Curable composition

Abstract

The present invention relates to a curable composition and an adhesive film including the same, and provides a curable composition and an adhesive film which may prevent damage to an element from moisture contained in the composition, ionic substances, and other foreign substances, and effectively block electrochemical corrosion, thereby improving a lifespan and durability of an organic electronic device.

Claims

1. A curable composition, comprising a curable adhesive resin, a silane coupling agent at less than 2 parts by weight, with respect to 100 parts by weight of the curable adhesive resin, and a high-molecular-weight resin of which a weight-average-molecular weight is 20,000 or more, and of which a content of halogen ions is 1,000 ppm or less as measured according to ASTM D 7359:2008, wherein the high-molecular-weight resin comprises a phenoxy resin, the composition satisfying the following Equations 1 and 2:
X1,000 ppm[Equation 1]
Y1,000 ppm,[Equation 2] wherein X in Equation 1 is an amount of volatile organic compounds, which is measured by preparing a film with the curable composition, maintaining 50 mg of the film sample at 150 C. for 1 hour, and using purge and trap-gas chromatography/mass spectrometry, and Y in Equation 2 is an amount of ionic substances contained in the curable composition, which is obtained by preparing a film with the curable composition, and measuring 50 mg of the film sample according to ASTM D 7359:2008, wherein a moisture content of a film sample formed of the curable composition is 0.01 wt % to 1 wt %, and the moisture content of the film sample is measured according to ASTM D3451-06 (2012) after preparing a film with the curable composition, and maintaining 50 mg of the film sample under conditions of 25 C. and a relative humidity of 50% for 24 hours.

2. The curable composition of claim 1, wherein the ionic substance is halogen ions.

3. The curable composition of claim 1, wherein the curable adhesive resin comprises one or more curable functional groups selected from a glycidyl group, an isocyanate group, a hydroxy group, a carboxyl group, an amide group, an epoxide group, a cyclic ether group, a sulfide group, an acetal group and a lactone group.

4. The curable composition of claim 1, wherein the curable adhesive resin is a silane-modified epoxy resin.

5. The curable composition of claim 1, wherein the curable adhesive resin is an epoxy resin of which a content of halogen ions is 1,000 ppm or less as measured according to ASTM D 7359:2008.

6. The curable composition of claim 1, further comprising an organic solvent of which a boiling point is 100 C. or less.

7. The curable composition of claim 1, further comprising a curing agent.

8. The curable composition of claim 7, wherein the curing agent is included at 0.5 to 20 parts by weight with respect to 100 parts by weight of the curable adhesive resin.

9. The curable composition of claim 7, wherein the curing agent is an imidazole curing agent which starts to cure at a temperature in a range of 50 to 170 C.

10. The curable composition of claim 1, wherein the high-molecular-weight resin is included at 20 to 200 parts by weight with respect to 100 parts by weight of the curable adhesive resin.

11. An adhesive film comprising the curable composition of claim 1.

12. An organic electronic device, comprising: a substrate; an organic electronic element formed on the substrate; and the adhesive film of claim 11 encapsulating the organic electronic element.

13. The organic electronic device of claim 12, wherein the organic electronic element is an organic light emitting diode.

14. A method of preparing an organic electronic device, comprising applying the adhesive film of claim 11 onto a substrate on which an organic electronic element is formed to cover the organic electronic element.

Description

BRIEF DESCRIPTION OF THE DRAWING

(1) FIG. 1 is a cross-sectional view illustrating an organic electronic device according to an embodiment of the present invention.

DESCRIPTION OF REFERENCE NUMERALS

(2) 12: adhesive film 21: substrate 22: cover substrate 23: organic electronic element

DETAILED DESCRIPTION OF EXEMPLARY EMBODIMENTS

(3) Hereinafter, the present invention will be described in detail in conjunction with examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not intended to be limited to the examples described below.

Example 1

(4) 100 g of low-chlorine BPA type epoxy (Epiclon 840S; DIC Corporation), 50 g of a phenoxy resin (PKFE; InChem Corporation), 0.5 g of a silane coupling agent (KBM-403) and 3 g of an imidazole curing agent (2PZ) were added with methyl ethylketone such that a content of solid fractions was 50%, and stirred to prepare a coating solution.

