Low outgassing photo or electron beam curable rubbery polymer material, preparation thereof and device comprising same

• US 7,256,221 B2
• Filed: 11/07/2003
• Issued: 08/14/2007
• Est. Priority Date: 11/07/2002
• Status: Active Grant

• Current Assignee: Corning Incorporated
• Original Assignee: Corning Incorporated
• Inventors: Sabia, Robert, Shustack, Paul J., Dewa, Paul G., Soni, Kamal K., Coykendall, Kelsee L., Sauer, David C.
• Primary Examiner(s): Berman; Susan
• Application Number:
  US10/703,800
• Publication Number:
  US 20040092618A1
• Time in Patent Office: 1,376 Days
• Field of Search: 522/81, 522/83, 522/120, 522/121, 522/142, 522/141, 522/157, 522/158, 522/159, 522/160, 522/161, 522/129, 522/64, 522/39, 522/66, 522/53, 522/46, 522/31, 522/14, 522/16, 522/23, 522/42
• US Class Current: 522/14
• CPC Class Codes: C08C 19/02 Hydrogenation
• CPC Class Codes: C08F 255/02 on to polymers of olefins having two or three carbon atoms
• CPC Class Codes: C08F 279/02 on to polymers of conjugated dienes
• CPC Class Codes: C08F 290/048 Polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
• CPC Class Codes: C08J 3/28 Treatment by wave energy or particle radiation
• CPC Class Codes: C08K 3/013 Fillers, pigments or reinforcing additives
• CPC Class Codes: C08K 5/0025 Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08L 15/00 Compositions of rubber derivatives C08L11/00, C08L13/00 take precedence
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

Disclosed are photo or electron beam polymerizable compositions, and preparation thereof and devices containing them. The composition contains completely or substantially completely hydrogenated hydrocarbon-based material completely free or substantially free of carbon-carbon double and triple bonds containing photo or electron beam curable terminal or pendant groups, low-outgassing photoinitiators, an optional viscosity adjustment component and an optional filler. The composition is visible light, UV or electron beam curable. It cures into a low-modulus, low outgassing polymer material. The composition can be used as an adhesive, sealant or lens potting material. It is ideal for use in lithographic tools involving deep or vacuum ultraviolet radiations, in particular, as lens potting materials for 157 nm lithographic tools.

Claims

1. A composition of matter consisting essentially of a reaction product of

(i) a photo or electron beam curable material component comprising a material having the backbone of a completely or substantially completely hydrogenated hydrocarbon based rubber material, which is completely or substantially free of carbon-carbon double and triple bonds, and bears at least one photo or electron beam polymerizable terminal or pendant group;

(ii) a photoinitiator/photosensitizer component having essentially no volatility at room temperature and also yielding photoproducts after exposure to actinic radiation that have minimal or no volatility at room temperature;

(iii) an optional viscosity adjustment component that is either homopolymerizable or is capable of copolymerizing with the photo or electron beam curable material component of(i); and

(iv) an optional inert filler,

wherein, the composition of matter, when cured, has a low outgassing rate such that it passes the ASTM-E-595-93 (1999) test and a low outgassing rate when exposed to ultraviolet radiation having a wavelength less than or equal to about 248 nm.

2. A composition of matter in accordance with claim 1, wherein the photo or electron beam curable material component of (i) comprises a functionalized material bearing at least one photo or electron beam polymerizable terminal or pendant group selected from the group consisting of:

polybutadiene, polyisoprene, polyethylene propylene rubber and combinations thereof, which material comprises a backbone that is completely hydrogenated or substantially completely hydrogenated and completely or substantially completely free of carbon-carbon double and triple bonds.

3. A composition of matter in accordance with claim 2, wherein the photo or electron beam curable material component of (i) is functionalized by at least one polymerizable terminal or pendant group selected from the group consisting of:

acrylate, methacrylate, acrylamide, maleimide, thioacrylate, thiomethacrylate, vinyl sulfide, itaconate, crotonate, styrene and N-vinyl amide, hydroxyl, thiol, epoxy, oxetane, episulfide, vinyl ether, propenyl ether, allyl ether, and compatible mixtures and/or combinations thereof.

4. A composition of matter in accordance with claim 3, wherein the photo or electron beam curable material component of(i) is functionalized by at least one polymerizable terminal or pendant group selected from the group consisting of:

epoxy, acrylate and methacrylate.

5. A composition of matter in accordance with claim 1, wherein the photoinitiator/photosensitizer is selected from the group consisting of the following compounds and/or mixtures in purified and/or diluted form:

oligo [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone];

oligo [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]Propanone], diluted in tripropylene glycol diacrylate (25% TPGDA);

1-[4-(4-benzoylphenylsulfonyl)phenyl]-2-methyl-2-(4-methylphenylsulfonyl) propan-1-one;

bis(2,4,6-trimethylbenzoyl)-Phenyl phosphine oxide;

2-benzyl-2-N,N-dimethylamino-1-(4-morpholino-phenyl)-1-butanone;

bis η

5-(2,4-cyclopentadien-1-yl) bis(2,6-difluoro-3-(1H-pyrrol-1-yl) phenyl)titanium;

bis (2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide;

2-oxepanone, homopolymer, 2-[[4-[2-methyl-2-(4-morpholinyl)-1-oxopropyl]phenyl]thio]ethyl ester;

mixture of 2-isopropylthioxanthone and 4-isopropylthioxanthone;

