CN110140425A - Sealing organic electroluminescent element composition - Google Patents
Sealing organic electroluminescent element composition Download PDFInfo
- Publication number
- CN110140425A CN110140425A CN201780081100.3A CN201780081100A CN110140425A CN 110140425 A CN110140425 A CN 110140425A CN 201780081100 A CN201780081100 A CN 201780081100A CN 110140425 A CN110140425 A CN 110140425A
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- Prior art keywords
- compound
- weight
- cationically polymerizable
- sealing
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- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 3
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- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- 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
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Epoxy Resins (AREA)
- Electroluminescent Light Sources (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
Abstract
The present invention provides a kind of organic EL element composition for sealing that can be steadily coated by ink jet printing method, can solidify rapidly by illumination and form the excellent solidfied material of moisture resistance.Organic EL element composition for sealing for being coated by ink jet printing method of the invention is the composition containing cationically polymerizable compound and cationic polymerization initiators, wherein, viscosity of the composition at 25 DEG C is 20mPas or less, the 50 weight % or more of cationically polymerizable total amount of compound contained in composition are epoxide and/or vinyl ether compound, the viscosity at 25 DEG C be 100mPas or more cationically polymerizable compound content be cationically polymerizable total amount of compound contained in composition 20 weight % or less, boiling point is that the content of 190 DEG C of cationically polymerizable compounds below is less than 20 weight % of cationically polymerizable total amount of compound contained in composition under normal pressure.
Description
Technical field
The present invention relates to the sealing organic electroluminescent element compositions for being coated by ink jet printing method.This
Japanese Patent Application 2016-256747 priority that application requires on December 28th, 2016 to propose in Japan, its content is quoted
In this.
Background technique
Organic electroluminescent (being sometimes referred to as " organic EL " in the present specification) element has to be clipped with a pair of of opposite electrode
Structural body made of luminescent layer, the electrode injection electronics from side, from the electrode injection hole of the other side.When the injected electrons
With hole in luminescent layer in conjunction with when, generate light emitting.From impact resistance, the power of visibility and illuminant colour
Diversity is set out, and is expected using the organic EL device comprising organic EL element as full color flat panel display or the substitute of LED.
However, organic EL element is easier to be influenced by moisture than other electronic components, exist because immersing organic EL member
The moisture of part and the problem of cause the oxidation of electrode, the denaturation of organic matter etc., the characteristics of luminescence caused to significantly reduce.It should as solution
The method of problem, it is known to utilize the method on the periphery of moisture resistance resin seal organic EL element.
Wherein, it describes in patent document 1 containing oxetane compound, epoxide and vinyl ether compound
As the composition of curability compound, the composition is able to use ink jet printing method and is easy to carry out coating, and the group
The moisture resistance for closing the solidfied material of object is excellent.
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 2014-225380 bulletin
Summary of the invention
Problems to be solved by the invention
But the composition recorded in patent document 1 is still insufficient in terms of moisture resistance.And, it has been found that the composition
In printing, mobility is reduced, and composition is easy to solidify and be attached to the jet hole of ink gun, therefore be will lead to injection and become not
Stable or jet hole occurs blocking and can not project.
Therefore, the purpose of the present invention is to provide a kind of organic EL element composition for sealing, the composition can pass through
Ink jet printing method and be steadily coated, can be solidified rapidly by illumination and form the excellent solidfied material of moisture resistance.
Another object of the present invention is to provide a kind of organic EL element composition for sealing, the composition can pass through spray
Ink print method and be steadily coated, can solidify rapidly and be formed moisture resistance by illumination and low out gassing is excellent consolidates
Compound.
It is organic to manufacture using above-mentioned organic EL element composition for sealing that another object of the present invention is to provide a kind of
The method of El element.
Another object of the present invention is to provide a kind of organic EL devices, have a structure in which in organic EL element
The solidfied material for stating sealing organic electroluminescent element composition seals the structure of (or cladding).
Solution to the problem
The present inventor has made intensive studies to solve the above-mentioned problems, as a result, it has been found that, for being applied by ink jet printing method
If the organic EL element composition for sealing of cloth contains the 50% oxetanes chemical combination for having more than curability compound total amount
Object (the aliphatic oxetane compound such as especially 3- ethyl -3- (2- Ethylhexoxymethyl) oxetanes) is as solid
The property changed compound, the then moisture resistance that will lead to gained solidfied material reduce.In addition, when the curability for being lower than 190 DEG C containing boiling point
When closing object, the volatilization of these compounds is easy to happen in printing and the mobility of composition is caused to reduce, composition solidifies simultaneously
It is attached to the jet hole of ink gun, thus causing to project becomes unstable or nozzle generation blocking and can not project.
And then find, while have it is following constitute [1]~[4] compositions can by ink jet printing method steadily into
Row coating, and can be solidified rapidly by illumination and form the excellent solidfied material of moisture resistance.The present invention is based on these discoveries
And complete.
[1] composition containing cationically polymerizable compound and cationic polymerization initiators, and the composition is at 25 DEG C
Under viscosity be 20mPas or less；
[2] in composition, as cationically polymerizable compound, contain cationically polymerizable chemical combination contained in composition
The epoxide and/or vinyl ether compound of the 50 weight % or more of object total amount；
[3] in composition, the content for the cationically polymerizable compound that the viscosity at 25 DEG C is 100mPas or more is
The 20 weight % or less of cationically polymerizable total amount of compound contained in composition；
[4] in composition, boiling point is that the content of 190 DEG C of cationically polymerizable compounds below is less than combination under normal pressure
20 weight % of cationically polymerizable total amount of compound contained in object.
That is, the present invention provides a kind of organic EL element composition for sealing, it is used to be coated by ink jet printing method,
The organic EL element composition for sealing contains cationically polymerizable compound and cationic polymerization initiators, wherein the group
Viscosity of the object at 25 DEG C is closed as 20mPas hereinafter, 50 weights of cationically polymerizable total amount of compound contained in composition
Amount % or more is epoxide and/or vinyl ether compound, the cation that the viscosity at 25 DEG C is 100mPas or more
The content of polymerizable compound is 20 weight % of cationically polymerizable total amount of compound contained in composition hereinafter, in normal pressure
Lower boiling point is that the content of 190 DEG C of cationically polymerizable compounds below is less than cationically polymerizable chemical combination contained in composition
20 weight % of object total amount.
The present invention also provides above-mentioned organic EL element composition for sealing, wherein the composition of cationically polymerizable compound
For following [1] or [2].
[1] following when the content of vinyl ether compound is less than 30 weight % of cationically polymerizable total amount of compound
The total content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) and diglycidyl ether type epoxy compound is cationic polymerization
The 50 weight % or more of property total amount of compound；
[2] when the content of vinyl ether compound is the 30 weight % or more of cationically polymerizable total amount of compound, under
State multifunctional alicyclic ring epoxy compound shown in formula (a-1) content be cationically polymerizable total amount of compound 5 weight % with
On, the total content of the multifunctional alicyclic ring epoxy compound and vinyl ether compound is cationically polymerizable total amount of compound
50 weight % or more,
[chemical formula 1]
(in formula, X indicates singly-bound or linking group).
The present invention also provides above-mentioned organic EL element composition for sealing, wherein multifunctional rouge shown in above-mentioned formula (a-1)
Ring epoxide is selected from 3,4- epoxycyclohexyl-methyl (3,4- epoxy) hexahydrobenzoid acid ester, (3,4,3 ', 4 '-diepoxies
Base) connection hexamethylene, bis- (3,4- epoxycyclohexyl-methyl) ethers, bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) second of 1,2- epoxy-1,2-
At least one of alkane and bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) propane of 2,2- compound.
The present invention also provides above-mentioned organic EL element composition for sealing, also contain list official shown in following formula (a-1 ')
Energy alicyclic ring epoxy compound is as cationically polymerizable compound.
[chemical formula 2]
(in formula, Ra1Indicate the reactive functional groups other than epoxycyclohexyl, Ra2And Ra3It is identical or different, indicate hydrogen atom
Or alkyl, L ' indicate singly-bound or linking group).
The present invention also provides above-mentioned organic EL element composition for sealing, wherein vinyl ether compound at least contains tool
The vinyl ether compound of circular structure.
The present invention also provides above-mentioned organic EL element composition for sealing, the amount of gas evolved when solidifying be 1000ppm with
Under.
The present invention also provides above-mentioned organic EL element composition for sealing, the moisture-vapor transmission of solidfied material is 200g/
(m2Dayatm) below.
In addition, the present invention provides a kind of manufacturing method of organic EL device comprising: it is coated with by ink jet printing method above-mentioned
Sealing organic electroluminescent element composition, to seal organic electroluminescent device.
In addition, the present invention provides a kind of organic EL device, have a structure in which that organic electroluminescent device is had by above-mentioned
The structure of the solidfied material sealing of electro-luminescence element composition for sealing.
The effect of invention
Organic EL element composition for sealing of the invention is due to above structure, from penetrating for the nozzle of ink gun
Excellent in stability out, can prevent the jet hole due to solidifying and being attached to ink gun and causing to project becomes unstable or can not
Project, can through when stably keep good injection.
In addition, organic EL element composition for sealing of the invention can be solid rapidly and irradiating ultraviolet light after coating
Change, forms moisture resistance and the excellent solidfied material of low out gassing.
Therefore, organic EL element composition for sealing of the invention can be suitable for sealing using ink jet printing method organic
The purposes of EL element.
Also, if ink jet printing method reality can be passed through using organic EL element composition for sealing of the invention
Now stable, high speed and uniform coating, workability are excellent.
In addition, if using organic EL element composition for sealing of the invention, then it can use that moisture resistance is excellent to be consolidated
Compound sealing organic el element, prevents from deteriorating, it is hereby achieved that high brightness and the organic EL device of long-life.
Specific embodiment
[organic EL element composition for sealing]
Organic EL element composition for sealing of the invention is drawn containing cationically polymerizable compound and cationic polymerization
Send out the composition of agent, wherein viscosity of the composition at 25 DEG C is 20mPas hereinafter, cation contained in composition is poly-
The 50 weight % or more of conjunction property total amount of compound are epoxide and/or vinyl ether compound, and the viscosity at 25 DEG C is
The content of the cationically polymerizable compound of 100mPas or more is cationically polymerizable total amount of compound contained in composition
20 weight % hereinafter, under normal pressure boiling point be 190 DEG C of cationically polymerizable compounds below content be less than composition in
20 weight % of contained cationically polymerizable total amount of compound.
[cationically polymerizable compound]
Organic EL element composition for sealing of the invention contains epoxide and/or vinyl ether compound as sun
Photopolymerizable compound.
<epoxide>
Epoxide is the compound that intramolecular has more than one epoxy group (epoxide ring), including alicyclic epoxy
Close object, aromatic epoxy compound and aliphatic epoxy compound.
