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(12) United States Patent (10) Patent No.: US 8,900,802 B2 Allen Et Al

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(12) United States Patent (10) Patent No.: US 8,900,802 B2 Allen Et Al USOO890O802B2 (12) United States Patent (10) Patent No.: US 8,900,802 B2 Allen et al. (45) Date of Patent: Dec. 2, 2014 (54) POSITIVE TONE ORGANIC SOLVENT (56) References Cited DEVELOPED CHEMICALLY AMPLIFIED RESIST U.S. PATENT DOCUMENTS 3,586,504 A 6, 1971 Coates et al. (71) Applicants: International Business Machines 4,833,067 A 5/1989 Tanaka et al. Corporation, Armonk, NY (US); JSR 5,126.230 A 6/1992 Lazarus et al. Corporation, Tokyo (JP) 5,185,235 A 2f1993 Sato et al. 5,266.424 A 1 1/1993 Fujino et al. 5,554.312 A 9, 1996 Ward (72) Inventors: Robert D. Allen, San Jose, CA (US); 5,846,695 A 12/1998 Iwata et al. Ramakrishnan Ayothi, San Jose, CA 6,599,683 B1 7/2003 Torek et al. (US); Luisa D. Bozano, Los Gatos, CA 7,585,609 B2 9, 2009 Larson et al. (US); William D. Hinsberg, Fremont, (Continued) CA (US); Linda K. Sundberg, Los Gatos, CA (US); Sally A. Swanson, San FOREIGN PATENT DOCUMENTS Jose, CA (US); Hoa D. Truong, San Jose, CA (US); Gregory M. Wallraff, JP 54143232 8, 1979 JP 58219549 12/1983 San Jose, CA (US) JP 6325.9560 10, 1988 (73) Assignees: International Business Machines OTHER PUBLICATIONS Corporation, Armonk, NY (US); JSR Corporation, Tokyo (JP) Ito et al., Positive/negative mid UV resists with high thermal stability, SPIE 0771:24-31 (1987). (*) Notice: Subject to any disclaimer, the term of this (Continued) patent is extended or adjusted under 35 U.S.C. 154(b) by 99 days. Primary Examiner — Brittany Raymond (74) Attorney, Agent, or Firm — Karen Canaan; CanaanLaw, (21) Appl. No.: 13/775,122 P.C. (22) Filed: Feb. 23, 2013 (57) ABSTRACT Prior Publication Data Provided is a method for developing positive-tone chemically (65) amplified resists with an organic developer solvent having at US 2014/0242526A1 Aug. 28, 2014 least one polyhydric alcohol. Such as ethylene glycol and/or glycerol, alone or in combination with an additional organic (51) Int. C. Solvent, such as isopropyl alcohol, and/or water. The organic GO3F 7/26 (2006.01) solvent developed positive tone resists described herein are GO3F 7/32 (2006.01) useful for lithography pattern forming processes; for produc (52) U.S. C. ing semiconductor devices, such as integrated circuits (IC); CPC ...................................... G03F 7/325 (2013.01) and for applications where basic solvents are not suitable, USPC .......................................................... 430/326 such as the fabrication of chips patterned with arrays of bio (58) Field of Classification Search molecules or deprotection applications that do not require the CPC ......... GO3F 7/0392: G03F 7/20: G03F 7/325 presence of acid moieties. USPC ...... - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 430/322, 326 See application file for complete search history. 