a coating material for coating an optical fiber, and a liquid crystal layer of a liquid crystal panel.

[0002]

2. Description of the Related Art In recent years, active energy ray-curable resin compositions have been increasingly used in the production of electronic equipment members or optical members. The reason is that the productivity is high and the working environment is improved because no organic solvent is used. From such a background, various physical properties have come to be required for the active energy ray-curable resin composition depending on the site where it is used. For example, in an analog resistance film type transparent touch panel, a resin dot spacer is generally used between the resistance films on the upper surface and the lower surface. In order to improve the sensitivity of the touch panel, the dot spacer needs to satisfy both a lower elastic modulus and an excellent resilience after a shape change at around room temperature. Also, in the case where a conductive film wiring made of silver or the like is provided on a resistance film such as ITO and the wiring is covered with a resin for insulation, considering the improvement in sensitivity, the insulating layer to be coated has a low elastic modulus. Yes, and it is necessary to have excellent resilience after a shape change. Here, it is preferable that the dot spacer and the insulating layer have excellent adhesion to a substrate such as an ITO vapor deposition film and silver. Further, since the dot spacers and the insulating layer are fine in shape, they are often applied by printing. In this case, the resin needs to have an appropriate viscosity according to the printing method. For example, in the case of gravure printing, it is preferable that the viscosity at room temperature is low,
Specifically, it is preferably several tens mPa · s or less, and particularly preferably several mPa · s.

Even in the conventional active energy ray-curable resin composition, a resin such as a UV-curable adhesive material exists if only the elastic modulus of the cured product is low. However, these are inferior in recoverability after shape change,
In other words, the tan δ in the dynamic viscoelasticity measurement is large. On the other hand, the elastic modulus (storage elastic modulus) near room temperature is low, and the resilience after shape change is excellent (ta
There are few active energy ray-curable resin compositions that give a cured product (having a small nδ), and the level thereof has a storage elastic modulus (G ′) of 1 in dynamic viscoelasticity measurement (25 ° C., 1 Hz).
When it is 0 ⁵ Pa or less and tan δ is 0.1 or less, it is not found in materials other than silicone-based materials. However, since the silicone-based resin has extremely poor adhesion to various base materials, it is not suitable for situations where adhesion to the base material is required.

Even with an active energy ray-curable resin composition containing no silicone resin, when the substrate is a metal oxide vapor deposition film having poor wettability, for example, an ITO vapor deposition film, sufficient adhesion is obtained. I couldn't get sex.
That is, in the conventional active energy ray-curable resin composition, the storage elastic modulus (G ′) is 10 ⁵ Pa or less and the tan δ is 0.1 in the dynamic viscoelasticity measurement (25 ° C., 1 Hz).
It was below, and it was not possible to give a cured product having excellent adhesion to the ITO vapor deposition film.

[0005]

The problem to be solved by the present invention is that it has a low elastic modulus and is excellent in recoverability after a shape change, and that it has good adhesion to a substrate having poor wettability such as an ITO vapor deposition film. Also provides an excellent cured product, and further provides an active energy ray-curable resin composition having low viscosity and good curability, which can be used for gravure printing and the like.

[0006]

As a result of intensive studies to solve the above problems, the present inventors have found that the following problems can be solved by the following invention, and have completed the present invention. 1 to 20 parts of a bisepoxy compound (component A) having a molecular weight of less than 2,000 represented by the following formula (1), 30 to 99 parts of an oxetane compound (component B) of the following formula (2),
And an active energy ray curable resin composition comprising a small amount of a cationic photopolymerization initiator.

[Chemical 4] In formula (1), R represents a divalent linking group.

[Chemical 5] In formula (2), R ¹ represents an alkyl group having 6 to 30 carbon atoms which may have a branch or a phenyl group substituted with an alkyl group having 4 to 10 carbon atoms, and R ² represents 1 to 1 carbon atoms. 6 represents an alkyl group which may have 6 branches. The curable resin composition preferably does not contain 10 parts or more of the polyfunctional epoxy compound and the polyfunctional oxetane compound other than the component A.
In the present invention, the compounding ratio is based on weight.