(cycloaliphatic epoxy)
Cycloaliphatic epoxy is the compound that intramolecular has more than one alicyclic ring and more than one epoxy group, including
Following compound.
(1) epoxy group that there is intramolecular adjacent two carbon atom by constituting alicyclic ring to constitute with oxygen atom is (in this theory
In bright book, sometimes referred to as " alicyclic epoxy group ".Alicyclic epoxy group includes epoxycyclohexyl) compound
(2) epoxy group directly passes through compound of the singly bound on alicyclic ring
(3) intramolecular has the compound (so-called diglycidyl ether type epoxy compound) of alicyclic ring and glycidyl ether
Above-mentioned compound of (1) intramolecular with alicyclic epoxy group includes the chemical combination that intramolecular has an alicyclic epoxy group
Object (1-1 '), intramolecular have the compound (1-1) of more than two alicyclic epoxy groups.
There is the compound (1-1) of more than two alicyclic epoxy groups as above-mentioned intramolecular, such as following formula (a- can be enumerated
1) multifunctional alicyclic ring epoxy compound shown in.
[chemical formula 3]
In above formula (a-1), X indicates singly-bound or linking group (bivalent group with more than one atom).Linker
The example of group includes: that some or all of bivalent hydrocarbon radical, carbon-to-carbon double bond have passed through epoxidised alkenylene, carbonyl, ehter bond, ester
Multiple groups being formed by connecting in key, carbonate group, amide groups and these groups etc..
The example of above-mentioned bivalent hydrocarbon radical include: carbon atom number be 1~18 straight or branched alkylidene, carbon atom number be
3~18 divalent alicyclic type hydrocarbon etc..Carbon atom number be 1~18 straight or branched alkylidene example include: methylene,
Methylmethylene, dimethylmethylene, ethylidene, propylidene, trimethylene etc..The divalent ester ring type that carbon atom number is 3~18
The example of alkyl includes: 1,2- cyclopentylene, 1,3- cyclopentylene, cyclopentylidene, 1,2- cyclohexylidene, 1,3- cyclohexylidene, 1,
Cycloalkylidenes such as 4- cyclohexylidene, cyclohexylidene (including cycloalkanes fork) etc..
It has passed through epoxidised alkenylene (sometimes referred to as " epoxidation Asia alkene as some or all of above-mentioned carbon-to-carbon double bond
Base ") in alkenylene, such as can enumerate: ethenylidene, allylidene, 1- butenylidene, 2- butenylidene, Aden's dialkylene,
The alkenylene of straight or branched etc. that the carbon atom numbers such as inferior pentenyl, sub- hexenyl, heptene base, sub- octenyl are 2~8.
In particular, preferably carbon-to-carbon double bond all have passed through epoxidised alkenylene, more preferably as above-mentioned epoxidation alkenylene
Carbon-to-carbon double bond all have passed through the alkenylene that epoxidised carbon atom number is 2~4.
In 2 cyclohexane rings in above-mentioned formula (a-1), other than the epoxy group shown in the formula, can also have respectively
One or more substituent group [for example, halogen atom (fluorine atom, chlorine atom etc.), optionally comprising oxygen atom or halogen atom
Alkyl is (for example, C1~4Alkyl, C1~4Halogenated alkyl, C1~4Alkoxy -C1~4Alkyl etc.), optionally with substituent group alkoxy (example
Such as, C1~4Alkoxy, halogenated C1~4Alkoxy etc.)].
It as the typical example of multifunctional alicyclic ring epoxy compound shown in above-mentioned formula (a-1), can enumerate: (3,4,3 ', 4 '-
Bicyclic oxygen) connection hexamethylene, bis- (3,4- epoxycyclohexyl-methyl) ethers, the bis- (3,4- 7-oxa-bicyclo[4.1.0-1- of 1,2- epoxy-1,2-
Base) it is ethane, bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) propane of 2,2-, bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) ethane of 1,2-, following
Formula (a-1-1)~(a-1-10) compound represented etc..It should be noted that it is 1 that the L in following formula (a-1-5), which is carbon atom number,
~8 alkylidene, wherein preferably the carbon atom numbers such as methylene, ethylidene, propylidene, isopropylidene be 1~3 straight chain or
Branched alkylidene.In addition, following formula (a-1-5), (a-1-7), (a-1-9), the n in (a-1-10)1~n8Respectively indicate 1~
30 integer.
[chemical formula 4]
[chemical formula 5]
There is the compound (1-1 ') of an alicyclic epoxy group as above-mentioned intramolecular, such as following formula (a-1 ') can be enumerated
Shown in simple function alicyclic ring epoxy compound.
[chemical formula 6]
In formula (a-1 '), Ra1Indicate the reactive functional groups (polymerizable functional group) in addition to epoxycyclohexyl, such as
It can enumerate: vinyl ether group, (methyl) acryloxy, epoxy group, glycidyl, oxetanylmethoxy etc..
In formula (a-1 '), Ra2、Ra3It is identical or different, indicate hydrogen atom or alkyl (for example, the carbon atoms such as methyl, ethyl
The alkyl that number is 1~5).
In formula (a-1 '), L ' indicates singly-bound or linking group.The example of above-mentioned linking group includes: bivalent hydrocarbon radical, carbonyl
Base (- CO-), ehter bond (- O-), thioether bond (- S-), ester bond (- COO-), amido bond (- CONH-), carbonic acid ester bond (- OCOO-) etc..
It as above-mentioned bivalent hydrocarbon radical, such as can enumerate: methylene, methylmethylene, dimethylmethylene, ethylidene, Asia
The straight or branched alkylidene that the carbon atom numbers such as propyl, trimethylene are 1~5.
There is the compound (1-1 ') of an alicyclic epoxy group as above-mentioned intramolecular, wherein it is preferred that 1,2:8,9- diepoxy
Limonene and/or 3,4- epoxycyclohexyl-methyl (methyl) acrylate.
Directly pass through compound of the singly bound on alicyclic ring as above-mentioned (2) epoxy group, such as following formula (a- can be enumerated
2) compound represented etc..
[chemical formula 7]
In formula (a-2), Ra4Be from the structural formula of p member alcohol remove p hydroxyl (- OH) obtained by group (p valence it is organic
Group), p, n9Respectively indicate natural number.P member alcohol [Ra4(OH)p] example include: that bis- (methylol)-n-butyl alcohols of 2,2- etc. are polynary
Alcohol (polyalcohol etc. that carbon atom number is 1~15) etc..P is preferably 1~6, n9Preferably 1~30.In the case that p is 2 or more, respectively
N in a [] in the group of (in the square brackets in outside)9It can be identical or different.Specifically, as shown in above-mentioned formula (a-2)
Compound, 1,2- epoxy -4- (2- Oxyranyle) hexamethylene addition product of bis- (the methylol)-n-butyl alcohols of 2,2- can be enumerated
[for example, trade name " EHPE3150 " (manufacture of Daicel Co., Ltd.) etc.] etc..
There is the compound of alicyclic ring and glycidyl ether as above-mentioned (3) intramolecular, such as alicyclic alcohol (spy can be enumerated
Be not ester ring type polyalcohol) glycidol ether.More specifically, it such as can enumerate: bisphenol A type epoxy compound is hydrogenated
Made of compound (hydrogenated bisphenol A type epoxide), bisphenol F type epoxy compound is hydrogenated made of compound (hydrogenation
Bisphenol F type epoxy compound)；Hydrogenated biphenyl phenolic epoxide；Hydrogenate phenol novolak-type epoxy compound；Hydrogenate first
Phenol novolak type epoxy compounds；The hydrogenation cresol novolak type epoxy compound of bisphenol-A；Hydrogenated naphthalene type epoxy compound
Object；By compound made of the epoxide obtained as tris-phenol hydrogenation etc..
(aromatic epoxy compound)
As above-mentioned aromatic epoxy compound, such as can enumerate: phenyl glycidyl ether, bisphenols [for example, bisphenol-A,
Bisphenol F, bisphenol S, fluorenes bis-phenol etc.] and bis- (epibis) the type diglycidyl ether types of epihalohydrin table as obtained from condensation reaction
Epoxide；Make these table dimorphism diglycidyl ether type epoxy compounds further with above-mentioned bisphenols carry out addition reaction and
Obtained macromolecule scale dimorphism diglycidyl ether type epoxy compound；By make by phenols [such as phenol, cresols, xylenol,
Resorcinol, catechol, bisphenol-A, Bisphenol F, bisphenol S etc.] and aldehyde [such as formaldehyde, acetaldehyde, benzaldehyde, hydroxy benzaldehyde, bigcatkin willow
Aldehyde etc.] through polyalcohols obtained from condensation reaction further with epihalohydrin carry out condensation reaction obtained from novolaks-
Alkyl type diglycidyl ether type epoxy compound；In 9 upper keys of fluorenes ring and there are two phenol skeleton and by these phenol skeletons
On oxygen atom after removing hydroxyl removal hydrogen atom immediately or via alkylidene oxygroup key and the epoxy for having glycidyl
Compound etc..
(aliphatic epoxy compound)
As above-mentioned aliphatic epoxy compound, such as can enumerate: (q is nature to the alcohol without cyclic structure of q member
Number) glycidol ether；Unitary or polybasic carboxylic acid [such as acetic acid, propionic acid, butyric acid, stearic acid, adipic acid, decanedioic acid, Malaysia
Acid, itaconic acid etc.] ethylene oxidic ester；Epoxidized linseed oil, epoxidised soybean oil, epoxidized castor oil etc. have double bond
The epoxides of grease；The epoxides etc. of the polyolefin such as epoxidized polybutadiene (including polyalkadiene).It should be noted that
It as the alcohol without cyclic structure of above-mentioned q member, such as can enumerate: methanol, ethyl alcohol, 1- propyl alcohol, isopropanol, n-butyl alcohol etc. one
First alcohol；Ethylene glycol, 1,2- propylene glycol, 1,3- propylene glycol, 1,4- butanediol, neopentyl glycol, 1,6-HD, diethylene glycol, three
The dihydric alcohols such as ethylene glycol, tetraethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol；Glycerol, diglycerol, antierythrite, three hydroxyls
Polyalcohols the etc. more than ternarys such as methyl ethane, trimethylolpropane, pentaerythrite, dipentaerythritol, D-sorbite.In addition, q
First alcohol can be polyether polyol, polyester polyol, polycarbonate polyol, polyolefin polyhydric alcohol etc..
