JP5865292B2 - Thermosetting epoxy-amine barrier sealant - Google Patents

Description

Detailed Description of the Invention

This invention was made with assistance from the United States government under contract number MDA972-93-2-0014 obtained from the Army Institute. The United States government has certain rights in the invention.

Related applications

The present invention relates to barrier sealants, adhesives, encapsulants and coatings for use in electronic and optoelectronic devices. (As used in this specification and claims, adhesives, sealants, encapsulants, and coatings are similar materials, all having adhesive, sealant, and coating properties and functions. Any one is listed. Other cases are also included).

background

Polymer barrier materials are widely used in many packaging and protection applications such as food, beverages, pharmaceuticals, cosmetics, agricultural products, electronic components, molded articles, pipes, and tubes. The barrier limits the exchange of permeant molecules between the environment and the protected system, so it preserves flavors and aromas of food or cosmetic ingredients and does not degrade electronic components with moisture or oxygen. And protect parts of automobile instrument panels from permeation of solvents commonly used in paints or primers. Because various systems require a variety of barrier performances, an excellent barrier in one application may be considered insufficient in other applications.

Many optoelectronic devices are moisture or oxygen sensitive and must be protected from moisture during their useful life. A common approach is to seal the device between an impervious substrate on which the device is placed and an impervious glass or metallic lid and use a curable adhesive or sealant And sealing or adhering to the periphery of the lid and the bottom substrate.

A typical example of this packaging shape is shown in FIG. 1, which is made of metal or glass on an organic light emitting diode (OLED) stack (3) formed on a glass substrate (4). The use of a curable peripheral sealant (1) to adhere to the lid (2) of Various structures exist, but typical devices are anode (5), cathode (6), and OLE.
Also includes some form of electrical interconnection between the D pixel / device and the external electrical circuit (7). For the purposes of the present invention, no special device shape is specified or required except that it includes an adhesive / sealant material such as peripheral sealant (1).

In many configurations, such as that shown in FIG. 1, both the glass substrate and the metal / glass lid are essentially impermeable to oxygen and moisture, and the sealant provides some permeability around the device. It is the only material that has it. For electronic and optoelectronic devices, moisture permeability (m
Oisture permeability is often much more important than oxygen permeability; therefore, oxygen barrier requirements are not imminent, so it is important for the good performance of the device that the moisture resistance of the peripheral sealant is important.
).

A good barrier sealant will exhibit low bulk moisture permeability, excellent adhesion, and strong interfacial adhesion / substrate interaction. If the quality of the substrate-sealant interface is poor, the interface functions as a weak boundary so that moisture can rapidly enter the device regardless of the bulk moisture permeability of the sealant. If the interface is at least continuous as a bulk sealant, typically the moisture permeability will depend on the bulk moisture permeability of the sealant itself.

Since the water vapor transmission rate is not standardized to a predetermined path thickness or path length for permeation, it is simply a water vapor transmission rate (WVTR).
It is important that moisture permeability (P) must be tested as a measure of effective barrier properties. Usually, permeability can be defined as WVTR multiplied by the permeation path length, so it is a preferred method for evaluating whether a sealant is an inherently good barrier material.

The most common method for expressing transparency is the permeability coefficient (permeability code).
ficient: eg g · mil / 100 square inch · day · atmosphere (this can be applied to any experimental condition) or permeation coef
ficient, for example g · mil / 100 square inches · day at a given temperature and relative humidity, which must refer to experimental conditions to define the partial pressure / concentration of permeate contained in the barrier material. Don't be. Usually, the passage of permeate through a barrier material (transmittance, P) can be described as the product of diffusion (D) and solubility (S): P = D · S.

The term solubility indicates the barrier's affinity for the permeate, and for water vapor, a low S is obtained from a hydrophobic material. The term diffusion is a measure of the permeate mobility in the barrier matrix and is directly related to barrier material properties such as free volume and molecular mobility. The low D is
Often obtained from highly cross-linked or crystalline materials (as opposed to less cross-linked or amorphous analogs). The permeability increases rapidly as the molecular motion increases (eg, as the temperature increases, especially when the Tg of the polymer increases).

A logical chemical approach to producing a good barrier must consider these two basic factors (D and S) that affect water vapor and oxygen permeability. Extrapolated to such chemical factors are physical variables: a long permeation path and a perfect adhesive layer (the adhesive on the substrate is well wetted), which enhances barrier performance and is therefore possible Should be applied as long as possible. An ideal barrier sealant provides excellent adhesion to all device substrates while exhibiting low D and S.

In order to obtain a high performance barrier material it is not sufficient to have only a low solubility (S) or only a low partial acidity (D). In a conventional example, it can be found in a general siloxane elastomer. Such materials are highly hydrophobic (low solubility, S), and also have high diffusivity (D) and high molecular mobility because rotation around the Si-O bond is not hindered. Low barrier. Thus, many systems that are simply hydrophobic are not good barrier materials, despite the fact that they exhibit low moisture solubility. Low water solubility must be combined with low molecular mobility and low permeate mobility or diffusivity.

Barriers based on epoxy-amine chemistry have long been used in food packaging. These crosslinked coatings have been found to have excellent oxygen barrier properties. However, it is generally known that oxygen and moisture permeability do not necessarily follow the same trend. Furthermore, to obtain the maximum potential of these coatings, the materials are usually cured at elevated temperatures for extended periods of time (typically 60 minutes at 100 ° C.). These harsh conditions include organic light emitting devices (
Used in many current and future display applications such as OLED), polymer light emitting devices, charge coupled device (CCD) sensors, liquid crystal displays (LCD), electrophoretic displays, and micro-electro-mechanical sensors (MEMS) Electroluminescence (e
It would be disadvantageous for the material.

Depending on the application, performance requirements are stringent and there is a need to further improve current barrier materials. In particular, there is a need for barrier materials that cure below 100 ° C. while maintaining good barrier performance, whether for food packaging or electronic and optoelectronic device packaging, or for other applications that require barrier performance.

Brief Description of Drawings

FIG. 1 shows an optoelectronic device having a sealed periphery. FIG. 2 is a differential scanning calorimetric overlay of an epoxy / TEPA (amine) blend cured isothermally at 75 ° C. with and without the use of a catalyst.

Summary of the Invention

The present invention is a barrier composition comprising a resin or resin / filler system that can be cured at low temperatures while maintaining excellent barrier performance. The composition comprises (a) an aromatic compound having a meta-substituted epoxy functionality, (b) a polyfunctional aliphatic amine, (c) optionally one or more fillers, and (d) optionally one or more adhesives. An accelerator, and (e) optionally a phenolic cure accelerator.

Such barrier compositions can be used alone or in combination with other curable resins and various fillers. The resulting composition exhibits a commercially acceptable cure rate, high crosslink density, and good adhesion so that it is efficient for use in sealing and encapsulating various manufactured articles, particularly electronic, optoelectronic and MEMS devices. To do.

In another aspect, the present invention provides epoxidized resole, bisphenol-F glycidyl ether, bisphenol-A diglycidyl ether, bisphenol-E diglycidyl ether, epoxidized phenol novolac resin, epoxidized cresol novolac resin, An aromatic epoxy compound selected from the group consisting of cyclic epoxy resins, naphthalene diglycidyl ethers and their halogenated derivatives; a low temperature curable barrier composition comprising a polyfunctional amine and optionally a phenolic cure accelerator; is there.

