TW201616225A - Photocurable composition and encapsulated apparatus including the same - Google Patents
Photocurable composition and encapsulated apparatus including the same Download PDFInfo
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- TW201616225A TW201616225A TW104130357A TW104130357A TW201616225A TW 201616225 A TW201616225 A TW 201616225A TW 104130357 A TW104130357 A TW 104130357A TW 104130357 A TW104130357 A TW 104130357A TW 201616225 A TW201616225 A TW 201616225A
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- Prior art keywords
- substituted
- unsubstituted
- photocurable composition
- meth
- acrylate
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- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 239000000178 monomer Substances 0.000 claims abstract description 93
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 48
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 119
- 239000011241 protective layer Substances 0.000 claims description 103
- -1 2-phenyl-2-(phenylthio)ethyl Chemical group 0.000 claims description 55
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
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- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
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- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 claims description 2
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- 229910001512 metal fluoride Inorganic materials 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- RHOOUTWPJJQGSK-UHFFFAOYSA-N 2-phenylsulfanylethyl prop-2-enoate Chemical group C=CC(=O)OCCSC1=CC=CC=C1 RHOOUTWPJJQGSK-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
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- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- HAZQZUFYRLFOLC-UHFFFAOYSA-N 2-phenyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=CC=CC=2)=N1 HAZQZUFYRLFOLC-UHFFFAOYSA-N 0.000 description 1
- 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices with at least one potential-jump barrier or surface barrier specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices with at least one potential-jump barrier or surface barrier specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
本發明是關於一種光固化性組成物、一種包含所述光固化性組成物之有機保護層以及一種包含所述光固化性組成物之裝置。The present invention relates to a photocurable composition, an organic protective layer comprising the photocurable composition, and an apparatus comprising the photocurable composition.
光學顯示器中所用之有機發光二極體由於環境濕氣或氣體而易於劣化或改變特徵。具體言之，有機發光二極體可在濕氣影響下在金屬層與有機發光層之間的界面處遭受分層，由於金屬氧化而增加電阻，且由濕氣或氧氣所導致之有機材料變形造成、或由內部或外部除氣所導致之有機材料與電極材料的氧化造成發光特徵劣化。因此，這類有機發光二極體必須用保護免受濕氣或氧氣之封裝用組成物封裝。Organic light-emitting diodes used in optical displays are susceptible to deterioration or changing characteristics due to ambient moisture or gases. Specifically, the organic light-emitting diode can be delaminated at the interface between the metal layer and the organic light-emitting layer under the influence of moisture, the resistance is increased due to oxidation of the metal, and the organic material is deformed by moisture or oxygen. Oxidation of the organic material and the electrode material caused by, or caused by, internal or external degassing causes degradation of the luminescent characteristics. Therefore, such organic light-emitting diodes must be packaged with a package composition that protects against moisture or oxygen.
以多層結構對有機發光二極體進行封裝，在所述多層結構中形成無機保護層及有機保護層。藉由電漿沈積形成無機阻擋層，電漿沈積可使有機保護層被電漿蝕刻。在有機保護層蝕刻期間，可能損壞有機保護層之封裝功能。因此，有機發光二極體之發光特性及可靠性可遭受劣化。The organic light-emitting diode is encapsulated in a multilayer structure in which an inorganic protective layer and an organic protective layer are formed. An inorganic barrier layer is formed by plasma deposition, and the plasma deposition allows the organic protective layer to be plasma etched. The encapsulation function of the organic protective layer may be damaged during the etching of the organic protective layer. Therefore, the light-emitting characteristics and reliability of the organic light-emitting diode can be deteriorated.
先前技術之一個實例揭露於韓國專利公開案第2011-0071039號中。An example of the prior art is disclosed in Korean Patent Publication No. 2011-0071039.
本發明之一個態樣提供一種能夠實現具有極佳耐電漿性之有機保護層之光固化性組成物。One aspect of the present invention provides a photocurable composition capable of realizing an organic protective layer having excellent plasma resistance.
本發明之另一態樣提供一種能夠實現具有顯著低的水蒸氣穿透率與氧氣穿透率之有機保護層之光固化性組成物。Another aspect of the present invention provides a photocurable composition capable of realizing an organic protective layer having a significantly low water vapor transmission rate and oxygen permeability.
本發明之另一態樣提供一種能夠實現可保護裝置免受周圍環境（諸如濕氣及氣體）影響且可因此隨時間推移提供裝置可靠性之有機保護層之光固化性組成物。Another aspect of the present invention provides a photocurable composition that is capable of achieving an organic protective layer that protects the device from the surrounding environment, such as moisture and gases, and that can provide device reliability over time.
本發明之又一態樣提供一種包含根據本發明之光固化性組成物之固化產物的封裝裝置。Yet another aspect of the present invention provides a package device comprising a cured product of a photocurable composition according to the present invention.
根據本發明之一個態樣，光固化性組成物之如由等式1表示之POC參數可為0.100至0.350，且可包含含有芳族烴基之光固化性單體及光起始劑。 ＜等式1＞ POC參數 =其中Pcn 為光固化性組成物之各單體之芳環數，Ocn 為光固化性組成物之各單體的O原子與S原子之總數，Wrn 為各單體以光固化性組成物之所有單體之總重量計的重量百分比（重量%），且Mwn 為光固化性組成物之各單體的重量平均分子量。According to an aspect of the present invention, the photocurable composition may have a POC parameter of from 0.100 to 0.350 as represented by the equation 1, and may include a photocurable monomer containing an aromatic hydrocarbon group and a photoinitiator. <Equation 1> POC parameter = Wherein Pc n is the number of aromatic rings of each monomer of the photocurable composition, Oc n is the total number of O atoms and S atoms of each monomer of the photocurable composition, and Wr n is a photocurable composition of each monomer. The weight percentage (% by weight) based on the total weight of all the monomers, and Mw n is the weight average molecular weight of each monomer of the photocurable composition.
根據本發明之另一態樣，封裝裝置可包含裝置用構件及形成於裝置用構件上之保護層，其中所述保護層可包含無機保護層及有機保護層，且所述有機保護層可包含如上文闡述之光固化性組成物之固化產物。According to another aspect of the present invention, a packaging device may include a member for a device and a protective layer formed on the member for the device, wherein the protective layer may include an inorganic protective layer and an organic protective layer, and the organic protective layer may include A cured product of the photocurable composition as set forth above.
根據本發明，有可能實現可展現高耐電漿性且保護裝置免受周圍環境（諸如濕氣及氣體）影響且可因此隨時間推移提供裝置可靠性之有機保護層。另外，包含根據本發明之光固化性組成物之固化產物的封裝裝置可展現高耐電漿性及顯著低的水蒸氣穿透率與氧氣穿透率。According to the present invention, it is possible to realize an organic protective layer which can exhibit high plasma resistance and protect the device from the surrounding environment such as moisture and gas and can thereby provide device reliability over time. Further, the encapsulating device comprising the cured product of the photocurable composition according to the present invention can exhibit high plasma resistance and remarkably low water vapor permeability and oxygen permeability.
在下文中，將參考隨附圖式詳細描述本發明之實施例。應理解，本發明不限於以下實施例且可以不同方式實施，且給出以下實施例以提供本發明之完整揭露內容且對所屬領域中具通常知識者提供本發明之充分理解。同樣，應注意，圖式未精確縮放，且為圖式中之描述清楚起見放大一些尺寸，諸如寬度、長度、厚度以及類似尺寸。儘管為描述方便起見在圖式中說明一些元件，但其他元件將易於由所屬領域中具通常知識者理解。另外，應理解，在不脫離本發明之範疇的情況下，本發明可由所屬領域中具通常知識者以不同方式實施。Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. It is to be understood that the invention is not to be construed as being limited to the embodiments of the invention, and the present invention is intended to provide a full understanding of the invention. Also, it should be noted that the drawings are not precisely scaled, and some dimensions, such as width, length, thickness, and the like, are exaggerated for clarity of the description in the drawings. Although some elements are illustrated in the drawings for convenience of description, other elements will be readily understood by those of ordinary skill in the art. In addition, it is to be understood that the invention may be carried out in various ways by those of ordinary skill in the art without departing from the scope of the invention.
如本文所用，參考隨附圖式定義諸如「上部」及「下部」之空間上相對術語。因此，應理解，「上部」可與「下部」互換使用。應理解，當一層被稱作「位於」另一層（或區域）「上」時，其可直接形成於另一層或區域上，或亦可存在中間層（區域）。因此，應理解，當一層被稱作「直接位於」另一層（或區域）「上」時，其間無中間層（區域）插入。As used herein, reference is made to the spatially relative terms such as "upper" and "lower" as used in the drawings. Therefore, it should be understood that the "upper" can be used interchangeably with the "lower". It will be understood that when a layer is referred to as being "on" another layer (or region), it may be formed directly on another layer or region, or an intermediate layer (area) may be present. Therefore, it should be understood that when a layer is referred to as being "directly on" another layer (or region), there is no intermediate layer (region) inserted therebetween.
如本文所用，術語「(甲基)丙烯基」是指丙烯基及/或甲基丙烯基。As used herein, the term "(meth)acrylyl" means propylene and/or methacryl.
如本文所用，除非另外陳述，否則術語「經取代」意謂本發明之官能基當中至少一個氫原子經下列各者取代：鹵素原子（F、Cl、Br或I）、羥基、硝基、亞胺基（=NH、=NR（R：C1 至C10 烷基））、甲脒基、肼基或腙基、羧酸基、C1 至C20 烷基、C6 至C30 芳基、C3 至C30 雜芳基、C2 至C30 雜環烷基或C3 至C20 環烷基。As used herein, unless otherwise stated, the term "substituted" means that at least one hydrogen atom of the functional group of the present invention is substituted by a halogen atom (F, Cl, Br or I), a hydroxyl group, a nitro group, or a sub Amino group (=NH, =NR (R: C 1 to C 10 alkyl)), indenyl, indenyl or fluorenyl, carboxylic acid, C 1 to C 20 alkyl, C 6 to C 30 aryl a C 3 to C 30 heteroaryl group, a C 2 to C 30 heterocycloalkyl group or a C 3 to C 20 cycloalkyl group.