As epoxide, intramolecular has the chemical combination of one or two alicyclic epoxy group (especially epoxycyclohexyl)
Object (=alicyclic ring epoxy compound) can play rapidly-curable due to low viscosity and higher boiling, therefore preferably
Contain the compound, wherein from the viewpoint of curability is especially excellent, preferably at least there are more than two rouge containing intramolecular
The compound (1-1) (multifunctional alicyclic ring epoxy compound shown in especially above-mentioned formula (a-1)) of ring epoxy group.Further, since
Compared with intramolecular has the compound (1-1) of more than two alicyclic epoxy groups, intramolecular has the change of an alicyclic epoxy group
Closing object (1-1 ') (simple function alicyclic ring epoxy compound shown in especially above-mentioned formula (a-1 ')) has more low viscosity and mobility
It is more excellent, therefore, from the viscosity of organic EL element composition for sealing of the invention can be made to reach 20mPas or less, can
From the perspective of playing ink-jet injection property and project the especially excellent effect of stability, preferably have containing above-mentioned intramolecular
There are two contain chemical combination of the above-mentioned intramolecular with an alicyclic epoxy group while compound (1-1) of the above alicyclic epoxy group
Object (1-1 ').
<vinyl ether compound>
Vinyl ether compound is the compound that intramolecular has more than one vinyl ether group.As such chemical combination
Object, such as following formula (b) compound represented can be enumerated.
Rb(O-CH=CH2)n (b)
(in formula, RbIndicate the alkyl of n valence, the heterocycle of n valence or the two or more in these groups via singly-bound or company
Connect group made of group bonding.N indicates 1 or more integer)
RbIn n valence alkyl include the aliphatic alkyl of n valence, the alicyclic type hydrocarbon of n valence and n valence aromatic hydrocarbon
Base.
It as the aliphatic alkyl of the monovalence in the aliphatic alkyl of n valence, such as can enumerate: methyl, ethyl, propyl, different
The carbon atom numbers such as propyl, butyl, isobutyl group, sec-butyl, tert-butyl, amyl, hexyl, decyl, dodecyl are 1~20 (preferably 1
~10, the alkyl of particularly preferred 1~3) left and right；Vinyl, allyl, methacrylic, 1- acrylic, isopropenyl, 1- fourth
The carbon atom numbers such as alkenyl, 2- cyclobutenyl, 3- cyclobutenyl, 1- pentenyl, 2- pentenyl, 3- pentenyl, 4- pentenyl, 5- hexenyl
For 2~20 (preferably 2~10, the alkenyl of particularly preferred 2~3) left and right；The carbon atom numbers such as acetenyl, propinyl are 2~20 (preferably
2~10, the alkynyl etc. of particularly preferred 2~3) left and right.
As the alicyclic type hydrocarbon of the monovalence in the alicyclic type hydrocarbon of n valence, can enumerate: cyclopropyl, cyclobutyl, cyclopenta,
The naphthenic base of (preferably 3~15 yuan, particularly preferred 5~8 yuan) of 3~20 yuan of cyclohexyl, cyclooctyl etc. left and right；Cyclopentenyl, hexamethylene
The cycloalkenyl of (preferably 3~15 yuan, particularly preferred 5~8 yuan) of 3~20 yuan of alkenyl etc. left and right；It is bicycloheptyl, bicycloheptenyl, complete
Hydrogen naphthalene -1- base, norborny, adamantyl, Fourth Ring [4.4.0.12,5.17,10] the endocyclics alkyl such as dodecane -3- base etc..
As the aromatic hydrocarbyl of the monovalence in the aromatic hydrocarbyl of n valence, can enumerate: the carbon atom numbers such as phenyl, naphthalene are about
For the aryl of 6~14 (preferably 6~10) left and right.
As the alkyl of n valence, can enumerate: a hydrogen of removal (n-1) is former in the structural formula of the monovalent hydrocarbon gone out from above-mentioned example
Group made of son.
As the heterocycle for the heterocycle for constituting n valence, such as can enumerate: contain oxygen atom as heteroatomic heterocycle (for example,
4 member ring such as oxetanes ring；Furan nucleus, tetrahydrofuran ring,It is azoles ring, different5 member rings such as azoles ring, gamma-butyrolacton ring；4-
6 member rings such as oxo -4H- pyranoid ring, amylene oxide ring, morpholine ring；Benzofuran ring, isobenzofuran ring, 4- oxo -4H- benzene
And the condensed ring such as pyranoid ring, chroman ring, heterochromatic full ring；3- oxatricyclo [4.3.1.14,8] hendecane -2- ketone ring, 3- oxa- three
Ring [4.2.1.04,8] bridged rings such as nonane -2- ketone ring), contain sulphur atom as heteroatomic heterocycle (for example, thiphene ring, thiazole
5 member rings such as ring, isothiazole ring, Thiadiazole；6 member rings such as 4- oxo -4H- thiapyran ring；Condensed ring such as benzothiophene ring etc.), contain
Nitrogen-atoms is as heteroatomic heterocycle (for example, 5 member rings such as pyrrole ring, nafoxidine ring, pyrazole ring, imidazole ring, triazole ring；Pyrrole
6 member rings such as phenazine ring, pyridazine ring, pyrimidine ring, pyridine ring, piperidine ring, piperazine ring；Indole ring, indoline ring, quinoline ring, acridine
Condensed ring such as ring, naphthyridines ring, quinazoline ring, purine ring etc.) etc..The heterocycle of n valence is that n are removed from the structural formula of above-mentioned heterocycle
Group made of hydrogen atom.
It as above-mentioned linking group, can enumerate: carbonyl, ehter bond and ester bond etc..
As vinyl ether compound, wherein from the viewpoint of with low viscosity and higher boiling, preferably at least comprising tool
The vinyl ether compound of circular structure, the particularly preferably R in above-mentioned formula (b)bFor the alicyclic type hydrocarbon of n valence, the aromatic series of n valence
The vinyl ether compound of the heterocycle of alkyl or n valence, in particular, from that with low viscosity and higher boiling and can play
Rapidly-curable is formed from the perspective of the excellent solidfied material of moisture resistance, vinyl ether compound preferably with alicyclic structure,
Vinyl ether compound with aromatic ring structure and the vinyl ether compound with cyclic annular ether structure are [in particular, (2- benzene
Phenoxyl) vinyl ether compound with aromatic ring structure such as ethyl vinyl ether is (for example, the simple function with aromatic ring structure
Vinyl ether compound)].
It as the above-mentioned vinyl ether compound with alicyclic structure, such as can enumerate: cyclohexanedimethanol divinyl base
Ether, A Hydrogenated Bisphenol A F type divinyl ether, hydrogenated biphenyl divinyl ether, hydrogenated bisphenol A type divinyl ether, tristane two
Methanol divinyl ether etc..
It as the above-mentioned vinyl ether compound with aromatic ring structure, such as can enumerate: (2- phenylphenoxy) ethyl second
Alkene ether, Bisphenol F bis- (vinyl oxygroup ethylethers), bisphenol-f type divinyl ether, biphenyl divinyl ether, bisphenol A-type diethyl
Alkene ether etc..
As the above-mentioned vinyl ether compound with cyclic annular ether structure, such as can enumerate: isobide divinyl ether,
Oxetanes divinyl ether, oxanorbornene divinyl ether etc..
In organic EL element composition for sealing of the invention, the vinyl ethers chemical combination with ring structure can also contained
While object, also containing has the structure for being bonded with aliphatic alkyl via the ehter bond as linking group (in particular, polyoxy
Ethylene chain) vinyl ether compound (for example, diethylene glycol divinyl ether, triethyleneglycol divinylether etc.).Due to upper
The viscosity for stating compound is low, mobility is excellent, therefore by containing the compound, it is close that organic EL element of the invention can be improved
The envelope injection of composition.
<other cationically polymerizable compounds>
In organic EL element composition for sealing of the invention, as cationically polymerizable compound, in addition to epoxy compound
, can also be containing other cationically polymerizable compounds outside object and vinyl ether compound, such as one kind or two can be contained
Kind or more oxetane compound (except the compound with epoxy group or vinyl ether group).
As oxetane compound, such as following formula (c) compound represented can be enumerated.
[chemical formula 8]
In formula (c), Rc1Indicate the organic group of monovalence, Rc2Indicate hydrogen atom or ethyl.M indicates 1 or more integer.
Above-mentioned Rc1In the organic group of monovalence include: monovalent hydrocarbon, monovalence heterocycle, substituted oxy carbonyl (alkoxy
Carbonyl, aryloxycarbonyl, aromatic alkoxy carbonyl, cyclo alkoxy carbonyl etc.), substituted-amino formoxyl (N- alkyl-carbamoyl,
N- aryl-amino-carbonyl etc.), the acyl group (aliphatic acyl radicals such as acetyl group；Aromatic acyls such as benzoyl etc.) and these
It is two or more via univalent perssad made of singly-bound or linking group bonding in group.
As monovalent hydrocarbon, monovalence heterocycle, can enumerate and the R in above formula (b)bThe identical example of example.
As above-mentioned linking group, such as can enumerate: carbonyl (- CO-), ehter bond (- O-), thioether bond (- S-), ester bond (-
COO-), multiple connections in amido bond (- CONH-), carbonic acid ester bond (- OCOO-), silane key (- Si-) and these groups and
At group.
The integer of above-mentioned 1 or more m expression, for example, 1~20, preferably 1.
It as oxetane compound, such as can enumerate: 3- ethyl -3- (2- Ethylhexoxymethyl) oxa- ring fourth
Alkane, 3- ethyl -3- (methoxy) oxetanes, 3- ethyl -3- (butoxymethyl) oxetanes, 3- ethyl -3-
R in (hexoxymethyl) oxetanes equation (c)c1For the compound (=aliphatic oxetanes of aliphatic alkyl
Close object)；R in 3- ethyl -3- (cyclohexyloxy methyl) oxetanes equation (c)c1For the compound (=rouge of alicyclic type hydrocarbon
Ring type oxetane compound)；R in (c) such as bis- { [1- ethyl (3- oxetanylmethoxy)] methyl } ethersc1For the change of heterocycle
It closes object (=heterocycle oxetane compound)；3- ethyl -3- [(phenoxy group) methyl] oxetanes, bis- [(the 3- second of 1,4-
Base -3- oxetanylmethoxy methoxyl group) methyl] R in benzene equation (c)c1For the compound (=aromatic series oxa- ring of aromatic hydrocarbyl
Butane compound) etc..
In the present invention, using oxetane compound, from the reduced sight for being able to suppress moisture resistance
Point sets out, it is preferable to use aromatic series oxetane compound.On the other hand, since the reduction of moisture resistance can be caused, no
It is preferred that largely using the aromatic series oxetane compound.
The present invention is not limited to specific theoretical, but it can consider that following several points are the originals for the difference for causing moisture resistance to reduce
Cause.Since aromatic ring facilitates water resistance, if ratio shared by intramolecular aromatic ring is high, the water resistance of oxetane compound
Be not easily deteriorated, and on the other hand, for aliphatic, although itself be it is hydrophobic, due to intermolecular free volume
Greatly, therefore it could be speculated that it is easy to cause water resistance to become when there are as oxetanylmethoxy hydrophilic functional group can be improved
Difference.