Detailed Description of the Invention

The present invention is a thermosetting barrier sealant comprising (a) an aromatic compound having a meta-substituted epoxy functionality and (b) a polyfunctional aliphatic amine. The barrier adhesive or sealant optionally includes (c) one or more fillers and (d) one or more adhesion promoters.

To cure at low temperatures while maintaining good transmission performance, this thermosetting barrier sealant
Furthermore, (e) a phenolic curing accelerator can be included.

In another aspect, the present invention provides an epoxidized resole, bisphenol-F glycidyl ether, bisphenol-A diglycidyl ether, bisphenol-E diglycidyl ether, epoxidized phenol novolac resin, epoxidized cresol novolac resin, polycyclic epoxy resin A low temperature curable barrier composition comprising an aromatic epoxy compound selected from the group consisting of naphthadiene glycidyl ether and halogenated derivatives thereof; a polyfunctional amine; and optionally a phenolic cure accelerator.

As used herein and in the claims, epoxies, epoxides, and oxiranes (and their plurals) are intended to refer to the same compound or compounds of this type.

Aromatic compounds having a meta-substituted epoxy functional group have the following structure:

｛式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４は、水素、ハロゲン、シアノ、アルキル、アリール及び
、置換アルキルまたはアリール基からなる群から選択され、これはエポキシ官能基を含ん
でいてもよく；Ｒ^５及びＲ^６は、一般構造：−Ｃ_nＨ_２ｎ−をもつ二価炭化水素結合基で
あり、ここでｎ＝０〜４であり（ｎが０であるときＲ^５及びＲ^６は存在しない）、ここで
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のいずれか二つは、同一環式構造の一部を形成し
ていてもよい；

{Wherein R ¹ , R ² , R ³ , R ⁴ are selected from the group consisting of hydrogen, halogen, cyano, alkyl, aryl, and substituted alkyl or aryl groups, which may contain epoxy functional groups Well; R ⁵ and R ⁶ are divalent hydrocarbon linking groups having the general structure: —C _n H _2n —, where n = 0-4 (when n is 0, R ⁵ and R ⁶ Where any ^two of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may form part of the same cyclic structure;

からなる群から選択される二価の結合基であり；
ＥＰ及びＥＰ’は、脂肪族エポキシ、グリシジルエーテル及び脂環式エポキシからなる
群から選択される硬化性エポキシ官能基である｝。 L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ are direct bonds, or

A divalent linking group selected from the group consisting of;
EP and EP ′ are curable epoxy functional groups selected from the group consisting of aliphatic epoxies, glycidyl ethers and alicyclic epoxies}.

｛式中、構造上の水素は、一つ以上のアルキルまたはハロゲン基によって置換されていて
もよい｝。 Examples of epoxy groups include, but are not limited to:

{Wherein the structural hydrogen may be substituted by one or more alkyl or halogen groups}.

Exemplary aromatic compounds having a meta-substituted epoxy functionality include, but are not limited to:

One or more additional epoxy resins can be used to meet various performance requirements, and these resins are preferably bisphenol F diglycidyl ether, novolac glycidyl ether, polycyclic epoxy, naphthalene diglycidyl ether And selected from the group consisting of these halogenated derivatives.

をもつアミンを意味し、式中、Ｒ’及びＲ”は、水素、アルキルまたは置換アルキル基か
らなる群から独立して選択される。Ｒ”’は水素または、二価アルキル／置換アルキル結
合基である。好適な多官能性脂肪族アミンとしては、

からなる群から選択されるものが挙げられるが、これらに限定されない。 As used herein, the term aliphatic amine refers to at least two of the following groups in the same molecule:

Wherein R ′ and R ″ are independently selected from the group consisting of hydrogen, alkyl or substituted alkyl groups. R ″ ′ is hydrogen or a divalent alkyl / substituted alkyl linking group. It is. Suitable polyfunctional aliphatic amines include

A material selected from the group consisting of, but not limited to.

As used herein and in the claims, the terms accelerator and catalyst shall refer to the same concept. Suitable accelerators are difunctional or polyfunctional phenolic compounds. Suitable phenol compounds include tris-2,4,6,-(dimethylaminomethyl) phenol, resorcinol, 4-ethylresorcinol, 2,5-dimethylresorcinol, phloroglucinol, 2-nitrofluoro-glucinol, 5-methoxy. Resorcinol, orcinol, 2-methylresorcinol, 4-bromoresorcinol, 4-chlororesorcinol, 4,6-dichlororesorcinol, 3,5-dihydroxy-benzaldehyde, 2,4-dihydroxy-benzaldehyde, methyl 3,5-dihydroxybenzoate, Methyl 2,4-dihydroxybenzoate, 1,2,4-benzenetriol, pyrogallol, 3,5-dihydroxybenzyl alcohol, 2 ′, 6′-dihydroxyacetophenone, 2 ′, 4′-dihydride Roxyacetophenone, 3 ′, 5′-dihydroxyacetophenone, 2 ′, 4′-dihydroxy-propiophenone, 2 ′, 4′-dihydroxy-3′-methylacetophenone, 2,4,5-trihydroxy-benzaldehyde, 2 ,
3,4-trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 3,5-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 2-nitroresorcinol, 1,3 -Dihydroxynaphthalene, hydroquinone, methylhydroquinone, 2,3-dimethylhydroquinone, 2-methoxyhydroquinone, chlorohydroquinone, 2 ', 5'-dihydroxyacetophenone, 2-isopropyl-
1,4-benzenediol, 2,5-dihydroxybenzoic acid, 2,3-dicyanohydroquinone, 1,4-dihydroxynaphthalene, 2 ′, 5′-dihydroxypropiophenone,
1- (2,5-dihydroxy-4-methylphenyl) ethanone, tert-butylhydroquinone, methyl 2,5-dihydroxybenzoate, (2,5-dihydroxyphenyl)
Acetic acid, 2,4,5-trihydroxybenzoic acid, 4,7-dihydroxy-3-methyl-1-
Indanone, 2,5-dichlorohydroquinone, tetrafluoro-hydroquinone, ethyl 2
, 5-dihydroxybenzoate, 2- (2,5-dihydroxybenzylidene) malononitrile, 2-bromo-1,4-benzenediol, ethyl (2,5-dihydroxyphenyl) acetate, 1- (2,4,5-tri Hydroxyphenyl) -1-butanone, methyl 2,5-dihydroxy-4-methoxybenzoate, 2,6-dinitro-1,4-benzenediol, 2,4,5-trihydroxyphenylalanine, (2,5-dihydroxyphenyl) )-(Phenyl) methanone, 2,5-ditert-butyl-1,4-benzenediol, 2- (6-methylheptyl) -1,4-benzenediol, 2- (1,1,3,3)
-Tetramethylbutyl) -1,4-benzenediol, dimethyl 2,5-dihydroxyterephthalate, 2,4,5-trichloro-3,6-dihydroxybenzonitrile, 2,5
Di-tert-pentyl-1,4-benzenediol, 2,5-dibromo-1,4-benzenediol, dimethyl 2,4-diethyl-3,6-dihydroxy-phenylphosphonate, pyrocatechol, 2,3-naphthalene Diol, 5-methyl-1,2,3-benzenetriol, 4-methylcatechol, 3-methylcatechol, 3-fluorocatechol,
3-methoxycatechol, 4-chlorocatechol, 4,5-dichlorocatechol, 4-t
tert-butylcatechol, 3,4,5,6-tetrachloro-1,2-benzenediol, 3-isopropyl-6-methylcatechol, 3-tert-butyl-6-methylcatechol, 3,4-dihydroxybenzonitrile 3,5-ditert-butylcatechol,
3,5-diisopropylcatechol, 3,4-dihydroxybenzaldehyde, 4- (1
, 1,3,3-tetramethylbutyl) -1,2-benzenediol, 4- (1,2-dihydroxyethyl) -1,2-benzenediol, 1- (3,4-dihydroxyphenyl)
Ethanone, 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzamide,
4-nitro-1,2-benzenediol, 4- (2-amino-1-hydroxyethyl)-
1,2-benzenediol, 5-methyl-3- (1,1,3,3-tetramethylbutyl)
-1,2-benzenediol, (3,4-dihydroxyphenyl) acetic acid, 2- (3,4-
Dihydroxybenzyl-idene) malononitrile, 3,5-dinitro-1,2-benzenediol, methyl 3,4-dihydroxybenzoate, 2-chloro-1- (3,4-dihydroxyphenyl) ethanone, phenyl (2,3,3) 4-trihydroxyphenyl) methanone, isopropyl 3,4,5-trihydroxybenzoate, 3,4-dihydroxy-2
-Methylphenylalanine, 3-bromo-4,5-dihydroxybenzoic acid, 2- (3,4
-Dihydroxy-5-methoxybenzylidene) malononitrile, ethyl 3- (3,4-dihydroxyphenyl) propanoate, 2-phenyl-1- (2,3,4-trihydroxy-phenyl) ethanone, and 3,4,5- Trihydroxy-N- (2-hydroxyethyl) benzamide can be mentioned, but is not limited thereto.