如本文所用，術語「雜」意謂碳原子經由N、O、S以及P所構成的族群中選出之原子取代。As used herein, the term "hetero" means that a carbon atom is substituted with an atom selected from the group consisting of N, O, S, and P.
如本文所用，可基於蝕刻速率評估「耐電漿性」，亦即光固化性組成物之固化產物在經受電漿處理時之蝕刻程度。較低蝕刻速率指示較佳耐電漿性。As used herein, the "plasma resistance" can be evaluated based on the etching rate, that is, the degree of etching of the cured product of the photocurable composition when subjected to plasma treatment. A lower etch rate indicates better plasma resistance.
根據本發明之實施例之光固化性組成物之如由等式1表示之POC參數可為0.100至0.350，且包含含有芳族烴基之光固化性單體及不含芳族烴基之光固化性單體中的至少一個作為光固化性單體。The photocurable composition according to the embodiment of the present invention may have a POC parameter of from 0.100 to 0.350 as represented by the formula 1, and contains a photocurable monomer containing an aromatic hydrocarbon group and photocurability without an aromatic hydrocarbon group. At least one of the monomers functions as a photocurable monomer.
根據本發明之一個實施例之光固化性組成物之如由等式1表示之POC參數可為0.100至0.350，且包含含有芳族烴基之光固化性單體及光起始劑。The photocurable composition according to one embodiment of the present invention may have a POC parameter of from 0.100 to 0.350 as represented by the formula 1, and includes a photocurable monomer containing an aromatic hydrocarbon group and a photoinitiator.
此外，根據本發明之另一實施例之光固化性組成物之如由等式1表示之POC參數可為0.100至0.350，且包含含有芳族烴基之光固化性單體、不含芳族烴基之光固化性單體以及光起始劑。 ＜等式1＞ POC參數 =其中Pcn 為光固化性組成物之各單體之芳環數，Ocn 為光固化性組成物之各單體的O原子與S原子之總數，Wrn 為各單體以光固化性組成物之所有單體之總重量計的重量百分比（重量%），且Mwn 為光固化性組成物之各單體的重量平均分子量。Further, the photocurable composition according to another embodiment of the present invention may have a POC parameter of from 0.100 to 0.350 as represented by the equation 1, and contains a photocurable monomer containing an aromatic hydrocarbon group, and does not contain an aromatic hydrocarbon group. A photocurable monomer and a photoinitiator. <Equation 1> POC parameter = Wherein Pc n is the number of aromatic rings of each monomer of the photocurable composition, Oc n is the total number of O atoms and S atoms of each monomer of the photocurable composition, and Wr n is a photocurable composition of each monomer. The weight percentage (% by weight) based on the total weight of all the monomers, and Mw n is the weight average molecular weight of each monomer of the photocurable composition.
POC參數（苯基氧參數）為藉由將由光固化性單體中芳環數減去O原子與S原子之數目所獲得的值除以組成物之重量平均分子量來獲得之值。組成物之POC參數可為0.100至0.350。當使用滿足上述POC參數之光固化性單體時，有可能提供具有顯著低的電漿蝕刻速率且因此展現高耐電漿性之有機保護層，其中電漿蝕刻速率是指在有機發光二極體上形成有機保護層或在有機發光二極體上形成無機保護層期間，有機保護層受電漿處理損壞之程度。The POC parameter (phenyloxy parameter) is a value obtained by dividing the value obtained by subtracting the number of O atoms and S atoms from the number of aromatic rings in the photocurable monomer by the weight average molecular weight of the composition. The composition may have a POC parameter of from 0.100 to 0.350. When a photocurable monomer satisfying the above POC parameters is used, it is possible to provide an organic protective layer having a remarkably low plasma etching rate and thus exhibiting high plasma resistance, wherein the plasma etching rate is referred to as an organic light emitting diode The organic protective layer is damaged by the plasma treatment during the formation of the organic protective layer or the formation of the inorganic protective layer on the organic light-emitting diode.
若POC參數小於0.100，則電漿蝕刻速率提高，藉此使有機膜損壞且因此使二極體之可靠性劣化，然而，若POC參數高於0.350，則組成物具有增加的黏度且可因此展現差的可加工性。If the POC parameter is less than 0.100, the plasma etching rate is increased, whereby the organic film is damaged and thus the reliability of the diode is deteriorated, however, if the POC parameter is higher than 0.350, the composition has an increased viscosity and can thus exhibit Poor processability.
POC參數可在例如0.100至0.230、0.100至0.190、0.101至0.216或0.108至0.187之範圍內。The POC parameter can be, for example, in the range of 0.100 to 0.230, 0.100 to 0.190, 0.101 to 0.216, or 0.108 to 0.187.
Pcn 為各單體之芳環數。芳環數是指單體中所含之單環數。在縮合環或稠合環之情況下，計數構成縮合環之單環數。舉例而言，當單體含有一個萘基時，Pcn 為2，因為萘基藉由縮合兩個單環苯環形成。當單體含有一個蒽基或菲基時，Pcn 為3。Pc n is the number of aromatic rings of each monomer. The number of aromatic rings means the number of single rings contained in the monomer. In the case of a condensed ring or a fused ring, the number of single rings constituting the condensed ring is counted. For example, when the monomer contains a naphthyl group, Pc n is 2 because the naphthyl group is formed by condensing two monocyclic benzene rings. When the monomer contains a mercapto group or a phenanthryl group, Pc n is 3.
儘管Ocn 為各單體中「O原子與S原子之總數」，Ocn 不包含(甲基)丙烯酸酯基中所含之「O」數目。舉例而言，當單體為十二烷二醇二甲基丙烯酸酯時，Ocn 為0，且當單體為丙烯酸苯硫基乙酯時，Ocn 為1。Although Oc n is the "total number of O atoms and S atoms" in each monomer, Oc n does not include the number of "O" contained in the (meth) acrylate group. For example, when the monomer is dodecanediol dimethacrylate, Oc n is 0, and when the monomer is phenylthioethyl acrylate, Oc n is 1.
Wrn 為各單體以所有單體之總重量計的重量%。舉例而言，當60公斤十二烷二醇二甲基丙烯酸酯與40公斤丙烯酸苯硫基乙酯之混合物包含於組成物中時，十二烷二醇二甲基丙烯酸酯之Wrn 為(60/100)×100= 60，且丙烯酸苯硫基乙酯之Wrn 為(40/100)×100= 40。Wr n is the weight % of each monomer based on the total weight of all monomers. For example, when a mixture of 60 kg of dodecanediol dimethacrylate and 40 kg of phenylthioethyl acrylate is contained in the composition, Wr n of dodecanediol dimethacrylate is ( 60/100) × 100 = 60, and Wr n of phenylthioethyl acrylate is (40/100) × 100 = 40.
在含有芳族烴基之光固化性單體中，Pcn 可大於或等於1或在1至5範圍內。在一些實施例中，Pcn 可大於或等於1、大於或等於2、大於或等於3，具體言之2至5、1至4或1至3。在此範圍內，電漿蝕刻速率可降低以防止損壞有機膜，藉此增強二極體之可靠性同時提供極佳的組成物可加工性。In the photocurable monomer containing an aromatic hydrocarbon group, Pc n may be greater than or equal to 1 or in the range of 1 to 5. In some embodiments, Pc n may be greater than or equal to 1, greater than or equal to 2, greater than or equal to 3, in particular 2 to 5, words to 4 or 1 to 3. Within this range, the plasma etch rate can be lowered to prevent damage to the organic film, thereby enhancing the reliability of the diode while providing excellent composition processability.
含有芳族烴基之光固化性單體及/或不含芳族烴基之光固化性單體是指可在光起始劑存在下經受固化反應之單體。光固化性單體可為非矽單體，其不含矽，且可包含例如僅由從C、H、O、N以及S中選出之元素組成之單體，但不限於此。光固化性單體可藉由任何典型方法製備，或可為市售產品。The photocurable monomer containing an aromatic hydrocarbon group and/or the photocurable monomer containing no aromatic hydrocarbon group means a monomer which can undergo a curing reaction in the presence of a photoinitiator. The photocurable monomer may be a non-fluorene monomer, which does not contain hydrazine, and may include, for example, a monomer composed only of elements selected from C, H, O, N, and S, but is not limited thereto. The photocurable monomer can be prepared by any typical method or can be a commercially available product.
含有芳族烴基之光固化性單體可單獨或以混合物形式使用。含有芳族烴基之光固化性單體可含有單環或多環芳族基（包括例如縮合芳族基）、具有至少兩個芳族單環之烴基或具有至少兩個芳族單環之含雜原子烴基，例如經取代或未經取代之C6 至C30 芳基與經取代或未經取代之C7 至C30 芳烷基中之至少一者。具體言之，芳族烴基可為下列各者中之至少一者：經取代或未經取代之苯基、經取代或未經取代之聯苯基、經取代或未經取代之萘基、經取代或未經取代之伸聯苯基、經取代或未經取代之三苯甲基、經取代或未經取代之聯三苯基、經取代或未經取代之聯四苯基、經取代或未經取代之蒽基、經取代或未經取代之菲基、經取代或未經取代之茀基、經取代或未經取代之聯伸三苯基、經取代或未經取代之聯伸四苯基、經取代或未經取代之2-苯基-2-(苯硫基)乙基、經取代或未經取代之3-苯基-2-(苯硫基)乙基、經取代或未經取代之2,2-二苯基丙烷基、經取代或未經取代之二苯基甲烷基、經取代或未經取代之聯苯氧基、經取代或未經取代之三苯氧基、經取代或未經取代之四苯氧基、經取代或未經取代之五苯氧基以及其結構異構體。具體言之，芳族烴基可包含至少兩個環彼此鄰接之結構。舉例而言，芳族烴基可包含經取代或未經取代之聯苯基、經取代或未經取代之三苯甲基、經取代或未經取代之伸聯苯基以及經取代或未經取代之2-苯基-2-(苯硫基)乙基，但不限於此。The photocurable monomer containing an aromatic hydrocarbon group may be used singly or in the form of a mixture. The photocurable monomer containing an aromatic hydrocarbon group may contain a monocyclic or polycyclic aromatic group (including, for example, a condensed aromatic group), a hydrocarbon group having at least two aromatic monocyclic groups, or a mixture having at least two aromatic monocyclic rings. A heteroatom hydrocarbon group such as at least one of a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 7 to C 30 aralkyl group. Specifically, the aromatic hydrocarbon group may be at least one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, Substituted or unsubstituted biphenyl, substituted or unsubstituted trityl, substituted or unsubstituted biphenyl, substituted or unsubstituted biphenyl, substituted or Unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted, extended triphenyl, substituted or unsubstituted, extended tetraphenyl Substituted, substituted or unsubstituted 2-phenyl-2-(phenylthio)ethyl, substituted or unsubstituted 3-phenyl-2-(phenylthio)ethyl, substituted or not Substituted 2,2-diphenylpropanyl, substituted or unsubstituted diphenylmethylalkyl, substituted or unsubstituted biphenyloxy, substituted or unsubstituted triphenyloxy, Substituted or unsubstituted tetraphenoxy, substituted or unsubstituted pentaceneoxy and structural isomers thereof. In particular, the aromatic hydrocarbon group may comprise a structure in which at least two rings are adjacent to each other. For example, the aromatic hydrocarbon group may comprise a substituted or unsubstituted biphenyl group, a substituted or unsubstituted trityl group, a substituted or unsubstituted stretched biphenyl group, and a substituted or unsubstituted group. 2-phenyl-2-(phenylthio)ethyl, but is not limited thereto.
