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US 7,408,013 B2Granted
Low-polydispersity photoimageable polymers and photoresists and processes for microlithography
AssigneeCommonwealth Scientific and Industrial Research Organization
InventorsAndrew Edward Feiring, Michael Fryd, Frank Leonard Schadt, III
Life of this patent
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Abstract
The invention pertains to low polydispersity copolymers useful for photoimaging and photoresist compositions, and to the photoimaging processes which use these compositions. The low polydispersity copolymers of this invention are prepared using controlled radical polymerization (CRP) techniques, such as RAFT (reversible addition fragmentation chain transfer) polymerization.
Claims33
A low polydispersity copolymer comprising:
- a. a repeat unit derived from an acrylic monomer selected from the group consisting of MAdA, HAdA, PinAc, PinMAc, and CH2═C(CH2OH)CO2R′″, wherein R′″ is a C1-C25 alkyl group, optionally substituted by one or more hydroxy, halogen, ether oxygen, ester or ketone carbonyl groups;
- b. a repeat unit derived from an unsaturated polycyclic monomer;
- and
- c. a functional group selected from the group of fluoroalcohol, protected fluoroalcohol and protected acid group;
- wherein at least 40 mole % of the repeat units of the low polydispersity copolymer are derived from acrylic monomers and the polydispersity is 1.05-2.0.
2 more elements
A low polydispersity copolymer comprising:
- a. a repeat unit derived from an acrylic monomer;
- b. a repeat unit derived from an unsaturated polycyclic monomer wherein the unsaturated polycyclic monomer is represented by structure I or structure II, wherein structure I is
- wherein
- v is 0, 1, or 2;
- A is O (oxygen) or NR27;
- R27 is selected from the group of H;
- C1-C10 alkyl or alkoxy, optionally substituted by halogen or ether oxygens;
- C6-C20 aryl;
- Y;
- C(Rf)(Rf′)OR28;R29Y;
- and OR29Y;
- R28 is a C1-C10 alkyl group;
- R29 is a C1-C20 alkylene group, optionally substituted by halogen or ether oxygen;
- Y is COZ′ or SO2Z′;
- Z′ is OH, halogen, R30 or OR30;
- R30 is a C1-C20 alkyl group, optionally substituted by halogen or ether oxygens;
- or C6-C20 aryl;
- Rf and Rf′ are the same or different fluoroalkyl groups of 1 to 10 carbon atoms or taken together are (CF2)n where n is 2 to 10;
- and
- R21 and R22 are independently selected from the group of H;
- halogen;
- C1-C10 alkyl or alkoxy, optionally substituted by halogen or ether oxygen;
- C6-C20 aryl;
- Y;
- C(Rf)(Rf′)OR28;
- R29Y;
- and OR29Y;
- or
- R21 and R22 taken together are =C(Rf)(Rf′) or C2-C9 alkylene, optionally substituted by halogen or incorporating an ether oxygen;
- and
- structure II is:
- w is 0, 1, or 2;
- R23, R24 and R25 are independently selected from the group of H;
- halogen;
- C1-C10 alkyl or alkoxy, optionally substituted by halogen or ether oxygen;
- C6-C20 aryl;
- Y;
- C(Rf)(Rf′)OR28;
- R29Y;
- and OR29Y;
- or
- R24 and R25 taken together are part of a double bond;
- R26 is hydrogen or an acid-labile protecting group;
- R28 is a C1-C10 alkyl group;
- R29 is a C1-C20 alkylene group, optionally substituted by halogen or ether oxygen;
- Y is COZ′ or SO2Z′;
- Z′ is OH, halogen, R30 or OR30;
- R30 is a C1-C20 alkyl group, optionally substituted by halogen or ether oxygens;
- or C6-C20 aryl;
- and
- Rf and Rf′ are the same or different fluoroalkyl groups of 1 to 10 carbon atoms or taken together are (CF2)n where n is 2 to 10;
- and
- c. a functional group selected from the group of fluoroalcohol, protected fluoroalcohol and protected acid group;
- wherein at least 40 mole% of the repeat units of the low polydispersity copolymer are derived from acrylic monomers and the polydispersity is 1.05-2.0.
