Device comprising low outgassing photo or electron beam cured rubbery polymer material

• US 7,232,595 B2
• Filed: 12/01/2004
• Issued: 06/19/2007
• Est. Priority Date: 11/07/2002
• Status: Active Grant

• Current Assignee: Corning Incorporated
• Original Assignee: Corning Incorporated
• Inventors: Soni, Kamal K., Coykendall, Kelsee L., Sauer, David, Sabia, Robert, Shustack, Paul J., Dewa, Paul G.
• Primary Examiner(s): McClendon; Sanza L.
• Application Number:
  US11/002,775
• Publication Number:
  US 20050152595A1
• Time in Patent Office: 930 Days
• Field of Search: 522/141, 522/142, 522/157, 522/158, 522/159, 522/160, 522/161, 522/71, 428/500, 428/523, 428/1.55, 428/343, 428/345, 428/355.R, 428/355.EP, 428/355.EN, 428/355.BL, 428/355.AC, 264/1.1, 264/1.32, 264/1.36, 264/1.38, 359/896
• US Class Current: 428/1.5
• CPC Class Codes: C08C 19/02 Hydrogenation
• CPC Class Codes: C08F 255/00 Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
• 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 290/06 Polymers provided for in subclass C08G
• 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 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C09J 123/02 not modified by chemical after-treatment
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• CPC Class Codes: C09K 2323/05 Bonding or intermediate layer characterised by chemical composition, e.g. sealant or spacer
• CPC Class Codes: C09K 2323/059 Unsaturated aliphatic polymer, e.g. vinyl
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer
• CPC Class Codes: Y10T 428/2809 including irradiated or wave energy treated component
• CPC Class Codes: Y10T 428/2852 Adhesive compositions
• CPC Class Codes: Y10T 428/287 including epoxy group or epoxy polymer
• CPC Class Codes: Y10T 428/2878 including addition polymer from unsaturated monomer
• CPC Class Codes: Y10T 428/2883 including addition polymer of diene monomer [e.g., SBR, SIS, etc.]
• CPC Class Codes: Y10T 428/2891 including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
• CPC Class Codes: Y10T 428/31855 : Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31938 : Polymer of monoethylenically unsaturated hydrocarbon

Abstract

Disclosed are photo or electron beam curable polymerizable compositions, and preparation thereof and devices containing such cured material. 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 and other optical devices involving deep or vacuum ultraviolet radiations, in particular, as lens potting materials for 248 nm, 193 nm and 157 nm lithographic tools, as well as other optical devices involving using high fluence irradiation.

Claims

1. An optical device comprising at least one lens element and, as lens potting material, a photo or electron beam cured composition of matter consisting essentially of a mixture, a blend or a reaction product of

(i) a photo or electron beam curable material component based on a completely or substantially completely hydrogenated hydrocarbon based rubber material having a backbone completely or substantially free of carbon-carbon double and triple bonds;

(ii) a photoinitiator/photosensitizer component having essentially no volatility at room temperature and also yield 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.

2. A device in accordance with claim 1, wherein the photo or electron beam curable material component of (i) is a functionalized material selected from the group consisting of:

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

3. A device 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:

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 device 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:

epoxy, acrylate and methacrylate.

5. A device in accordance with claim 1, wherein the photoinitiator/photosensitizer in the composition of matter is selected from 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 and/or combinations thereof.

6. A device in accordance with claim 1, wherein the inert filler in the composition of matter 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 and combinations thereof.

7. A device in accordance with claim 1, wherein the cured composition of matter has a low modulus ranging from 25 to 10,000 psi (1.7×

10⁵ to 6.8×

10⁷ Pa).

8. A device in accordance with claim 1, wherein the cured composition of matter has a low outgassing rate.

9. A device in accordance with claim 1, wherein the cured composition of matter has a T_g of equal to or lower than 25°

C.

10. A device in accordance with claim 1, which is for use in connection with electromagnetic irradiation at a high fluence.

11. A device in accordance with claim 1, which is for use in connection with electromagnetic irradiation having a wavelength less than 500 nm.

12. A device in accordance with claim 11 which is a lithographic device involving using deep and/or vacuum ultraviolet irradiation.

13. A device in accordance with claim 12 wherein the wavelength of the lithographic radiation is approximately 157 nm or shorter.

14. A device in accordance with claim 12, wherein the lens material is doped or undoped high purity fused silica or crystalline CaF₂, optionally coated with antireflective material selected from the group consisting of:

magnesium fluoride, aluminum fluoride, calcium fluoride, gadolinium fluoride, thorium fluoride, lanthanum fluoride, yttrium fluoride, neodymium fluoride, dysprosium fluoride, sodium aluminum fluoride, alumina, silica, fluorine-containing silica, hafnia, scandium oxide, thorium oxide, zirconia, yttria, and compatible combinations thereof.

15. A device in accordance with claim 11, wherein minimal or no purging of the light path is required.

16. A device in accordance with claim 1, which is selected from the group consisting of stepper lens, stepper lens assembly, semiconductor inspection device, etalon and laser generator.