含有芳族烴基之光固化性單體可含有1至20個、具體言之1至5個經取代或未經取代之乙烯基或(甲基)丙烯基。The photocurable monomer containing an aromatic hydrocarbon group may contain 1 to 20, specifically 1 to 5, substituted or unsubstituted vinyl or (meth) propylene groups.
具體言之，含有芳族烴基之光固化性單體可包含(甲基)丙烯酸2-苯基苯氧乙酯、(甲基)丙烯酸3-苯基苯氧乙酯、(甲基)丙烯酸4-苯基苯氧乙酯、(甲基)丙烯酸苯氧乙酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸苯氧酯、(甲基)丙烯酸2-乙基苯氧酯、(甲基)丙烯酸3-乙基苯氧酯、(甲基)丙烯酸4-乙基苯氧酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯乙酯、(甲基)丙烯酸苯丙酯、二(甲基)丙烯酸2,2'-苯基苯氧乙酯、(甲基)丙烯酸2-苯基苯氧丙酯、(甲基)丙烯酸3-苯基苯氧丙酯、(甲基)丙烯酸4-苯基苯氧丙酯、二(甲基)丙烯酸2,2'-苯基苯氧丙酯、(甲基)丙烯酸2-苯基苯氧丁酯、二(甲基)丙烯酸2,2'-苯基苯氧丁酯、(甲基)丙烯酸4-苯丁酯、(甲基)丙烯酸2-苯丁酯、(甲基)丙烯酸3-苯丁酯、(甲基)丙烯酸2-(2-甲基苯基)乙酯、(甲基)丙烯酸2-(3-甲基苯基)乙酯、(甲基)丙烯酸2-(4-甲基苯基)乙酯、(甲基)丙烯酸2-(4-丙基苯基)乙酯、(甲基)丙烯酸2-(4-(1-甲基乙基)苯基)乙酯、(甲基)丙烯酸2-(4-甲氧基苯基)乙酯、(甲基)丙烯酸2-(4-環己基苯基)乙酯、(甲基)丙烯酸2-(2-氯苯基)乙酯、(甲基)丙烯酸2-(3-氯苯基)乙酯、(甲基)丙烯酸2-(4-氯苯基)乙酯、(甲基)丙烯酸2-(4-溴苯基)乙酯、(甲基)丙烯酸2-(3-苯基苯基)乙酯、(甲基)丙烯酸2-苯基-2-(苯硫基)乙酯、(甲基)丙烯酸2-(三苯基甲氧基)乙酯、(甲基)丙烯酸4-(三苯基甲氧基)丁酯、(甲基)丙烯酸3-(聯苯-2-基氧基)丁酯、(甲基)丙烯酸2-(聯苯-2-基氧基)丁酯、(甲基)丙烯酸4-(聯苯-2-基氧基)丙酯、(甲基)丙烯酸3-(聯苯-2-基氧基)丙酯、(甲基)丙烯酸2-(聯苯-2-基氧基)丙酯、(甲基)丙烯酸4-(聯苯-2-基氧基)乙酯、(甲基)丙烯酸3-(聯苯-2-基氧基)乙酯、(甲基)丙烯酸2-(4-苄基苯基)乙酯、(甲基)丙烯酸1-萘酯、(甲基)丙烯酸2-萘酯、二(甲基)丙烯酸1,4-伸苯酯、雙酚-A二(甲基)丙烯酸酯、乙氧基化雙酚-A二(甲基)丙烯酸酯、雙酚-F二(甲基)丙烯酸酯、乙氧基化雙酚-F二(甲基)丙烯酸酯、丙烯酸4-異丙苯基苯氧乙酯、乙氧基化雙酚茀二丙烯酸酯以及其結構異構體或混合物，但不限於此。此外，含有芳族烴基之光固化性單體可包含前述單(甲基)丙烯酸酯之二(甲基)丙烯酸酯、三(甲基)丙烯酸酯以及四(甲基)丙烯酸酯，其具有與單(甲基)丙烯酸酯之中心部分相同的中心部分且以對稱形式末端丙烯酸化。舉例而言，當含有芳族烴基之光固化性單體為(甲基)丙烯酸苄酯時，可包含製備實例4中所製備之單體。Specifically, the photocurable monomer containing an aromatic hydrocarbon group may include 2-phenylphenoxyethyl (meth)acrylate, 3-phenylphenoxyethyl (meth)acrylate, or (meth)acrylic acid 4 -Phenylphenoxyethyl ester, phenoxyethyl (meth)acrylate, phenyl (meth)acrylate, phenoxy (meth)acrylate, 2-ethylphenoxy (meth)acrylate, (A) 3-ethylphenoxyacrylate, 4-ethylphenoxy (meth)acrylate, benzyl (meth)acrylate, phenethyl (meth)acrylate, phenylpropyl (meth)acrylate, 2,2'-phenylphenoxyethyl bis(meth)acrylate, 2-phenylphenoxypropyl (meth)acrylate, 3-phenylphenoxypropyl (meth)acrylate, (methyl) 4-phenylphenoxypropyl acrylate, 2,2'-phenylphenoxypropyl bis(meth)acrylate, 2-phenylphenoxybutyl (meth)acrylate, di(meth)acrylic acid 2, 2'-Phenylphenoxybutyl ester, 4-phenylbutyl (meth)acrylate, 2-phenylbutyl (meth)acrylate, 3-phenylbutyl (meth)acrylate, 2-(meth)acrylate (2-methylphenyl)ethyl ester, 2-(3-methylphenyl)ethyl (meth)acrylate, 2-(4-methylphenyl)ethyl (meth)acrylate, (methyl) ) C 2-(4-propylphenyl)ethyl acid, 2-(4-(1-methylethyl)phenyl)ethyl (meth)acrylate, 2-(4-methoxy) (meth)acrylate Ethylphenyl)ethyl ester, 2-(4-cyclohexylphenyl)ethyl (meth)acrylate, 2-(2-chlorophenyl)ethyl (meth)acrylate, 2-((meth)acrylate) 3-chlorophenyl)ethyl ester, 2-(4-chlorophenyl)ethyl (meth)acrylate, 2-(4-bromophenyl)ethyl (meth)acrylate, 2-(meth)acrylate (3-phenylphenyl)ethyl ester, 2-phenyl-2-(phenylthio)ethyl (meth)acrylate, 2-(triphenylmethoxy)ethyl (meth)acrylate, ( 4-(triphenylmethoxy)butyl methacrylate, 3-(biphenyl-2-yloxy)butyl (meth)acrylate, 2-(biphenyl-2-(meth)acrylate Butyloxy)butyl, 4-(biphenyl-2-yloxy)propyl (meth)acrylate, 3-(biphenyl-2-yloxy)propyl (meth)acrylate, (methyl) ) 2-(biphenyl-2-yloxy)propyl acrylate, 4-(biphenyl-2-yloxy)ethyl (meth)acrylate, 3-(biphenyl-2-(meth)acrylate Ethyloxy)ethyl ester, 2-(4-benzylphenyl)ethyl (meth)acrylate, 1-naphthyl (meth)acrylate, 2-naphthyl (meth)acrylate, di(methyl) Acrylic acid 1,4-benzene , bisphenol-A di(meth) acrylate, ethoxylated bisphenol-A di(meth) acrylate, bisphenol-F di(meth) acrylate, ethoxylated bisphenol-F II (Meth) acrylate, 4-isopropylphenylphenoxyethyl acrylate, ethoxylated bisphenol fluorene diacrylate, and structural isomers or mixtures thereof, but are not limited thereto. Further, the photocurable monomer containing an aromatic hydrocarbon group may include the above-mentioned mono(meth)acrylate di(meth)acrylate, tri(meth)acrylate, and tetra(meth)acrylate, which have The central portion of the mono(meth) acrylate is the same central portion and is acrylated in a symmetrical form. For example, when the photocurable monomer containing an aromatic hydrocarbon group is benzyl (meth)acrylate, the monomer prepared in Preparation Example 4 may be contained.
另外，由於如本文所闡述之(甲基)丙烯酸酯是藉助於實例提供，含有芳族烴基之光固化性單體不限於此且因此包含（但不限於）其任何結構異構體。舉例而言，儘管在本文中已藉助於實例提及單獨的二(甲基)丙烯酸1,4-伸苯酯，但本發明亦可包含二(甲基)丙烯酸1,2-伸苯酯及二(甲基)丙烯酸1,3-伸苯酯。In addition, since the (meth) acrylate as set forth herein is provided by way of example, the photocurable monomer containing an aromatic hydrocarbon group is not limited thereto and thus includes, but is not limited to, any structural isomer thereof. For example, although a single 1,4-phenylene bis(meth)acrylate has been mentioned herein by way of example, the present invention may also comprise 1,2-phenylene bis(meth)acrylate and 1,3-(phenyl) acrylate.
