) BPA ECN EPICLON N-600 Fig.2 Fig Fig.4 DCPD EPICLON HP-7200 ECN Fig.5 DCPD ECN DCPD 6-28) Table 1 BPA Fig.4 Chemical str

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1 Relation between Chemical Structures and Characteristics on Epoxy Resins OGURA Ichiro This paper presents the study of the relation between chemical structures and characteristics of epoxy resins with respect to the technological trends in recent electronics epoxy applications and DIC novel high performance epoxy resins. The aim of this study was to reveal this relation in order to quickly and efficiently develop novel high performance epoxy resins without a lot of trial and error. We reanalyzed and rearranged the data obtained by previous R&D activities from the viewpoint of this theme in order to frame the theories described in this paper. 1 1) Fig.1 [A] [B] [C] BPA [A] ECN [B] [A] [B] Fig.1 Basic chemical structures of glycidyl ether type epoxy resins. DIC Technical Review No.7 /

2 ) BPA ECN EPICLON N-600 Fig.2 Fig Fig.4 DCPD EPICLON HP-7200 ECN Fig.5 DCPD ECN DCPD 6-28) Table 1 BPA Fig.4 Chemical structure of dicyclopentadiene (DCPD) type epoxy resin. Fig.2 Relation between molecular weight and softening point / melt viscosity on BPA type epoxy resins. Fig.5 Relation between softening point and melt viscosity regarding ECN and DCPD type epoxy resins. Table 1 Effect of Hydrogen Bond on Viscosity Fig.3 Relation between molecular weight and softening point / melt viscosity on cresol novolac type epoxy resins (ECN). 2 DIC Technical Review No.7 / 2001

3 29) ECN Fig.1[C] BGA Fig.6 EPICLON EXA ,7-2,7-DHN Table 2 2,7-2,7-DHN 30-33) (EPICLON EXA-7035) 1,5-1,5-DHN Fig.7 1,5-DHN [a] [a][b][c] ) Fig.6 Chemical structure of tetra-functional naphthalene type epoxy resin. 3.2 Table 2 Difference of Molecular Structures of Multifunctional Naphthalene Type Epoxy Resins Derived from DHN Isomers Fig.7 Adjustment method of crystalline type epoxy resin's mp by using the resonance effect among different kinds of epoxy resin with similar structures. DIC Technical Review No.7 /

4 3.2.1 Table 3 EPICLON HP-4032 BPA Fig ) Table Fig.9 BPA Fig.10 Table 4 Effect of Substituted Group at Epoxy Group on Curability Table 3 Comparison of Gel Time between Naphthalene and BPA Type Epoxy Resin Fig.9 Effect of epoxy group content (EEW) on curability. Fig.8 Three-dimensional chemical structure model of naphthalene type epoxy resin with smaller steric hindrance (plane skeleton). Fig.10 Effect of functionality on curability regarding phenol novolac type epoxy resins (EPN). 4 DIC Technical Review No.7 / 2001

5 3.2.4 Table 5 BPA Fig.11 - Table 5 Effect of Hydroxyl Group on Curability 3.3 Tg Tg Tg Tg Tg Tg Tg Table 6 BPA BPF Tg Tg BPA BPF Tg pp EPICLON EXA-4700 Tg Table 7 ECN Tg 300 Tg BPA EPICLON EXA BPA Table 8 BPA Tg Tg Table 6 Comparison of Tg among Naphthalene, BPA and BPF Type Epoxy Resin Fig.11 Effect of impurities (Hyd.Cl and -Glycol) on curability. DIC Technical Review No.7 /

6 Tg Tg Fig.12 Tg BPA Table 7 Comparison of Tg between Tetra-functional Naphthalene and ECN Type Epoxy Resin with Same Viscosity ( ) Tg Table 9 BPA Tg Tg Fig.13 ECN Tg Tg Tg DCPD Fig.14 Tg ECN DCPD EPICLON HP-7200 DCPD ECN 1/3 Tg DCPD Table 9 Comparison of Tg between Two Kinds of BPA Type Epoxy Resins with Different E.E.W. Table 8 Comparison of Tg between Normal and Hydrogenated BPA Type Epoxy Resin Fig.12 Difference of Tg between imidazole system and acid-anhydride system. Fig.13 Relation between functionality and Tg regarding ECN. 6 DIC Technical Review No.7 / 2001

