US006482565Bl  (12)  United States Patent  Jung et al.  (10)  Patent No.:  US 6,482,565 Bl  (45)  Date of Patent:  Nov.  19, 2002  (54)  PHOTORESIST CROSS-LINKER AND  PHOTORESIST COMPOSITION  COMPRISING THE SAME  (75)  Inventors:  Jae Chang Jung; Keun Kyu Kong;  Myoung Soo Kim; Hyoung Gi Kim;  Hyeong Soo Kim; Ki Ho Baik,  all of  Kyoungki-do  (KR)  (73)  Assignee:  Hyundai Electronics Industries Co.,  Ltd. (KR)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (21)  Appl. No.:  09/448,964  (22)  Filed:  Nov. 24, 1999  (51)  Int. Cl.7  ................................................  G03F 7/004  (52)  U.S. Cl.  ....................  430/270.1;  430/325; 526/266;  526/320; 526/271; 549/347; 549/369; 549/430  (58)  Field of Search  .............................. 430/270.1, 325;  549/347, 369, 430; 526/266, 320, 271  (30)  Foreign Application Priority Data  Nov. 27, 1998  Feb. 22, 1999  (KR) ............................................ 98-51356  (KR) ............................................. 99-5825  3,468,857 A  5,049,463 A  *  5,059,698 A  5,412,041 A  *  6,060,212 A  *  9/1969  9/1991  10/1991  5/1995  5/2000  Graver ...................... 260/80.3  Kato et al. .................... 430/49  Schulthess et al. ......... 549/375  Lesko et al. ................ 525/340  McCulloch et al. ..... 430/270.1  DE  EP  EP  EP  GB  JP  JP  WO  3714276 Al  0 347 381 Al  0 422 888 A2  875 789 Al  922747  4-5040054  5-216294  WO 99/61497  11/1988  12/1989  4/1991  11/1998  4/1963  *  12/1970  *  8/1993  12/1999  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OIBER PUBLICATIONS  1970: 100663 Ca plus Abstract.*  1971:65746 Caplus Abstract.*  1967:10943 Caplus Abstract.*  1984:10943 Caplus Abstract.*  1972:552633 Caplus Abstract.*  1970:477088 Caplus Abstract.*  1998:604944 Caplus Abstract.*  1971:112779 CaplusAbstract of JP 45040054, Dec. 1970.*  1970:510169 Caplus Abstract to Ouchi, T. et al. Kogyo  Kagaku Zasshi, 1970, 73(7), 1717-19.*  Anionic polymerizabilities of 2-vinyl-1,3-dioxolane and  2-vinyl-1,3---dioxane, Yamashita, N. et al., J. Polym.Sci.,  Polym.Lett.Ed., 1979, 17, 521-6.*  1994:496066 Caplus Abstract of JP 5216294, Aug. 1993. *  Chemical Abstract No. 131:337017 & JP 11315075.  Chemical Abstract No. 128:295769 & JP 10088419.  Chemical Abstract No. 118:102825 & J. Maslinska-Solich  et al., React. Polym. (1992), 18(2), 159-166.  J.Maslinska-Solich et al., "Studies on Co(II) and Mn(II)  complesex of some maleic anhydride copolymers,"  Reactive  Polymers,  vol. 18, 1992, pp. 159-166.  * cited by examiner  Primary Examiner-Rosemary  E. Ashton  (74)  Attorney, Agent, or  Firm-Townsend and Townsend  and Crew  LLP  The present invention relates to a cross-linker for use in a  photoresist which is suitable for a photolithography process  using KrF (248 ru), ArF (193 nm), E-beam, ion beam or  EUV light source. According to the present invention, pre› ferred cross-linkers comprise a copolymer having repeating  units derived from: (i) a compound represented by following  Chemical Formula 1 and/or (ii) one or more compound(s)  selected from the group consisting of acrylic acid, meth› acrylic acid and maleic anhydride.  wherein,  R$_{1}$, R 2  and  R  individually represent straight or  branched C$_{1}$ _ $_{10 }$alkyl, straight or branched C$_{1}$ _ $_{10 }$ester,  straight or branched C$_{1}$ _ $_{10 }$ketone, straight or branched  C$_{1}$ _ $_{10 }$carboxylic acid, straight or branched C$_{1}$ _ $_{10 }$acetal,  straight or branched C$_{1}$ _ $_{10 }$alkyl including at least one  hydroxyl group, straight or branched C$_{1}$ _ $_{10 }$ester includ› ing at least one hydroxyl group, straight or branched  C$_{1}$ _ 10  ketone including at least one hydroxyl group,  straight or branched C$_{1}$ _ $_{10 }$carboxylic acid including at  least one hydroxyl group, and straight or branched  C$_{1}$ _ $_{10 }$acetal including at least one hydroxyl group;  R$_{3 }$ represents hydrogen or methyl; m represents  O  or 1; and  n represents a number of 1 to 5.  16 Claims, 5 Drawing Sheets  (57)  ABSTRACT  <Chemical Formula 1> 