KR101663479B1 - Vl-curable self-healing optically clear bonding materials and method for manufacturing the same - Google Patents

Vl-curable self-healing optically clear bonding materials and method for manufacturing the same Download PDF

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KR101663479B1
KR101663479B1 KR1020150124113A KR20150124113A KR101663479B1 KR 101663479 B1 KR101663479 B1 KR 101663479B1 KR 1020150124113 A KR1020150124113 A KR 1020150124113A KR 20150124113 A KR20150124113 A KR 20150124113A KR 101663479 B1 KR101663479 B1 KR 101663479B1
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South Korea
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visible light
healing
self
binder resin
resin
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KR1020150124113A
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Korean (ko)
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이준협
손인태
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명지대학교 산학협력단
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays

Abstract

The present invention relates to a visible light-curable, self-healing and transparent optical bonding material and a method for producing the same, and more specifically, to a visible light-curable, self-healing and transparent optical bonding material which utilizes self-healing reactions of a polymer, and to a method for producing the same. According to the present invention, despite deterioration of the bonding material due to repeated flexural deformation of a display device, excellent reliability of the display device can be realized through a self-healing property, and accordingly, the problem of the prior art, functional degradation of the display device associated with deterioration of the bonding material, can be resolved. More particularly, when a fissure occurs in the bonding material of the present invention, monomers inside capsules are released and come into contact with a photoinitiator, whereby polymerization is initiated by visible light, causing the fissured area in the bonding material to self-heal.

Description

TECHNICAL FIELD [0001] The present invention relates to a viscoelastic self-healing transparent optical adhesive material and a method of manufacturing the same, and a method of manufacturing the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a visible light curable self-healing transparent optical adhesive material and a method of manufacturing the same. More particularly, the present invention relates to a visible light curable self-healing transparent optical adhesive material using a self-healing reaction of a polymer and a method for producing the same.

Transparent flexible displays consist of transparent plastic substrates and organic transistors. Although research on element technologies such as organic transistor and plastic substrate have been carried out to a great extent and industrialization has been advanced to the present level, research on optical adhesive materials for bonding optical films and touch screen panels existing on the outside of the display has been insufficient . In the case of the adhesive material applied to the conventional display, there is a fatal reliability problem in which display performance is deteriorated due to the destruction of the optical adhesive layer due to fatigue accumulation during repetitive deflection over a long period of time.

Korean Patent No. 10-0942311 Korean Patent No. 10-1362463 Korean Patent No. 10-1399987

The present invention provides a visible light curable self-healing transparent optical adhesive material using a self-healing reaction of a polymer and a process for producing the same.

The present invention also provides a visible light curable self-healing transparent optical adhesive material for a transparent flexible display and a method of manufacturing the same.

The present invention relates to a photoinitiator which acts on visible light; A capsule comprising a monomer having a functional group that can be polymerized by visible light; And a binder resin, wherein the viscoelastic curable self-healing transparent optical adhesive material is provided.

The visible light may be visible light having a wavelength range of 400 to 700 nm.

The photoinitiator,

Figure 112015085302716-pat00001
,
Figure 112015085302716-pat00002
,
Figure 112015085302716-pat00003
,
Figure 112015085302716-pat00004
,
Figure 112015085302716-pat00005
,
Figure 112015085302716-pat00006
,
Figure 112015085302716-pat00007
,
Figure 112015085302716-pat00008
And
Figure 112015085302716-pat00009
2-chlorothioxanten-9-one, 4- (dimethylamino) benzophenone, 9,10-phenanthrenequinone, and thioxanthene (Irgacure 784, Irgacure OXE-01, Irgacure OXE-02, MIchler's ketone, 4,4'- -9-one). ≪ / RTI >

The photoinitiator may be included in an amount of 0.01 to 5 parts by weight, and more preferably 0.05 to 3 parts by weight based on 100 parts by weight of the binder resin. When the above range is maintained, the adhesive strength and hardness of the adhesive material are not lowered.

The monomer includes at least one member selected from the group consisting of dicylcopentadiene, brominated epoxy, cinnamate, multifunctional cinnamate, and furfuryl methacrylate .

The capsule may be contained in an amount of 0.05 to 40 parts by weight, and more preferably 0.1 to 20 parts by weight, based on 100 parts by weight of the binder resin. When the above range is maintained, it is possible to induce an effective self-healing reaction at breakage by cracking without changing the physical properties of the adhesive material.

The capsule may be of nanoscale size. Specifically, it may have a diameter of 5 to 500 nm. In the case of nano-sized capsule particles, since they can be implemented in a transparent form, they may be preferable for display purposes. However, micro-sized capsule particles may be unsuitable for display applications because they are implemented in opaque form with increased scattering and reflection depending on size.