51 more elements
A photoresist comprising:
- a. a photoactive component;
- and
- b. a low polydispersity copolymer comprising:
- a repeat unit derived from an acrylic monomer selected from the group consisting of MAdA, HAdA, PinAc, PinMAc, and CH2═C(CH2OH)CO2R′″, wherein R′″ is a C1-C25 alkyl group. optionally substituted by one or more hydroxy, halogen, ether oxygen, ester or ketone carbonyl groups;
- ii. a repeat unit derived from an unsaturated polycyclic monomer;
- and
- iii. a functional group selected from the group of fluoroalcohol, protected fluoroalcohol, and protected acid groups;
- wherein at least 40 mole% of the repeat units of the low polydispersity copolymer are derived from acrylic monomers and the polydispersity is 1.05-2.0.
5 more elements
A photoresist comprising:
- a. a photoactive component;
- and
- b. a low polydispersity copolymer comprising:
- i. a repeat unit derived from an acrylic monomer;
- ii. a repeat unit derived from an unsaturated polycyclic monomer wherein the unsaturated polycyclic monomer is represented by structure I or structure II, wherein structure I is
- wherein
- v is 0, 1, or 2;
- A is O (oxygen) or NR27;
- R27 is selected from the group of H;
- C1-C10 alkyl or alkoxy, optionally substituted by halogen or ether oxygens;
- C6-C20 aryl;
- Y;
- C(Rf)(Rf′)OR28;
- R29Y;
- and OR29Y;
- R28 is a C1-C10 alkyl group;
- R29 is a C1-C20 alkylene group, optionally substituted by halogen or ether oxygen;
- Y is COZ′ or SO2Z′;
- Z′ is OH, halogen, R30 or OR30;
- R30 is a C1-C20 alkyl group, optionally substituted by halogen or ether oxygens;
- or C6-C20 aryl;
- Rf and Rf′ are the same or different fluoroalkyl groups of 1 to 10 carbon atoms or taken together are (CF2)n where n is 2 to 10;
- and
- R21 and R22 are independently selected from the group of H;
- halogen;
- C1-C10 alkyl or alkoxy, optionally substituted by halogen or ether oxygen;
- C6-C20 aryl;
- Y;
- C(Rf)(Rf′)OR28;
- R29Y;
- and OR29Y;
- or R21 and R22 taken together are =C(Rf)(Rf′) or C2-C9 alkylene, optionally substituted by halogen or incorporating an ether oxygen;
- and
- structure II is:
- w is 0, 1, or 2;
- R23, R24 and R25 are independently selected from the group of H;
- halogen;
- C1-C10 alkyl or alkoxy, optionally substituted by halogen or ether oxygen;
- C6-C20 aryl;
- Y;
- C(Rf)(Rf′)OR28;
- R29Y;
- and OR29Y;
- or
- R24 and R25 taken together are part of a double bond;
- R26 is hydrogen or an acid-labile protecting group;
- R28 is a C1-C10 alkyl group;
- R29 is a C1-C20 alkylene group, optionally substituted by halogen or ether oxygen;
- Y is COZ′ or SO2Z′;
- Z′ is OH, halogen, R30 or OR30;
- R30 is a C1l -C20 alkyl group, optionally substituted by halogen or ether oxygens;
- or C6-C20 aryl;
- and
- Rf and Rf′ are the same or different fluoroalkyl groups of 1 to 10 carbon atoms or taken together are (CF2)n where n is 2 to 10;
- and
- iii. a functional group selected from the group of fluoroalcohol, protected fluoroalcohol, and protected acid groups;
- wherein at least 40 mole% of the repeat units of the low polydispersity copolymer are derived from acrylic monomers and the polydispersity is 1.05-2.0.
54 more elements
Dependencies are inferred from the claim text.