Another aspect of the present invention is a cured product obtained by subjecting the above-mentioned active energy ray-curable resin composition to a curing treatment of irradiating with active energy rays, which is at 25 ° C. for 1H.
The physical property value of the dynamic viscoelasticity measurement in z was achieved by a cured product characterized by a storage elastic modulus (G ′) of 10 ⁵ Pa or less and a tan δ of 0.1 or less.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The active energy ray-curable resin composition of the present invention will be described in detail below. The active energy ray-curable resin composition of the present invention comprises a bisepoxy compound represented by the formula (1) and having a molecular weight of less than 2,000 (component A) and an oxetane compound represented by the formula (2) (component B). And a photocationic polymerization initiator (component X) which can be activated by a small amount of active energy ray to initiate cationic polymerization
May be contained as an optional component, and a compound having a hydroxyl group and being liquid at room temperature (component C), a polyfunctional epoxy compound other than component A or a polyfunctional oxetane compound, a thermal cationic polymerization initiator, and the like may be contained as optional components. .

(Component A) The compound (Component A) used in the present invention has two glycidyloxy groups in one molecule and has a molecular weight of less than 2,000, preferably 1,000.
Less than the compound. The compound of component A acts as a crosslinking agent and plays a role of curing the curable resin composition. Here, since the epoxy group is a glycidyloxy type, the curable resin composition of the present invention exhibits excellent adhesion even to a substrate having extremely poor wettability such as an ITO vapor deposition film. In addition, by setting the number of glycidyloxy groups contained in one molecule to be two, the elastic modulus of the cured product can be kept low. The epoxy equivalent of the bisepoxy compound of component A is preferably 80 to 900 g / eq,
It is more preferably 100 to 450 g / eq. Another role of the compound (component A) used in the present invention is
The purpose is to shorten the polymerization initiation induction period that would be expected if the composition were only oxetanyl groups derived from component B. The shortening of the polymerization initiation induction period leads to the improvement of the curability of the composition. The molecular weight of component A is 2,000
When it is less than 0, the viscosity of the curable resin composition can be lowered.

The bisglycidyloxy compound (component A) used in the present invention may have various structures. Specific examples of R in the formula (1) include those having 6 to 6 carbon atoms.
40 alkylene, a polyoxyethylene group, a polyoxypropylene group, an alkylene diarylen group etc. can be illustrated. Specific examples of the compounds belonging to component A are 1,6
-Hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, polypropylene glycol diglycidyl ether, bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and the like.

The compounding part of the compound (component A) used in the present invention is 1 to 20 parts, more preferably 5 to 10 parts, based on 100 parts of the entire resin component. If it is less than 1 part, the curability will be poor, and if it is more than 20 parts, the elastic modulus of the cured product will be high, such being undesirable. In the composition of the present invention, the compounding parts of the polyfunctional epoxy compound and the polyfunctional oxetane compound other than the compound (component A) is preferably less than 10 parts. Thereby, the adhesiveness of the cured product can be made excellent. Also, this is
It is also important for lowering the elastic modulus of the cured product.

(Component B) The oxetane compound (component B) in the present invention lowers the viscosity of the composition, improves the wettability, improves the curability, lowers the glass transition temperature of the cured product, and improves the composition for various substrates. It has the function of improving the adhesiveness of. Reducing the glass transition temperature of the cured product is important for reducing the elastic modulus of the cured product and improving the recoverability after shape change. Here, R ¹ of the compound (component B) has 6 to 6 carbon atoms.
An alkyl group which may have 30 branches or a carbon number of 4 to
10 shows a phenyl group substituted with an alkyl group, for example, a hexyl group, an octyl group, a 2-ethylhexyl group,
Examples thereof include an octadecyl group, a 2,4-di-tert-butylphenyl group, and a 2,4-di-tert-amylphenyl group, and a 2-ethyl-hexyl group is particularly preferable.
The reason for this is that the compound of component B having this substituent has no crystallinity, the glass transition temperature of the cured product is lowered, and the raw materials are easily available. Also,
R ² is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a branch, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, t
-Butyl group, amyl group, isoamyl group, hexyl group and the like can be mentioned.