The capsule may be a structure in which the SiO 2 to form an outer layer. In the case of a structure in which SiO 2 is formed as an outer layer, when a crack is generated in the adhesive material, the capsule contained in the adhesive material easily breaks, so that the monomer in the capsule can easily flow and contact with the initiator.

The binder resin may include an epoxy or an acrylic monomer.

The binder resin may further comprise silicon.

The epoxy or acrylic monomer and silicon may be included in a weight ratio of 8: 2 to 5: 5, and more preferably 6: 4. When the above range is maintained, there is an advantage that an excellent adhesive force can be secured without lowering the optical transparency.

The binder resin may be at least one selected from the group consisting of bisphenol A glycidyl methacrylate resin, bisphenol A epoxy resin, acrylated bisphenol A epoxy resin, A polyurethane resin, a polyurethane resin, a polyurethane acrylate resin, and a polyurethane acrylate-epoxy resin.

In addition, the present invention relates to a photopolymerization initiator comprising a photoinitiator acting on visible light, a capsule containing a monomer having a functional group capable of being polymerized by visible light, and a binder resin And agitating the mixture at 50 to 200 DEG C for 10 to 180 minutes to provide a visible light curable self-healing transparent optical adhesive material. More preferably at 150 < 0 > C for 60 minutes. When the above range is maintained, the capsule is uniformly dispersed in the binder, and self-healing reaction occurs uniformly over the entire surface.

The photoinitiator may be mixed in an amount of 0.01 to 5 parts by weight, more preferably 0.05 to 3 parts by weight, based on 100 parts by weight of the binder resin.

The capsules may be mixed in an amount of 0.05 to 40 parts by weight, more preferably 0.1 to 20 parts by weight, based on 100 parts by weight of the binder resin.

The binder resin may include epoxy or acrylic monomer and silicone. The epoxy or acrylic monomer and silicone may be mixed in a weight ratio of 8: 2 to 5: 5, and more preferably 6: 4. Can be mixed.

The detailed contents of the photoinitiator, capsule, binder resin and the like are the same as those described above, so they are omitted here.

The present invention also relates to a photoinitiator which acts on visible light; A capsule comprising a monomer having a functional group that can be polymerized by visible light; And a binder resin. The transparent self-curing transparent optical adhesive material for visible light curing for a transparent flexible display is provided. The specific contents of the photoinitiator, the capsule, the adhesive resin and the like are the same as those described above, so they are omitted here.

The present invention also relates to a transparent flexible display device comprising a photoinitiator acting on visible light, a capsule containing a monomer having a functional group capable of being polymerized by visible light, and a step of stirring the binder resin at 50 to 200 DEG C for 10 to 180 minutes. The present invention provides a method of manufacturing a transparent optical adhesive material for visible light curing self-healing. The detailed contents of the photoinitiator, capsule, binder resin and the like are the same as those described above, so they are omitted here.

According to the present invention, it is possible to realize excellent reliability of the display through self-healing even when the adhesive material is broken due to repetitive bending deformation of the display, so that the problem of the prior art in which the performance of the display deteriorates due to the destruction of the adhesive material can be solved have.

More specifically, when a crack is applied to the adhesive material according to the present invention, the monomer in the capsule flows out and comes into contact with the photoinitiator, and the polymerization reaction is caused by the visible light, thereby self-healing the cracked portion of the adhesive material. In addition, the present invention has a merit that the polymerization reaction is caused by visible light and can be self-healed by backlight irradiation without any additional processing.

1 is a schematic view showing a configuration of an adhesive material according to an embodiment of the present invention.
Fig. 2 is a graph showing shear strengths of Examples and Comparative Examples of the present invention.

Hereinafter, the present invention will be described in more detail with reference to the drawings and examples. The objects, features and advantages of the present invention will be readily understood through the following drawings and examples. The present invention is not limited to the embodiments described herein, but may be embodied in other forms. The embodiments described herein are provided to enable those skilled in the art to fully understand the spirit of the present invention. Therefore, the present invention should not be limited by the following examples.

The present invention will be described with reference to FIG. The self-healing adhesive material 100 according to one embodiment of the present invention includes a binder resin 110, a capsule 120 including a monomer having a functional group capable of being polymerized by visible light (wavelength band of 400 to 700 nm) And a photoinitiator 130 functioning as a photoinitiator. Capsule 120 may be nano-sized. The photoinitiator 130 may serve to assist the polymerization reaction.