In addition, simple function oxetanes is more likely to that water resistance deterioration occurs compared with multifunctional oxetanes.Its
Reason can estimate are as follows: in the case where simple function, also will do it molecular motion in solidfied material, therefore free volume further increases
Add, water resistance further deteriorates.
[cationic polymerization initiators]
Organic EL element composition for sealing of the invention contains while containing above-mentioned cationically polymerizable compound
One or more kinds of cationic polymerization initiators.
As cationic polymerization initiators, particularly preferred light cationic polymerization initiator.Light cationic polymerization initiator is
Cation kind can be generated because of the irradiation of light (such as ultraviolet light), to cause the curing reaction of cationically polymerizable compound
Compound, the anion portion of the occurring source comprising light absorbing cation portion and as acid.
It as light cationic polymerization initiator, such as can enumerate: diazols compound, iodineSalt compounds, sulfonium salt
Class compound,Salt compounds, selenium salt compounds, oxygenSalt compounds, ammonium salt compounds, bromine salt compounds
Deng.
In the present invention, from the viewpoint of it can form the solidfied material with excellent curability, wherein it is preferable to use sulfoniums
Salt compounds.As the cationic portion of sulfonium salt compounds, such as can enumerate: (4- hydroxy phenyl) methylbenzyl sulfonium cation,
Triphenylsulfonium ion, diphenyl [4- (thiophenyl) phenyl] sulfonium cation, 4- (4- xenyl sulfenyl) phenyl -4- xenyl phenyl sulfonium
The aryl sulfonium cations such as ion, tri-p-tolylsulfonium ion (especially triaryl matte ion).
It as the anion portion of light cationic polymerization initiator, such as can enumerate: [(Y)sB(Phf)4-s]-(in formula, Y is indicated
Phenyl or xenyl.Phf indicate at least one of hydrogen atom by perfluoroalkyl, perfluoro alkoxy and halogen atom extremely
Phenyl made of a kind of few substitution.S is 0~3 integer), BF4 -、[(Rf)tPF6-t]-(Rf: 80% or more quilt in hydrogen atom
Fluorine atom replace made of alkyl, t:0~5 integer), AsF6 -、SbF6 -、SbF5OH-Deng.In the present invention, wherein from conduct
The activity of initiator is high, with high solidification, the solidfied material of excellent heat resistance can be obtained from the perspective of, preferably anion
Portion is SbF6 -Or above-mentioned [(Y)sB(Phf)4-s]-Light cationic polymerization initiator.
It as light cationic polymerization initiator, such as can enumerate: (4- hydroxy phenyl) methylbenzyl sulfonium four (pentafluorophenyl group)
Borate, four (pentafluorophenyl group) borate of 4- (4- xenyl sulfenyl) phenyl -4- xenyl phenyl sulfonium, 4- (phenylsulfartyl) phenyl
Diphenyl sulfonium phenyl three (pentafluorophenyl group) borate, [4- (4- xenyl sulfenyl) phenyl] -4- xenyl phenyl sulfonium phenyl three (five
Fluorophenyl) borate, diphenyl [4- (phenylsulfartyl) phenyl sulfonium] fluorine antimonate, diphenyl [4- (phenylsulfartyl) phenyl] sulfonium three
(pentafluoroethyl group) three fluorophosphate, diphenyl [4- (phenylsulfartyl) phenyl] sulfonium four (pentafluorophenyl group) borate, diphenyl [4-
(phenylsulfartyl) phenyl] sulfonium hexafluorophosphate, three (pentafluoroethyl groups) three of 4- (4- xenyl sulfenyl) phenyl -4- xenyl phenyl sulfonium
Fluorophosphate, bis- [4- (diphenyl sulfonium) phenyl] thioether phenyl three (pentafluorophenyl group) borates, [4- (2- thioxanthene ketone group sulfenyl) benzene
Base] three (pentafluorophenyl group) borate of phenyl -2- thioxanthene ketone group sulfonium phenyl, trade name " Cyracure UVI-6970 ",
" Cyracure UVI-6974 ", " Cyracure UVI-6990 ", " Cyracure UVI-950 " are (above-mentioned to be carbonized by American Association
Object company manufacture), " Irgacure 250 ", " Irgacure 261 ", " Irgacure264 " (above-mentioned to be manufactured by BASF AG),
" CG-24-61 " (being manufactured by Ciba-Geigy company), " Optomer SP-150 ", " Optomer SP-151 ", " Optomer
SP-170 ", " Optomer SP-171 " (above-mentioned to be manufactured by ADEKA Corp.), " DAICAT II " (Daicel Co., Ltd.
Manufacture), " UVAC1590 ", " UVAC1591 " (above-mentioned to be manufactured by Daicel-Cytec company), " CI-2064 ", " CI-2639 ",
" CI-2624 ", " CI-2481 ", " CI-2734 ", " CI-2855 ", " CI-2823 ", " CI-2758 ", " CIT-1682 " (it is above-mentioned by
Tso Tat Co., Ltd., Japan manufacture), " PI-2074 " (by Rhodia company manufacture, four (pentafluorophenyl group) borate tolyl isopropyls
Phenyl-iodideSalt), " FFC509 " (being manufactured by 3M company), " BBI-102 ", " BBI-101 ", " BBI-103 ", " MPI-103 ",
" TPS-103 ", " MDS-103 ", " DTS-103 ", " NAT-103 ", " NDS-103 " are (above-mentioned by Midori Kagaku Co., Ltd.
Manufacture), " CD-1010 ", " CD-1011 ", " CD-1012 " (above-mentioned by Sartomer America company manufacture), " CPI-
The commercially available products such as 100P ", " CPI-101A " (above-mentioned to be manufactured by SAN-APRO company).
[organic EL element composition for sealing]
The viscosity of organic EL element composition for sealing of the invention at 25 DEG C be 20mPas or less (such as 10~
20mPas), preferably 15mPas or less.Since viscosity is in above range, organic EL element of the invention, which seals, to be used
Composition has excellent injection, can accurately be ejected into required position.On the other hand, when viscosity is more than above range
When, organic EL element composition for sealing of the invention is easy to happen the jet hole for solidifying and being attached to ink gun, causes to project
Become unstable, therefore not preferably.
Organic EL element composition for sealing of the invention contains above-mentioned epoxide and/or vinyl ether compound is made
For cationically polymerizable compound.These compounds can also combine individually containing one kind containing two or more.
The total content of epoxide and vinyl ether compound is in organic EL element composition for sealing of the invention
The 50 weight % or more (such as 50~100 weight %) of the cationically polymerizable total amount of compound contained, preferably 60 weight %
More than, particularly preferably 70 weight % or more, most preferably 80 weight % or more, especially preferably 90 weight % or more.
The cation that viscosity in organic EL element composition for sealing of the invention at 25 DEG C is 30mPas or more
The content of polymerizable compound, 30~60 weights of the cationically polymerizable total amount of compound for example, contained in above-mentioned composition
Measure %, preferably 30~55 weight %.
The cation that viscosity in organic EL element composition for sealing of the invention at 25 DEG C is 100mPas or more
The content of polymerizable compound, for the 20 weight % or less of the cationically polymerizable total amount of compound contained in above-mentioned composition
(for example, 0~20 weight %).The viscosity of the composition is low as a result, and injection property is excellent.
Further, from the viewpoint of can further improve it is ejection, group is used in organic EL element sealing of the invention
The content for closing the cationically polymerizable compound that the viscosity in object at 25 DEG C is 2000mPas or more is preferably 15 weight %
(for example, 0~15 weight %) below, particularly preferably 10 weight % or less.
In addition, boiling point is 190 DEG C of cations below under normal pressure in organic EL element composition for sealing of the invention
The content of polymerizable compound, less than 20 weight % of the total amount for the cationically polymerizable compound for including in above-mentioned composition
(for example, 0 weight % is more than and less than 20 weight %), preferably 15 weight % are hereinafter, particularly preferably 10 weight % are hereinafter, most
Preferably 5 weight % are hereinafter, especially preferably 1 weight % or less.It is used thus, it is possible to prevent organic EL element of the invention from sealing
Composition solidifies and is attached to the jet hole of ink gun, is able to maintain good injection.
In addition, from that can prevent organic EL element composition for sealing of the invention from solidifying and be attached to the spray of ink gun
It at mouthpiece, is able to maintain good ejaculatory viewpoint and sets out, at 25 DEG C in organic EL element composition for sealing of the invention
Under viscosity be less than 3mPas and under normal pressure boiling point be 190 DEG C of cationically polymerizable compounds below content, it is preferably small
(preferably 5 weight % are hereinafter, especially excellent by 10 weight % of the cationically polymerizable total amount of compound contained in above-mentioned composition
It is selected as 3 weight % or less).
In addition, from the viewpoint of it can be further improved the injection stability based on ink-jet, organic EL member of the invention
Boiling point is the content of 160 DEG C of cationically polymerizable compounds below under normal pressure in part composition for sealing, is less than above-mentioned group
Such as 20 weight % of the cationically polymerizable total amount of compound contained in object are closed (for example, 0 weight % is more than and less than 20 weights
Measure %), more preferable 15 weight % hereinafter, further preferred 10 weight % hereinafter, particularly preferred 5 weight % hereinafter, most preferably 3 weights
% is measured hereinafter, particularly preferred 1 weight % or less.
From the aspect of making ink-jet injection property and injection have good stability, group is used in organic EL element sealing of the invention
Close the composition that the cationically polymerizable compound contained in object preferably has following [1] or [2].
[1] when the content of vinyl ether compound is less than 30 weight % of cationically polymerizable total amount of compound, formula (a-
1) total content of multifunctional alicyclic ring epoxy compound and diglycidyl ether type epoxy compound shown in is cationically polymerizable
Close the 50 weight % or more of object total amount.
[2] when the content of vinyl ether compound is the 30 weight % or more of cationically polymerizable total amount of compound, formula
(a-1) content of multifunctional alicyclic ring epoxy compound shown in is the 5 weight % or more of cationically polymerizable total amount of compound, on
The total content for stating multifunctional alicyclic ring epoxy compound and vinyl ether compound is 50 weights of cationically polymerizable total amount of compound
Measure % or more
In the case where above-mentioned [1], the content of vinyl ether compound is less than the 30 of cationically polymerizable total amount of compound
Weight % (for example, 0 weight % is more than and less than 30 weight %), preferably 20 weight % hereinafter, particularly preferred 10 weight % hereinafter,
Most preferably 5 weight % or less.
In the case where above-mentioned [1], the content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) is, for example, cation
The 10 weight % or more (for example, 10~70 weight %) of polymerizable compound total amount, preferably 20~60 weight %, particularly preferably
For 30~55 weight %, most preferably 35~55 weight %.
In the case where above-mentioned [1], the content of diglycidyl ether type epoxy compound is, for example, cationically polymerizable chemical combination
The 5 weight % or more (such as 5~80 weight %) of object total amount, preferably 10~50 weight %, particularly preferably 15~30 weights
Measure %, most preferably 15~25 weight %.
