Photocurable adhesive film for organic electronic device seal, organic electronic device, and method for sealing same

Patent metadata

Field	Value
Publication number	US-9966562-B2
Application number	US-201414263677-A
Country	US
Kind code	B2
Filing date	Apr 28, 2014
Priority date	Nov 18, 2011
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

Provided are a photocurable pressure-sensitive adhesive composition including an acrylic polymer, an epoxy resin, and a cationic photopolymerization initiator, an organic electronic device having an encapsulant including a photocured product of the composition using a curable pressure-sensitive adhesive film which is a film-state product including the composition, and a method for manufacturing an organic electronic device using the curable pressure-sensitive adhesive film. Particularly, due to the method including laminating a photocurable pressure-sensitive adhesive film including a curable pressure-sensitive adhesive layer including an acrylic polymer, an epoxy resin, and a cationic photopolymerization initiator to an top substrate, and radiating light to an entire surface of the curable pressure-sensitive adhesive layer to perform photocuring, and laminating the photocured curable pressure-sensitive adhesive layer to a bottom substrate on which an organic light emitting element is formed to cover an entire surface of the organic light emitting element, mechanical strength and a simple process caused by photocuring to the organic light emitting element without direct light irradiation may be achieved, and a lifespan of the element may be increased.

First claim

What is claimed is:

1. An organic electronic device, comprising:
a substrate on which an organic light emitting element is formed; and
a cured pressure-sensitive adhesive film encapsulating an entire surface of the organic light emitting element on the substrate,
wherein the cured pressure-sensitive adhesive film comprises a cured pressure-sensitive adhesive layer comprising a photocured-product of a photocurable pressure-sensitive adhesive composition comprising an acrylic polymer, an epoxy resin in an amount of 1 to 30 parts by weight relative to 100 parts by weight of the acrylic polymer, and a cationic photopolymerization initiator,
wherein the pressure-sensitive adhesive has a viscosity before light irradiation of 10 5 to 10 7 Pa·s and a viscosity after light irradiation of 10 6 to 10 8 Pa·s,
wherein the viscosity of the pressure-sensitive adhesive after light irradiation is higher than the viscosity of the pressure-sensitive adhesive before light irradiation,
wherein the cured pressure-sensitive adhesive film is a film which is partially photocured and then fully heat-cured, and
wherein the organic light emitting element is not irradiated during photocuring.

2. The device of claim 1 ,
wherein the cured pressure-sensitive adhesive film has a water vapor transmission rate of less than 150 g/m 2 ·day after photo-curing and heat-curing.

3. The device of claim 1 ,
wherein the cured pressure-sensitive adhesive layer of the cured pressure-sensitive adhesive film comprises a non-reacted component of a photocurable pressure-sensitive adhesive composition at less than 100 ppm after light irradiation and heat-curing are sequentially performed.

4. The device of claim 1 ,
wherein the acrylic polymer has a glass transition temperature of −60 to −10° C., and a weight average molecular weight of 50,000 to 2,000,000.

5. The device of claim 1 ,
wherein the acrylic polymer comprises a crosslinkable functional group, and comprises an alkyl (meth)acrylate and a copolymerizable monomer having a crosslinkable functional group in a polymerized form.

6. The device of claim 5 ,
wherein the crosslinkable functional group is at least one or more selected from a glycidyl group, an isocyanate group, a hydroxyl group, a carboxyl group, an amide group, an epoxide group, a cyclic ether group, a sulfide group, an acetal group and a lactone group.

7. The device of claim 1 ,
wherein the epoxy resin is at least one or more selected from the group consisting of a multifunctional epoxy resin, a bisphenol-based epoxy resin, a novolac-type epoxy resin, a naphthalene-type epoxy resin, a trisphenolmethane-type epoxy resin, a glycidyl amine-type epoxy resin and a cycloaliphatic epoxy resin.

8. The device of claim 1 ,
wherein the cationic photopolymerization initiator is an aromatic diazonium salt, an aromatic iodine aluminum salt, an aromatic sulfonium salt or an iron-arene complex.

9. The device of claim 1 ,
wherein the photocurable pressure-sensitive adhesive composition comprises the cationic photopolymerization initiator in an amount of 0.01 to 10 parts by weight, relative to 100 parts by weight of the acrylic polymer.

10. The device of claim 1 ,
wherein the photocurable pressure-sensitive adhesive composition further comprises a crosslinking agent.

11. The device of claim 10 ,
wherein the crosslinking agent is an isocyanate-based compound, an epoxy-based compound, an aziridine-based compound or a metal chelate-based compound.

12. The device of claim 10 ,
wherein the photocurable pressure-sensitive adhesive composition comprises the crosslinking agent in an amount of 0.01 to 10 parts by weight, relative to 100 parts by weight of the acrylic polymer.

13. The device of claim 1 ,
wherein the photocurable pressure-sensitive adhesive composition further comprises a moisture adsorbent.

14. The device of claim 13 ,
wherein the moisture adsorbent is alumina, a metal oxide, an organic metal oxide, a metal salt or phosphorus pentoxide.

15. The device of claim 14 ,
wherein the moisture adsorbent comprises at least one or more selected from the group consisting of P 2 O 5 , Li 2 O, Na 2 O, BaO, CaO, MgO, Li 2 SO 4 , Na 2 SO 4 , CaSO 4 , MgSO 4 , CoSO 4 , Ga 2 (SO 4 ) 3 , Ti(SO 4 ) 2 , NiSO 4 , CaCl 2 , MgCl 2 , SrCl 2 , YCl 3 , CuCl 2 , CsF, TaF 5 , NbF 5 , LiBr, CaBr 2 , CeBr 3 , SeBr 4 , VBr 3 , MgBr 2 , BaI 2 , MgI 2 , Ba(ClO 4 ) 2 and Mg(ClO 4 ).

16. The device of claim 1 ,
wherein the photocurable pressure-sensitive adhesive composition further comprises a filler.

17. The device of claim 16 ,
wherein the filler comprises at least one or more selected from the group consisting of clay, talc, silica, barium sulfate, aluminum hydroxide, calcium carbonate, magnesium carbonate, zeolite, zirconia, titania and montmorillonite.

18. The device of claim 1 , further comprising:
a protective layer encapsulating the organic light emitting element and being between the cured pressure-sensitive adhesive film and the organic light emitting element.

19. A photocurable pressure-sensitive adhesive composition for encapsulating an organic electronic device of claim 1 , comprising:
an acrylic polymer, an epoxy resin in an amount of 1 to 30 parts by weight relative to 100 parts by weight of the acrylic polymer and a cationic photopolymerization initiator.

20. A photocurable pressure-sensitive adhesive film for encapsulating an organic electronic device, which is a film-state product comprising the composition of claim 19 , comprising:
a curable pressure-sensitive adhesive layer having a viscosity of 10 5 to 10 7 Pa·s before light irradiation and a viscosity of 10 6 to 10 8 Pa·s after light irradiation.

Assignees

• Lg Chemical Ltd

Inventors

• Cho Yoon Gyung
• Yoo Hyun Jee
• Shim Jung Sup
• Chang Suk Ky

Classifications

• C08G18/003

  with epoxy compounds having no active hydrogen (with epoxy resins containing active hydrogen C08G18/58) · CPC title

• C09J7/10

  without carriers · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C09J133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title