需要i）當單獨使用含有芳族烴基之光固化性單體時，含有芳族烴基之光固化性單體滿足Pcn -Ocn ≥1，及ii）當兩個或多於兩個芳族烴基用於混合物中時，混合物滿足∑(Pcn -Ocn )≥1。It is required that i) when a photocurable monomer containing an aromatic hydrocarbon group is used alone, the photocurable monomer containing an aromatic hydrocarbon group satisfies Pc n -Oc n ≥ 1, and ii) when two or more than two aromatic groups When the hydrocarbon group is used in the mixture, the mixture satisfies ∑(Pc n -Oc n )≥1.
含有芳族烴基之光固化性單體之存在量以光固化性單體之總重量計可為5重量%至50重量%，具體言之10重量%至45重量%或30重量%至50重量%。在此範圍內，組成物可具有極佳耐電漿性。The photocurable monomer containing an aromatic hydrocarbon group may be present in an amount of from 5% by weight to 50% by weight, based on the total weight of the photocurable monomer, specifically from 10% by weight to 45% by weight or from 30% by weight to 50% by weight. %. Within this range, the composition can have excellent plasma resistance.
含有芳族烴基之光固化性單體之重量平均分子量可為100.00公克/莫耳至1000.00公克/莫耳，100.00公克/莫耳至500.00公克/莫耳，100.00公克/莫耳至300.00公克/莫耳，130.00公克/莫耳至700.00公克/莫耳，或150.00公克/莫耳至600.00公克/莫耳。在此範圍內，組成物就可加工性而言可展現極佳特性。The photocurable monomer having an aromatic hydrocarbon group may have a weight average molecular weight of 100.00 g/m to 1000.00 g/m, 100.00 g/m to 500.00 g/m, 100.00 g/m to 300.00 g/m Ear, 130.00 g/m to 700.00 g/m, or 150.00 g/m to 600.00 g/m. Within this range, the composition exhibits excellent properties in terms of processability.
不含芳族烴基之光固化性單體不含芳族烴基，可含有1至20個、具體言之1至5個經取代或未經取代之乙烯基或(甲基)丙烯酸酯基，且可單獨或以混合物形式使用。The photo-curable monomer containing no aromatic hydrocarbon group does not contain an aromatic hydrocarbon group, and may contain 1 to 20, specifically 1 to 5, substituted or unsubstituted vinyl or (meth) acrylate groups, and It can be used singly or in the form of a mixture.
具體言之，不含芳族烴基之(甲基)丙烯酸酯單體可包含不飽和羧酸酯，包含(甲基)丙烯酸酯，諸如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸2-羥丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十一烷基酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸環己酯以及類似酯；不飽和羧酸胺基烷基酯，諸如(甲基)丙烯酸2-胺基乙酯、(甲基)丙烯酸2-二甲胺基乙酯以及類似酯；飽和或不飽和羧酸乙烯酯，諸如乙酸乙烯酯；氰化乙烯化合物，諸如(甲基)丙烯腈；不飽和醯胺類化合物，諸如(甲基)丙烯醯胺；乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、辛二醇二(甲基)丙烯酸酯、壬二醇二(甲基)丙烯酸酯、癸二醇二(甲基)丙烯酸酯、十一烷二醇二(甲基)丙烯酸酯、十二烷二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、季戊四醇二(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇二(甲基)丙烯酸酯、二季戊四醇三(甲基)丙烯酸酯、二季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯或其混合物，但不限於此。Specifically, the (meth) acrylate monomer containing no aromatic hydrocarbon group may contain an unsaturated carboxylic acid ester, and contains a (meth) acrylate such as methyl (meth) acrylate or ethyl (meth) acrylate. , (butyl) (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, (methyl) ) decyl acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, cyclohexyl (meth) acrylate and similar esters; unsaturated carboxylic acid Aminoalkyl esters such as 2-aminoethyl (meth)acrylate, 2-dimethylaminoethyl (meth)acrylate and similar esters; saturated or unsaturated vinyl carboxylates such as vinyl acetate a vinyl cyanide compound such as (meth)acrylonitrile; an unsaturated guanamine compound such as (meth) acrylamide; ethylene glycol di(meth) acrylate, triethylene glycol di(methyl) Acrylate, trimethylolpropane tri(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, octanediol II (methyl) propyl Oleate, decanediol di(meth) acrylate, decanediol di(meth) acrylate, undecanediol di(meth) acrylate, dodecanediol di(meth) acrylate Ester, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol di(meth)acrylate Dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate or a mixture thereof, but is not limited thereto.
不含芳族烴基之光固化性單體可為不含芳族烴基之(甲基)丙烯酸酯單體，具體言之，含有經取代或未經取代之C1 至C20 烷基、經取代或未經取代之C1 至C20 烷基矽烷基或經取代或未經取代之環烷基的單(甲基)丙烯酸酯、二(甲基)丙烯酸酯、三(甲基)丙烯酸酯或四(甲基)丙烯酸酯。The photocurable monomer containing no aromatic hydrocarbon group may be a (meth) acrylate monomer not containing an aromatic hydrocarbon group, specifically, a substituted or unsubstituted C 1 to C 20 alkyl group, substituted Or unsubstituted C 1 to C 20 alkyl decyl or substituted or unsubstituted cycloalkyl mono (meth) acrylate, di (meth) acrylate, tri (meth) acrylate or Tetra (meth) acrylate.
在本發明之一個實施例中，不含芳族烴基之(甲基)丙烯酸酯單體可為含有經取代或未經取代之C1 至C20 烷基的單(甲基)丙烯酸酯，含有經取代或未經取代之C1 至C20 伸烷基或經取代或未經取代之C1 至C20 烷基的二(甲基)丙烯酸酯，含有經取代或未經取代之C1 至C20 伸烷基或經取代或未經取代之C1 至C20 烷基的三(甲基)丙烯酸酯，含有經取代或未經取代之C1 至C20 伸烷基或經取代或未經取代之C1 至C20 烷基的四(甲基)丙烯酸酯，或其混合物。In one embodiment of the present invention, the (meth) acrylate monomer having no aromatic hydrocarbon group may be a mono(meth) acrylate containing a substituted or unsubstituted C 1 to C 20 alkyl group, and contains a substituted or unsubstituted C 1 to C 20 alkyl or substituted or unsubstituted C 1 to C 20 alkyl di(meth) acrylate containing substituted or unsubstituted C 1 to C 20 alkyl or substituted or unsubstituted C 1 to C 20 alkyl tri(meth) acrylate containing substituted or unsubstituted C 1 to C 20 alkyl or substituted or not a substituted C 1 to C 20 alkyl tetrakis (meth) acrylate, or a mixture thereof.
在本發明之一個實施例中，不含芳族烴基之(甲基)丙烯酸酯單體可為含有經取代或未經取代之C1 至C20 烷基的單(甲基)丙烯酸酯，或含有經取代或未經取代之C1 至C20 伸烷基或經取代或未經取代之C1 至C20 烷基的二(甲基)丙烯酸酯。具體言之，含有經取代或未經取代之C1 至C20 烷基的單(甲基)丙烯酸酯可為(甲基)丙烯酸癸酯、(甲基)丙烯酸十一酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸十三酯、(甲基)丙烯酸十四酯、(甲基)丙烯酸十五酯、(甲基)丙烯酸十六酯、(甲基)丙烯酸十七酯、(甲基)丙烯酸十八酯、(甲基)丙烯酸十九酯、(甲基)丙烯酸二十酯或其混合物，但不限於此。含有經取代或未經取代之C1 至C20 烷基的二(甲基)丙烯酸酯可為辛二醇二(甲基)丙烯酸酯、壬二醇二(甲基)丙烯酸酯、癸二醇二(甲基)丙烯酸酯、十一烷二醇二(甲基)丙烯酸酯、十二烷二醇二(甲基)丙烯酸酯或其混合物，但不限於此。In one embodiment of the present invention, the (meth) acrylate monomer having no aromatic hydrocarbon group may be a mono (meth) acrylate having a substituted or unsubstituted C 1 to C 20 alkyl group, or A di(meth)acrylate containing a substituted or unsubstituted C 1 to C 20 alkyl group or a substituted or unsubstituted C 1 to C 20 alkyl group. Specifically, the mono(meth)acrylate containing a substituted or unsubstituted C 1 to C 20 alkyl group may be decyl (meth) acrylate, eleven (meth) acrylate, (methyl) Lauryl acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, fifteen (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, ( Methyl) octadecyl acrylate, pentadecyl (meth) acrylate, stearyl (meth) acrylate or a mixture thereof, but is not limited thereto. The di(meth)acrylate containing a substituted or unsubstituted C 1 to C 20 alkyl group may be octanediol di(meth)acrylate, decanediol di(meth)acrylate, decanediol. Di(meth)acrylate, undecanediol di(meth)acrylate, dodecanediol di(meth)acrylate or a mixture thereof, but is not limited thereto.
不含芳族烴基之光固化性單體之存在量以包含於根據本發明之組成物中的光固化性單體之總重量計可為30重量%至95重量%，具體言之50重量%至95重量%、50重量%至70重量%。The photocurable monomer containing no aromatic hydrocarbon group may be present in an amount of 30% by weight to 95% by weight, specifically 50% by weight, based on the total weight of the photocurable monomer contained in the composition according to the present invention. Up to 95% by weight, 50% by weight to 70% by weight.
不含芳族烴基之光固化性單體之重量平均分子量可為100.00公克/莫耳至500.00公克/莫耳，100.00公克/莫耳至300.00公克/莫耳，或130.00公克/莫耳至400.00公克/莫耳。在此範圍內，組成物可展現極佳可加工性。The photo-curable monomer having no aromatic hydrocarbon group may have a weight average molecular weight of 100.00 g/mole to 500.00 g/mole, 100.00 g/m to 300.00 g/m, or 130.00 g/m to 400.00 g / Mo Er. Within this range, the composition exhibits excellent processability.