In the case where above-mentioned [1], multifunctional alicyclic ring epoxy compound and diglycidyl ether type epoxy shown in formula (a-1)
The total content of compound is 50 weight % or more, the more preferably 55 weight % or more of cationically polymerizable total amount of compound, special
It You Xuanwei not 60 weight % or more, most preferably 65 weight % or more.The upper limit is, for example, 95 weight %, preferably 90 weight %, special
Not preferably 85 weight %, most preferably 80 weight %, particularly preferred 75 weight %.
In the case where above-mentioned [1], multifunctional alicyclic ring epoxy compound and diglycidyl ether type epoxy shown in formula (a-1)
The ratio between content of compound (the former/the latter；Weight ratio) it is, for example, 50/50~90/10, preferably 60/40~85/15, it is especially excellent
Select 60/40~80/20, most preferably 60/40~75/25, particularly preferred 60/40~70/30.
In the case where above-mentioned [1], from the ejaculatory viewpoint of ink-jet can be improved by lowering viscousity, as ring
Oxygen compound preferably also includes shown in formula (a-1 ') while containing multifunctional alicyclic ring epoxy compound shown in formula (a-1)
Simple function alicyclic ring epoxy compound, the total content of above-mentioned multifunctional alicyclic ring epoxy compound and simple function alicyclic ring epoxy compound
The for example, 50 weight % or more of cationically polymerizable total amount of compound, preferably 55 weight % or more, particularly preferably 60 weights
Measure % or more, most preferably 65 weight % or more.It should be noted that the upper limit is, for example, 95 weight %, preferably 90 weight %,
Particularly preferably 85 weight %.
In the case where above-mentioned [1], multifunctional alicyclic ring epoxy compound shown in formula (a-1) and list shown in formula (a-1 ')
The ratio between content of function alicyclic ring epoxy compound [above-mentioned multifunctional alicyclic ring epoxy compound/above-mentioned simple function alicyclic epoxy chemical combination
Object；Weight ratio] it is, for example, 50/50~90/10, preferably 51/49~85/15, particularly preferred 52/48~80/20, most preferably 55/
45~70/30, particularly preferred 55/45~65/35.
In the case where above-mentioned [1], the content of simple function alicyclic ring epoxy compound shown in formula (a-1 ') be, for example, sun from
5~50 weight % of sub- polymerizable compound total amount, preferably 10~45 weight %, more preferable 15~45 weight %, particularly preferably
20~45 weight %, most preferably 25~40 weight %.
In the case where above-mentioned [2], multifunctional alicyclic ring epoxy compound shown in formula (a-1) and vinyl ether compound
Total content is, for example, the 50 weight % or more of cationically polymerizable total amount of compound, preferably 55 weight % or more, and particularly preferred 60
Weight % or more, most preferably 65 weight % or more.The upper limit is, for example, 100 weight %, preferably 95 weight %, particularly preferred 90 weight
Measure %, most preferably 85 weight %.
In the case where above-mentioned [2], the content of vinyl ether compound is 30 weights of cationically polymerizable total amount of compound
It measures % or more (such as 30~100 weight %), preferably 30~90 weight %, particularly preferred 30~70 weight %, most preferably 40~
60 weight %.
In the case where above-mentioned [2], the content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) is, for example, cation
0~40 weight % of polymerizable compound total amount, preferably 5~35 weight %, particularly preferred 10~35 weight %.
In addition, multifunctional alicyclic ring epoxy compound shown in formula (a-1) and vinyl are etherified in the case where above-mentioned [2]
The ratio between content of conjunction object (the former/the latter；Weight ratio) it is, for example, 0/100~50/50, preferably 10/90~45/55, particularly preferably
10/90~40/60.
In addition, in the case where above-mentioned [2], from the ejaculatory viewpoint of ink-jet can be improved by lowering viscousity,
It preferably also include formula (a- while containing multifunctional alicyclic ring epoxy compound shown in formula (a-1) as epoxide
1 ') simple function alicyclic ring epoxy compound shown in, above-mentioned multifunctional alicyclic ring epoxy compound and simple function alicyclic ring epoxy compound
Total content be, for example, cationically polymerizable total amount of compound 20 weight % or more, preferably 25 weight % or more, particularly preferably
30 weight % or more, most preferably 40 weight % or more.It should be noted that the upper limit is, for example, 75 weight %, preferably 70 weight %,
Particularly preferred 65 weight %.
In addition, in the case where above-mentioned [2], multifunctional alicyclic ring epoxy compound shown in formula (a-1) and formula (a-1 ') institute
The ratio between content of the simple function alicyclic ring epoxy compound shown [above-mentioned multifunctional alicyclic ring epoxy compound/above-mentioned simple function alicyclic ring ring
Oxygen compound；Weight ratio] it is, for example, 10/90~70/30, preferably 20/80~60/40, particularly preferred 30/70~55/45.
In the case where above-mentioned [2], the content of simple function alicyclic ring epoxy compound shown in formula (a-1 ') be, for example, sun from
5~50 weight % of sub- polymerizable compound total amount, preferably 10~45 weight %, preferably 15~45 weight %, particularly preferred 20
~45 weight %, most preferably 25~40 weight %.
The content of oxetane compound (especially aliphatic oxetane compound) is organic EL of the invention
50 weight % of the cationically polymerizable total amount of compound contained in component seal composition hereinafter, it is preferred that 45 weight % with
Under, particularly preferred 30 weight % hereinafter, most preferably 20 weight % hereinafter, particularly preferred 15 weight % or less.It should be noted that
Lower limit is zero.When the content excess of oxetane compound (especially aliphatic oxetane compound), it is difficult to obtain
Sufficient moisture resistance is obtained, it is not preferable.
Organic EL element composition for sealing of the invention contains while containing above-mentioned cationically polymerizable compound
One or more kinds of cationic polymerization initiators.Relative to what is contained in organic EL element composition for sealing of the invention
100 parts by weight of cationically polymerizable compound, the content of cationic polymerization initiators are, for example, 0.01~5 parts by weight, preferably
0.05~3 parts by weight, particularly preferred 0.1~2 parts by weight.
Organic EL element composition for sealing of the invention is since with above structure, viscosity is low and mobility is excellent
Different, ink-jet injection property is excellent.Therefore, although organic EL element composition for sealing of the invention also can according to need and contain
Other components than that described above, but do not need particularly to contain solvent, the content of solvent is that group is used in organic EL element sealing
Close object total amount such as 30 weight % hereinafter, it is preferred that 20 weight % hereinafter, particularly preferred 15 weight % hereinafter, most preferably 10 weights
% is measured hereinafter, particularly preferred 5 weight % or less.It should be noted that lower limit is zero.Group is used in organic EL element sealing of the invention
It closes in object, the content of solvent can be suppressed to zero or extremely low, therefore be able to suppress and take off as caused by non-volatile and remaining solvent
The generation of gas.
Organic EL element composition for sealing of the invention can by by above-mentioned cationically polymerizable compound and sun from
Sub- polymerization initiator is stirred, mixes to prepare.They can be used alone or be applied in combination respectively two or more.Make
It for the method for above-mentioned stirring, mixing, is not particularly limited, the various mixing machines such as dissolvers, homogenizer, kneading can be used for example
Machine, roller, ball mill, rotation-revolution type agitating device etc..In addition, volume can carry out deaeration under vacuum after stirring, mixing.
Organic EL element composition for sealing of the invention is 20mPas hereinafter, therefore gluing due to the viscosity at 25 DEG C
The injection for spending nozzle low and from ink gun is excellent.
In addition, the viscosity at 25 DEG C is 100mPas or more in organic EL element composition for sealing of the invention
The content of cationically polymerizable compound be 20 weights of cationically polymerizable total amount of compound contained in above-mentioned composition
% is measured hereinafter, since the content of the cationically polymerizable compound of low-flow is suppressed in low-level, from ink gun
The injection of nozzle is excellent.
In addition, in organic EL element composition for sealing of the invention, under normal pressure boiling point be 190 DEG C of sun below from
The content of sub- polymerizable compound is less than 20 weight % of the total amount of the cationically polymerizable compound in above-mentioned composition included,
Since the content of low-boiling cationically polymerizable compound is suppressed in low-level, organic EL of the invention can be prevented
Component seal composition solidifies and is attached to the jet hole of ink gun, is able to maintain good injection.That is, ink-jet can be passed through
Print process is steadily coated.
After carrying out ultraviolet light irradiation to organic EL element composition for sealing, if it is low to remain volatile unreacted
Then there is the tendency of amount of gas evolved rising in molecular weight cure compound, but due to organic EL element sealing combination of the invention
It uses the compound with rapidly-curable as curability compound in object, therefore can be irradiated promptly by ultraviolet light
Polymerization reaction occurs, to inhibiting the residual of unreacted low molecular weight curability compound in low-level.Therefore, can will consolidate
Amount of gas evolved when change inhibits in low-level.Amount of gas evolved is, for example, 1000ppm hereinafter, it is preferred that 800ppm is hereinafter, more preferable 700ppm
Hereinafter, particularly preferably 550ppm hereinafter, most preferably 350ppm hereinafter, particularly preferably 200ppm or less.It should be noted that degassing
Amount can be measured using the method recorded in embodiment.
Organic EL element composition for sealing of the invention can be solidified rapidly by irradiating ultraviolet light, form solidfied material.
As the light source of ultraviolet light, as long as the light source for generating acid in solidification compound can be made by illumination, such as can
It uses: mercury vapor lamp, mercury xenon lamp, metal halide lamp, tengsten lamp, arc light as UV-LED, basic, normal, high medium pressure mercury lamp
Lamp, Excimer lamp, excimer laser, semiconductor laser, YAG laser, laser and nonlinear optical crystal combination and
At laser system, high-frequency induction ultraviolet ray generating apparatus etc..Ultraviolet irradiation amount (accumulated light) is, for example, 1000~
2000mJ/cm2Left and right.
For organic EL element composition for sealing of the invention, can also further implement to heat after uv irradiation
Processing.By implementing to heat, curing degree can be further improved.Implement heat treatment in the case where, heating temperature be 40~
200 DEG C or so, heating time is 1 minute~15 hours or so.
The solidfied material of organic EL element composition for sealing of the invention has excellent moisture resistance, moisture-vapor transmission example
For example 200g/ (m2Dayatm) (such as 50~200g/ (m below2Dayatm)), preferably 180g/ (m2·day·
Atm) hereinafter, particularly preferably 160g/ (m2Dayatm) hereinafter, most preferably 120g/ (m2Dayatm) hereinafter, especially excellent
Select 100g/ (m2Dayatm) below.It should be noted that moisture-vapor transmission can method by recording in embodiment
It is measured.
The transparency of above-mentioned solidfied material is excellent, and light transmittance (wavelength 400nm) is, for example, 80% or more (preferably 86% or more).
