US006368773Bl  (12)  United States Patent  Jung et al.  (10)  Patent No.:  US 6,368,773 Bl  (45)  Date of Patent:  Apr. 9, 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; Jin  Soo Kim,  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.:  09/448,916  (22)  Filed:  Nov. 24, 1999  (30)  Foreign Application Priority Data  (51)  Int. Cl.7  ................................................  G03F 7/027  (52)  U.S. Cl.  ................................  430/281.1;  430/270.1;  430/325  (58)  Field of Search  ........................... 430/270.1, 281.1,  430/325; 526/271, 317.1, 333; 568/594,  596  Nov. 27, 1998  Feb. 22, 1999  (KR) ............................................ 98-51355  (KR) ............................................. 99-5823  DE  EP  GB  3714276 Al  0 100 071 A2  695789  11/1988  2/1984  8/1953  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OIBER PUBLICATIONS  Academic Press Dictionary of Science and Technology  definitions of acetal, alkyl, carboxylic acid, ester and  ketone.*  2,866,813 A  *  12/1958 McTeer ...................... 260/488  3,468,857 A  9/1969 Graver ...................... 260/80.3  4,562,009 A  *  12/1985 Lysenko et al. ... ... ... 260/465.6  4,579,979 A  *  4/1986 Andrade et al. ............ 568/596  4,607,126 A  *  8/1986 Sajtos ........................ 568/385  5,200,051 A  *  4/1993 Cozzette et al. ............ 204/403  5,290,894 A  *  3/1994 Melrose et al. ............. 526/315  5,645,969 A  *  7/1997 Matsuo et al. .............. 430/165  6,121,399 A  *  9/2000 Webster et al. ............. 525/320  6,184,263  Bl  *  2/2001 Narang et al. ................ 522/11  CA90:138248, Sastre et al,Angew. Makromol. Chem. 1978,  73, 25-33.*  U.S. application No. 09/448,964, Jung et al., filed Nov. 24,  1999.  Chemical Abstract No. 110:96578.  * cited by examiner  Primary Examiner-Rosemary  Ashton  (74)  Attorney, Agent, or  Firm-Townsend and Townsend  and Crew  LLP  The present invention relates to a cross-linker for photoresist  compositions which is suitable for a photolithography pro› cess using KrF (248 mn), ArF (193 mn), E-beam, ion beam  or EUV light sources. Preferred cross-linkers, according to  the present invention, comprise a copolymer of (i) a com› pound represented by following Chemical Formula 1 and/or  (ii) one or more compound(s) selected from the group  consisting of acrylic acid, methacrylic acid and maleic  anhydride.  (57)  ABSTRACT  wherein,  R$_{1 }$ and  R$_{2 }$ 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; and  R$_{3 }$ represents hydrogen or methyl.  10 Claims, 12 Drawing Sheets  <Chemical Formula 1> 