CA2045093A1 - A process for making low optical density polymers and copolymers for photoresists and optical applications - Google Patents
A process for making low optical density polymers and copolymers for photoresists and optical applicationsInfo
- Publication number
- CA2045093A1 CA2045093A1 CA 2045093 CA2045093A CA2045093A1 CA 2045093 A1 CA2045093 A1 CA 2045093A1 CA 2045093 CA2045093 CA 2045093 CA 2045093 A CA2045093 A CA 2045093A CA 2045093 A1 CA2045093 A1 CA 2045093A1
- Authority
- CA
- Canada
- Prior art keywords
- polymers
- transesterification
- optical density
- over
- low optical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title abstract 7
- 230000003287 optical effect Effects 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 229920002120 photoresistant polymer Polymers 0.000 title abstract 2
- 229920001577 copolymer Polymers 0.000 title 1
- 239000000178 monomer Substances 0.000 abstract 5
- 238000005809 transesterification reaction Methods 0.000 abstract 5
- -1 poly(4-hydroxystyrene) Polymers 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 230000005855 radiation Effects 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000002835 absorbance Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000012986 chain transfer agent Substances 0.000 abstract 1
- 238000003384 imaging method Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000001429 visible spectrum Methods 0.000 abstract 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention pertains to a process for the preparation of polymers comprising poly(4-hydroxystyrene) or substituted poly(4-hydroxystyrene) or both. The polymers have low optical density (absorbance) over a wavelength range from about 240 to about 260 nm, as well as low optical density over the near UV and visible spectrum (310 to 800 nm). Such polymers arc produced by polymerizing 4-acetoxystyrene and/or substituted 4-aeetoxystyrene monomers, with or without other comonomers, and subsequently performing transesterification. In the most preferred embodiment of the present invention, the polymers are produced using at least one alcohol as a reaction medium, a chain transfer agent and a transesterification reactant, providing an unusually economic process. These polymers are particularly useful as photoresist components for use in combination with deep UV, X-ray, and E-Beam imaging systems.
To obtain polymers having low optical density over the 240 to 260 nm radiation wavelength range, it is necessary to use an initiator which does not comprise a substantially absorbant structure over the 240 to 260 nm range or to use an initiator concentration of less than about 3 mole % of the monomer(s), to obtain a polymerization conversion of the initial polymerization monomers of at least about 90% by weight, or to remove residual monomer(s) from the reaction medium prior to transesterification, and to obtain a transesterification conversion of the polymerized monomers of at least 85% by weight. It is also necessary to avoid the use of transesterification catalysts which can cause the formation of chemical structures which can absorb over the 240 to 260 nm radiation wavelength range.
To obtain polymers having low optical density over the 240 to 260 nm radiation wavelength range, it is necessary to use an initiator which does not comprise a substantially absorbant structure over the 240 to 260 nm range or to use an initiator concentration of less than about 3 mole % of the monomer(s), to obtain a polymerization conversion of the initial polymerization monomers of at least about 90% by weight, or to remove residual monomer(s) from the reaction medium prior to transesterification, and to obtain a transesterification conversion of the polymerized monomers of at least 85% by weight. It is also necessary to avoid the use of transesterification catalysts which can cause the formation of chemical structures which can absorb over the 240 to 260 nm radiation wavelength range.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60484790A | 1990-10-26 | 1990-10-26 | |
US07/604,847 | 1990-10-26 | ||
US07/706,601 | 1991-05-28 | ||
US07/706,601 US5239015A (en) | 1990-06-29 | 1991-05-28 | Process for making low optical density polymers and copolymers for photoresists and optical applications |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2045093A1 true CA2045093A1 (en) | 1992-04-27 |
CA2045093C CA2045093C (en) | 2004-02-03 |
Family
ID=27084782
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA 2045093 Expired - Lifetime CA2045093C (en) | 1990-10-26 | 1991-06-20 | A process for making low optical density polymers and copolymers for photoresists and optical applications |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2045093C (en) |
-
1991
- 1991-06-20 CA CA 2045093 patent/CA2045093C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2045093C (en) | 2004-02-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed | ||
MKEC | Expiry (correction) |
Effective date: 20121202 |