在一個實施例中，光固化性組成物可包含5重量%至50重量%之含有芳族烴基的光固化性單體及50重量%至95重量%之不含芳族烴基的光固化性單體。在一個實施例中，光固化性組成物可包含30重量%至50重量%之含有芳族烴基的光固化性單體及50重量%至70重量%之不含芳族烴基的光固化性單體。在此範圍內，光固化性組成物可展現適用於形成有機發光二極體用封裝層之黏度。In one embodiment, the photocurable composition may comprise from 5% by weight to 50% by weight of the photo-curable monomer containing an aromatic hydrocarbon group and from 50% by weight to 95% by weight of the photocurable single group containing no aromatic hydrocarbon group. body. In one embodiment, the photocurable composition may comprise 30% to 50% by weight of an aromatic hydrocarbon group-containing photocurable monomer and 50% to 70% by weight of an aromatic hydrocarbon group-free photocurable single body. Within this range, the photocurable composition can exhibit a viscosity suitable for forming an encapsulation layer for an organic light-emitting diode.
光起始劑可包含能夠進行光固化反應之任何典型光起始劑。舉例而言，光起始劑可包含三嗪、苯乙酮、二苯甲酮、噻噸酮、安息香、磷、肟起始劑或其混合物。The photoinitiator can comprise any typical photoinitiator capable of undergoing a photocuring reaction. For example, the photoinitiator can comprise triazine, acetophenone, benzophenone, thioxanthone, benzoin, phosphorus, hydrazine initiators, or mixtures thereof.
三嗪起始劑之實例可包含2,4,6-三氯-s-三嗪、2-苯基-4,6-雙(三氯甲基)-s-三嗪、2-(3',4'-二甲氧基苯乙烯基)-4,6-雙(三氯甲基)-s-三嗪、2-(4'-甲氧基萘基)-4,6-雙(三氯甲基)-s-三嗪、2-(對甲氧基苯基)-4,6-雙(三氯甲基)-s-三嗪、2-(對甲苯基)-4,6-雙(三氯甲基)-s-三嗪、2-聯苯-4,6-雙(三氯甲基)-s-三嗪、雙(三氯甲基)-6-苯乙烯基-s-三嗪、2-(萘并-1-基)-4,6-雙(三氯甲基)-s-三嗪、2-(4-甲氧基萘并-1-基)-4,6-雙(三氯甲基)-s-三嗪、2,4-三氯甲基(向日葵基)-6-三嗪、2,4-(三氯甲基(4'-甲氧基苯乙烯基)-6-三嗪以及其混合物。Examples of the triazine initiator may include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3' , 4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis (three Chloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6- Bis(trichloromethyl)-s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s Triazine, 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthen-1-yl)-4, 6-Bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl(safflower-based)-6-triazine, 2,4-(trichloromethyl(4'-methoxybenzene) Vinyl)-6-triazine and mixtures thereof.
苯乙酮起始劑之實例可包含2,2'-二乙氧基苯乙酮、2,2'-二丁氧基苯乙酮、2-羥基-2-甲基苯丙酮、對第三丁基三氯苯乙酮、對第三丁基二氯苯乙酮、4-氯苯乙酮、2,2'-二氯-4-苯氧基苯乙酮、2-甲基-1-(4-(甲硫基)苯基)-2-嗎啉基丙-1-酮、2-苄基-2-二甲胺基-1-(4-嗎啉基苯基)-丁-1-酮以及其混合物。Examples of the acetophenone initiator may include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, and third Butyl trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1- (4-(Methylthio)phenyl)-2-morpholinylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-but-1 a ketone and a mixture thereof.
二苯甲酮起始劑之實例可包含二苯甲酮、苯甲酸苄醯酯、苄醯基苯甲酸甲酯、4-苯基二苯甲酮、羥基二苯甲酮、丙烯酸化二苯甲酮、4,4'-雙(二甲胺基)二苯甲酮、4,4'-二氯二苯甲酮、3,3'-二甲基-2-甲氧基二苯甲酮以及其混合物。Examples of the benzophenone starter may include benzophenone, benzalkonium benzoate, methyl benzalkonium benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone Ketone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and Its mixture.
噻噸酮起始劑之實例可包含噻噸酮、2-甲基噻噸酮、異丙基噻噸酮、2,4-二乙基噻噸酮、2,4-二異丙基噻噸酮、2-氯噻噸酮以及其混合物。Examples of the thioxanthone starter may include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthene Ketones, 2-chlorothioxanthone, and mixtures thereof.
安息香起始劑之實例可包含安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香異丁醚、苄基二甲基縮酮以及其混合物。Examples of the benzoin starter may include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and mixtures thereof.
磷起始劑之實例可包含二苄醯基苯基氧化膦、苄醯基(二苯基)氧化膦以及其混合物。Examples of the phosphorus initiator may include dibenzyl phenyl phosphine oxide, benzindenyl (diphenyl) phosphine oxide, and a mixture thereof.
肟起始劑之實例可包含2-(鄰苄醯肟)-1-[4-(苯硫基)苯基]-1,2-辛二酮、1-(鄰乙醯肟)-1-[9-乙基-6-(2-甲基苄醯基)-9H-咔唑-3-基]乙酮以及其混合物。Examples of the hydrazine initiator may include 2-(o-benzylidene)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-ethylidene)-1- [9-Ethyl-6-(2-methylbenzylindenyl)-9H-indazol-3-yl]ethanone and mixtures thereof.
光起始劑之存在量以光固化性單體之100重量份計可為0.1重量份至20重量份。在此範圍內，光固化性組成物可允許足夠光聚合且可防止因光聚合之後剩餘的未反應起始劑所致之透射率劣化。具體言之，光起始劑之存在量以光固化性單體之100重量份計可為0.5重量份至10重量份，更具體言之1重量份至8重量份。此外，光起始劑就固體含量而言可以0.1重量%至5重量%之量存在於光固化性組成物中。在此範圍內，光固化性組成物可允許足夠光聚合且可防止因光聚合之後剩餘的未反應起始劑所致之透射率劣化。The photoinitiator may be present in an amount of from 0.1 part by weight to 20 parts by weight based on 100 parts by weight of the photocurable monomer. Within this range, the photocurable composition can allow sufficient photopolymerization and can prevent deterioration of transmittance due to unreacted starter remaining after photopolymerization. Specifically, the photoinitiator may be present in an amount of from 0.5 part by weight to 10 parts by weight, more specifically from 1 part by weight to 8 parts by weight, based on 100 parts by weight of the photocurable monomer. Further, the photoinitiator may be present in the photocurable composition in an amount of from 0.1% by weight to 5% by weight in terms of solid content. Within this range, the photocurable composition can allow sufficient photopolymerization and can prevent deterioration of transmittance due to unreacted starter remaining after photopolymerization.
另外，可使用光酸產生劑或包括咔唑、二酮、鋶、碘鎓、重氮或聯咪唑之光起始劑替代前述光起始劑。Alternatively, a photoacid generator or a photoinitiator comprising oxazole, diketone, hydrazine, iodonium, diazo or biimidazole may be used in place of the above photoinitiator.
根據本發明之另一實施例之光固化性組成物可更包含抗氧化劑。The photocurable composition according to another embodiment of the present invention may further comprise an antioxidant.
抗氧化劑可改良封裝層之熱穩定性。抗氧化劑可包含酚、醌、胺以及亞磷酸酯抗氧化劑中之至少一者，但不限於此。舉例而言，抗氧化劑可包含肆[亞甲基(3,5-二-第三丁基-4-羥基氫化肉桂酸酯)]甲烷、三(2,4-二-第三丁基苯基)亞磷酸酯以及類似物。Antioxidants improve the thermal stability of the encapsulation layer. The antioxidant may include at least one of a phenol, a hydrazine, an amine, and a phosphite antioxidant, but is not limited thereto. For example, the antioxidant may comprise hydrazine [methylene (3,5-di-t-butyl-4-hydroxyhydrocinnamate)] methane, tris(2,4-di-t-butylphenyl) Phosphite and analogs.
抗氧化劑之存在量以光固化性單體與光起始劑之總數的100重量份計可為0.01重量份至3重量份，具體言之0.01重量份至1重量份。在此範圍內，組成物可展現極佳熱穩定性。The antioxidant may be present in an amount of from 0.01 part by weight to 3 parts by weight, specifically from 0.01 part by weight to 1 part by weight, based on 100 parts by weight of the total of the photocurable monomer and the photoinitiator. Within this range, the composition exhibits excellent thermal stability.
光固化性組成物可經由在10毫瓦/平方公分至500毫瓦/平方公分下UV照射1秒至100秒來固化，但不限於此。The photocurable composition may be cured by UV irradiation at 10 mW/cm 2 to 500 mW/cm 2 for 1 second to 100 seconds, but is not limited thereto.
光固化性組成物在固化之後的電漿蝕刻速率可為12%或小於12%，具體言之0%至10%，更具體言之0%至8.0%。在此範圍內，有可能實現展現極佳耐電漿性及極佳可靠性之有機保護層。The plasma etch rate of the photocurable composition after curing may be 12% or less, specifically 0% to 10%, more specifically 0% to 8.0%. Within this range, it is possible to realize an organic protective layer exhibiting excellent plasma resistance and excellent reliability.
蝕刻速率可藉由將光固化性組成物沈積至特定厚度T0且固化形成有機保護層之程序獲得。隨後，量測電漿處理之後有機保護層之厚度T1，且藉由等式2計算蝕刻速率： ＜等式2＞ 電漿蝕刻速率（%）= {(T0-T1)/T0}×100The etch rate can be obtained by depositing a photocurable composition to a specific thickness T0 and curing to form an organic protective layer. Subsequently, the thickness T1 of the organic protective layer after the plasma treatment is measured, and the etching rate is calculated by Equation 2: <Equation 2> Plasma etching rate (%) = {(T0 - T1) / T0} × 100
舉例而言，將光固化性組成物噴塗於矽晶圓上，隨後經由在100焦耳/平方公分下UV照射10秒來UV固化，藉此形成塗層厚度為5微米之樣品。在下列條件下使用ICP乾式刻蝕器（電漿實驗室系統133，牛津儀器（Oxford Instruments））用氬氣使樣品經受乾式蝕刻：ICP功率：2500瓦，RE功率：300瓦，DC偏壓：200伏，Ar流量：50標準立方公分/分鐘，壓力：10毫托，以及蝕刻時間：1分鐘。量測乾式蝕刻之前有機保護層之厚度T0及乾式蝕刻之後有機保護層之厚度T1，藉此根據等式2計算電漿蝕刻速率。For example, a photocurable composition was sprayed onto a tantalum wafer and subsequently UV cured by UV irradiation at 100 Joules/cm 2 for 10 seconds, thereby forming a sample having a coating thickness of 5 microns. The sample was subjected to dry etching with argon using an ICP dry etcher (plasma laboratory system 133, Oxford Instruments) under the following conditions: ICP power: 2500 watts, RE power: 300 watts, DC bias: 200 volts, Ar flow: 50 standard cubic centimeters per minute, pressure: 10 millitorr, and etching time: 1 minute. The thickness T0 of the organic protective layer before dry etching and the thickness T1 of the organic protective layer after dry etching are measured, whereby the plasma etching rate is calculated according to Equation 2.