Suitable fillers include powdered quartz, fused silica, amorphous silica, talc, glass beads, graphite, carbon black, alumina, clay, and nanoclay, mica,
Examples include, but are not limited to, vermiculite, aluminum nitride, and boron nitride. Additional suitable fillers include metal powders and metal flakes such as silver, copper, gold,
Tin, tin / lead alloys and other alloys are included. Organic filler powders such as poly (tetrachloroethylene), poly (chlorotrifluoroethylene), and poly (vinylidene chloride)
Can also be used. Examples of fillers that function as desiccants or oxygen scavengers include Ca
O, BaO, Na ₂ SO ₄ , CaSO ₄ , MgSO ₄ , zeolite, silica gel, P ₂ O
₅ , CaCl ₂ and Al ₂ O ₃ can also be used, but are not limited thereto.

The epoxy-amine based components can be premixed or stored in separate containers and mixed in-situ using equipment such as a static mixer. The components can also be partially premixed, such as by adding a small amount of an epoxy component to the amine to form an amine oligomer / prepolymer. The amount of epoxy must be small enough so that gelation does not occur. This mixture is then further mixed with the remaining epoxy components. Alternatively, one or more components can be dissolved in one or more solvents before application.

Applications of these formulations include syringe dispensing, screen printing, stencil printing, spraying, roll coating, ink jet printing,
It can be performed by various processes such as, but not limited to, processes such as spin coating, dip coating, and vapor deposition. The choice of application method depends on the product, but such choice is within the expertise of one skilled in the art.

Example

Example 1. Epoxy-amine blends in various ratios

This example demonstrates the importance of epoxy-amine stoichiometry in thermoset blends. Bisphenol F diglycidyl ether (Hexion Specialty Chemi
Mixtures of cals Epoxy Research Resin RSL-1739 and triethylenetetramine (TETA, Aldrich) or tetraethylenepentamine (TEPA, ACROS) are shown in Table 1 (TETA sample) and Table 2 (TE
(PA samples) were mixed at various ratios. All the samples listed in the table contained 0.2% by weight of a silicone surface additive BYK-310. Each sample was mixed and then degassed in a vacuum chamber and cured on a glass plate at 100 ° C. for 100 minutes. The transmission coefficient of the cured sample was measured with Mocon Permetran 3/33 at 50 ° C. and 100% RH. As shown in these tables, the molar ratio of epoxy to amine molecules and the ratio of epoxy groups to amine nitrogen and epoxy groups to amine hydrogen were calculated. For TETA (Table 1), the lowest moisture permeability coefficient 3.4-3.
7 g · mil / 100 square inches · day was achieved about 1 to 1 epoxy group to amine hydrogen. This proved to be an optimal ratio. With higher amounts of epoxy, the film became more brittle and much more difficult to remove from the glass without breaking. With higher amounts of amine, the film became soft and did not cure sufficiently. Samples containing TEPA and RSL-1739 (Table 2) showed similar trends. The lowest moisture permeability coefficient was 3.6 to 4.0 g · mil / 100 square inches · day, which was also obtained with a 1: 1 ratio of epoxy groups to amine hydrogen.

Example 2 Blends with various epoxies

This example shows the effect of epoxy structure on permeation performance. The TEPA formulation may be another epoxy or ERL-4221 (Dow Chemical), resorcinol diglycidyl ether (CVC Specialty Chem as ERISYS RDGE).
available from Icals), and Epilon EXA-835LV (Danipo)
n Ink and Chemicals Co. ) And other epoxy combinations. Table 3 shows the composition and the permeation results. All formulations are epoxy groups vs. amine hydrogen 1:
1 with 0.2% by weight BYK-310 as an antifoaming agent, unless otherwise stated in Table 3,
Cured on glass at 100 ° C. for 100 minutes. Formulations containing alicyclic epoxy ERL-4221 did not fully cure. The RDGE formulation performed well and had a low permeability coefficient (2.0-2.5 g · mil / 100 square inches · day) alone and blended with other glycidyl epoxies.

Example 3 FIG. Blends with various amines

This example shows the effect of amine structure on the moisture permeability of various cured epoxy / amine blends. Several blends were studied using 80/20 RDGE / 835LV as the epoxy option. As shown in Table 4 below, amines with various backbone structures were tested and all had a 1: 1 ratio of epoxy groups to amine hydrogens. All samples are 10
Cured at 0 ° C. for 100 minutes. In systems containing polyfunctional aliphatic amines such as TEPA (tetraethylenepentamine), TETA (triethylene-tetramine) or DETA (ethylene triamine), low moisture permeability was observed. As can be seen from the table, the aromatic amine / epoxy system did not melt and did not cure.

Example 4 Curing under various conditions

This example shows the effect of a phenol catalyst in an epoxy-amine system. To a vial containing a clear solution of 1.32 g RDGE and 0.33 g Epiclon EXA-835LV was added 0.37 g TEPA. The entire mixture was blended for 1 minute using a vortex mixer. Isothermal curing studies were performed at 75 ° C and 100 ° C with Perkin Elmer DS
The results are shown in Table 5.