The alkyl group represented by R ¹ or R ² may have a substituent. As this substituent, any substituent is acceptable as long as it does not inhibit cationic polymerization, and the alkyl group can be substituted with any substituent that does not adversely affect cationic polymerization. Substituent groups that are permissible for this alkyl group include C1-12 alkoxy groups and C
2-12 acyloxy group, a C2-12 alkoxycarbonyl group, and a halogen atom can be illustrated.

The blending part of component B in the composition of the present invention is 30 to 99 parts, preferably 50 to 90 parts, based on 100 parts of the entire resin component. When the content of component B is less than 30 parts, the compounding effect is small, that is, a composition having low viscosity, excellent wettability, excellent curability, low elastic modulus, excellent restoration after shape change, and excellent adhesion. It can no longer be a thing. In addition, in this invention, a "resin component" means what removed the polymerization initiator from the resin composition. Furthermore, when a filler, a bulking agent, and other additives are used, they are those excluding them.

(Component C) In the composition of the present invention, in addition to the compound (Component A) and the compound (Component B), a compound having a hydroxyl group, which is liquid at room temperature (Component C), and a resin component are added.
As 0 part, 0 to 30 parts can be blended. As a result, the storage elastic modulus of the cured product can be reduced.
Here, the fact that the compound (component C) contains a hydroxyl group means
It is preferable in the sense that the compound (component C) is incorporated into the resin skeleton to prevent exudation from the cured product. Compound (component C)
Has a molecular weight of 2,000 in order to keep the viscosity of the composition low.
It is preferably less than 0. The preferable compounding part number of the compound (component C) is 0 to 30 parts. When the amount is more than 30 parts, the compound (component C) that is not incorporated into the resin skeleton during curing increases, and the exudation of these components remarkably occurs during heating, which is not preferable.

In the composition of the present invention, in addition to the above components, R ¹ of the compound (component B) is replaced with various substituents, for example, an unsubstituted or C 6-10 alkyl group. It is also possible to blend a compound substituted with benzene ring or the like. However, it is preferable to appropriately adjust the number of parts to be mixed so that the storage elastic modulus (G ′) or tan δ of the cured product is not increased, and specifically, it is preferably kept within a range of 0 to 30 parts.

In addition to the above components, the composition of the present invention may contain a monofunctional epoxy compound having 6 to 30 carbon atoms. However, it is preferable to appropriately adjust the number of parts to be mixed so that the curability of the composition is not extremely deteriorated, and specifically, it is preferable to keep it in the range of 0 to 30 parts.

It is preferable that the composition of the present invention does not contain 10 parts or more of the polyfunctional epoxy compound and the polyfunctional oxetane compound other than the component A, in other words, contains less than 10 parts even if included. As the polyfunctional epoxy compound other than the component A, for example, dicyclopentadiene dioxide, limonene dioxide, 4-vinylcyclohexene dioxide, 3,4-epoxycyclohexylmethyl-3 ′, 4′-epoxycyclohexanecarboxylate, di ( Examples include 3,4-epoxycyclohexyl) adipate, o-, m-, p-cresol novolac type epoxy resin, phenol novolac type epoxy resin, and the like.

Examples of polyfunctional oxetane compounds include compounds represented by the following formula (4).

[Chemical 6] In the formula, m represents a natural number of 2 or more, R ₃ is an alkyl group having 1 to 6 carbon atoms which may have a branch, preferably a methyl group or an ethyl group, and R ₄ represents a m-valent linking group. .

The composition of the present invention must contain a photocationic polymerization initiator (component X) which initiates cationic polymerization by irradiation with active energy rays. The cationic polymerization initiator needs to be dissolved in the resin composition and is preferably one having excellent curability. Examples of the cationic polymerization initiator include a diazonium salt, an iodonium salt, a sulfonium salt, a selenium salt, a pyridinium salt, a ferrocenium salt, and a phosphonium salt, but an aromatic iodonium salt and an aromatic that are relatively stable thermally Onium salt photoinitiators such as sulfonium salts are preferably used. In order to activate the onium salt photoinitiator, it is preferable to irradiate ultraviolet rays or visible light as an active energy ray.

