Source: https://patents.google.com/patent/US7897319?oq=7%2C172%2C682
Timestamp: 2018-03-24 05:35:12
Document Index: 661941026

Matched Legal Cases: ['§371', '§119', 'Application No. 2004', 'Application No. 2004', 'Application No. 10', 'Application No. 2004', 'Application No. 2004', 'Application No. 2004', 'Application No. 2004', 'Application No. 10', 'Application No. 10', 'Application No. 2005', 'Application No. 094104523', 'Application No. 10', 'Application No. 10', 'Application No. 10']

US7897319B2 - Positive resist composition and method of forming resist pattern - Google Patents
US7897319B2
US7897319B2 US11572630 US57263005A US7897319B2 US 7897319 B2 US7897319 B2 US 7897319B2 US 11572630 US11572630 US 11572630 US 57263005 A US57263005 A US 57263005A US 7897319 B2 US7897319 B2 US 7897319B2
US11572630
US20070259273A1 (en )
This application is the U.S. National Phase filing under 35 U.S.C. §371 of PCT/JP2005/013564, filed Jul. 25, 2005, which designated the United States and was published in a language other than English, which claims priority under 35 U.S.C. §119(a)-(d) to Japanese Patent Application No. 2004-220111, filed Jul. 28, 2004. The content of these applications is incorporated herein by reference in their entireties.
In this description, the term “exposure” is used as a general concept that includes irradiation with any form of radiation.
Furthermore, specific examples of poly(bis-sulfonyl)diazomethanes include the structures shown below, such as 1,3-bis(phenylsulfonyldiazomethylsulfonyl)propane (compound A, decomposition point 135° C.), 1,4-bis(phenylsulfonyldiazomethylsulfonyl)butane (compound B, decomposition point 147° C.), 1,6-bis(phenylsulfonyldiazomethylsulfonyl)hexane (compound C, melting point 132° C., decomposition point 145° C.), 1,10-bis(phenylsulfonyldiazomethylsulfonyl)decane (compound D, decomposition point 147° C.), 1,2-bis(cyclohexylsulfonyldiazomethylsulfonyl)ethane (compound E, decomposition point 149° C.), 1,3-bis(cyclohexylsulfonyldiazomethylsulfonyl)propane (compound F, decomposition point 153° C.), 1,6-bis(cyclohexylsulfonyldiazomethylsulfonyl)hexane (compound G, melting point 109° C., decomposition point 122° C.), and 1,10-bis(cyclohexylsulfonyldiazomethylsulfonyl)decane (compound H, decomposition point 116° C.).
Namely, a positive resist composition described above is first applied to the surface of a substrate such as a silicon wafer using a spinner or the like, a prebake is conducted under temperature conditions of 80 to 150° C. for 40 to 120 seconds, and preferably for 60 to 90 seconds, and the resulting film is then subjected to selective exposure with an electron beam or extreme ultraviolet radiation or the like, using an electron beam lithography apparatus or the like. In other words, following exposure through a mask pattern or patterning of the resist film by direct irradiation with an electron beam without using a mask pattern, PEB (post exposure baking) is conducted under temperature conditions of 70 to 150° C. for 40 to 500 seconds, and preferably for 60 to 400 seconds. Subsequently, developing is conducted using an alkali developing solution such as a 0.1 to 10% by weight aqueous solution of tetramethylammonium hydroxide. In this manner, a resist pattern that is faithful to the mask pattern can be obtained.
Using a 400 MHz proton NMR apparatus manufactured by JEOL Ltd., the number of phenolic hydroxyl groups within the MBSA protector (a1), and the number of phenolic hydroxyl groups protected with 1-ethoxyethyl groups were measured, and determination of the protection ratio (mol %) revealed a value of 19.9 mol %. The protection ratio is determined using the formula: {number of phenolic hydroxyl groups protected with 1-ethoxyethyl groups/(number of phenolic hydroxyl groups+number of phenolic hydroxyl groups protected with 1-ethoxyethyl groups)}1×100.
Subsequently, the thus obtained positive resist composition solution was applied uniformly, using a spinner, to the surface of an 8-inch silicon substrate that had been treated with hexamethyldisilazane, and was then subjected to a bake treatment (post applied bake (PAB)) at 120° C. for 90 seconds, thus forming a resist film (film thickness: 150 nm).
This resist film was then subjected to direct patterning with an electron beam lithography apparatus (HL-800D, manufactured by Hitachi Ltd., accelerating voltage: 70 kV), and was then subjected to a bake treatment (post exposure baking (PEB)) at 100° C. for 90 seconds, developed for 60 seconds in a 2.38% by weight aqueous solution (at 23° C.) of tetramethylammonium hydroxide (TMAH), and rinsed in pure water for 30 seconds, thus forming a line and space (L/S) pattern. The thus obtained resist pattern was subjected to the evaluations described below. The results of the evaluations are shown in Table 1.