1,3-dimethyl-2-hydroxy-9H-thioxanthen-9-one, 2-ethylhexyl ester;

4,4′

-bis(methylethylamino)benzophenone;

4,4′

-bis(isopropylphenoxy)benzophenone;

4-benzoyl-4′

-methyldiphenyl sulfide;

2-chloro-thioxanthone;

1-chloro-4-propoxythioxanthone;

2,4-diethylthioxanthone;

poly[oxy(methyl-1,2-ethanediyl)], α

-[4-(dimethylamino)benzoyl-ω

-butoxy-;

2,2′

-bis-(2-chlorophenyl)-4,5,4′

,5′

-tetraphenyl-2′

H-<

1,2′

>

biimidazolyl;

(tolylcumyl)iodonium tetrakis(pentafluorophenyl) borate;

[4-[(2-hydroxytetradecyl)oxy]phenyl]phenyliodonium hexafluoro antimonate;

mixture of bis(4-dodecylphenyl)iodonium hexafluoroantimonate, isopropylthioxanthone, and C12+C14 alkylglycidyl ethers;

mixture of bis(4-dodecylphenyl)iodonium hexafluoroantimonate and C12+C14 alkylglycidyl ethers;

phenyl-4-octyloxyphenyl iodonium hexafluoro antimonate;

mixture of triaryl sulfonium hexafluoroantimonate salts;

mixture of triaryl sulfonium hexafluorophosphate salts;

perylene;

anthracene;

1,2-benzanthracene;

9-n-butoxyanthracene;

9,10-di-n-butoxy anthracene;

9,10-di-n-propoxy anthracene;

9,10-diethoxy anthracene;

anthrone;

pyrene;

2-ethyl-9,10-dimethoxy anthracene;

2,5-diphenyl-1,3,4-oxadiazole;

diphenyl anthracene;

9,10-dimethylanthracene;

1,3-diphenyl-2-pyrazoline;

1,3-diphenylisobenzofuran;

N,N,N′

,N′

-tetraphenyl benzidine; and

N,N,N′

,N′

-tetraphenyl phenylene diamine;

and compatible mixtures thereof and/or compatible combinations thereof.

6. A composition of matter in accordance with claim 1, wherein the inert filler is an inorganic filler selected from the group consisting of alumina, crystobalite, aluminum trihydroxide, talc, feldspar, calcium carbonate, mica, clay, wallastonite, nepeleline syenite, silica, and compatible mixtures thereof and compatible combinations thereof.

7. A cured composition of matter obtained by exposing the composition of claim 1 to visible light, ultraviolet light or electron beam.

8. A composition of matter in accordance with claim 7, which has a low modulus ranging from 25 to 10,000 psi (1.7×

10⁵ to 6.8×

10⁷ Pa).

9. A composition of matter in accordance with claim 7, which has a Tg of equal to or lower than 25°

C.

12. A composition of matter in accordance with claim 1, wherein the photo or electron beam curable material component of (i) is functionalized by at least one polymerizable terminal or pendant group selected from the group consisting of:

acrylate, methacrylate, acrylamide, maleimide, thioacrylate, thiomethacrylate, vinyl sulfide, itaconate, crotonate, styrene and N-vinyl amide, hydroxyl, thiol, oxetane, episulfide, vinyl ether, propenyl ether, allyl ether, and compatible mixtures and/or combinations thereof.

13. A composition of matter in accordance with claim. 1, which is essentially free of silicone.

14. A process according to claim 12, wherein steps (B) and (C) are performed in an environment essentially free of silicone.

10. A process for producing a cured composition of matter having low outgassing rate and low modulus between 25 and 10,000 psi (1.7×

10⁵ to 6.8×

10⁷ Pa), comprising the following steps of;

(A) providing a rubber material (i) (a) having a backbone that is completely or substantially completely free of carbon-carbon double bond and triple bond and (b) comprising terminal and/or pendant groups tat are photo and/or electron beam polymerizable;

(B) mixing the material (i) with a photoinitiator/photosensitizer (ii) having essentially no volatility at room temperature and also yielding photoproducts after exposure to actinic radiation that have minimal or no volatility at room temperature;

(iii) an optional viscosity adjustment component that is either homopolymerizable or is capable of copolymerizing wit material (i); and

(iv) an optional inert filler;

(C) curing the mixture resulting from step (B) by visible light, UV light or electron beam to form a cured composition of matter having low outgassing rate and low modulus, wherein the cured composition has an outgassing rate tat is sufficient to pass the ASTM-E-595-93 (1999) test and a low outgassing rate when exposed to ultraviolet radiation having a wavelength less than or equal to about 248 nm.

11. A process in accordance with claim 10, wherein step (A) comprises the following steps:

(A1) providing a completely or substantially completely hydrogenated hydrocarbon-based rubber material (i′

) completely or substantially completely free of carbon-carbon double bond and triple bond having reactive terminal and/or pendant groups; and

(A2) modifying the rubber material (i′

) into material (i) by introducing photo and/or electron beam polymerizable terminal and/or pendant groups to the rubber material (i′

) by allowing the reactive terminal and/or pendant groups of (i′

) to react with agents having the photo and/or electron beam polymerizable groups.