As shown in the table, when cured at 75 ° C., no catalyst is used.
It takes significantly longer than curing at 0 ° C. This is indicated by the long time to reach the exothermic peak and the time required to obtain 90% cure. Another sample was 0.082 g resorcinol, 1.32 g RDGE and 0.33 g Epic.
It was blended into a mixture of lon EXA-835LV (5 wt% resorcinol based on epoxy) and heated to 100 ° C. for 10 minutes to make a clear solution. After cooling to room temperature, 0.37 g of TETA was added and the solution was mixed with a vortex mixer. Again isothermal curing was studied with this formulation. The formulation using the catalyst was greatly improved in curing performance. The time to peak temperature and the time to reach 90% of the total exotherm were reduced compared to the sample without catalyst. The film cured for 20 minutes at 75 ° C. without the use of a catalyst was tacky, but when the catalyst was added, the film was non-tacky and scratch resistant (s
(crack resistant).

Embodiment 5 FIG. Effect of phenol loading on curing behavior

This example shows the effect of phenol catalyst loading on cure behavior. Samples were prepared as in Example 4 and Perkin Elmer D while heating to 150 ° C. at 10 ° C./min.
Analyzed by SC. All formulations were prepared with 1: 1 epoxy group to amine hydrogen. Table 6 shows the results.
Shown in For samples that did not use bisphenol-A or 1.5-5% bisphenol-A, curing began at about 65 ° C. Bisphenol-A level is 1
When increased to 0%, curing began at a low temperature of about 55 ° C. As the bisphenol-A loading increased, the cure peak temperature decreased.

Example 6 Comparison of various phenols to catalyze epoxy-amine curing

This example shows the effect of a phenolic catalyst on curing behavior and moisture permeability after curing. Several epoxy-TETA samples using different phenol catalysts were compared. in this case,
6.64 g RDGE, 1.67 g Epiclon 835LV, and 1.67 g T
Produces a mixture of ETA, cure temperature and exotherm information (Delta H, J / g)
Obtained by heating to 150 ° C. at 10 ° C./min in Elmer DSC. As shown by the examples, resorcinol reduces the curing temperature and is 100 at 100 ° C.
Permeation performance comparable to the sample without the use of a minute cured catalyst could be achieved. Transmission data was collected at 50 ° C. and 100% RH. In the case of bisphenol-A, a significant increase in permeation was observed. Another phenol, 2-hydroxy-4-methoxybenzophenone (
HMBP) did not help at all in curing.

Example 7 Various substituted resorcinol cure accelerators

Several substituted forms of resorcinol were screened at 5% by weight to determine if the cure temperature could be further reduced. As shown in Table 8 below, all resorcinol analogs reduced the cure peak, but none were as good as resorcinol itself.

Example 8 FIG. Filled two-part formulation

A silica-filled two-part epoxy-amine system was prepared with micron sized silica and fumed silica rheology modifier. The ingredients are listed in Table 9.

Epoxy and resorcinol were heated at 110 ° C. to dissolve resorcinol. After cooling
Silane adhesion promoter was added and the sample was mixed with a vortex mixer. The filler and rheology modifier were then added and the sample was mixed with a 3 roll mixer followed by degassing overnight. T
EPA was added to the filled epoxy system and stirred well with a wooden stick and a vortex mixer.

Adhesion performance was tested by applying two pieces of tape (~ 5 mils) about 1/4 inch apart on a TEFLON coated aluminum plate. Using a blade, the formulation was placed between tapes to form a film. A glass slide and several 4 × 4 mm glass dies were cleaned by wiping with isopropanol and immersed in isopropanol for 24 hours. Slides and dies were removed from isopropanol, air dried and then UV ozone cleaned for 5 minutes. The die was then placed on the film of the formulation and tapped lightly to immerse the entire die. The die was removed from the formulation coating and placed on a slide. The die was tapped and wetted between the die and the slide with the formulation. The sealant formulation was cured in an oven at 75-80 ° C. for 20 minutes. The shear adhesion of the cured sample was adjusted to 100 kg head and 300
Tested using a Royce Instrument 552 100K equipped with a mill die tool. The dry adhesion was found to exceed 40 kg, and this level was maintained even after 1 and 2 weeks of moist heat degradation at 65 ° C. and 80% RH.

｛式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４は、水素、ハロゲン、シアノ、アルキル、アリール及び
、置換アルキルまたはアリール基からなる群から選択され、これはエポキシ官能基を含ん
でいてもよく；Ｒ^５、Ｒ^６は、一般構造：−Ｃ_nＨ_２ｎ−をもつ二価炭化水素結合基であ
り、ここでｎ＝０〜４であり、ここでＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６のいずれか
二つは、同一環式構造の一部を形成していてもよく；
Ｌ^１、Ｌ^２、Ｌ^３、Ｌ^４、Ｌ^５、Ｌ^６は直接結合であるか、または

からなる群から選択される二価の結合基であり；
ＥＰ及びＥＰ’は、脂肪族エポキシ、グリシジルエーテル及び脂環式エポキシからなる
群から選択される硬化性エポキシ官能基であり；ここで前記エポキシ中の水素は一つ以上
のアルキルまたはハロゲン基で置換されていてもよい｝をもつ芳香族化合物；
（ｂ）多官能性脂肪族アミン；
（ｃ）場合により一種以上の充填剤；
（ｄ）場合により一種以上の接着促進剤。
(２) ＥＰ及びＥＰ’官能基が、

｛式中、ＥＰ及びＥＰ’構造上の水素は、一つ以上のアルキルまたはハロゲン基によって
置換されていてもよい｝からなる群から選択される、請求項１に記載の硬化性バリヤ組成
物。
(３) さらに（ｅ）フェノール性硬化促進剤を含む、請求項１に記載の硬化性バリヤ組成物。
(４) 前記多官能性脂肪族アミンが、