Aromatic iodonium salt and aromatic sulfone
When using an onium salt photoinitiator such as an onium salt,
BF for Nion_Four ⁻, AsF₆ ⁻, SbF₆ ⁻, P
F₆ ⁻, B (C₆F₅)_Four ⁻And these
Among them, B (C₆F₅)_Four ⁻As an anion
Umium salts are suitable because they have good compatibility with oxetane compounds.
It

In the present invention, an active energy ray is used.
X-rays, electron beams, etc. can also be used, but ultraviolet rays
Is preferably used. In the present invention, the active energy
When using ultraviolet rays as the radiation, the wavelength range is
Although not particularly limited, it may be 150 to 400 nm.
200 to 380 nm is more preferable.
Yes. When using ultraviolet light, the various photocationic weights mentioned above are used.
Of the curable resin composition of the present invention by activating the polymerization initiator
On-polymerization can be efficiently initiated. In the resin composition of the present invention
On the other hand, a suitable cationic photopolymerization initiator has a cationic component.
Bis (alkylphenyl) iodonium, anion component
Is PF₆ ⁻, SbF₆ ⁻Or (C₆F ₅)_FourB⁻And
The most suitable ones are listed below.
Su (dodecylphenyl) iodonium hexafluoroa
Antimonate (GE Toshiba Silicone, UV-938
0C main component), trilycumyl iodonium tetrakis
(Pentafluorophenyl) borate (Rhodia
Manufactured by PHOTOINITIATOR 2074) and the like.
To be

If desired, a sensitizer may be used in combination with the resin composition of the present invention. The sensitizer used in combination with the above cationic photopolymerization initiator is not particularly limited, and generally used photoradical polymerization initiators can be preferably used. As a typical sensitizer that can be used in the present invention, it is possible to use the compound disclosed by Krivero in Advanced in Polymer Science (Adv. In Plymer. Sci., 62, 1 (1984)). . Specific examples include pyrene, perylene, acridine orange, thioxanthone, 2-chlorothioxanthone, and penzoflavin. In the present invention, thioxanthones are most preferable because they enhance the activity of the onium salt as the photocationic polymerization initiator.

Further, as photoradical polymerization initiators which can be generally used, benzophenone, 2,4-diethylthioxanthone, 2-isopropylthioxanthone, 2,
Thioxanthones such as 4-dichlorothioxanthone, benzoin methyl ether, benzoin ethyl ether,
Benzoin ethers such as benzoin isopropyl ether, benzyl dimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one,
1- (4-isopropylphenyl) -2-hydroxy-
Examples thereof include α-hydroxyalkylphenones such as 2-methylpropan-1-one and 1-hydroxycyclohexyl phenyl ketone, and α-dicarbonyl compounds such as camphorquinone.

The amounts of the photo-cationic polymerization initiator and the sensitizer can be appropriately adjusted according to the irradiation amount of ultraviolet rays and the curability of the resin.
It is preferably 0.1 to 10 parts, and particularly preferably 0.5 to 5 parts. In the present invention, the "small amount of cationic photopolymerization initiator" means the above-mentioned addition amount. 0.
If it is less than 1 part, the curability is poor, and if it is more than 10 parts, the components that are truly necessary for the cured product may be reduced and the physical properties of the cured product may deteriorate, or the coloring of the cured product may become severe. is there.

The active energy ray-curable resin composition of the present invention is expected to improve the polymerization rate and / or the adhesion by heating after being cured by irradiation with active energy rays. In this case, it is preferable to add a thermal cationic polymerization initiator. With this thermal cationic polymerization initiator,
It is activated by heating and induces ring-opening polymerization of the ring-opening polymerizable group possessed by epoxy compounds and oxetane compounds, and various onium salts such as quaternary ammonium salts, phosphonium salts and sulfonium salts are included. It can be illustrated. Examples of the onium salts as the above-mentioned thermal cationic polymerization initiator include Adeka Opton CP-66.
And Adeka Opton CP-77 (all are trade names, manufactured by Asahi Denka Co., Ltd.), San-Aid SI-60L, Sun-Aid SI-80L and San-Aid SI-100L (all are trade names, manufactured by Sanshin Chemical Industry Co., Ltd.), And commercially available compounds such as CI series (manufactured by Nippon Soda Co., Ltd.) can be used. The mixing ratio of the thermal cationic polymerization initiator is
The amount is preferably 0.01 to 5 parts with respect to 100 parts of the resin composition. If the blending ratio is less than 0.01 part, the ring-opening reaction of the ring-opening polymerizable group may not be able to proceed sufficiently even if it is activated by the action of heat. Further, even if it is blended in an amount of more than 5 parts by weight, the action of promoting the polymerization is not further enhanced, and conversely the curing performance may be lowered.

