Patterning process, resist composition, polymer, and monomer
US-9213235-B2 · Dec 15, 2015 · US
US9856341B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9856341-B2 |
| Application number | US-201514732941-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jun 8, 2015 |
| Priority date | Dec 26, 2014 |
| Publication date | Jan 2, 2018 |
| Grant date | Jan 2, 2018 |
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A polymer including a first repeating unit represented by Formula 1, a second repeating unit represented by Formula 2, and a third repeating unit: wherein R 1 to R 3 , X, and Rf in Formula 1 and R 4 to R 6 , R, and a in Formula 2 are the same as those defined in the detailed description, and wherein the polymer has a glass transition temperature of about 25° C. or less or a Young's modulus of about 10 megaPascals or greater.
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What is claimed is: 1. A polymer comprising: a first repeating unit represented by Formula 1; a second repeating unit represented by Formula 2; and a third repeating unit represented by Formula 3: wherein in Formula 1, R 1 to R 3 each independently represent hydrogen, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 1 -C 20 heteroalkyl group, or an unsubstituted or substituted C 6 -C 20 aryl group, X represents a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 1 -C 20 heteroalkylene group a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, or —C(═O)O(CH 2 ) n — (where n is an integer between 1 and 10), and Rf represents fluorine, a C 1 -C 20 perfluorinated alkyl group, a C 3 -C 20 perfluorinated carbocyclic group, a C 6 -C 20 perfluorinated aryl group, or a C 2 -C 20 perfluorinated heteroaryl group, wherein in Formula 2, R 4 to R 6 each independently represent hydrogen, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 1 -C 20 heteroalkyl group, or an unsubstituted or substituted C 6 -C 20 aryl group, R represents hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 heteroalkyl group a C 6 -C 20 aryl group, a C 2 -C 20 heteroaryl group, a C 2 -C 20 heterocyclic group, a C 4 -C 20 carbocyclic group, —PO 3 Li, or —SO 2 Li, and a is an integer between 1 and 20, wherein in Formula 3, R 7 to R 9 each independently represent hydrogen, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 1 -C 20 heteroalkyl group or an unsubstituted or substituted C 6 -C 20 aryl group, L represents a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 1 -C 20 heteroalkylene group a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, or a substituted or unsubstituted C 4 -C 20 carbocyclic group, b is 0 or an integer between 1 and 5, and G is a group represented by Formula 3a, or a group represented by Formula 3f, wherein in Formula 3a, R 10 to R 12 each independently represent hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 heteroalkyl group, a C 6 -C 20 aryl group, a C 2 -C 20 carbocyclic group, or a C 2 -C 20 heterocyclic group, and —Si k O 1.5k (R 13 ) a (R 14 ) b (R 15 ) c Formula 3f wherein in Formula 3f, R 13 , R 14 , and R 15 each independently represent hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, or a C 1 -C 20 silicon-containing functional group, and k=a+b+c and 6≦k≦20, wherein the polymer has a glass transition temperature of about 25° C. or less or a Young's modulus of about 10 megaPascals or greater. 2. The polymer of claim 1 , wherein X in Formula 1 is phenylene or —C(═O)O(CH 2 ) n —, (wherein n is an integer between 1 and 5). 3. The polymer of claim 1 , wherein Rf is —F, —CF 3 , or —CF 2 CF 3 . 4. The polymer of claim 1 , wherein an amount of the third repeating unit represented by Formula 3 is in a range of about 0.1 moles to about 0.8 moles based on 1 mole of the second repeating unit. 5. The polymer of claim 1 , wherein an amount of the first repeating unit represented by Formula 1 is in a range of about 0.2 moles to about 0.9 moles based on 1 mole of the second repeating unit. 6. The polymer of claim 1 , wherein the polymer is a polymer represented by Formula 4: wherein in Formula 4, l+m+n=1, 0.1≦l≦0.3, 0.4≦m≦0.6, and 0.2≦n≦0.4, R 1 to R 9 each independently represent hydrogen, a C 6 -C 20 alkyl group, or a C 6 -C 20 aryl group, Rf represents fluorine, a C 1 -C 12 perfluorinated alkyl group, or a C 3 -C 12 perfluorinated carbocyclic group, a is an integer between 1 and 20, R represents a C 1 -C 20 alkyl group, a C 6 -C 20 aryl group, —PO 3 Li, or —SO 2 Li, L represents an unsubstituted or substituted C 1 -C 20 alkylene group, or an unsubstituted or substituted C 6 -C 20 arylene group, b is 0 or an integer between 1 and 5, and G is a group represented by Formula 3a, or a group represented by Formula 3f, wherein in Formula 3a, R 10 to R 12 each independently represent hydrogen, a C 1 -C 20 alkyl group, or a C 6 -C 20 aryl group, and —Si k O 1.5k (R 13 ) a (R 14 ) b (R 15 ) c Formula 3f wherein in Formula 3f, R 13 , R 14 , and R 15 each independently represent hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, or a C 1 -C 20 silicon-containing functional group, and k=a+b+c and 6≦k≦20. 7. The polymer of claim 1 , wherein G in Formula 3 is one selected from groups represented by Formulae 3b to 3d: wherein in Formula 3b, R 1 , R 3 to R 6 each independently represent hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, or a C 1 -C 20 silicon-containing functional group, wherein in Formula 3c, R 1 , R 2 , R 4 to R 8 each independently represent hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a subs
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