からなる群から選択される、請求項１、２または３のいずれかに記載の硬化性バリヤ組成
物。
(５) 前記フェノール性硬化促進剤が、トリス−２，４，６，−（ジメチルアミノメチル）フェノール、レゾルシノール、４−エチルレゾルシノール、２，５−ジメチルレゾルシノール、フロログルシノール、２−ニトロフロロ−グルシノール、５−メトキシレゾルシノール、オルシノール、２−メチルレゾルシノール、４−ブロモレゾルシノール、４−クロロレゾルシノール、４，６−ジクロロレゾルシノール、３，５−ジヒドロキシ−ベンズアルデヒド、２，４−ジヒドロキシ−ベンズアルデヒド、メチル３，５−ジヒドロキシベンゾエート、メチル２，４−ジヒドロキシベンゾエート、１，２，４−ベンゼントリオール、ピロガロール、３，５−ジヒドロキシベンジルアルコール、２’、６’−ジヒドロキシアセトフェノン、２’、４’−ジヒドロキシアセトフェノン、３’，５’−ジヒドロキシアセトフェノン、２’，４’−ジヒドロキシ−プロピオフェノン、２’，４’−ジヒドロキシ−３’−メチルアセトフェノン、２，４，５−トリヒドロキシ−ベンズアルデヒド、２，３，４−トリヒドロキシベンズアルデヒド、２，４，６−トリヒドロキシベンズアルデヒド、３，５−ジヒドロキシ安息香酸、２，４−ジヒドロキシ安息香酸、２，６−ジヒドロキシ安息香酸、２−ニトロレゾルシノール、１，３−ジヒドロキシナフタレン、ヒドロキノン、メチルヒドロキノン、２，３−ジメチルヒドロキノン、２−メトキシヒドロキノン、クロロヒドロキノン、２’，５’−ジヒドロキシアセトフェノン、２−イソプロピル−１，４−ベンゼンジオール、２，５−ジヒドロキシ安息香酸、２，３−ジシアノヒドロキノン、１，４−ジヒドロキシナフタレン、２’，５’−ジヒドロキシプロピオフェノン、１−（２，５−ジヒドロキシ−４−メチルフェニル）エタノン、ｔｅｒｔ−ブチルヒドロキノン、メチル２，５−ジヒドロキシベンゾエート、（２，５−ジヒドロキシフェニル）酢酸、２，４，５−トリヒドロキシ安息香酸、４，７−ジヒドロキシ−３−メチル−１−インダノン、２，５−ジクロロヒドロキノン、テトラフルオロ−ヒドロキノン、エチル２，５−ジヒドロキシベンゾエート、２−（２，５−ジヒドロキシベンジリデン）マロノニトリル、２−ブロモ−１，４−ベンゼンジオール、エチル（２，５−ジヒドロキシフェニル）アセテート、１−（２，４，５−トリヒドロキシフェニル）−１−ブタノン、メチル２，５−ジヒドロキシ−４−メトキシベンゾエート、２，６−ジニトロ−１，４−ベンゼンジオール、２，４，５−トリヒドロキシフェニルアラニン、（２，５−ジヒドロキシフェニル）−（フェニル）メタノン、２，５−ジｔｅｒｔ−ブチル−１，４−ベンゼンジオール、２−（６−メチルヘプチル）−１，４−ベンゼンジオール、２−（１，１，３，３−テトラメチルブチル）−１，４−ベンゼンジオール、ジメチル２，５−ジヒドロキシテレフタレート、２，４，５−トリクロロ−３，６−ジヒドロキシベンゾニトリル、２，５−ジｔｅｒｔ−ペンチル−１，４−ベンゼンジオール、２，５−ジブロモ−１，４−ベンゼンジオール、ジメチル２，４−ジエチル−３，６−ジヒドロキシ−フェニルホスホネート、ピロカテコール、２，３−ナフタレンジオール、５−メチル−１，２，３−ベンゼントリオール、４−メチルカテコール、３−メチルカテコール、３−フルオロカテコール、３−メトキシカテコール、４−クロロカテコール、４，５−ジクロロカテコール、４−ｔｅｒｔ−ブチルカテコール、３，４，５，６−テトラクロロ−１，２−ベンゼンジオール、３−イソプロピル−６−メチルカテコール、３−ｔｅｒｔ−ブチル−６−メチルカテコール、３，４−ジヒドロキシベンゾニトリル、３，５−ジｔｅｒｔ−ブチルカテコール、３，５−ジイソプロピルカテコール、３，４−ジヒドロキシベンズアルデヒド、４−（１，１，３，３−テトラメチルブチル）−１，２−ベンゼンジオール、４−（１，２−ジヒドロキシエチル）−１，２−ベンゼンジオール、１−（３，４−ジヒドロキシフェニル）エタノン、３，４−ジヒドロキシ安息香酸、３，４，５−トリヒドロキシベンズアミド、４−ニトロ−１，２−ベンゼンジオール、４−（２−アミノ−１−ヒドロキシエチル）−１，２−ベンゼンジオール、５−メチル−３−（１，１，３，３−テトラメチルブチル）−１，２−ベンゼンジオール、（３，４−ジヒドロキシフェニル）酢酸、２−（３，４−ジヒドロキシベンジル−イデン）マロノニトリル、３，５−ジニトロ−１，２−ベンゼンジオール、メチル３，４−ジヒドロキシベンゾエート、２−クロロ−１−（３，４−ジヒドロキシフェニル）エタノン、フェニル（２，３，４−トリヒドロキシフェニル）メタノン、イソプロピル３，４，５−トリヒドロキシベンゾエート、３，４−ジヒドロキシ−２−メチルフェニルアラニン、３−ブロモ−４，５−ジヒドロキシ安息香酸、２−（３，４−ジヒドロキシ−５−メトキシベンジリデン）マロノニトリル、エチル３−（３，４−ジヒドロキシフェニル）プロパノエート、２−フェニル−１−（２，３，４−トリヒドロキシ−フェニル）エタノン、及び３，４，５−トリヒドロキシ−Ｎ−（２−ヒドロキシエチル）ベンズアミドからなる群から選択される、請求項１または２のいずれかに記載の硬化性バリヤ組成物。
(６) 一種以上の充填剤が存在し、且つ粉末石英、溶融シリカ、アモルファスシリカ、タルク、ガラスビーズ、グラファイト、カーボンブラック、アルミナ、クレー、及びナノクレー、マイカ、バーミキュライト、窒化アルミニウム、窒化ホウ素、金属粉末、金属フレーク、ポリ（テトラクロロエチレン）、ポリ（クロロトリフルオロエチレン）、ポリ（塩化ビニリデン）、ＣａＯ、ＢａＯ、Ｎａ_２ＳＯ_４、ＣａＳＯ_４、ＭｇＳＯ_４、ゼオライト、シリカゲル、Ｐ_２Ｏ_５、ＣａＣｌ_２及びＡｌ_２Ｏ_３からなる群から選択される、請求項１に記載の硬化性バリヤ組成物。
(７) （ａ）エポキシ化レゾール、ビスフェノール−Ｆグリシジルエーテル、ビスフェノール−Ａジグリシジルエーテル、ビスフェノール−Ｅジグリシジルエーテル、エポキシ化フェノールノボラック樹脂、エポキシ化クレゾールノボラック樹脂、多環式エポキシ樹脂、ナフタレンジグリシジルエーテル、及びそのハロゲン化誘導体からなる群から選択される芳香族エポキシ化合物；
（ｂ）多官能性脂肪族アミン；
（ｃ）場合により一種以上の充填剤；
（ｄ）場合により一種以上の接着促進剤；及び
（ｅ）場合によりフェノール性硬化促進剤
を含む硬化性バリヤ組成物。
(８) 前記多官能性脂肪族アミンが、