The resin composition of the present invention may contain a filler such as silica fine particles for the purpose of adjusting viscosity and imparting thixotropy. The addition amount of the filler can be appropriately adjusted, but it is preferably 0 to 10 parts from the viewpoint of maintaining a low elastic modulus and the like. Further, a coupling agent such as a silane coupling agent can be added to the resin composition of the present invention for the purpose of further improving the adhesiveness.

The resin composition of the present invention gives a cured product which has a very low elastic modulus at room temperature, is excellent in the resilience after shape change, and is excellent in adhesion to a substrate having poor wettability. It can be suitably used as a material for electronic device members and optical members that require such physical properties. Also,
Since the viscosity at room temperature can be adjusted to several mPa · s to several tens of mPa · s, it can be applied in a fine shape by gravure printing, spraying or the like, or can be thin film coated. Specifically, it is used for manufacturing transparent touch panels, optical fibers, and the like. In the former case, for example, it can be used as an insulating layer for covering a resistance film such as an ITO vapor deposition film and / or a conductive film formed thereon, or as a dot spacer.
Further, in the latter case, it can be used as a coating material.

The production of the touch panel coating will be described below. In order to use the resin composition of the present invention as a coating material for a touch panel, it is necessary to mix a cationic polymerization initiator that initiates cationic polymerization by irradiation with active energy rays. Further, a sensitizer may be used in combination to accelerate the polymerization. After the composition is irradiated with active energy rays to be cured, the composition may be post-polymerized by irradiation with active energy rays again or heating to increase the degree of polymerization. When performing thermal polymerization, it is preferable to mix a thermal cationic polymerization initiator. Further, in order to impart thixotropy, a filler such as silica fine particles may be blended.

When used as a dot spacer, ITO formed on a transparent insulating substrate by a sputtering method or the like
The resin composition of the present invention is printed on the vapor-deposited film by a method such as gravure printing to form dots having a vertical and horizontal height of several to several tens of μm. The printed resin composition is cured by irradiating it with active energy rays such as ultraviolet rays. The resin composition of the present invention has a very low elastic modulus and is excellent in resilience after a shape change, and thus is suitably used when a touch panel having high sensitivity is produced. It should be noted that since it has good adhesion to an ITO vapor deposition film having poor wettability, it is also excellent in reliability. Here, the film thickness of this resin is thinned to several μm, and another low elastic modulus and low tan are formed on top of this.
The resin of δ may be applied and cured.

Even when a conductive film of silver or the like formed on the ITO vapor-deposited film is coated to form an insulating layer, gravure printing or the like can be used as in the case of the dot spacer described above. For example, to briefly describe the structure of a resistive film type touch panel, a transparent resistive film made of an ITO vapor deposition film is formed on the entire panel, and conductive films such as silver are formed in strips at both ends thereof. When the resin is applied so as to cover the conductive film, gravure printing or the like may be used. After that, the resin is cured by irradiation with active energy rays,
It is possible to obtain an insulating layer having a low elastic modulus and an excellent restoring property after a shape change. This makes it possible to provide a touch panel with high sensitivity even at both ends. The positions of the conductive film are not limited to the positions at both ends of the panel.

The production of the optical fiber coating will be described below. The resin composition of the present invention can also be suitably used as a coating for optical fibers. The resin composition used for the primary coating layer of the optical fiber has physical properties such as low viscosity with excellent coatability, excellent curability, flexibility, little change in physical properties in a wide temperature range, and low water absorption. is necessary. The resin composition of the present invention has a viscosity of several to several tens mP.
Since it can be adjusted within the range of a · s, it has excellent coatability. Further, the resin composition of the present invention exhibits excellent curability, especially when formed into a thin film, because it does not suffer from polymerization inhibition by oxygen which is found in radically polymerized resins such as acrylate resins. Further, the main cured product is designed to have a glass transition temperature of minus several tens of degrees in order to lower the elastic modulus (G ′) and tan δ near room temperature. This means that there is little change in physical properties even at a considerably low temperature. Further, the main cured product has excellent heat resistance, and has an advantage that physical property changes are small even in a wide temperature range. Further, although the acrylate resin has a relatively high absorption rate, the present composition is also advantageous in that the water absorption rate of the cured product is low because the composition has a butadiene skeleton and a polyether structure. Since it has the above physical properties, the resin composition of the present invention can be suitably used as a primary coating material for optical fibers.