Subsequently, the thus obtained positive resist composition solution was subjected to the same evaluations as those described in the example 1. During these evaluations, the PAB conditions were altered to 110° C. for 90 seconds and the PEB conditions were altered to 90° C. for 90 seconds. The results are shown in Table 1.
Subsequently, the thus obtained positive resist composition solution was subjected to the same evaluations as those described in the example 1. During these evaluations, the PAB conditions were altered to 110° C. for 90 seconds and the PEB conditions were altered to 110° C. for 90 seconds. The results are shown in Table 1.
Sensitivity Resolution (L/S)
[μC/cm2] Pattern shape [nm]
Example 1 16 Rectangular 60
Example 2 22 Rectangular 60
Comparative example 1 15 T-top 90
US11572630 2004-07-28 2005-07-25 Positive resist composition and method of forming resist pattern Active 2026-10-19 US7897319B2 (en)
JP2004220111A JP3946715B2 (en) 2004-07-28 2004-07-28 The positive resist composition and a resist pattern forming method
JP2004-220111 2004-07-28
PCT/JP2005/013564 WO2006011442A1 (en) 2004-07-28 2005-07-25 Positive resist composition and method of forming resist pattern
US20070259273A1 true US20070259273A1 (en) 2007-11-08
US7897319B2 true US7897319B2 (en) 2011-03-01
ID=35786192
US11572630 Active 2026-10-19 US7897319B2 (en) 2004-07-28 2005-07-25 Positive resist composition and method of forming resist pattern
US (1) US7897319B2 (en)
JP (1) JP3946715B2 (en)
KR (2) KR20070043861A (en)
WO (1) WO2006011442A1 (en)
JP4444854B2 (en) 2005-02-25 2010-03-31 東京応化工業株式会社 The positive resist composition, a resist pattern forming method and compounds
JP2006347892A (en) * 2005-06-13 2006-12-28 Tokyo Ohka Kogyo Co Ltd Compound, positive resist composition and method for forming resist pattern
WO2006134811A1 (en) * 2005-06-13 2006-12-21 Tokyo Ohka Kogyo Co., Ltd. Polyhydric phenol compound, compound, positive resist composition, and method of forming resist pattern
JP4823578B2 (en) * 2005-06-13 2011-11-24 東京応化工業株式会社 Polyhydric phenol compounds, compounds, a positive resist composition and a resist pattern forming method
JP4879559B2 (en) * 2005-09-20 2012-02-22 東京応化工業株式会社 The compounds and methods of manufacturing
JP5000241B2 (en) * 2005-11-04 2012-08-15 東京応化工業株式会社 Compound, a positive resist composition and a resist pattern forming method
JP5031277B2 (en) 2006-06-20 2012-09-19 東京応化工業株式会社 The positive resist composition and a resist pattern forming method
JPH09160246A (en) * 1995-12-01 1997-06-20 Shin Etsu Chem Co Ltd Chemically amplified positive resist material
US7504196B2 (en) * 2005-02-25 2009-03-17 Tokyo Ohka Kogyo Co., Ltd. Positive resist composition, method for resist pattern formation and compound
Decision to Grant a Patent issued in corresponding Japanese Patent Application No. 2004-182301, dated Jan. 6, 2009.
European Search Report issued in related European Patent Application No. EP 06732357.6, dated Aug. 30, 2010.
Hirayama et al, "Development of Amorphous PolyPhenol Resists with Low Molecular Weight and Narrow Dispersion for EB Lithography", IEEE Xplore, Oct. 22, 2004, pp. 10-11.
Hirayama et al. "Development of Electron Beam Resists Based on Amorphous Polyphenols with Low Molecular Weight and Narrow Dispersion" Proceedings of SPIE vol. 5753, p. 738-745.
Hirayama et al., "Development of Amorphous Polyphenol Resists with Low Molecular Weight and Narrow Dispersion for EB Lithography", IEEE Xplore, pp. 10-11, (Oct. 22, 2004). *
Hirayama et al., "Development of Electron Beam Resists based on Amorphous Polyphenols with Low Molecular Weight and Narrow Dispersion", Proceedings of SPIE, vol. 5753, pp. 738-745, (Mar. 2, 2005). *
International Search Report dated Sep. 6, 2005, for PCT/JP2005/013564 filed Jul. 28, 2004.
International Search Report from PCT/JP2006/302271, mailed on Mar. 7, 2006.
International Search Report issued in corresponding PCT application No. PCT/JP2005/018143, mailed Nov. 15, 2005.