36 Claims, 14 Drawing Sheets 630 Siggs -ie- EG (100) p: 3-, -- 2G/PA 70/30) s -A- EGEPA 50/50) -v- EGAAater (90:0 480 - k -Q-TRAH (0.28 N) - 3. : 300- 18 v i A \ ?f: A \ & l, \, W. 18- \, - & - 8.33333333333333339 -g-s-s-s-s-s-s-s-s-s-s-s-s- -------------------------------------------------------------------- 8 O 2 A. 8 20 22 24 28 28 30 32 EDse (milcm) US 8,900,802 B2 Page 2 (56) References Cited 2007,0269749 A1 11/2007 Schenker U.S. PATENT DOCUMENTS OTHER PUBLICATIONS RE42,1287,851,140 B2E 12/20102/2011 TsubakiEgbe Maltabes et al., lx Deep UV Lithography With Chemical Amplifica 2002/0106589 A1 8/2002 Rodney et al. tion for 1-Microti DRAM Production, SPIE 1262:3-7 (1990). U.S. Patent US 8,900,802 B2 f U.S. Patent Dec. 2, 2014 Sheet 2 of 14 US 8,900,802 B2 Kr imaging Results for NORA-MAdMA Resists PA Developer (100); CD - 200 nm S F.G. 2A KrF imaging Results for NORA-MAdMA Resists EG (100) Developer, CD - 200 nm LS F.G. 2B U.S. Patent Dec. 2, 2014 Sheet 3 of 14 US 8,900,802 B2 Krf imaging Results for NORA-MAdMA Resists EGIPA Developer (70/30); CD - 200 nm S FG. 2C Krf imaging Results for NORA-MAdMA Resists & EGIWater Developer (90/10); CD - 200 nm S FG. 2D U.S. Patent Dec. 2, 2014 Sheet 4 of 14 US 8,900,802 B2 60 -- EG (00) -o- EGARA (70:30) 50 -A - EG-IRA 50/50) -v- EGANater (90i40) 40 - ----<-- TMAH (0.26 N} ts 300 d 20 O y \ O - 33-3-3-3-3-3-3-3-3-s-s-s-s 4 6 8 to 12 14 16 18 20 22 24 26 28 30 32 Dose (m.J.lcm) FG. 3 U.S. Patent Dec. 2, 2014 Sheet 5 of 14 US 8,900,802 B2 TMA Developer (0.26N), CD is 60 nm LS FG. 4A E-Beam imaging Results for NORA-MAdMA Resists MA Developer (0.28N), CD is 40 nm S FG. 4B U.S. Patent Dec. 2, 2014 Sheet 6 of 14 US 8,900,802 B2 E-Bear inaging Resuits for NORA-WAdvA Resists EG Developer (100); CD is 60 frn LS F.G. 4C E-Beam imaging Results for NORA-MAdMA Resists EG Developer (100); CD as 40 nm S F.G. D. U.S. Patent Dec. 2, 2014 Sheet 7 of 14 US 8,900,802 B2 i : s - s. n . S U.S. Patent Dec. 2, 2014 Sheet 8 of 14 US 8,900,802 B2 70) -- EG (90) 8) -o- EG/Water (90/10)* &- EG|Water (85.15) 50 -v- EG|Water (75.25) -e- (TMAH) (0.26 N) 400 - 30 20) OO ... XXX & X { -8-8-8-8-8-8 4 6 & 10 12 4 6 18 20 22 24 26 28 30 32 Dose indicin) F.G. 6 U.S. Patent Dec. 2, 2014 Sheet 9 of 14 US 8,900,802 B2 Etv imaging Resuits for PS-AAAA Resists Resis fo: S-AdA Resists EG leveloper 100); C is 32 nm S EG Reveloper (GO), CE - 36 am S FG. A FG. 78 U.S. Patent Dec. 2, 2014 Sheet 10 of 14 US 8,900,802 B2 9 O - - - - - --------------- -----f------------ -----r-- - - - - - - - --------- -----frn -----r - - - - - - - - -f -8- NBHFA. AAAMAResist (EMA; 26 N) -O- NEHFA-RAAdMA Resis: (Eg: 103} t ~&^ NBHFA. AAdiA Resist (ESAPA is 70:30) ...K. NEHFA. AchAA Resis: EGFIFA : 50:50 r KX -(- NBHA - EcoMA Resist (EGPA - 70:30) - 8s - R.A. --> -- hid-MCpl.A Resist (EGl; A = 70:33} 23 KX \\ N -- He-MCpi/A Resist (EGl:PA = 70:30) - , ( V. 3 8-os res f -o- d -c.c. *- C - C - C - C - C - C - ---.E is \W. i A - : - . &e $3. &gs:som - & \e s *:::crease - &x- skissez-85-stressras, & 3 & sers: 2 - - 8 2 4 6 8 20 22 24 28 28 3 U.S. Patent Dec. 2, 2014 Sheet 11 of 14 US 8,900,802 B2 FO) 600-siss -- NBHFA - MAdMA Resist (EGEPA : 70:30) - as A-AA A ~0- N8HFA. AAiMA f\8HFA-8:Cpi/A A& iResist (EGPA : 70:30) SO) -A- N84FA - EcEcMA Resist (EGPA is 