Various methods can be used for coating the optical fiber, and the method is not particularly limited. For example, the glass fiber is passed through the resin layer immediately after being melt-spun and irradiated with ultraviolet rays. The method of hardening is mentioned. However, the method is not limited to the above,
It is possible to appropriately change the method such as spray coating. Further, not only glass fiber but also plastic fiber can be used.

From a viewpoint different from the above, the resin composition of the present invention gives a cured product having a low elastic modulus and excellent resilience after a shape change, and therefore, it can be used as a resin for a pressure-sensitive conductor. It is possible. For example, in the resin composition of the present invention, conductive fine particles, and heat-expandable microcapsules are blended, cured with active energy rays, and then heated to expand the microcapsules, only when pressure is applied. It is possible to use a pressure-sensitive conductor that exhibits conductivity. It is also possible to create various switches and transparent touch panels using such pressure-sensitive conductors. The composition of the present invention containing liquid crystal is placed between a counter electrode and a pixel electrode made of a transparent electrode such as ITO and irradiated with an active energy ray such as ultraviolet rays to polymer dispersed liquid crystal (liquid crystal layer). Then, a liquid crystal panel can be manufactured. After curing by irradiating with active energy rays, heat is applied to cure and / or
Alternatively, the adhesiveness can be improved. Polymer-dispersed liquid crystal is a type in which liquid crystal in the form of water droplets is dispersed in a polymer, and a type in which liquid crystal is present continuously without being in the form of water droplets, that is, a type in which liquid crystal is present in a polymer network. It is a liquid crystal dispersed in the molecule. As the liquid crystal, nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal or the like can be used. Since the cured product from the composition of the present invention has excellent adhesiveness, there is no peeling between the electrode and the liquid crystal layer, and the occurrence of defective products can be greatly reduced.

[0035]

EXAMPLES The present invention will be described in more detail below by showing Examples and Comparative Examples. However, the present invention is not limited to these examples. All "parts" and "%" are based on weight.

The components shown in Table 1 were mixed according to a conventional method to prepare an active energy ray-curable resin composition, and then the physical properties were evaluated. Abbreviations in Table 1 indicate the following compounds. EHOX: Component B, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane (Aron Oxetane OXT-212 manufactured by Toagosei Co., Ltd.) POX: 3-Ethyl-3-phenoxymethyloxetane (Toagosei Co., Ltd.) Manufactured by Aron Oxetane OXT-211) D-OH: Component C, a compound having 2 hydroxyl groups in one molecule and having 36 carbon atoms (DIMERDI manufactured by UNIQEMA).
OL) EP828: Component A, bisphenol A-type epoxy resin (Yukaka Shell Epoxy Co., Ltd., Epicoat 828) EPL1600: Component A, 1,6-hexanediol diglycidyl ether (Kyoeisha Chemical Co., Ltd., Eporite 1600). UV9380C: Component X, a photocationic initiator whose main component is bis (dodecylphenyl) iodonium hexafluoroantimonate (UV manufactured by GE Toshiba Silicones Co., Ltd.)
-9380C) UVR6110: 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (UVR-6110 manufactured by Dow Chemical Japan Co., Ltd.) UVR6216: 2-tetradecyloxirane (Dow.
UVR-6216 manufactured by Chemical Japan Co., Ltd.)

Examples 1 to 3 and Comparative Examples 1 to 2 The components shown in Table 1 were mixed according to a conventional method to prepare an active energy ray-curable resin composition, and the following physical properties were evaluated. The evaluation results are shown in Table 2.