The viscosity of organic EL element composition for sealing of the invention is low, and is able to suppress volatilization when printing, therefore
Be able to suppress through when caused viscosity increase, can prevent above-mentioned composition from solidify and be attached to the jet hole of ink gun, holding
Good injection.Furthermore, it is possible to rapidly form low out gassing and the excellent transparent cured of moisture resistance by irradiating ultraviolet light
Object.Therefore, organic EL element composition for sealing of the invention can be suitable for carrying out sealing organic el using ink jet printing method
The purposes of element.
[manufacturing method of organic EL device]
The manufacturing method of organic EL device of the invention is characterized in that, above-mentioned organic EL is coated with by ink jet printing method
Component seal composition, thus sealing organic el element.
Then, the above-mentioned composition being coated with by ink jet printing method can form solidfied material by irradiating ultraviolet light.Make
For ultraviolet irradiation method, the above method can be used.
According to the present invention, having for stability is projected with excellent ink-jet injection property and ink-jet as described above due to using
Machine EL element composition for sealing, therefore can be stablized by ink jet printing method, quickly and uniformly be coated with the composition.This
Outside, above-mentioned composition can be irradiated by ultraviolet light and be solidified rapidly.Therefore, it can be made well with excellent workability, efficiency
Make organic EL device.
[organic EL device]
Organic EL device (for example, organic el display etc.) of the invention, which has, uses group by the sealing of above-mentioned organic EL element
It closes the solidfied material of object and seals the composition of organic EL element.
As described above, the moisture resistance and low out gassing of the solidfied material of above-mentioned organic EL element composition for sealing are excellent, and
And there is the transparency.Therefore, organic EL device of the invention can inhibit the element deterioration as caused by moisture, brightness height and service life
It is long.
Embodiment
Hereinafter, the present invention is further illustrated in conjunction with the embodiments, but the present invention is not limited to the examples.
Preparation example 1 (preparation of (2- phenylphenoxy) ethyl vinyl ether)
Sodium hydride (55% is accounted in mineral oil) (30.8g, 705.8mmol) and DMSO (509.4g) are dosed to equipped with cold
Solidifying pipe, blender, thermometer 2L four-neck flask in, be added dropwise thereto at 0 DEG C o-phenyl phenol (50.2g,
DMSO (171.6g) solution 250.7mmol).
Then, above-mentioned four-neck flask is placed in 60 DEG C of oil bath, be added dropwise 2- chloroethyl vinyl ether (58.6g,
DMSO (46.0g) solution 550.0mmol).
Reaction solution is stirred 4 hours, 0 DEG C is subsequently cooled to, water is then slowly added dropwise and is quenched, and is transferred to liquid separation leakage
In bucket.
Water layer is extracted with ethyl acetate, saturated salt solution is added into organic layer and is washed.Then, it isolates organic
Layer, is dehydrated using anhydrous sodium sulfate, solvent is then distilled off, obtain liquid crude product.Pass through silica gel column chromatography (oneself
Alkane/ethyl acetate=10/1) the above-mentioned crude product of purifying, obtain the target product (37.5g, 44%) of white solid forms.
1H-NMR(CDCl3, 500MHz) and δ $och 3.85 (s, 1.40H), 3.91 (s, 0.47H), 3.98-4.05 (m,
4.13H),4.14-4.16(m,4H),4.22-4.25(m,2H),6.47-6.54(m,2H),6.80-6.89(m,2H),7.06-
7.09(m,4H),7.12-7.16(m,4H).
Preparation example 2 (preparation of Bisphenol F bis- (ethyleneoxy ethylethers))
In addition to replace o-phenyl phenol and used dihydroxydiphenyl methane (2,2 '-dihydroxydiphenyl methane, 3,
3 '-dihydroxydiphenyl methane and 4, the mixture of 4 '-dihydroxydiphenyl methane) except, in the same manner as preparation example 1 into
Row, has obtained target product (37.5g, 44%).
1H-NMR(CDCl3, 500MHz) and δ $och 3.85 (s, 1.40H), 3.91 (s, 0.47H), 3.98-4.05 (m,
4.13H),4.14-4.16(m,4H),4.22-4.25(m,2H),6.47-6.54(m,2H),6.80-6.89(m,2H),7.06-
7.09(m,4H),7.12-7.16(m,4H).
Examples 1 to 22, the Comparative Examples 1 to 5
Each component is mixed according to the formula (unit: parts by weight) recorded in following table, obtains composition for sealing.By with
Lower method determines the gained viscosity of composition for sealing, property is projected in ink-jet, project stability, UV curability, taking off when solidify
The water vapo(u)r transmission of tolerance and gained solidfied material.
(viscosity)
Using E type viscosimeter, the viscosity of composition for sealing obtained in embodiment and comparative example is determined at 25 DEG C.
(ink-jet injection)
Based on viscosity, has rated the ink-jet of composition for sealing obtained in embodiment and comparative example by the following method and penetrate
Property out.
Evaluation criterion
◎ (very good): the viscosity at 25 DEG C is 15mPas or less
Zero (good): the viscosity at 25 DEG C is greater than 15mPas and is 20mPas or less
× (bad): the viscosity at 25 DEG C is greater than 20mPas
(ink-jet injection stability)
Stability is projected in the ink-jet for having rated composition for sealing obtained in embodiment and comparative example by the following method.
That is, for composition for sealing obtained in embodiment and comparative example, using ink-jet printer (trade name " DMP-2831 ",
The manufacture of Fujifilm Co., Ltd.) it has carried out projecting test, and evaluated based on following standard.
Evaluation criterion
Zero (good): it can project with high precision
× (bad): generating flight bending or jet hole is blocked and fails to project
(UV solidification)
The UV curability of composition for sealing obtained in embodiment and comparative example is evaluated by following manner:
It is coated with (thickness: 20 μm) composition for sealing on glass substrate, utilizes the mercury light irradiation (exposure: 2000mJ/ of 200W/cm
cm2) after ultraviolet light, viscosity is checked for by finger touch, and evaluated based on following standard.
Evaluation criterion
Zero: inviscid
△: slightly sticky
×: toughness
(amount of gas evolved when solidification)
Sealing compositions 60mg obtained in embodiment and comparative example is put into phial, UV irradiation (2000mJ/ is carried out
cm2) after, measure the amount of gas evolved in phial.Wherein, use toluene titer [as the toluene of standard substance: 100ppm (60 μ
G), solvent: hexane (60mg)] make calibration curve.In addition, as determining instrument, used trade name " HP-6890N " (by
The manufacture of Hewlett Packard company), chromatographic column has used trade name " DB-624 " (being manufactured by Agilent company).
(moisture-vapor transmission)
For carrying out UV irradiation (2000mJ/ by the film to composition for sealing obtained in embodiment and comparative example
cm2) obtained from solidfied material (thickness: 100 μm), according to JIS L 1099 and JIS Z 0208 (agar diffusion method), in 60 DEG C, 90%RH
Under the conditions of determine its moisture-vapor transmission.
[table 1]
* boiling point: being the boiling point under normal pressure in addition to the case where describing pressure.
<cationically polymerizable compound>
E-1:(3,4,3 ', 4 '-bicyclic oxygens) connection hexamethylene, it is manufactured by Daicel Co., Ltd.
E-2: bis- (3,4- epoxycyclohexyl-methyl) ethers are manufactured by Daicel Co., Ltd.
E-3:3,4- epoxycyclohexyl-methyl (3,4- epoxy) hexahydrobenzoid acid ester, trade name " CELLOXIDE
2021P " is manufactured by Daicel Co., Ltd.
Bis- (3, the 4- epoxycyclohexyl) ethylene oxide of e-4:2,3-, are manufactured by Daicel Co., Ltd.
Bis- (3, the 4- 7-oxa-bicyclo[4.1.0-1- base) propane of e-5:2,2-, are manufactured by Daiicel company
OPP-EOVE:(2- phenylphenoxy) ethyl vinyl ether, use the substance obtained in preparation example 1
ONB-DVE:7- oxabicyclo [2.2.1] hept-2-ene" divinyl ether (Oxanorbornene divinyl
Ether), manufactured by Daicel Co., Ltd.
Bis- [(3- ethyl -3- oxetanylmethoxy) methoxy] biphenyl of OXBP:4,4-, by Industries plants of Ube
The manufacture of formula commercial firm
Bis- [(3- ethyl -3- oxetanylmethoxy methoxyl group) methyl] benzene of OXT-121:1,4-, trade name " Aron
Oxetane OXT-121 " is manufactured by Toagosei Co., Ltd.
OXT-DVE: oxetanes divinyl ether is manufactured by Daicel Co., Ltd.
YL-983U: Bisphenol F diglycidyl ether is manufactured by Mitsubishi Chemical Co., Ltd.
HRM-C01:N- vinyl carbazole is manufactured by Nisshoku Techno Fine Chemical Co., Ltd..
CELLOXIDE 3000:1,2:8,9- diepoxy limonene, is manufactured by Daicel Co., Ltd.
CYCLOMER M100:3,4- epoxycyclohexyl-methyl methacrylate, is manufactured by Daicel Co., Ltd.
ISB-DVE: isobide divinyl ether is manufactured by Daicel Co., Ltd.
CHDVE: cyclohexanedimethanol divinyl base ether, by Nippon Carbide Industries Co. Ltd. system
It makes
TEGDVE: triethyleneglycol divinylether is manufactured by Nippon Carbide Industries Co., Ltd.
DEGDVE: diethylene glycol divinyl ether is manufactured by Nippon Carbide Industries Co., Ltd.
BisF-bis (VOE) E: Bisphenol F is bis- (ethyleneoxy ethylether), has used substance obtained in preparation example 2
OXT-221:3- ethyl -3 { [(3- Ethyloxetane -3- base) methoxyl group] methyl } oxetanes, by
The manufacture of Toagosei Co., Ltd.
SR-16HJ:1,6- hexanediol diglycidyl ether are manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.
SR-14BJ:1,4- butanediol diglycidyl ether are manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.
SR-PG: propylene glycol diglycidylether is manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.
SR-NPG: neopentylglycol diglycidyl ether is manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.
PGE: phenyl glycidyl ether is manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.
CELLOXIDE 2000:1,2- epoxy -4- vinyl cyclohexane, is manufactured by Daicel Co., Ltd.
OXT-212:3- ethyl -3- [(2- ethyl hexyl oxy) methyl] oxetanes, trade name " Aron Oxetane
OXT-212 " is manufactured by Toagosei Co., Ltd.
BDVE:1,4- butanediol divinyl ether are manufactured by Nippon Carbide Industries Co., Ltd.
<cationic polymerization initiators>
Four (pentafluorophenyl group) borate of 4- (4- xenyl sulfenyl) phenyl -4- xenyl phenyl sulfonium
It is as summary above, technical solution of the present invention and its denaturation note is as follows.