からなる群から選択される、請求項７に記載の硬化性バリヤ組成物。
(９) 前記フェノール性硬化促進剤が、トリス−２，４，６，−（ジメチルアミノメチル）フェノール、レゾルシノール、４−エチルレゾルシノール、２，５−ジメチルレゾルシノール、フロログルシノール、２−ニトロフロロ−グルシノール、５−メトキシレゾルシノール、オルシノール、２−メチルレゾルシノール、４−ブロモレゾルシノール、４−クロロレゾルシノール、４，６−ジクロロレゾルシノール、３，５−ジヒドロキシ−ベンズアルデヒド、２，４−ジヒドロキシ−ベンズアルデヒド、メチル３，５−ジヒドロキシベンゾエート、メチル２，４−ジヒドロキシベンゾエート、１，２，４−ベンゼントリオール、ピロガロール、３，５−ジヒドロキシベンジルアルコール、２’、６’−ジヒドロキシアセトフェノン、２’、４’−ジヒドロキシアセトフェノン、３’，５’−ジヒドロキシアセトフェノン、２’，４’−ジヒドロキシ−プロピオフェノン、２’，４’−ジヒドロキシ−３’−メチルアセトフェノン、２，４，５−トリヒドロキシ−ベンズアルデヒド、２，３，４−トリヒドロキシベンズアルデヒド、２，４，６−トリヒドロキシベンズアルデヒド、３，５−ジヒドロキシ安息香酸、２，４−ジヒドロキシ安息香酸、２，６−ジヒドロキシ安息香酸、２−ニトロレゾルシノール、１，３−ジヒドロキシナフタレン、ヒドロキノン、メチルヒドロキノン、２，３−ジメチルヒドロキノン、２−メトキシヒドロキノン、クロロヒドロキノン、２’，５’−ジヒドロキシアセトフェノン、２−イソプロピル−１，４−ベンゼンジオール、２，５−ジヒドロキシ安息香酸、２，３−ジシアノヒドロキノン、１，４−ジヒドロキシナフタレン、２’，５’−ジヒドロキシプロピオフェノン、１−（２，５−ジヒドロキシ−４−メチルフェニル）エタノン、ｔｅｒｔ−ブチルヒドロキノン、メチル２，５−ジヒドロキシベンゾエート、（２，５−ジヒドロキシフェニル）酢酸、２，４，５−トリヒドロキシ安息香酸、４，７−ジヒドロキシ−３−メチル−１−インダノン、２，５−ジクロロヒドロキノン、テトラフルオロ−ヒドロキノン、エチル２，５−ジヒドロキシベンゾエート、２−（２，５−ジヒドロキシベンジリデン）マロノニトリル、２−ブロモ−１，４−ベンゼンジオール、エチル（２，５−ジヒドロキシフェニル）アセテート、１−（２，４，５−トリヒドロキシフェニル）−１−ブタノン、メチル２，５−ジヒドロキシ−４−メトキシベンゾエート、２，６−ジニトロ−１，４−ベンゼンジオール、２，４，５−トリヒドロキシフェニルアラニン、（２，５−ジヒドロキシフェニル）−（フェニル）メタノン、２，５−ジｔｅｒｔ−ブチル−１，４−ベンゼンジオール、２−（６−メチルヘプチル）−１，４−ベンゼンジオール、２−（１，１，３，３−テトラメチルブチル）−１，４−ベンゼンジオール、ジメチル２，５−ジヒドロキシテレフタレート、２，４，５−トリクロロ−３，６−ジヒドロキシベンゾニトリル、２，５−ジｔｅｒｔ−ペンチル−１，４−ベンゼンジオール、２，５−ジブロモ−１，４−ベンゼンジオール、ジメチル２，４−ジエチル−３，６−ジヒドロキシ−フェニルホスホネート、ピロカテコール、２，３−ナフタレンジオール、５−メチル−１，２，３−ベンゼントリオール、４−メチルカテコール、３−メチルカテコール、３−フルオロカテコール、３−メトキシカテコール、４−クロロカテコール、４，５−ジクロロカテコール、４−ｔｅｒｔ−ブチルカテコール、３，４，５，６−テトラクロロ−１，２−ベンゼンジオール、３−イソプロピル−６−メチルカテコール、３−ｔｅｒｔ−ブチル−６−メチルカテコール、３，４−ジヒドロキシベンゾニトリル、３，５−ジｔｅｒｔ−ブチルカテコール、３，５−ジイソプロピルカテコール、３，４−ジヒドロキシベンズアルデヒド、４−（１，１，３，３−テトラメチルブチル）−１，２−ベンゼンジオール、４−（１，２−ジヒドロキシエチル）−１，２−ベンゼンジオール、１−（３，４−ジヒドロキシフェニル）エタノン、３，４−ジヒドロキシ安息香酸、３，４，５−トリヒドロキシベンズアミド、４−ニトロ−１，２−ベンゼンジオール、４−（２−アミノ−１−ヒドロキシエチル）−１，２−ベンゼンジオール、５−メチル−３−（１，１，３，３−テトラメチルブチル）−１，２−ベンゼンジオール、（３，４−ジヒドロキシフェニル）酢酸、２−（３，４−ジヒドロキシベンジル−イデン）マロノニトリル、３，５−ジニトロ−１，２−ベンゼンジオール、メチル３，４−ジヒドロキシベンゾエート、２−クロロ−１−（３，４−ジヒドロキシフェニル）エタノン、フェニル（２，３，４−トリヒドロキシフェニル）メタノン、イソプロピル３，４，５−トリヒドロキシベンゾエート、３，４−ジヒドロキシ−２−メチルフェニルアラニン、３−ブロモ−４，５−ジヒドロキシ安息香酸、２−（３，４−ジヒドロキシ−５−メトキシベンジリデン）マロノニトリル、エチル３−（３，４−ジヒドロキシフェニル）プロパノエート、２−フェニル−１−（２，３，４−トリヒドロキシ−フェニル）エタノン、及び３，４，５−トリヒドロキシ−Ｎ−（２−ヒドロキシエチル）ベンズアミドからなる群から選択される、請求項７に記載の硬化性バリヤ組成物。
(１０)充填剤が存在し、且つ粉末石英、溶融シリカ、アモルファスシリカ、タルク、ガラスビーズ、グラファイト、カーボンブラック、アルミナ、クレー、及びナノクレー、マイカ、バーミキュライト、窒化アルミニウム、窒化ホウ素、金属粉末、金属フレーク、ポリ（テトラクロロエチレン）、ポリ（クロロトリフルオロエチレン）、ポリ（塩化ビニリデン）、ＣａＯ、ＢａＯ、Ｎａ_２ＳＯ_４、ＣａＳＯ_４、ＭｇＳＯ_４、ゼオライト、シリカゲル、Ｐ_２Ｏ_５、ＣａＣｌ_２及びＡｌ_２Ｏ_３からなる群から選択される、請求項７に記載の硬化性バリヤ組成物。
(１１) 請求項１又は７に記載の硬化性バリヤ組成物でシール、コーティングまたは封入された電子または光電子デバイス。
(１２) 前記デバイスがＯＬＥＤデバイスである、請求項１１に記載の電子または光電子デバイス。
(１３) 前記デバイスが電気泳動デバイスである、請求項１１に記載の電子または光電子デバイス。
(１４) 前記デバイスがＬＣＤデバイスである、請求項１１に記載の電子または光電子デバイス。
The moisture permeability coefficient of the above formulation was found to be 1.1 g · mil / 100 square inches · day. Transmission data was collected at 50 ° C. and 100% RH.