70:30) - A -v- He-MCpMA Resist (EGAPA - 70:30) 400 - y -K- He-MCpl.A Resist (EGPA is 50:50) | \ sa 300 1 \ - : o v. -d AéréY ré-a-3-3-&-8-é-a -g-g-ga-gi-a-g-g-e- - ---------------------------- 2 4 6 8 2 4 6 8 20 22 24, 26 Dose (m3/cm’) FG. 9 U.S. Patent Dec. 2, 2014 Sheet 12 of 14 US 8,900,802 B2 ST; U.S. Patent Dec. 2, 2014 Sheet 14 of 14 US 8,900,802 B2 Kf CQiast Clive Data for NORA - A.A Resists f -R- Glycerol (400) 600 Q -O-Glycerol Water 80/20) -A'r Glycero, PA 70/30) SO - v \\y/ -v- Glycero, PA 50/50) S 400 - Soros,'a-o-o-o-o-o-o-o-o-o Y "- sis - a -a -a- fs 3. 2O - { 8 8 2 4 6 S 2 22 24 28 28 S. 32 FG. 2 US 8,900,802 B2 1. 2 POSITIVE TONE ORGANIC SOLVENT water or another organic solvent. In one embodiment, the DEVELOPED CHEMICALLY AMPLIFED developer comprises a mixture of ethylene glycol and isopro RESIST pyl alcohol. In another embodiment, the developer comprises a mixture of ethylene glycol and water. In a further embodi JOINT RESEARCH AGREEMENT ment, the developer comprises a mixture of glycerol and isopropyl alcohol. The invention described herein is subject to a joint research In another embodiment, the chemically amplified resist agreement between International Business Machines Corpo comprises a composition selected from the group consisting ration and JSR Corporation. 10 of molecular glasses, polyhydroxystyrenes, styrenes having one or more pendant hexafluoroalcohol groups, acrylates, TECHNICAL FIELD methacrylates, and methacrylate fluoroalcohols. The present invention relates generally to photoresists. In one embodiment, the chemically amplified resist com More specifically, the present invention relates to positive prises styrenic NORIA molecular glass protected with a tone resists that are capable of being developed with polyhy 15 2-methyl-2-adamantyl group (NORIA-MAdMA). dric alcohol-based solvents for high resolution imaging. In another embodiment, the chemically amplified resist comprises the polyhydroxystyrene polymer, poly(4-hy BACKGROUND OF THE INVENTION droxystyrene-co-2-methyl-2-adamanty1 methacrylate) As semiconductor device features continue to shrink in (PHS-MAdMA). size, the task of meeting photoresist performance require In a further embodiment, the chemically amplified resist ments for high resolution, low line edge roughness (LER) and comprises a methacrylate-fluoroalcohol polymer selected high photo speed grows increasingly difficult. The challenges from the group consisting of poly(5-acryloyloxy-2,6-norbor in simultaneously meeting the requirements for resolution, nanecarbolactone-co-2-methyl-2-adamantyl methacrylate LER, and sensitivity are known in the art as the “RLS 25 co-2-1,1,1-trifluoro-2'-(trifluoromethyl)-2'-hydroxy)pro Tradeoff.” Current generation chemically amplified photore pyl-3-norbornyl methacrylate) (NBHFA-MAdMA); poly(5- sists, designed to be developed in alkaline base, are capable of acryloyloxy-2,6-norbornanecarbolactone-co-2-methyl-2- high photo speeds, but exhibit unsatisfactory resolution and cyclopentay1 methacrylate-co-2-1,1,1-trifluoro-2'- LER as feature sizes approach 20 nm.
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