根據本發明之光固化性組成物可為用作下列各者之封裝材料之光固化性組成物：可撓性有機發光二極體、有機發光二極體、照明器件、金屬感測器墊、微盤雷射器、電致變色器件、光致變色器件、微機電系統、太陽能電池、積體電路、電荷耦合器件以及發光聚合物。The photocurable composition according to the present invention may be a photocurable composition used as a packaging material for each of: a flexible organic light emitting diode, an organic light emitting diode, a lighting device, a metal sensor pad, Microdisk lasers, electrochromic devices, photochromic devices, microelectromechanical systems, solar cells, integrated circuits, charge coupled devices, and luminescent polymers.
根據一個實施例之光固化性組成物可為用作有機發光二極體（OLED）、發光二極體（LED）以及OLED或LED照明器件之顯示器封裝材料之光固化性組成物。The photocurable composition according to one embodiment may be a photocurable composition used as a display encapsulant material for an organic light emitting diode (OLED), a light emitting diode (LED), and an OLED or LED lighting device.
根據本發明之實施例之光固化性組成物可用作有機發光二極體之封裝材料。具體言之，光固化性組成物可用作用於形成有機保護層之封裝材料，有機保護層保護有機發光二極體免受周圍環境以防止有機發光二極體受周圍環境（例如液體或氣體，具體言之濕氣或氧氣）或用於製造包含有機發光二極體的裝置之化學品損壞或特徵惡化。The photocurable composition according to an embodiment of the present invention can be used as an encapsulating material for an organic light emitting diode. Specifically, the photocurable composition can be used as an encapsulating material for forming an organic protective layer, and the organic protective layer protects the organic light emitting diode from the surrounding environment to prevent the organic light emitting diode from being subjected to the surrounding environment (for example, liquid or gas, specifically In case of moisture or oxygen) or chemical damage or deterioration of features used to manufacture devices containing organic light-emitting diodes.
根據本發明之實施例之光固化性組成物可用於在有機發光二極體上形成有機保護層，或在形成於有機發光二極體上之無機保護層上形成有機保護層。有機保護層可使用沈積、噴墨印刷以及類似者形成，但不限於此。The photocurable composition according to an embodiment of the present invention can be used to form an organic protective layer on the organic light emitting diode or to form an organic protective layer on the inorganic protective layer formed on the organic light emitting diode. The organic protective layer may be formed using deposition, inkjet printing, and the like, but is not limited thereto.
根據本發明之實施例之光固化性組成物可用作裝置用構件之封裝材料。具體言之，光固化性組成物可用作用於形成有機保護層之封裝材料，有機保護層保護裝置用構件免受周圍環境以防止裝置用構件受周圍環境（例如液體或氣體，具體言之濕氣或氧氣）或用於製造包含有機發光二極體的裝置之化學品損壞或特徵惡化。裝置用構件之實例可包含可撓性有機發光二極體、有機發光二極體、照明器件、金屬感測器墊、微盤雷射器、電致變色器件、光致變色器件、微機電系統、太陽能電池、積體電路、電荷耦合器件、發光聚合物以及發光二極體，但不限於此。The photocurable composition according to an embodiment of the present invention can be used as an encapsulating material for a member for a device. Specifically, the photocurable composition can be used as an encapsulating material for forming an organic protective layer, and the organic protective layer protects the member for the device from the surrounding environment to prevent the device member from being subjected to the surrounding environment (for example, liquid or gas, specifically moisture). Or oxygen) or chemical damage or deterioration of features used to make devices containing organic light-emitting diodes. Examples of components for the device may include a flexible organic light emitting diode, an organic light emitting diode, an illumination device, a metal sensor pad, a microdisk laser, an electrochromic device, a photochromic device, a microelectromechanical system. , solar cells, integrated circuits, charge coupled devices, light-emitting polymers, and light-emitting diodes, but are not limited thereto.
根據本發明之另一態樣，封裝裝置可包含裝置用構件及形成於裝置用構件上之保護層。保護層可包含無機保護層及有機保護層，其中所述有機保護層可由根據本發明之實施例之光固化性組成物形成。According to another aspect of the present invention, a packaging device may include a member for a device and a protective layer formed on the member for the device. The protective layer may include an inorganic protective layer and an organic protective layer, wherein the organic protective layer may be formed of a photocurable composition according to an embodiment of the present invention.
隨後，將參考圖1描述根據本發明之一個實施例之封裝裝置。Subsequently, a packaging device according to an embodiment of the present invention will be described with reference to FIG.
圖1為根據本發明之一個實施例之封裝裝置之截面視圖。封裝裝置100包含基板10；裝置用構件20，形成於基板10上；以及複合保護層30，形成於裝置用構件20上且包含無機保護層31及有機保護層32，其中無機保護層31毗連裝置用構件20且有機保護層32可由根據本發明之實施例之光固化性組成物形成。1 is a cross-sectional view of a packaged device in accordance with one embodiment of the present invention. The packaging device 100 includes a substrate 10; a device member 20 is formed on the substrate 10; and a composite protective layer 30 is formed on the device member 20 and includes an inorganic protective layer 31 and an organic protective layer 32, wherein the inorganic protective layer 31 is adjacent to the device The member 20 is used and the organic protective layer 32 can be formed of a photocurable composition according to an embodiment of the present invention.
裝置用構件之實例可包含可撓性有機發光二極體、有機發光二極體、照明器件、金屬感測器墊、微盤雷射器、電致變色器件、光致變色器件、微機電系統、太陽能電池、積體電路、電荷耦合器件以及發光聚合物，但不限於此。在一個實施例中，裝置用構件可為由下列各者中選出之一個：有機發光二極體（OLED）、發光二極體（LED）、OLED照明器件以及LED照明器件。Examples of components for the device may include a flexible organic light emitting diode, an organic light emitting diode, an illumination device, a metal sensor pad, a microdisk laser, an electrochromic device, a photochromic device, a microelectromechanical system. , solar cells, integrated circuits, charge coupled devices, and luminescent polymers, but are not limited thereto. In one embodiment, the device component can be one selected from the group consisting of an organic light emitting diode (OLED), a light emitting diode (LED), an OLED lighting device, and an LED lighting device.
基板10不受特定限制且可包含透明玻璃、塑膠膜以及矽或金屬基板。The substrate 10 is not particularly limited and may include a transparent glass, a plastic film, and a tantalum or metal substrate.
裝置用構件20可為例如有機發光二極體，且包含第一電極、第二電極以及形成於第一電極與第二電極之間的有機發光層，其中所述有機發光層可具有電洞注入層、電洞傳輸層、發光層、電子傳輸層以及電子注入層依次堆疊之結構，但不限於此。The device member 20 may be, for example, an organic light emitting diode, and includes a first electrode, a second electrode, and an organic light emitting layer formed between the first electrode and the second electrode, wherein the organic light emitting layer may have a hole injection The structure in which the layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer are sequentially stacked is not limited thereto.
複合保護層30包含無機保護層31及有機保護層32，其中無機保護層31及有機保護層32分別由不同材料形成且可充當裝置用構件之封裝材料。The composite protective layer 30 includes an inorganic protective layer 31 and an organic protective layer 32, wherein the inorganic protective layer 31 and the organic protective layer 32 are respectively formed of different materials and can serve as an encapsulating material for the device member.
無機保護層31由不同於有機保護層32之材料組成，且因此可補充有機保護層32之作用。無機保護層31可由具有極佳透光率及優良的濕氣及/或氧氣障壁特性之無機材料形成。舉例而言，無機保護層31可由下列各者形成：金屬、非金屬、金屬間化合物或合金、非金屬間化合物或合金、金屬或非金屬之氧化物、金屬或非金屬之氟化物、金屬或非金屬之氮化物、金屬或非金屬之碳化物、金屬或非金屬之氮氧化物、金屬或非金屬之硼化物、金屬或非金屬之硼氧化物、金屬或非金屬之矽化物以及其組合。金屬或非金屬可包含矽（Si）、鋁（Al）、硒（Se）、鋅（Zn）、銻（Sb）、銦（In）、鍺（Ge）、錫（Sn）、鉍（Bi）、過渡金屬以及鑭系金屬，但不限於此。具體言之，無機保護層可為氧化矽（SiOx ）、氮化矽（SiNx ）、氮氧化矽（SiOx Ny ）、ZnSe、ZnO、Sb2 O3 、AlOx （包含Al2 O3 ）、In2 O3 或SnO2 ，其中x及y各自獨立地為1至5。The inorganic protective layer 31 is composed of a material different from the organic protective layer 32, and thus can complement the role of the organic protective layer 32. The inorganic protective layer 31 can be formed of an inorganic material having excellent light transmittance and excellent moisture and/or oxygen barrier properties. For example, the inorganic protective layer 31 may be formed of a metal, a non-metal, an intermetallic compound or alloy, a non-intermetallic compound or alloy, a metal or non-metal oxide, a metal or non-metal fluoride, a metal or Non-metallic nitrides, metal or non-metal carbides, metal or non-metal oxynitrides, metal or non-metal borides, metal or non-metal oxyborides, metal or non-metal bismuth compounds, and combinations thereof . The metal or non-metal may comprise bismuth (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), antimony (Bi). , transition metals and lanthanide metals, but are not limited to this. Specifically, the inorganic protective layer may be cerium oxide (SiO x ), cerium nitride (SiN x ), cerium oxynitride (SiO x N y ), ZnSe, ZnO, Sb 2 O 3 , AlO x (including Al 2 O). 3 ), In 2 O 3 or SnO 2 , wherein x and y are each independently from 1 to 5.