When cracks are applied to the adhesive material 100 applied to the display due to repetitive bending deformation of the flexible display, the capsules 120 at the positions are broken and the monomer (healing material) in the capsules 120 flows out and comes into contact with the photoinitiator 130 And a polymerization reaction is caused by visible light, so that the cracked portion of the adhesive material is self-healing. The adhesive material 100 may be composed of organic molecules as shown in Table 1 below (A: a binder resin, B: a capsule material, and C: a photoinitiator).

[Table 1]

Figure 112015085302716-pat00010

Example : Manufacture of self-healing adhesive materials

A mixture of a silicone / epoxy resin (polydimethylsiloaxne / bisphenol A epoxy) and a capsule and initiator (Irgacure OXE-02) capable of exhibiting adhesion properties was prepared. The silicone and the epoxy resin were mixed in a ratio of 4: 6 (weight ratio). Then, 10 parts by weight and 1 part by weight of the capsule and initiator were added to 100 parts by weight of the resin, and the mixture was stirred at 80 DEG C for about 60 minutes, Thereby completing the adhesive material.

The capsules were prepared using the following sol-gel method. Sol-gel solutions containing monomers with trimethylolpropane triacrylate (TMPTA), which can be polymerized by visible light, were synthesized by sol-gel precursor tetraethylorthosilicate (TEOS), 3- (trimethoxysilyl) propyl methacrylate (MPTS), C 2 H 5 OH, (TMPTA) having a functional group capable of being polymerized by the addition of a monomer. At this time, NH 4 OH was added as a catalyst. Then, a dispersant (Igepal NP12) was added and mixed at room temperature for 2 hours. The sol-gel solution was mixed at a weight ratio of TEOS: MPTS: TMPTA: C 2 H 5 OH = 1: 1: 1: 8 and NH 4 OH: Igepal = 3.5:

Comparative Example: Production of Adhesive Material

Silicone and epoxy resin were mixed in a 4: 6 ratio (weight ratio), and then stirred at 80 DEG C for about 60 minutes to complete the adhesive material.

Experimental Example: Measurement of Shear Strength of Self-Healing Adhesive

As a result of measuring the shear strength of the two substrates with the adhesive, the new self-healing adhesive material according to Example 1 exhibited a shear strength of 85% of that of conventional adhesive materials using silicone / epoxy resin (Fig. 1 Reference). Shear strength was analyzed using Universal Testing Machine (UTM) (Lloyd, UK) according to ASTM D1002. The adhesive specimens were prepared by applying an adhesive between steel plates and curing at room temperature for 24 hours. The specimens were fixed at a thickness of 2 mm, a width of 25.4 mm, and a length of 101 mm. The cured specimens used for the adhesion measurement were averaged with a minimum of 5 specimens.

100: Visible light curable self-healing transparent optical adhesive material
110: binder resin
120: a capsule comprising a monomer having a functional group capable of being polymerized by visible light
130: Photoinitiator acting on the visible light region

Claims (18)