[1] a kind of sealing organic electroluminescent element composition, is used to be coated by ink jet printing method,
The sealing organic electroluminescent element is containing cationically polymerizable compound and cationic polymerization with composition
The composition of initiator, wherein
Viscosity of the composition at 25 DEG C be 20mPas hereinafter,
The 50 weight % or more of cationically polymerizable total amount of compound contained in composition are epoxide and/or second
Alkenyl ether compound,
The content for the cationically polymerizable compound that viscosity at 25 DEG C is 100mPas or more is contained in composition
Cationically polymerizable total amount of compound 20 weight % hereinafter,
Boiling point is that the content of 190 DEG C of cationically polymerizable compounds below is less than sun contained in composition under normal pressure
20 weight % of photopolymerizable total amount of compound.
[2] the sealing organic electroluminescent element composition according to [1], wherein
The group of cationically polymerizable compound becomes following [I] or [II]:
[I] is following when the content of vinyl ether compound is less than 30 weight % of cationically polymerizable total amount of compound
The total content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) and diglycidyl ether type epoxy compound is cationic polymerization
The 50 weight % or more of property total amount of compound,
[II] when the content of vinyl ether compound be cationically polymerizable total amount of compound 30 weight % or more when, under
State multifunctional alicyclic ring epoxy compound shown in formula (a-1) content be cationically polymerizable total amount of compound 5 weight % with
On, the total content of the multifunctional alicyclic ring epoxy compound and vinyl ether compound is cationically polymerizable total amount of compound
50 weight % or more,
[chemical formula 9]
In formula (a-1), X indicates singly-bound or linking group.
[3] the sealing organic electroluminescent element composition according to [2], wherein
Multifunctional alicyclic ring epoxy compound shown in above-mentioned formula (a-1) is selected from 3,4- epoxycyclohexyl-methyl (3,4- ring
Oxygen) hexahydrobenzoid acid ester, (3,4,3 ', 4 '-bicyclic oxygen) connection hexamethylene, bis- (3,4- epoxycyclohexyl-methyl) ethers, 1,2- ring
In bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) ethane of oxygen-1,2- and bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) propane of 2,2- extremely
A kind of few compound.
[4] the sealing organic electroluminescent element composition according to [2] or [3], also contains following formula (a-
1 ') simple function alicyclic ring epoxy compound shown in as cationically polymerizable compound,
[chemical formula 10]
In formula (a-1 '), Ra1Indicate the reactive functional groups other than epoxycyclohexyl, Ra2And Ra3It is identical or different, it indicates
Hydrogen atom or alkyl, L ' indicate singly-bound or linking group.
[5] the sealing organic electroluminescent element composition according to any one of [1]~[4], wherein
Vinyl ether compound at least contains the vinyl ether compound with ring structure.
[6] the sealing organic electroluminescent element composition according to any one of [1]~[5], in solidification
Amount of gas evolved be 1000ppm or less.
[7] the sealing organic electroluminescent element composition according to any one of [1]~[6], solidfied material
Moisture-vapor transmission is 200g/ (m2Dayatm) below.
[8] the sealing organic electroluminescent element composition according to any one of [1]~[7], at 25 DEG C
Viscosity be 10 or more and 20mPas or less or 15mPas or less.
[9] the sealing organic electroluminescent element composition according to any one of [1]~[8], wherein
It, can be containing in above-mentioned epoxide and/or vinyl ether compound as cationically polymerizable compound
Individually one kind or combination contain two or more, and the total content of epoxide and vinyl ether compound is cationically polymerizable
Close the 50 weight % or more of object total amount, 50~100 weight %, 60 weight % or more, 70 weight % or more, 80 weight % or more,
Or 90 is more than weight %.
[10] the sealing organic electroluminescent element composition according to any one of [1]~[9], wherein
The content for the cationically polymerizable compound that viscosity at 25 DEG C is 30mPas or more is cationically polymerizable
30~60 weight % or 30~55 weight % of total amount of compound.
[11] the sealing organic electroluminescent element composition according to any one of [1]~[10], wherein
The content for the cationically polymerizable compound that viscosity at 25 DEG C is 100mPas or more is in above-mentioned composition
0~20 weight % of the cationically polymerizable total amount of compound for including.
[12] the sealing organic electroluminescent element composition according to any one of [1]~[11], wherein
The content for the cationically polymerizable compound that viscosity at 25 DEG C is 2000mPas or more be 15 weight % with
Under, 0~15 weight % or 10 weight % or less.
[13] the sealing organic electroluminescent element composition according to any one of [1]~[12], wherein
Boiling point is that the content of 190 DEG C of cationically polymerizable compounds below is less than cationically polymerizable chemical combination under normal pressure
20 weight % of object total amount or for 0 weight % more than and less than 20 weight % or be 15 weight % or less, 10 weight % or less,
5 weight % or less or 1 weight % or less.
[14] the sealing organic electroluminescent element composition according to any one of [1]~[13], wherein
Viscosity is less than 3mPas at 25 DEG C and boiling point is 190 DEG C of cationically polymerizable chemical combination below under normal pressure
The content of object is less than 10 weight % of cationically polymerizable total amount of compound or is 5 weight % or less or 3 weight % or less.
[15] the sealing organic electroluminescent element composition according to any one of [1]~[14], wherein
Boiling point is that the content of 160 DEG C of cationically polymerizable compounds below is less than cationically polymerizable chemical combination under normal pressure
20 weight % of object total amount or for 0 weight % more than and less than 20 weight % or be 15 weight % or less, 10 weight % or less,
5 weight % or less, 3 weight % or less or 1 weight % or less.
[16] the sealing organic electroluminescent element composition according to any one of [1]~[15], wherein
The content of vinyl ether compound is less than 30 weight % of cationically polymerizable total amount of compound or is 0 weight %
It more than and less than 30 weight % or is 20 weight % or less, 10 weight % or less or 5 weight % or less.
[17] the sealing organic electroluminescent element composition according to any one of [1]~[16], wherein
The content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) is 10 weights of cationically polymerizable total amount of compound
Amount % or more is 10~70 weight %, 20~60 weight %, 30~55 weight % or 35~55 weight %.
[18] the sealing organic electroluminescent element composition according to any one of [1]~[17], wherein
The content of diglycidyl ether type epoxy compound be cationically polymerizable total amount of compound 5 weight % or more, 5~
80 weight %, 10~50 weight %, 15~30 weight % or 15~25 weight %.
[19] the sealing organic electroluminescent element composition according to any one of [1]~[18], wherein
The total content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) and diglycidyl ether type epoxy compound is sun
50 weight % or more, 55 weight % or more, 60 weight % or more, the 65 weight % or more of photopolymerizable total amount of compound, on
It is limited to 95 weight %, 90 weight %, 85 weight %, 80 weight % or 75 weight %.
[20] the sealing organic electroluminescent element composition according to any one of [1]~[19], wherein
The ratio between multifunctional alicyclic ring epoxy compound and the content of diglycidyl ether type epoxy compound shown in formula (a-1)
(the former/the latter；Weight ratio) it is 50/50~90/10,60/40~85/15,60/40~80/20,60/40~75/25 or 60/
40~70/30.
[21] the sealing organic electroluminescent element composition according to any one of [1]~[20], wherein
Also contain formula while containing multifunctional alicyclic ring epoxy compound shown in formula (a-1) as epoxide
Simple function alicyclic ring epoxy compound shown in (a-1 '), above-mentioned multifunctional alicyclic ring epoxy compound and simple function alicyclic epoxy chemical combination
The total content of object is 50 weight % or more, 55 weight % or more, the 60 weight % or more, 65 of cationically polymerizable total amount of compound
Weight % or more, the upper limit are 95 weight %, 90 weight %, 85 weight %.
[22] the sealing organic electroluminescent element composition according to any one of [1]~[21], wherein
Multifunctional alicyclic ring epoxy compound shown in formula (a-1) and simple function alicyclic ring epoxy compound shown in formula (a-1 ')
The ratio between content [above-mentioned multifunctional alicyclic ring epoxy compound/above-mentioned simple function alicyclic ring epoxy compound；Weight ratio] be 50/50~
90/10,51/49~85/15,52/48~80/20,55/45~70/30,55/45~65/35.
[23] the sealing organic electroluminescent element composition according to any one of [1]~[22], wherein
The content of simple function alicyclic ring epoxy compound shown in formula (a-1 ') be cationically polymerizable total amount of compound 5~
50 weight %, 10~45 weight %, 15~45 weight %, 20~45 weight % or 25~40 weight %.
[24] the sealing organic electroluminescent element composition according to any one of [1]~[23], wherein
The total content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) and vinyl ether compound is cationic polymerization
Property total amount of compound 50 weight % or more, 55 weight % or more, 60 weight % or more, 65 weight % or more, the upper limit be 100 weights
Measure %, 95 weight %, 90 weight %, 85 weight %.
[25] the sealing organic electroluminescent element composition according to any one of [1]~[24], wherein
The content of vinyl ether compound is the 30 weight % or more of cationically polymerizable total amount of compound, 30~100 weights
Measure %, 30~90 weight %, 30~70 weight % or 40~60 weight %.
[26] the sealing organic electroluminescent element composition according to any one of [1]~[25], wherein
The content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) be cationically polymerizable total amount of compound 0~
40 weight %, 5~35 weight %, 10~35 weight %.
[27] the sealing organic electroluminescent element composition according to any one of [1]~[26], wherein
The ratio between content of multifunctional alicyclic ring epoxy compound shown in formula (a-1) and vinyl ether compound (the former/after
Person；Weight ratio) it is 0/100~50/50,10/90~45/55,10/90~40/60.
[28] the sealing organic electroluminescent element composition according to any one of [1]~[27], wherein
Also contain formula while containing multifunctional alicyclic ring epoxy compound shown in formula (a-1) as epoxide
Simple function alicyclic ring epoxy compound shown in (a-1 '), above-mentioned multifunctional alicyclic ring epoxy compound and simple function alicyclic epoxy chemical combination
The total content of object is 20 weight % or more, 25 weight % or more, the 30 weight % or more, 40 of cationically polymerizable total amount of compound
Weight % or more, the upper limit are 75 weight %, 70 weight % or 65 weight %.
[29] the sealing organic electroluminescent element composition according to any one of [1]~[28], wherein
Multifunctional alicyclic ring epoxy compound shown in formula (a-1) and simple function alicyclic ring epoxy compound shown in formula (a-1 ')
The ratio between content [above-mentioned multifunctional alicyclic ring epoxy compound/above-mentioned simple function alicyclic ring epoxy compound；Weight ratio] it is, for example, 10/
90~70/30,20/80~60/40,30/70~55/45.
[30] the sealing organic electroluminescent element composition according to any one of [1]~[29], wherein
The content of simple function alicyclic ring epoxy compound shown in formula (a-1 ') be cationically polymerizable total amount of compound 5~
50 weight %, 10~45 weight %, 15~45 weight %, 20~45 weight % or 25~40 weight %.