(1) Curable barrier composition comprising:
(A) Meta-substituted epoxy functional group:

{Wherein R ¹ , R ² , R ³ , R ⁴ are selected from the group consisting of hydrogen, halogen, cyano, alkyl, aryl, and substituted alkyl or aryl groups, which may contain epoxy functional groups Well; R ⁵ , R ⁶ are divalent hydrocarbon linking groups having the general structure: —C _n H _2n —, where n = 0-4, where R ¹ , R ² , R ³ , Any two of R ⁴ , R ⁵ and R ⁶ may form part of the same cyclic structure;
L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ are direct bonds, or

A divalent linking group selected from the group consisting of;
EP and EP ′ are curable epoxy functional groups selected from the group consisting of aliphatic epoxies, glycidyl ethers and alicyclic epoxies; wherein the hydrogen in the epoxy is substituted with one or more alkyl or halogen groups Aromatic compounds that may be
(B) a polyfunctional aliphatic amine;
(C) optionally one or more fillers;
(D) optionally one or more adhesion promoters.
(2) EP and EP ′ functional groups are

The curable barrier composition of claim 1, wherein {wherein the hydrogens on the EP and EP ′ structures may be substituted by one or more alkyl or halogen groups}.
(3) The curable barrier composition according to claim 1, further comprising (e) a phenolic curing accelerator.
(4) The polyfunctional aliphatic amine is

4. A curable barrier composition according to any of claims 1, 2 or 3, selected from the group consisting of:
(5) The phenolic curing accelerator is tris-2,4,6,-(dimethylaminomethyl) phenol, resorcinol, 4-ethylresorcinol, 2,5-dimethylresorcinol, phloroglucinol, 2-nitrofluoro-glucinol 5-methoxyresorcinol, orcinol, 2-methylresorcinol, 4-bromoresorcinol, 4-chlororesorcinol, 4,6-dichlororesorcinol, 3,5-dihydroxy-benzaldehyde, 2,4-dihydroxy-benzaldehyde, methyl 3,5 -Dihydroxybenzoate, methyl 2,4-dihydroxybenzoate, 1,2,4-benzenetriol, pyrogallol, 3,5-dihydroxybenzyl alcohol, 2 ', 6'-dihydroxyacetophenone, 2', 4'-dihi Droxyacetophenone, 3 ′, 5′-dihydroxyacetophenone, 2 ′, 4′-dihydroxy-propiophenone, 2 ′, 4′-dihydroxy-3′-methylacetophenone, 2,4,5-trihydroxy-benzaldehyde, 2,3,4-trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 3,5-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 2-nitroresorcinol, 1 , 3-dihydroxynaphthalene, hydroquinone, methylhydroquinone, 2,3-dimethylhydroquinone, 2-methoxyhydroquinone, chlorohydroquinone, 2 ′, 5′-dihydroxyacetophenone, 2-isopropyl-1,4-benzenediol, 2,5- Dihydroxybenzoic acid, 2,3-di Anohydroquinone, 1,4-dihydroxynaphthalene, 2 ′, 5′-dihydroxypropiophenone, 1- (2,5-dihydroxy-4-methylphenyl) ethanone, tert-butylhydroquinone, methyl 2,5-dihydroxybenzoate, (2,5-dihydroxyphenyl) acetic acid, 2,4,5-trihydroxybenzoic acid, 4,7-dihydroxy-3-methyl-1-indanone, 2,5-dichlorohydroquinone, tetrafluoro-hydroquinone, ethyl 2, 5-dihydroxybenzoate, 2- (2,5-dihydroxybenzylidene) malononitrile, 2-bromo-1,4-benzenediol, ethyl (2,5-dihydroxyphenyl) acetate, 1- (2,4,5-trihydroxy Phenyl) -1-butanone, methyl 2,5-dihydro Xyl-4-methoxybenzoate, 2,6-dinitro-1,4-benzenediol, 2,4,5-trihydroxyphenylalanine, (2,5-dihydroxyphenyl)-(phenyl) methanone, 2,5-ditert -Butyl-1,4-benzenediol, 2- (6-methylheptyl) -1,4-benzenediol, 2- (1,1,3,3-tetramethylbutyl) -1,4-benzenediol, dimethyl 2,5-dihydroxyterephthalate, 2,4,5-trichloro-3,6-dihydroxybenzonitrile, 2,5-ditert-pentyl-1,4-benzenediol, 2,5-dibromo-1,4-benzene Diol, dimethyl 2,4-diethyl-3,6-dihydroxy-phenylphosphonate, pyrocatechol, 2,3-naphthalenedio 5-methyl-1,2,3-benzenetriol, 4-methylcatechol, 3-methylcatechol, 3-fluorocatechol, 3-methoxycatechol, 4-chlorocatechol, 4,5-dichlorocatechol, 4-tert -Butylcatechol, 3,4,5,6-tetrachloro-1,2-benzenediol, 3-isopropyl-6-methylcatechol, 3-tert-butyl-6-methylcatechol, 3,4-dihydroxybenzonitrile, 3,5-ditert-butylcatechol, 3,5-diisopropylcatechol, 3,4-dihydroxybenzaldehyde, 4- (1,1,3,3-tetramethylbutyl) -1,2-benzenediol, 4- ( 1,2-dihydroxyethyl) -1,2-benzenediol, 1- (3,4-dihydroxy) Phenyl) ethanone, 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzamide, 4-nitro-1,2-benzenediol, 4- (2-amino-1-hydroxyethyl) -1,2- Benzenediol, 5-methyl-3- (1,1,3,3-tetramethylbutyl) -1,2-benzenediol, (3,4-dihydroxyphenyl) acetic acid, 2- (3,4-dihydroxybenzyl- Iden) malononitrile, 3,5-dinitro-1,2-benzenediol, methyl 3,4-dihydroxybenzoate, 2-chloro-1- (3,4-dihydroxyphenyl) ethanone, phenyl (2,3,4-tri Hydroxyphenyl) methanone, isopropyl 3,4,5-trihydroxybenzoate, 3,4-dihydroxy-2-methylphenyl Alanine, 3-bromo-4,5-dihydroxybenzoic acid, 2- (3,4-dihydroxy-5-methoxybenzylidene) malononitrile, ethyl 3- (3,4-dihydroxyphenyl) propanoate, 2-phenyl-1- ( 3. The method of claim 1 or 2, selected from the group consisting of 2,3,4-trihydroxy-phenyl) ethanone and 3,4,5-trihydroxy-N- (2-hydroxyethyl) benzamide. Curable barrier composition.
(6) One or more fillers are present and powdered quartz, fused silica, amorphous silica, talc, glass beads, graphite, carbon black, alumina, clay, and nanoclay, mica, vermiculite, aluminum nitride, boron nitride, metal Powder, metal flakes, poly (tetrachloroethylene), poly (chlorotrifluoroethylene), poly (vinylidene chloride), CaO, BaO, Na ₂ SO ₄ , CaSO ₄ , MgSO ₄ , zeolite, silica gel, P ₂ O ₅ , CaCl ₂ And a curable barrier composition according to claim 1, selected from the group consisting of Al ₂ O ₃ .
(7) (a) Epoxidized resole, bisphenol-F glycidyl ether, bisphenol-A diglycidyl ether, bisphenol-E diglycidyl ether, epoxidized phenol novolac resin, epoxidized cresol novolac resin, polycyclic epoxy resin, naphthalene An aromatic epoxy compound selected from the group consisting of glycidyl ether and halogenated derivatives thereof;
(B) a polyfunctional aliphatic amine;
(C) optionally one or more fillers;
(D) a curable barrier composition optionally comprising one or more adhesion promoters; and (e) optionally comprising a phenolic curing accelerator.
(8) The polyfunctional aliphatic amine is