Photoinitiators acting on visible light;
A capsule of 5 to 500 nm in diameter containing a monomer having a functional group that can be polymerized by visible light; And
A transparent optical adhesive material for visible light curing self-healing, comprising a binder resin.
The method according to claim 1,
The photoinitiator,
Figure 112015085302716-pat00011
,
Figure 112015085302716-pat00012
,
Figure 112015085302716-pat00013
,
Figure 112015085302716-pat00014
,
Figure 112015085302716-pat00015
,
Figure 112015085302716-pat00016
,
Figure 112015085302716-pat00017
,
Figure 112015085302716-pat00018
And
Figure 112015085302716-pat00019
Wherein the viscoelastic curable self-healing transparent optical adhesive material comprises at least one member selected from the group consisting of acrylic acid,
The method according to claim 1,
Wherein the photoinitiator is included in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the binder resin.
The method according to claim 1,
Wherein the monomer comprises at least one member selected from the group consisting of dicyclopentadiene, brominated epoxy, cinnamate, and furfuryl methacrylate.
The method according to claim 1,
Wherein the capsule is contained in an amount of 0.05 to 40 parts by weight based on 100 parts by weight of the binder resin.
The method according to claim 1,
The transparent self-healing transparent optical adhesive material of visible light curing type is characterized in that the capsule is of nano size.
The method according to claim 1,
The capsule is visible light-curable self-healing transparent optical adhesive material, it characterized in that the structure in which the SiO 2 to form an outer layer.
The method according to claim 1,
Wherein the binder resin comprises an epoxy or acrylic monomer. ≪ RTI ID = 0.0 > 11. < / RTI >
The method of claim 8,
Wherein the binder resin further comprises a silicone resin. ≪ RTI ID = 0.0 > 11. < / RTI >
The method of claim 9,
An epoxy or acrylic monomer, and a silicone resin in a weight ratio of 8: 2 to 5: 5.
The method according to claim 1,
The binder resin is selected from the group consisting of bisphenol A glycidyl methacrylate resin, bisphenol A epoxy resin, acrylated bisphenol A epoxy resin, polyurethane resin, polyurethane acrylate resin and polyurethane acrylate-epoxy resin Of the transparent self-healing self-healing transparent optical adhesive material.
Mixing a 5 to 500 nm diameter capsule containing a monomer having a functional group capable of being polymerized by visible light and a binder resin and stirring the mixture at 50 to 200 DEG C for 10 to 180 minutes, A method for manufacturing a visible light curable self - healing transparent optical adhesive material.
The method of claim 12,
Wherein the photoinitiator is mixed in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the binder resin.
The method of claim 12,
Wherein the capsules are mixed in an amount of 0.05 to 40 parts by weight based on 100 parts by weight of the binder resin.
The method of claim 12,
Wherein the capsule is formed by a sol-gel method.
The method of claim 12,
Wherein the binder resin comprises an epoxy or acrylic monomer and a silicone resin,
Wherein the epoxy or acrylic monomer and the silicone resin are mixed in a weight ratio of 8: 2 to 5: 5.
Photoinitiators acting on visible light; A capsule of 5 to 500 nm in diameter containing a monomer having a functional group that can be polymerized by visible light; And a binder resin, wherein the visible light curable self-healing transparent optical adhesive material for transparent flexible display.
A step of stirring a capsule having a diameter of 5 to 500 nm containing a monomer having a functional group capable of being polymerized by visible light and a binder resin at 50 to 200 DEG C for 10 to 180 minutes, a photoinitiator acting on visible light, a transparent flexible display A method for manufacturing a viscoelastic self - healing transparent optical adhesive material.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180090424A (en) 2017-02-02 2018-08-13 한양대학교 산학협력단 Self-healing transistor and self-healing method of transistor
CN108893078A (en) * 2018-05-25 2018-11-27 安徽工业大学 A kind of preparation method of the flexible selfreparing electroconductive binder for imbrication component

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KR100942311B1 (en) 2009-10-14 2010-02-16 (주)신광화학산업 Ultraviolet hardening type adhesive, making method thereof, and flat panel display front adhesion method using it
KR101362463B1 (en) 2013-07-05 2014-02-12 주식회사 신광화학산업 Ultraviolet hardening typed adhesive compound with excellent adhesion and anti-environment property, manufacturing method thereof, and method for bonding cover window on panel display
KR101399987B1 (en) 2006-11-17 2014-05-27 린텍 가부시키가이샤 Pressure sensitive adhesive composition for display
US8865798B2 (en) * 2006-10-17 2014-10-21 Valorbec Societe En Commandite Self healing composite material and method of manufacturing same
KR20140123735A (en) * 2013-04-15 2014-10-23 삼성디스플레이 주식회사 Adhesive having adhesive capsule and organic light emitting display device comprising adhesive layer formed by the adhesive
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8865798B2 (en) * 2006-10-17 2014-10-21 Valorbec Societe En Commandite Self healing composite material and method of manufacturing same
KR101399987B1 (en) 2006-11-17 2014-05-27 린텍 가부시키가이샤 Pressure sensitive adhesive composition for display
KR100942311B1 (en) 2009-10-14 2010-02-16 (주)신광화학산업 Ultraviolet hardening type adhesive, making method thereof, and flat panel display front adhesion method using it
KR20150079692A (en) * 2012-10-24 2015-07-08 도아고세이가부시키가이샤 Active energy ray-curable adhesive composition and method for producing laminate
KR20140123735A (en) * 2013-04-15 2014-10-23 삼성디스플레이 주식회사 Adhesive having adhesive capsule and organic light emitting display device comprising adhesive layer formed by the adhesive
KR101362463B1 (en) 2013-07-05 2014-02-12 주식회사 신광화학산업 Ultraviolet hardening typed adhesive compound with excellent adhesion and anti-environment property, manufacturing method thereof, and method for bonding cover window on panel display

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180090424A (en) 2017-02-02 2018-08-13 한양대학교 산학협력단 Self-healing transistor and self-healing method of transistor
CN108893078A (en) * 2018-05-25 2018-11-27 安徽工业大学 A kind of preparation method of the flexible selfreparing electroconductive binder for imbrication component
CN108893078B (en) * 2018-05-25 2019-10-25 安徽工业大学 A kind of preparation method of the flexible selfreparing electroconductive binder for imbrication component

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