[31] the sealing organic electroluminescent element composition according to any one of [1]~[30], wherein
Above-mentioned epoxide and/or vinyl ether compound are following [i], [ii] or [iii],
The ring that there is [i] intramolecular one or more to be made of the two neighboring carbon atom and oxygen atom that constitute alicyclic ring
The compound and diglycidyl ether type epoxy compound of oxygroup；
There is [ii] intramolecular one or more to be made of the two neighboring carbon atom and oxygen atom for constituting alicyclic ring
The compound of epoxy group and selected from the vinyl ether compound with aromatic ring structure and with cyclic annular ether structure vinyl etherificate
Close the vinyl ether compound in object；
[iii] is selected from the vinyl ether compound with aromatic ring structure and the vinyl ether compound with cyclic annular ether structure
In vinyl ether compound.
[32] the sealing organic electroluminescent element composition according to any one of [1]~[31], it includes divide
The compound for the epoxy group being made of there are two tools the two neighboring carbon atom and oxygen atom that constitute alicyclic ring in sub, the compound are
Multifunctional alicyclic ring epoxy compound shown in following formula (a-1),
[chemical formula 11]
In formula (a-1), X indicates singly-bound or linking group.
[33] the sealing organic electroluminescent element composition according to any one of [1]~[32], it includes divide
The compound of the epoxy group constituted in sub with a two neighboring carbon atom by constituting alicyclic ring and oxygen atom, the compound are
Simple function alicyclic ring epoxy compound shown in following formula (a-1 '),
[chemical formula 12]
In formula (a-1 '), Ra1Indicate the reactive functional groups other than epoxycyclohexyl, Ra2And Ra3It is identical or different, it indicates
Hydrogen atom or alkyl, L ' indicate singly-bound or linking group.
[34] a kind of manufacturing method of organic electroluminescence device comprising:
Sealing organic electroluminescent element combination described in any one of [1]~[33] is coated with by ink jet printing method
Object, to seal organic electroluminescent device.
[35] a kind of organic electroluminescence device, has a structure in which
Organic electroluminescent device sealing organic electroluminescent element composition described in any one of [1]~[33]
The structure that is sealed to form of solidfied material.
Industrial applicibility
Present invention offer can be steadily coated, can be solidified rapidly by illumination by ink jet printing method and shape
At the organic EL element composition for sealing of the excellent solidfied material of moisture resistance.
Claims (9)
1. a kind of sealing organic electroluminescent element composition, is used to be coated by ink jet printing method,
The sealing organic electroluminescent element with composition is caused containing cationically polymerizable compound and cationic polymerization
The composition of agent,
Wherein,
Viscosity of the composition at 25 DEG C be 20mPas hereinafter,
The 50 weight % or more of cationically polymerizable total amount of compound contained in composition are epoxide and/or vinyl
Ether compound,
The content for the cationically polymerizable compound that viscosity at 25 DEG C is 100mPas or more is sun contained in composition
20 weight % of photopolymerizable total amount of compound hereinafter,
Boiling point is that the content of 190 DEG C of cationically polymerizable compounds below is less than cation contained in composition under normal pressure
20 weight % of polymerizable compound total amount.
2. sealing organic electroluminescent element composition according to claim 1, wherein
The group of cationically polymerizable compound becomes following [1] or [2],
[1] when the content of vinyl ether compound is less than 30 weight % of cationically polymerizable total amount of compound, following formula (a-
1) total content of multifunctional alicyclic ring epoxy compound and diglycidyl ether type epoxy compound shown in is cationically polymerizable
Close the 50 weight % or more of object total amount；
[2] when the content of vinyl ether compound is the 30 weight % or more of cationically polymerizable total amount of compound, following formula
(a-1) content of multifunctional alicyclic ring epoxy compound shown in is the 5 weight % or more of cationically polymerizable total amount of compound, institute
The total content for stating multifunctional alicyclic ring epoxy compound and vinyl ether compound is 50 weights of cationically polymerizable total amount of compound
% or more is measured,
In formula (a-1), X indicates singly-bound or linking group.
3. sealing organic electroluminescent element composition according to claim 2, wherein
Multifunctional alicyclic ring epoxy compound shown in above-mentioned formula (a-1) is at least one of to be selected from the group compound: 3,4- ring
Oxygen cyclohexyl methyl (3,4- epoxy) hexahydrobenzoid acid ester, (3,4,3 ', 4 '-bicyclic oxygen) join hexamethylene, bis- (3,4- epoxide rings
Hexyl methyl) ether, bis- (3,4- 7-oxa-bicyclo[4.1.0-1- base) ethane of 1,2- epoxy-1,2- and bis- (the 3,4- epoxy hexamethylenes of 2,2-
Alkane -1- base) propane.
4. sealing organic electroluminescent element composition according to claim 2 or 3 also contains following formula (a-1 ')
Shown in simple function alicyclic ring epoxy compound as cationically polymerizable compound,
In formula (a-1 '), Ra1Indicate the reactive functional groups other than epoxycyclohexyl, Ra2And Ra3It is identical or different, indicate that hydrogen is former
Son or alkyl, L ' indicate singly-bound or linking group.
5. sealing organic electroluminescent element composition according to any one of claims 1 to 4, wherein
Vinyl ether compound at least contains the vinyl ether compound with ring structure.
6. sealing organic electroluminescent element composition according to any one of claims 1 to 5, de- when solidifying
Tolerance is 1000ppm or less.
7. sealing organic electroluminescent element composition described according to claim 1~any one of 6, the water of solidfied material
Vapor transmission rates are 200g/ (m2Dayatm) below.
8. a kind of manufacturing method of organic electroluminescence device comprising:
It is coated with sealing organic electroluminescent element composition according to any one of claims 1 to 7 by ink jet printing method,
Seal organic electroluminescent device.
9. a kind of organic electroluminescence device, has a structure in which
Organic electroluminescent device is by sealing organic electroluminescent element composition according to any one of claims 1 to 7
The structure that is sealed to form of solidfied material.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016256747A JP6228289B1 (en) | 2016-12-28 | 2016-12-28 | Composition for sealing an organic electroluminescence device |
| JP2016-256747 | 2016-12-28 | ||
| PCT/JP2017/045572 WO2018123738A1 (en) | 2016-12-28 | 2017-12-19 | Composition for sealing organic electroluminescence element |
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| Publication Number | Publication Date |
|---|---|
| CN110140425A true CN110140425A (en) | 2019-08-16 |
Family
ID=60265862
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|---|---|---|---|
| CN201780081100.3A Pending CN110140425A (en) | 2016-12-28 | 2017-12-19 | Sealing organic electroluminescent element composition |
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| JP (1) | JP6228289B1 (en) |
| KR (1) | KR102518942B1 (en) |
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| JP6410158B2 (en) * | 2016-10-07 | 2018-10-24 | パナソニックＩｐマネジメント株式会社 | Ultraviolet curable resin composition, organic EL light emitting device manufacturing method, and organic EL light emitting device |
| JP6228289B1 (en) * | 2016-12-28 | 2017-11-08 | 株式会社ダイセル | Composition for sealing an organic electroluminescence device |
| JP6653842B2 (en) * | 2017-06-30 | 2020-02-26 | 協立化学産業株式会社 | Cationic polymerization-curable resin composition for sealing an organic EL device, and an organic EL device using the same |
| JPWO2019146736A1 (en) * | 2018-01-26 | 2021-01-28 | 味の素株式会社 | Curable resin composition for sealing |
| WO2019198470A1 (en) * | 2018-04-09 | 2019-10-17 | 積水化学工業株式会社 | Sealant for organic electroluminescent display element |
| WO2019203180A1 (en) * | 2018-04-20 | 2019-10-24 | 積水化学工業株式会社 | Sealant for organic el display element |
| JP7039391B2 (en) * | 2018-05-25 | 2022-03-22 | 三井化学株式会社 | Sealant for display element, sealant for organic EL element and its cured product |
| KR102490648B1 (en) * | 2018-06-20 | 2023-01-19 | 미쓰이 가가쿠 가부시키가이샤 | Encapsulant for display element and cured product thereof |
| WO2020031941A1 (en) * | 2018-08-10 | 2020-02-13 | 三井化学株式会社 | Sealant |
| KR102541648B1 (en) * | 2020-06-03 | 2023-06-08 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same |
| WO2023182281A1 (en) * | 2022-03-25 | 2023-09-28 | デンカ株式会社 | Encapsulant for organic electroluminescent element, encapsulation material, and organic electroluminescent display device |
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| KR100799146B1 (en) * | 2003-08-21 | 2008-01-29 | 아사히 가세이 케미칼즈 가부시키가이샤 | Photosensitive composition and cured product thereof |
| JP2011153255A (en) * | 2010-01-28 | 2011-08-11 | Tokyo Printing Ink Mfg Co Ltd | Cationically photocurable composition and cured product |
| JP5812993B2 (en) * | 2010-08-12 | 2015-11-17 | 株式会社ダイセル | Low moisture-permeable resin composition and cured product thereof |
| JP6200203B2 (en) * | 2013-05-16 | 2017-09-20 | 積水化学工業株式会社 | Sealant for organic electroluminescence display element and method for producing organic electroluminescence display element |
| JP5764687B1 (en) * | 2014-03-31 | 2015-08-19 | 古河電気工業株式会社 | Organic electronic device element sealing resin composition, organic electronic device element sealing resin sheet, organic electroluminescence element, and image display device |
| TWI695059B (en) * | 2015-04-17 | 2020-06-01 | 日商積水化學工業股份有限公司 | Sealant for electronic device and manufacturing method of electronic device |
| JP2017082160A (en) * | 2015-10-30 | 2017-05-18 | 三洋化成工業株式会社 | Photocurable composition |
| JP2017228414A (en) * | 2016-06-22 | 2017-12-28 | 積水化学工業株式会社 | Sealant for organic electroluminescent display element |
| JP6228289B1 (en) * | 2016-12-28 | 2017-11-08 | 株式会社ダイセル | Composition for sealing an organic electroluminescence device |
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2016
- 2016-12-28 JP JP2016256747A patent/JP6228289B1/en active Active
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2017
- 2017-12-19 CN CN201780081100.3A patent/CN110140425A/en active Pending
- 2017-12-19 KR KR1020197017559A patent/KR102518942B1/en active IP Right Grant
- 2017-12-19 WO PCT/JP2017/045572 patent/WO2018123738A1/en active Application Filing
- 2017-12-27 TW TW106146003A patent/TW201833254A/en unknown
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| KR20190098743A (en) | 2019-08-22 |
| KR102518942B1 (en) | 2023-04-07 |
| JP6228289B1 (en) | 2017-11-08 |
| TW201833254A (en) | 2018-09-16 |
| JP2018110056A (en) | 2018-07-12 |
| WO2018123738A1 (en) | 2018-07-05 |
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