7 / DCPD Tg Tg DCPD ) Fig.15 Fig.16 Fig.17 Fig.14 Relation between cross-linking density and Tg regarding ECN and DCPD type epoxy resin. Fig.16 Relation between E.E.W. and moisture absorption. Fig.15 Chemical structures of various alkyl phenol novolac type epoxy resins. Fig.17 Relation between hydroxyl content in cured resin and moisture absorption. DIC Technical Review No.7 /

8 3.4.2 Table Table 11 Table 10 Effect of Hydrophilic Group on Moisture Absorption Table 11 Comparison of Moisture Absorption of Various Naphthalene Type Epoxy Resins Derived from Monoand Dihydroxy Naphthalene Tg Fig.18 Tg Tg Tg DCPD EPICLON HP Tg 10 DCPD DCPD Tg Tg Fig.19 Tg ECN DCPD Fig.18 Relation between Tg and moisture absorption. 8 DIC Technical Review No.7 / 2001

9 Tg DCPD ( / ) 1 - ( / ) Clausius-Mossotti 45) :Molar polarization :Molar volume Table 12 46) Fig.20 Fig.21 Fig.19 Relation between Tg and moisture absorption regarding ECN and DCPD type epoxy resin. Fig.20 Relation between E.E.W. and dielectric constant. Table 12 Molar Polarization and Molar Volume of Various Functional Groups Fig.21 Relation between hydroxyl content in cured resin and dielectric constant. DIC Technical Review No.7 /

10 Clausius-Mossotti Tg Tg Tg Fig.22 Tg =3.0 Tg 80 DCPD Tg Tg Fig.22 DCPD Fig.23 DCPD Tg Tg DCPD DCPD Fig.22 Relation between Tg and dielectric constant. Fig.23 Comparison of relation between Tg and dielectric constant between alkyl phenol novolac type and DCPD type epoxy resins (with different functionalities). Table 13 Causal Relationship between Features of Chemical Structures and Characteristics Regarding Epoxy Resins 10 DIC Technical Review No.7 / 2001

11 4 Table 13 Tg / 24 1) ) K. Iko,Y.Nakamura, Encapsulating Resins for Semiconductors, IEEE Electrical Insukation Magazine, /August, 6(4) (1990) 3) Electronic Packaging Technology,8 5 85(1992) 4), Semiconductor World No.9,p (1992) 5),28(2)(1990) 6) ) 7) ) 8) ) ) (1998) 11) (1998) 12) (1997) 13) (1997) 14) (1997) 15) (1997) DIC Technical Review No.7 / ) (1998) 17) (1997) 18) (1996) 19) (1995) 20) (1995) 21) (1995) 22) (1995) 23) (1994) 24) (1995) 25) 17(2)29 (1996) 26) DIC Technical Review (3) ) ) ) ) 30) ) 31) ) ) 33) I. Ogura, K. Takahashi, Proc.3rd Japan International SAMPE Symposium, Vol.1(1991) 34) (1998) 35) DIC Technical Review (5) ) ) p ),,,, :, 11 2 (1990) 39),,,15(1)(1994) 40) J.B.Enns,J.K.Gillham J. Appl. Polym. Sci., 28, 2831 (1983) 41) V.B. Gupta, L. T. Drazal Appl. Polym. Sci., 30, 4467 (1985) 42) E. Morel, V. Bellenger, J. Verdu, Polym., 26, 1719 (1985) 43) C. Carfagna, A. Apicella, L. Nicolais J. Appl. Polym. Sci., 27, 105 (1982) 44) V.Bellenger, J.Verdu,J.Mater. Sci., 24, 63 (1989) 45) D. W. VanKrevelen, : "Properties of Polymer, 2nd Ed.", pp , Scientific Publishing Company (1991) 46) I. Ogura, High Dielectric Constant Material and Their Low Dielectric Constant Applications, Low Dielectric Constant Epoxy Resin, Academic Press (1999) 11

12 OGURA Ichiro 12 DIC Technical Review No.7 / 2001

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