(IO)  Patent No.:  US 10,520,820 B2  Dec. 31, 2019  (45)  Date of Patent:  Liu et al.  (54)  NEGATIVE TONE DEVELOPER FOR  EXTREME ULTRAVIOLET LITHOGRAPHY  (56)  References Cited  U.S. PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  20 Claims, 5 Drawing Sheets  Related U.S. Application Data  (65)  Prior Publication Data  c12)  United States Patent  USO 10520820B2  John  J  Biafore et al., "Statistical Simulation of Resist at EUV and  ArF," Proceedings of SPIE-The International Society for Optical  Engineering-Mar. 2009, vol. 7273 (11 pages).  Primary Examiner  - Christopher G Young  (74)  Attorney, Agent, or Firm  - Haynes and Boone, LLP  The present disclosure provides NTD developers and cor› responding lithography techniques that can overcome reso› lution, line edge roughness (LER), and sensitivity (RLS)  tradeoff barriers particular to extreme ultraviolet (EUV)  technologies, thereby achieving high patterning fidelity for  advanced technology nodes.  An exemplary lithography  method includes forming a negative tone resist layer over a  workpiece; exposing the negative tone resist layer to EUV  radiation; and removing an unexposed portion of the nega› tive tone resist layer in a negative tone developer, thereby  forming a patterned negative tone resist layer. The negative  tone developer includes an organic solvent having a log P  value greater than 1.82. The organic solvent is an ester  acetate derivative represented by R$_{1}$COOR$_{2}$ .  R$_{1 }$ and R$_{2 }$ are  hydrocarbon chains having four or less carbon atoms. In  some implementations, R$_{1}$ ,  R$_{2}$ ,  or both R$_{1 }$ and R$_{2 }$ are propyl  functional groups, such as n-propyl, isopropyl, or 2-meth› ylpropyl.  US 2018/0341177 Al  Nov. 29, 2018  8,796,666 Bl  8,900,802 B2  9,012,132 B2  9,028,915 B2  9,093,530 B2  9,146,469 B2  9,213,234 B2  9,223,220 B2  9,256,133 B2  9,459,536 Bl  9,536,759 B2  9,548,303 B2  8/2014 Huang et al.  12/2014 Allen et al.  4/2015 Chang  5/2015 Chang et al.  7/2015 Huang et al.  9/2015 Liu et al.  12/2015 Chang  12/2015 Chang  2/2016 Chang  10/2016 Laietal.  1/2017 Yang et al.  1/2017 Lee et al.  (71)  Applicant:  Taiwan Semiconductor  Manufacturing Co., Ltd.,  Hsinchu  (TW)  (72)  Inventors:  Chen-Yu Liu,  Kaohsiung (TW);  Wei-Han Lai,  New Taipei (TW);  Tzu-Yang Lin,  Tainan (TW);  Ming-Hui  Weng,  New Taipei (TW);  Ching-Yu  Chang,  Yilang County (TW);  Chin-Hsiang Lin,  Hsin-Chu (TW)  (73)  Assignee:  TAIWAN SEMICONDUCTOR  MANUFACTURING CO., LTD.,  Hsinchu (TW)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 155 days.  (21)  Appl. No.:  15/694,222  (22)  Filed:  Sep. 1, 2017  (60)  Provisional application No. 62/511,758, filed on May  26, 2017.  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ................  G03F  71325  (2013.01);  G03F 7/16  (2013.01);  G03F 7/20  (2013.01);  G03F 7/2004  (2013.01)  (58)  Field of Classification Search  CPC . G03F 7/16; G03F 7/20; G03F 7/2004; G03F  7/038; G03F 7/325  USPC ......................... 430/296, 325, 330, 331, 942  See application file for complete search history.  G03F  7132  G03F  7116  G03F  7120  (2006.01)  (2006.01)  (2006.01) 