JP 09-160246 English translation. *
Notice of Allowance issued in related Korean Patent Application No. 10-2009-7006750, dated Feb. 16, 2010.
Notice of Allowance issued on corresponding Japanese Patent Application No. 2004-260764, dated Feb. 16, 2010.
Office Action issued in corresponding U.S. Appl. No. 10/590,046, dated Apr. 24, 2009.
Office Action issued in corresponding U.S. Appl. No. 10/590,046, dated Mar. 17, 2010.
Office Action issued in corresponding U.S. Appl. No. 10/590,046, dated Sep. 21, 2009.
Office Action issued in corresponding U.S. Appl. No. 10/590,046, dated Sep. 26, 2008.
Office Action issued in corresponding U.S. Appl. No. 11/574,805 dated Aug. 19, 2008.
Office Action issued in corresponding U.S. Appl. No. 11/574,805 dated Aug. 4, 2009.
Office Action issued in corresponding U.S. Appl. No. 11/574,805 dated Feb. 10, 2009.
Office Action issued in corresponding U.S. Appl. No. 11/574,805 dated Feb. 26, 2010.
Office Action issued in corresponding U.S. Appl. No. 11/574,805 dated May 19, 2009.
Office Action issued in corresponding U.S. Appl. No. 11/718,091 dated Apr. 23, 2010.
Office Action issued in corresponding U.S. Appl. No. 11/718,091 dated Sep. 14, 2009.
Office Action issued in corresponding U.S. Appl. No. 11/813,511, dated Apr. 28, 2010.
Office Action issued in corresponding U.S. Appl. No. 11/813,511, dated Oct. 8, 2009.
Office Action issued in corresponding U.S. Appl. No. 11/884,748, dated Jul. 7, 2008.
Office Action issued in corresponding U.S. Appl. No. 11/914,451 dated May 3, 2010.
Office Action issued in corresponding U.S. Appl. No. 11/914,451 dated Oct. 8, 2009.
Office Action issued in corresponding U.S. Appl. No. 11/917,458, dated Apr. 5, 2010.
Office Action issued in corresponding U.S. Appl. No. 11/994,602, dated Mar. 8, 2010.
Office Action issued in counterpart Japanese Patent Application No. 2004-182300, dated May 27, 2008.
Office Action issued in counterpart Japanese Patent Application No. 2004-182301, dated Aug. 26, 2008.
Office Action issued in counterpart Japanese Patent Application No. 2004-182301, dated Jun. 3, 2008.
Office Action issued in counterpart Japanese Patent Application No. JP 2005-050721, dated Jul. 28, 2009.
Office Action issued in Korean Patent Application No. 10-2007-7004390, dated Dec. 17, 2008.
Office Action issued in Korean Patent Application No. 10-2008-7025851, dated Jan. 7, 2009.
Office Action issued in the counterpart Japanese Patent Application No. 2005-050721, dated Mar. 3, 2009.
Office Action issued in the counterpart Taiwanese Patent Application No. 094104523, dated May 12, 2008.
Office Action issued on Apr. 14, 2008 on the counterpart Korean Patent Application No. 10-2007-7004390.
Office Action issued on the counterpart Korean Patent Application No. 10-2007-7019433, dated Jun. 5, 2008.
Office Action issued Sep. 16, 2008 in the counterpart Korean Patent Application No. 10-2007-7010473.
JP3946715B2 (en) 2007-07-18 grant
US20070259273A1 (en) 2007-11-08 application
JP2006039281A (en) 2006-02-09 application
KR20070043861A (en) 2007-04-25 application
WO2006011442A1 (en) 2006-02-02 application
KR20080098690A (en) 2008-11-11 application
US20090317745A1 (en) 2009-12-24 Positive resist composition and method of forming resist pattern
JP2010204187A (en) 2010-09-16 Positive resist composition, method for forming resist pattern, and polymer compound
JP2009191055A (en) 2009-08-27 Resist composition, resist pattern forming method, new compound and acid generator
US20100015552A1 (en) 2010-01-21 Resist composition, method of forming resist pattern, compound and acid generator
US20090104563A1 (en) 2009-04-23 Resist composition, method of forming resist pattern, novel compound, and acid generator
EP2088466A1 (en) 2009-08-12 Resist composition for immersion exposure, method of forming resist pattern using the same, and fluorine-containing compound
US20090162781A1 (en) 2009-06-25 Resist composition, resist pattern forming method and compound
US20070224520A1 (en) 2007-09-27 Polymer Compound, Photoresist Composition Containing Such Polymer Compound, and Method for Forming Resist Pattern
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SHIONO, DAIJU;HIRAYAMA, TAKU;HADA, HIDEO;REEL/FRAME:018848/0090