無機保護層31可藉由電漿製程或真空製程，例如濺鍍、化學氣相沈積、電漿化學氣相沈積、蒸發、昇華、電子迴旋共振-電漿增強式化學氣相沈積或其組合來沈積。The inorganic protective layer 31 can be processed by a plasma process or a vacuum process such as sputtering, chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma enhanced chemical vapor deposition or a combination thereof. Deposition.
無機保護層31之厚度可為100埃至2000埃，但不限於此。The inorganic protective layer 31 may have a thickness of 100 angstroms to 2000 angstroms, but is not limited thereto.
有機保護層32可藉由沈積、噴墨印刷、網版印刷、旋塗、刮塗或固化根據本發明之實施例之光固化性組成物來形成。這些製程可單獨或以其組合形式進行。舉例而言，有機保護層可藉由塗佈厚度為約1微米至約50微米之光固化性組成物，隨後經由在10毫瓦/平方公分至500毫瓦/平方公分下照射1秒至100秒來固化組成物而形成。The organic protective layer 32 can be formed by deposition, inkjet printing, screen printing, spin coating, blade coating or curing of a photocurable composition according to an embodiment of the present invention. These processes can be carried out either singly or in combination. For example, the organic protective layer can be applied by applying a photocurable composition having a thickness of from about 1 micron to about 50 microns, followed by irradiation at 10 mW/cm 2 to 500 mW/cm 2 for 1 second to 100. It is formed by curing the composition in seconds.
儘管圖1中未展示，有機保護層與無機保護層可交替沈積，使得層之總數變為3或大於3。當有機保護層沈積於兩個或多於兩個無機保護層之間時，有可能確保無機保護層之平滑度且防止一個無機保護層鋪展至其他無機保護層之缺陷。此外，沈積於兩個或多於兩個有機保護層之間的無機保護層可補充或增強裝置之封裝效果。Although not shown in FIG. 1, the organic protective layer and the inorganic protective layer may be alternately deposited such that the total number of layers becomes 3 or more. When the organic protective layer is deposited between two or more inorganic protective layers, it is possible to ensure the smoothness of the inorganic protective layer and prevent the defects of one inorganic protective layer from spreading to other inorganic protective layers. In addition, an inorganic protective layer deposited between two or more organic protective layers may complement or enhance the packaging effect of the device.
複合保護層30包含一個交替堆疊於另一個上之無機保護層31與有機保護層32，其中無機保護層31與有機保護層32之總數不受特定限制。無機保護層31與有機保護層32之總數可視對氧氣及/或濕氣及/或水蒸氣及/或化學品之耐滲透性水準而變化。舉例而言，無機保護層31與有機保護層32可以總計10層或少於10層、例如以總計2層至7層存在，且具體言之，可以總計7層按無機保護層/有機保護層/無機保護層/有機保護層/無機保護層/有機保護層/無機保護層之順序交替沈積。The composite protective layer 30 includes an inorganic protective layer 31 and an organic protective layer 32 which are alternately stacked on the other, wherein the total number of the inorganic protective layer 31 and the organic protective layer 32 is not particularly limited. The total number of inorganic protective layers 31 and organic protective layers 32 may vary depending on the level of resistance to oxygen and/or moisture and/or water vapor and/or chemicals. For example, the inorganic protective layer 31 and the organic protective layer 32 may be present in a total of 10 layers or less, for example, in a total of 2 to 7 layers, and in particular, a total of 7 layers may be used as the inorganic protective layer/organic protective layer. The order of the inorganic protective layer/organic protective layer/inorganic protective layer/organic protective layer/inorganic protective layer is alternately deposited.
封裝裝置之除氣量可為百萬分之2000或小於百萬分之2000。在此範圍內，有可能延長裝置用構件之壽命，藉此增強可靠性。具體言之，封裝裝置之除氣量可為百萬分之10至百萬分之1000。The degassing capacity of the packaged device can be 2000 parts per million or less than 2000 parts per million. Within this range, it is possible to extend the life of the components for the device, thereby enhancing reliability. Specifically, the degassing amount of the packaging device may be 10 parts per million to 1000 parts per million.
隨後，將參考圖2描述根據本發明之另一實施例之封裝裝置。圖2為根據本發明之另一實施例之封裝裝置之截面視圖。Subsequently, a packaging device according to another embodiment of the present invention will be described with reference to FIG. 2 is a cross-sectional view of a package device in accordance with another embodiment of the present invention.
參考圖2，根據本發明之實施例之封裝裝置200包含基板10；裝置用構件20，形成於基板10上；以及複合保護層30，形成於裝置用構件20上且包含無機保護層31及有機保護層32，其中無機保護層31將容納裝置用構件20之內部空間封裝，且有機保護層32可由根據本發明之實施例之光固化性組成物形成。由於除無機保護層31不毗連裝置用構件20以外，此封裝裝置與根據本發明之上述實施例之有機發光二極體顯示器實質上相同，因此將省略其詳細描述。Referring to FIG. 2, a packaging apparatus 200 according to an embodiment of the present invention includes a substrate 10; a device member 20 formed on the substrate 10; and a composite protective layer 30 formed on the device member 20 and including an inorganic protective layer 31 and organic The protective layer 32 in which the inorganic protective layer 31 encapsulates the inner space of the accommodating member 20, and the organic protective layer 32 may be formed of a photocurable composition according to an embodiment of the present invention. Since the package device is substantially the same as the organic light-emitting diode display according to the above-described embodiment of the present invention except that the inorganic protective layer 31 is not adjacent to the device member 20, detailed description thereof will be omitted.
在下文中，將參考一些實例更詳細描述本發明。然而，應理解提供這些實例僅為說明，且不應以任何方式解釋為限制本發明。為清楚起見，將省略所屬領域中具通常知識者顯而易知之細節描述。製備實例 1 Hereinafter, the present invention will be described in more detail with reference to some examples. However, it is to be understood that these examples are provided for illustration only and are not to be construed as limiting the invention in any way. For the sake of clarity, detailed descriptions that are apparent to those of ordinary skill in the art will be omitted. Preparation example 1
在具有冷卻管及攪拌器之3000毫升反應器中，置放300毫升二氯甲烷（西格瑪奧德里奇公司（Sigma Aldrich Corporation））、200公克4-羥丁基丙烯酸酯（新中村化工（Shin Nakamura Chemical））以及168公克三乙胺，隨後將燒瓶冷卻至0℃且攪拌2小時，同時向其中逐滴添加藉由將278公克對甲苯磺醯氯（西格瑪奧德里奇公司）溶解於500毫升二氯甲烷中所得溶液。額外攪拌5小時之後，藉由真空蒸餾移除殘餘溶劑。將300公克所得化合物置放於1000毫升乙腈（西格瑪奧德里奇公司）中，且隨後向其中添加220公克碳酸鉀（奧德里奇有限公司（Aldrich Co., Ltd.））及141公克2-苯基苯酚（西格瑪奧德里奇公司），隨後在80℃下攪拌。移除殘餘溶劑及反應殘基，藉此獲得由式1表示之化合物。所得化合物（重量平均分子量：296.36）之HPLC純度為93%。 ＜式1＞ 製備實例 2 In a 3000 ml reactor equipped with a cooling tube and a stirrer, 300 ml of dichloromethane (Sigma Aldrich Corporation) and 200 g of 4-hydroxybutyl acrylate (Shin Nakamura) were placed. Chemical)) and 168 g of triethylamine, then the flask was cooled to 0 ° C and stirred for 2 hours while being added dropwise thereto by dissolving 278 g of p-toluenesulfonyl chloride (Sigma Aldrich) in 500 ml. The resulting solution in methyl chloride. After stirring for an additional 5 hours, the residual solvent was removed by vacuum distillation. 300 g of the obtained compound was placed in 1000 ml of acetonitrile (Sigma Aldrich), and then 220 g of potassium carbonate (Aldrich Co., Ltd.) and 141 g of 2-benzene were added thereto. Phenol (Sigma Aldrich), followed by stirring at 80 °C. The residual solvent and the reaction residue are removed, whereby the compound represented by Formula 1 is obtained. The obtained compound (weight average molecular weight: 296.36) had an HPLC purity of 93%. <Formula 1> Preparation example 2
在具有冷卻管及攪拌器之1000毫升反應器中，置放200毫升二氯甲烷（西格瑪奧德里奇公司）、100公克苯硫酚（奧德里奇有限公司）以及109公克氧化苯乙烯（西格瑪奧德里奇公司），隨後將燒瓶冷卻至0℃。隨後，將4公克過氯酸鋅（西格瑪奧德里奇公司）置放於燒瓶中，隨後攪拌8小時且藉由真空蒸餾移除殘餘溶劑。將150公克所得化合物置放於500毫升二氯甲烷中，且向其中添加70公克三乙胺（大中化學化工（Daejungchem Chemicals）），隨後在0℃下攪拌，同時滴加65公克甲基丙烯醯氯（梯希愛有限公司（TCI Co., Ltd.））2小時。額外攪拌5小時之後，移除殘餘溶劑及反應殘基，藉此獲得由式2表示之化合物。所得化合物（重量平均分子量：284.37）之HPLC純度為94%。 ＜式2＞ 製備實例 3 In a 1000 ml reactor with a cooling tube and stirrer, place 200 ml of dichloromethane (Sigma Aldrich), 100 g of thiophenol (Aldrich Co., Ltd.) and 109 g of styrene oxide (Sigma) The company was then cooled to 0 ° C. Subsequently, 4 g of zinc perchlorate (Sigma Aldrich) was placed in the flask, followed by stirring for 8 hours and the residual solvent was removed by vacuum distillation. 150 g of the obtained compound was placed in 500 ml of dichloromethane, and 70 g of triethylamine (Daejungchem Chemicals) was added thereto, followed by stirring at 0 ° C while dropwise adding 65 g of methacrylic acid. Chlorine (TCI Co., Ltd.) 2 hours. After additional stirring for 5 hours, the residual solvent and the reaction residue were removed, whereby the compound represented by Formula 2 was obtained. The obtained compound (weight average molecular weight: 284.37) had an HPLC purity of 94%. <Formula 2> Preparation Example 3