Viscosity The viscosity at 25 ° C. was measured with an E type viscometer. ○ The composition was applied to ITO vapor-deposited on leveling PET with a bar coater adjusted to have a thickness of 10 μm, and when observed immediately after coating, those with no streaks were marked with ○, and those with streaks remained. It was evaluated as x. The curable composition was cured by irradiating it with ultraviolet rays to the article to be evaluated for its leveling property. UV irradiation condition is 160W
/ Cm condensing type high pressure mercury lamp (one lamp), mercury lamp height 10c
m, conveyor speed 10 m / min. The curability was evaluated to be better as the number of passes required for curing was smaller. However, those that did not cure even after 10 passes of irradiation were evaluated as poor curability, and other evaluations were not performed. The adhesion-cured material was subjected to a 5-pass UV irradiation after curing, and then evaluated according to the JIS K-5400 X-cut tape method. ○ Dynamic viscoelasticity measurement (G 'and tan δ) A frame having a thickness of 1 mm was prepared on a plate made of polytetrafluoroethylene, the composition was poured, and then ultraviolet rays were irradiated by a mercury lamp. Intensity at 365 nm 25 mW / cm
Irradiation was performed at ² for 2 minutes, and the cured state was confirmed. After that, the cured product was once taken out from the frame, the front and the back were reversed, and the back was irradiated under the same conditions, and this operation was repeated 4 times in total.
The dynamic viscoelasticity of the obtained cured product was measured at a measurement temperature of 25 ° C.
Performed at a frequency of 1 Hz, storage elastic modulus (G ') and tan
δ was evaluated.

[0039]

[Table 1]

The evaluation results are summarized below.

[Table 2] (Note) In Comparative Example 1, the curability did not cure even after 10 passes, and the curability was poor.

From the results shown in Table 2, the resin composition of the present invention has a low viscosity and is excellent in leveling property and curability, and the cured product has excellent adhesion to an ITO vapor deposition film having poor wettability. In addition, it is found that the elastic modulus is low and the resilience after shape change is excellent.

[0042]

EFFECT OF THE INVENTION The active energy ray-curable resin composition of the present invention has a very low elastic modulus at room temperature and is excellent in recoverability after a shape change and has poor wettability such as an ITO vapor deposition film. In the case of producing an electronic device member or an optical member that requires such physical properties, since it is a composition having a low viscosity and good curability excellent in coating property and leveling property, it gives a cured product having excellent adhesion. Can be suitably used.

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 2H025 AA14 AB05 AB14 AB17 AC01                       AD01 BD03 BD23 CA48 CB30                       FA17                 4J036 AB01 AB09 AB10 AD08 FA10                       FA11 GA01 GA03 GA04 GA22                       GA24 GA25 HA01 HA03 JA01                       JA09 JA15

Claims (5)

[Claims] 1. A molecular weight of 2,000 represented by the following formula (1):
1 to 20 parts of a bisepoxy compound (component A) of less than 0,
The oxetane compound (component B) of the following formula (2) was added in an amount of 30 to 9
An active energy ray-curable resin composition comprising 9 parts and a small amount of a cationic photopolymerization initiator. [Chemical 1] In formula (1), R represents a divalent linking group. [Chemical 2] In formula (2), R ¹ represents an alkyl group having 6 to 30 carbon atoms which may have a branch or a phenyl group substituted with an alkyl group having 4 to 10 carbon atoms, and R ² represents 1 to 1 carbon atoms. 6 represents an alkyl group which may have 6 branches. 2. The active energy ray-curable resin composition according to claim 1, which does not contain 10 parts or more of a polyfunctional epoxy compound and a polyfunctional oxetane compound other than the component A. 3. The active energy ray-curable resin composition according to claim 1, wherein the oxetane compound (component B) is the following compound (3). [Chemical 3] 4. The active energy ray curing according to claim 1, wherein the curable resin composition further contains 0 to 30 parts by weight of a compound having a hydroxyl group and being liquid at room temperature (component C). Type resin composition. 5. A cured product obtained by subjecting the active energy ray-curable resin composition according to any one of claims 1 to 4 to a curing treatment for irradiating an active energy ray.
A cured product characterized by having a storage elastic modulus (G ′) of 10 ⁵ Pa or less and a tan δ of 0.1 or less as physical properties measured by dynamic viscoelasticity at 25 ° C. and 1 Hz.