(5) The prepared solution was applied onto a release surface of a release PET film using a comma coater, and dried at 110 C. for 3 minutes, and then an adhesive film having a thickness of 20 m was formed.

Example 2

(6) An adhesive film was prepared in the same method as Example 1 except that a silane-modified epoxy resin (KSR-177) was added instead of the low-chlorine BPA type epoxy, and a silane coupling agent was not added.

Example 3

(7) An adhesive film was prepared in the same method as Example 1 except that C11ZA (SHIKOKU CHEMICALS CORPORATION) which starts to cure at a high temperature was added instead of the imidazole curing agent 2PZ.

Comparative Example 1

(8) An adhesive film was prepared in the same method as Example 1 except that an epoxy resin (Epiclon 840) was added instead of the low-chlorine BPA type epoxy, and 3 phr of a reactive dilution agent (PG-202; Kukdo Chemical Co., Ltd.) was added.

Comparative Example 2

(9) An adhesive film was prepared in the same method as Example 1 except that 2 parts by weight of a silane coupling agent was added with respect to 100 parts by weight of a resin, xylene was added instead of the methyl ethylketone as an organic solvent, and the applied solution was dried at 100 C. for 1 minute.

Experimental Example 1: Total Volatile Organic Compounds (VOC) Measurement

(10) Measurement device: Purge & Trap sampler-GC/MSD system (P & T: JAI JTD-505III, GC/MS: Agilent 7890B/5977A)

(11) Samples of the films prepared in examples and comparative examples were weighed to about 50 mg, passed through purge and trap at 150 C. for 1 hour, and a total amount of VOCs was measured through GC-MS. The measured volatilization amount was quantified using toluene as a standard reagent.

Experimental Example 2: Ionic Substance (Trace Element) Measurement

(12) Preprocessing of the samples weighed to about 50 mg and having films applied thereto was performed according to EN 50267-2-1 & 502672-2, and a trace element was measured according to ASTM D 7395:2008.

(13) Evaluation Method: Dark Spot

(14) An element available for a lighting test was deposited on a glass substrate. After the adhesive film on a coated sheet was heat-laminated on the glass substrate for encapsulating, the film was vacuum-pressed for 3 minutes at a pressure of 5 kg/cm.sup.2 while being heated at 80 C. on the substrate. The pressed sample was thermally cured at 100 C. for 2 hours in an oven. The thermally cured sample was observed under conditions of a constant temperature and humidity of 85 C. and 85% RH, and checked for dark spots. Through an observation for 300 hours, it was checked whether or not dark spots were generated on the sample.

(15) Evaluation Method: Wire Corrosion and Bubble Formation

(16) An element was deposited on a glass substrate. After the adhesive film on a coated sheet was heat laminated on the glass substrate for encapsulating, the film was vacuum-pressed for 3 minutes at a pressure of 5 kg/cm.sup.2 while being heated at 80 C. on the substrate. The pressed sample was thermally cured at 100 C. for 2 hours in an oven. After applying the adhesive film on the organic electronic element as described above, the film was checked with the naked eye for wire corrosion and bubbles.

(17) TABLE-US-00001 TABLE 1 Ionic Etc. (Wire VOCs substance corrosion and (ppm) (ppm) Dark spot bubbles) Example 1 193 510 None Good Example 2 156 675 None Good Example 3 164 509 None Good Comparative 1183 1288 Generated Wire corrosion Example 1 Comparative 1567 555 Generated Bubbles formed on Example 2 pressing/curing

(18) As shown in Table 1, in Example 1 in which the low-chlorine BPA type epoxy resin was used, and a small amount of the silane coupling agent was used, VOCs and ionic substances were both effectively suppressed. In Example 2 in which a silane coupling agent was not included and the silane-modified epoxy resin was used, an amount of an alcoholic volatile material that caused significant damage to the organic elements was decreased. Further, in Example 3 in which the imidazole curing agent was changed, storing stability and heat stability in the process were improved by controlling a curing temperature while maintaining other conditions to be the same.

(19) On the other hand, in Comparative Example 1 in which a generally used epoxy resin was used, a great amount of VOCs and ionic substances were generated, and in Comparative Example 2 in which 2 parts by weight of a silane coupling agent was used and xylene was used as an organic solvent, a great amount of VOCs were generated.