在具有冷卻管及攪拌器之2000毫升燒瓶中，置放600毫升二氯甲烷（西格瑪奧德里奇公司）、58.8公克2-甲基丙烯酸羥基乙酯（奧德里奇有限公司）以及52.2公克三乙胺（西格瑪奧德里奇公司），隨後在0℃下攪拌同時緩慢地引入100公克三苯基氯甲烷（三苯甲基氯，西格瑪奧德里奇公司）。將燒瓶加熱至25℃，隨後攪拌4小時。隨後，藉由真空蒸餾移除二氯甲烷，隨後矽膠管柱層析，藉此獲得124公克由式3表示之化合物。所得化合物之HPLC純度為97%。 ＜式3＞ 製備實例 4 In a 2000 ml flask with a cooling tube and a stirrer, 600 ml of dichloromethane (Sigma Aldrich), 58.8 g of 2-hydroxyethyl methacrylate (Aldrich Co., Ltd.) and 52.2 g of tribride were placed. Amine (Sigma Aldrich) was then slowly introduced at 0 ° C while slowly introducing 100 grams of triphenylchloromethane (trityl chloride, Sigma Aldrich). The flask was heated to 25 ° C and then stirred for 4 hours. Subsequently, dichloromethane was removed by vacuum distillation, followed by silica gel column chromatography, whereby 124 g of the compound represented by Formula 3 was obtained. The obtained compound had an HPLC purity of 97%. <Formula 3> Preparation Example 4
在具有冷卻管及攪拌器之2000毫升燒瓶中，置放800毫升乙腈（西格瑪奧德里奇公司）、180公克碳酸鉀（奧德里奇有限公司）以及108公克丙烯酸，隨後在0℃下攪拌同時緩慢地引入150公克4,4'-雙(氯甲基)聯苯（梯希愛有限公司）。將燒瓶加熱至70℃，隨後攪拌12小時。隨後，藉由真空蒸餾移除乙腈，隨後矽膠管柱層析，藉此獲得177公克由式4表示之化合物。所得化合物之HPLC純度為97%。 ＜式4＞ In a 2000 ml flask with a cooling tube and a stirrer, 800 ml of acetonitrile (Sigma Aldrich), 180 g of potassium carbonate (Aldrich Co., Ltd.) and 108 g of acrylic acid were placed, followed by stirring at 0 ° C while slowly 150 grams of 4,4'-bis(chloromethyl)biphenyl (Tie Xi Ai Co., Ltd.) was introduced. The flask was heated to 70 ° C and then stirred for 12 hours. Subsequently, acetonitrile was removed by vacuum distillation, followed by silica gel column chromatography, whereby 177 g of the compound represented by Formula 4 was obtained. The obtained compound had an HPLC purity of 97%. <Formula 4>
實例及比較例中所用之組分的細節如下： （A）光固化性單體 （a1）十二烷二醇二甲基丙烯酸酯（施他默化學品（Satomer Chemical）） （a2）三羥甲基丙烷三丙烯酸酯（巴斯夫有限公司（BASF Co., Ltd.）） （a3）1,3-雙(3-甲基丙烯醯氧基丙基)四甲基二矽氧烷（SIB1402.0，蓋勒斯特公司（Gelest Inc.）） （a4）丙烯酸2-苯基苯氧乙酯（FA-301A，日立化成（Hitachi Chemical）） （a5）製備實例1中所製備之含有芳族烴基之光固化性單體 （a6）製備實例2中所製備之含有芳族烴基之光固化性單體 （a7）製備實例3中所製備之含有芳族烴基之光固化性單體 （a8）丙烯酸苯硫基乙酯（KOREMUL-PT-011，韓農化工（Hannong Chemicals）） （a9）製備實例4中所製備之含有芳族烴基之光固化性單體 （B）光起始劑：磷起始劑（達若可TPO，巴斯夫有限公司）實例 1 The details of the components used in the examples and comparative examples are as follows: (A) Photocurable monomer (a1) dodecanediol dimethacrylate (Satomer Chemical) (a2) trishydroxyl Methylpropane triacrylate (BASF Co., Ltd.) (a3) 1,3-bis(3-methylpropenyloxypropyl)tetramethyldioxane (SIB1402.0) , Gelest Inc. (a4) 2-Phenylphenoxyethyl acrylate (FA-301A, Hitachi Chemical) (a5) Preparation of aromatic hydrocarbon group prepared in Example 1 Photocurable monomer (a6) Preparation of the aromatic hydrocarbon group-containing photocurable monomer (a7) prepared in Example 2 Preparation of the aromatic hydrocarbon group-containing photocurable monomer (a8) acrylic acid prepared in Example 3. Phenylthioethyl ester (KOREMUL-PT-011, Hannon Chemicals) (a9) Preparation of photo-curable monomer (B) photoinitiator containing aromatic hydrocarbon group prepared in Example 4: phosphorus Starting agent (Daroco TPO, BASF Co., Ltd.) Example 1
在125毫升棕色聚丙烯瓶中，置放60重量份（a1）、40重量份（a4）以及5重量份（B），隨後使用振盪器混合3小時，藉此製備實例1之光固化性組成物。藉由以下等式計算POC參數。結果展示於表1中。 POC參數=其中Pcn 為光固化性組成物之各單體之芳環數，Ocn 為光固化性組成物之各單體的O原子與S原子之總數，Wrn 為各單體以光固化性組成物之所有單體之總重量計的重量百分比（重量%），且Mwn 為光固化性組成物之各單體的重量平均分子量。實例 2 至實例 11 及比較例 1 至比較例 3 60 parts by weight (a1), 40 parts by weight (a4), and 5 parts by weight (B) were placed in a 125 ml brown polypropylene bottle, followed by mixing with a shaker for 3 hours, thereby preparing a photocurable composition of Example 1. Things. The POC parameters are calculated by the following equation. The results are shown in Table 1. POC parameter = Wherein Pc n is the number of aromatic rings of each monomer of the photocurable composition, Oc n is the total number of O atoms and S atoms of each monomer of the photocurable composition, and Wr n is a photocurable composition of each monomer. The weight percentage (% by weight) based on the total weight of all the monomers, and Mw n is the weight average molecular weight of each monomer of the photocurable composition. Example 2 to Example 11 and Comparative Example 1 to Comparative Example 3
除各組分之種類及量如表1中所列改變以外，以與實例1中相同之方式製備光固化性組成物。計算每種光固化性組成物之POC參數。結果展示於表1中。特性評估 A photocurable composition was prepared in the same manner as in Example 1 except that the kinds and amounts of the components were changed as listed in Table 1. The POC parameters of each photocurable composition were calculated. The results are shown in Table 1. Characteristic evaluation
（1）電漿蝕刻速率（%）：將實例及比較例中之每種光固化性組成物噴塗於矽晶圓上，隨後經由在100焦耳/平方公分下UV照射10秒來UV固化，藉此形成5微米厚有機保護層樣品。在下列條件下使用ICP乾式刻蝕器（電漿實驗室系統133，牛津儀器）用氬氣使樣品經受乾式蝕刻：ICP功率：2500瓦，RE功率：300瓦，DC偏壓：200伏，Ar流量：50標準立方公分/分鐘，壓力：10毫托，以及蝕刻時間：1分鐘。在量測乾式蝕刻之前有機保護層之厚度T0及乾式蝕刻之後有機保護層之厚度T1之後，藉由以下等式計算電漿蝕刻速率。 電漿蝕刻速率（%）= {(T0-T1)/T0}×100表 1
根據表1及表2中所展示之結果，可見實例之POC參數在本發明範圍內之光固化性組成物具有顯著低的電漿蝕刻速率且因此展現顯著極佳耐電漿性。相反，比較例之POC參數在本發明範圍以外之光固化性組成物與實例相比具有相對高的電漿蝕刻速率。From the results shown in Tables 1 and 2, it can be seen that the photocurable compositions of the examples having POC parameters within the scope of the present invention have significantly lower plasma etch rates and thus exhibit significantly superior plasma resistance. In contrast, the photocurable compositions of the comparative examples having POC parameters outside the scope of the present invention have a relatively high plasma etch rate compared to the examples.
展示本發明之簡單修改或改變可易於由所屬領域中具通常知識者實施，且所述修改或改變將由本發明之範疇涵蓋。Simple modifications or variations of the present invention can be readily implemented by those of ordinary skill in the art, and such modifications or variations are encompassed by the scope of the invention.
10‧‧‧基板
20‧‧‧裝置用構件
30‧‧‧複合保護層
31‧‧‧無機保護層
32‧‧‧有機保護層
100‧‧‧封裝裝置
200‧‧‧封裝裝置10‧‧‧Substrate
20‧‧‧Device components
30‧‧‧Composite protective layer
31‧‧‧Inorganic protective layer
32‧‧‧Organic protective layer
100‧‧‧Package
200‧‧‧Package
圖1為根據本發明之一個實施例之封裝裝置之截面視圖。 圖2為根據本發明之另一實施例之封裝裝置之截面視圖。1 is a cross-sectional view of a packaged device in accordance with one embodiment of the present invention. 2 is a cross-sectional view of a package device in accordance with another embodiment of the present invention.
10‧‧‧基板 10‧‧‧Substrate
20‧‧‧裝置用構件 20‧‧‧Device components
30‧‧‧複合保護層 30‧‧‧Composite protective layer
31‧‧‧無機保護層 31‧‧‧Inorganic protective layer
32‧‧‧有機保護層 32‧‧‧Organic protective layer
100‧‧‧封裝裝置 100‧‧‧Package
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| CN115003705A (en) * | 2020-01-22 | 2022-09-02 | 可隆工业株式会社 | Polymeric composition having excellent storage stability, encapsulating material and display device |
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| WO2022039019A1 (en) * | 2020-08-19 | 2022-02-24 | コニカミノルタ株式会社 | Composition for electronic device sealing, method for forming electronic device sealing film, and electronic device sealing film |
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