The curable barrier composition according to claim 7, selected from the group consisting of:
(9) The phenolic curing accelerator is tris-2,4,6,-(dimethylaminomethyl) phenol, resorcinol, 4-ethylresorcinol, 2,5-dimethylresorcinol, phloroglucinol, 2-nitrofluoro-glucinol 5-methoxyresorcinol, orcinol, 2-methylresorcinol, 4-bromoresorcinol, 4-chlororesorcinol, 4,6-dichlororesorcinol, 3,5-dihydroxy-benzaldehyde, 2,4-dihydroxy-benzaldehyde, methyl 3,5 -Dihydroxybenzoate, methyl 2,4-dihydroxybenzoate, 1,2,4-benzenetriol, pyrogallol, 3,5-dihydroxybenzyl alcohol, 2 ', 6'-dihydroxyacetophenone, 2', 4'-dihi Droxyacetophenone, 3 ′, 5′-dihydroxyacetophenone, 2 ′, 4′-dihydroxy-propiophenone, 2 ′, 4′-dihydroxy-3′-methylacetophenone, 2,4,5-trihydroxy-benzaldehyde, 2,3,4-trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 3,5-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 2-nitroresorcinol, 1 , 3-dihydroxynaphthalene, hydroquinone, methylhydroquinone, 2,3-dimethylhydroquinone, 2-methoxyhydroquinone, chlorohydroquinone, 2 ′, 5′-dihydroxyacetophenone, 2-isopropyl-1,4-benzenediol, 2,5- Dihydroxybenzoic acid, 2,3-di Anohydroquinone, 1,4-dihydroxynaphthalene, 2 ′, 5′-dihydroxypropiophenone, 1- (2,5-dihydroxy-4-methylphenyl) ethanone, tert-butylhydroquinone, methyl 2,5-dihydroxybenzoate, (2,5-dihydroxyphenyl) acetic acid, 2,4,5-trihydroxybenzoic acid, 4,7-dihydroxy-3-methyl-1-indanone, 2,5-dichlorohydroquinone, tetrafluoro-hydroquinone, ethyl 2, 5-dihydroxybenzoate, 2- (2,5-dihydroxybenzylidene) malononitrile, 2-bromo-1,4-benzenediol, ethyl (2,5-dihydroxyphenyl) acetate, 1- (2,4,5-trihydroxy Phenyl) -1-butanone, methyl 2,5-dihydro Xyl-4-methoxybenzoate, 2,6-dinitro-1,4-benzenediol, 2,4,5-trihydroxyphenylalanine, (2,5-dihydroxyphenyl)-(phenyl) methanone, 2,5-ditert -Butyl-1,4-benzenediol, 2- (6-methylheptyl) -1,4-benzenediol, 2- (1,1,3,3-tetramethylbutyl) -1,4-benzenediol, dimethyl 2,5-dihydroxyterephthalate, 2,4,5-trichloro-3,6-dihydroxybenzonitrile, 2,5-ditert-pentyl-1,4-benzenediol, 2,5-dibromo-1,4-benzene Diol, dimethyl 2,4-diethyl-3,6-dihydroxy-phenylphosphonate, pyrocatechol, 2,3-naphthalenedio 5-methyl-1,2,3-benzenetriol, 4-methylcatechol, 3-methylcatechol, 3-fluorocatechol, 3-methoxycatechol, 4-chlorocatechol, 4,5-dichlorocatechol, 4-tert -Butylcatechol, 3,4,5,6-tetrachloro-1,2-benzenediol, 3-isopropyl-6-methylcatechol, 3-tert-butyl-6-methylcatechol, 3,4-dihydroxybenzonitrile, 3,5-ditert-butylcatechol, 3,5-diisopropylcatechol, 3,4-dihydroxybenzaldehyde, 4- (1,1,3,3-tetramethylbutyl) -1,2-benzenediol, 4- ( 1,2-dihydroxyethyl) -1,2-benzenediol, 1- (3,4-dihydroxy) Phenyl) ethanone, 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzamide, 4-nitro-1,2-benzenediol, 4- (2-amino-1-hydroxyethyl) -1,2- Benzenediol, 5-methyl-3- (1,1,3,3-tetramethylbutyl) -1,2-benzenediol, (3,4-dihydroxyphenyl) acetic acid, 2- (3,4-dihydroxybenzyl- Iden) malononitrile, 3,5-dinitro-1,2-benzenediol, methyl 3,4-dihydroxybenzoate, 2-chloro-1- (3,4-dihydroxyphenyl) ethanone, phenyl (2,3,4-tri Hydroxyphenyl) methanone, isopropyl 3,4,5-trihydroxybenzoate, 3,4-dihydroxy-2-methylphenyl Alanine, 3-bromo-4,5-dihydroxybenzoic acid, 2- (3,4-dihydroxy-5-methoxybenzylidene) malononitrile, ethyl 3- (3,4-dihydroxyphenyl) propanoate, 2-phenyl-1- ( The curable barrier composition of claim 7 selected from the group consisting of 2,3,4-trihydroxy-phenyl) ethanone and 3,4,5-trihydroxy-N- (2-hydroxyethyl) benzamide. object.
(10) Filler is present and powdered quartz, fused silica, amorphous silica, talc, glass beads, graphite, carbon black, alumina, clay, and nanoclay, mica, vermiculite, aluminum nitride, boron nitride, metal powder, metal Flakes, poly (tetrachloroethylene), poly (chlorotrifluoroethylene), poly (vinylidene chloride), CaO, BaO, Na ₂ SO ₄ , CaSO ₄ , MgSO ₄ , zeolite, silica gel, P ₂ O ₅ , CaCl ₂ and Al ₂ The curable barrier composition according to claim 7, which is selected from the group consisting of O ₃ .
(11) An electronic or optoelectronic device sealed, coated or encapsulated with the curable barrier composition according to claim 1 or 7.
12. The electronic or optoelectronic device according to claim 11, wherein the device is an OLED device.
(13) The electronic or optoelectronic device according to claim 11, wherein the device is an electrophoretic device.
14. The electronic or optoelectronic device according to claim 11, wherein the device is an LCD device.

FIG. 1 shows an optoelectronic device having a sealed periphery. FIG. 2 is a differential scanning calorimetric overlay of an epoxy / TEPA (amine) blend cured isothermally at 75 ° C. with and without a catalyst.

Claims (3)

A curable barrier composition used to reduce moisture permeability,
(A) an aromatic epoxy compound selected from bisphenol-F diglycidyl ether, resorcinol diglycidyl ether, and combinations thereof;
(B) a polyfunctional aliphatic amine selected from tetraethylenepentamine, triethylenetetramine, and diethylenetriamine;
(C) one or more fillers ;
(D) one or more adhesion promoters ;
(E) a phenolic curing accelerator , wherein the weight ratio of the polyfunctional aliphatic amine to the aromatic epoxy compound is 1.35: 8.65 to 0.73: 3.27 And a composition. The curable barrier composition of claim 1, wherein the phenolic cure accelerator is resorcinol, 5-methoxyresorcinol, orcinol, 4-bromoresorcinol, 2,4-dihydroxy-benzaldehyde, and methyl 3,5. A composition selected from the group consisting of dihydroxybenzoates. The curable barrier composition according to claim 1, wherein the one or more fillers are powdered quartz, fused silica, amorphous silica, talc, glass beads, graphite, carbon black, alumina, clay, nanoclay, mica , Vermiculite, aluminum nitride, boron nitride, metal powder, metal flakes, poly (tetrachloroethylene), poly (chlorotrifluoroethylene), poly (vinylidene chloride), CaO, BaO, Na ₂ SO ₄ , CaSO ₄ , MgSO ₄ , zeolite , A composition selected from the group consisting of silica gel, P ₂ O ₅ , CaCl ₂ and Al ₂ O ₃ .

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