Epoxy compound, composition prepared therefrom, semiconductor device prepared therefrom, electronic device prepared therefrom, article prepared therefrom, and method of preparing epoxy compound
An epoxy compound having an aromatic ring represented by Formula 1 or Formula 2, a composition prepared from the epoxy compound, a semiconductor device prepared from the epoxy compound, an electronic device prepared from the epoxy compound, an article prepared from the epoxy compound, and a method of preparing the epoxy compound: E1-(M1) a1 -(L1) b1 -(M2) a2 -L2-A1-L3-(M3) a3 -(L4) b2 -(M4) a4 -E2 Formula 1 E3-(A2) c1 -(L5) b3 -(M5) a5 -L6-(M6) a6 -L7-(M7) a7 -(L8) b4 -(A3) c2 -E4 Formula 2 In Formulae 1 and 2, M1, M2, M3, M4, M5, M6, M7, A1, A2, A3, L1, L2, L3, L4, L5, L6, L7, L8, E1, E2, E3, E4, a1, a2, a3, a4, a5, a6, a7, b1, b2, b3, b4, c1, and c2 are the same as defined in the detailed description.
1. An epoxy compound including an aromatic ring represented by one of Formulae 4a to 4f:
E1-M2-L2-A1-L3-M3-E2 Formula 4a
E1-M1-L1-M2-L2-A1-L3-M3-E2 Formula 4b
E1-M2-L2-A1-L3-M3-L4-M4-E2 Formula 4c
E1-M1-L1-M2-L2-A1-L3-M3-L4-M4-E2 Formula 4d
E1-M1-M2-L2-A1-L3-M3-L4-M4-E2 Formula 4e
E1-M1-L1-M2-L2-A1-L3-M3-M4-E2 Formula 4f
wherein, in Formulae 4a to 4f,
M1 and M4 are each independently an arylene group represented by Formulae 3a to 3j,
M2 and M3 are each independently a naphthalene group represented by Formulae 3g to 3j,
wherein, in Formulae 3a to 3j,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are each independently a hydrogen, a halogen, a hydroxy group, or a substituted or unsubstituted C1-C10 alkyl group;
A1 is a substituted or unsubstituted C4-C12 alkylene group, a substituted or unsubstituted C4-C12 alkenylene group, a substituted or unsubstituted C4-C12 alkynylene group, a substituted or unsubstituted C4-C12 alkadienylene group, or a (poly)oxyalkylene group comprising a substituted or unsubstituted C1-C5 alkylene group;
L1, L2, L3, and L4 are each independently —C(═O)O— or —OC(═O)—, and
E1 and E2 are each independently an epoxy-containing group.
2. The epoxy compound of claim 1 , wherein A1 is an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decylene group, an undecylene group, a dodecylene group, a butadienylene group, a pentadienylene group, a hexadienylene group, a heptadienylene group, an octadienylene group, a nonadienylene group, a decadienylene group, an undecadienylene group, a dodecadienylene group, or —(CH 2 O)p-, where p is a real number of 1 to 10.
3. The epoxy compound of claim 1 , wherein E1 and E2 are each independently an epoxy-containing group represented by Formulae 6a to 6f:
wherein, in Formulae 6a to 6f,
R a , and R b are each independently a hydrogen, a halogen, a hydroxy group, or a substituted or unsubstituted C1-C10 alkyl group,
n1 is 2 to 10, and n2 is 1 to 10.
4. The epoxy compound of claim 1 , wherein
M1 and M4 are each independently an arylene group represented by Formula 7a to 7j,
M2 and M3 are each independently a naphthalene group represented by Formula 7g to 7j, and
E1 and E2 are each independently an epoxy-containing group represented by Formulae 8a to 8f:
wherein, in Formulae 8a to 8f, n1 is 1 to 10, and
n2 is 2 to 10.
5. The epoxy compound of claim 1 , wherein the epoxy compound represented by Formula 1 is represented by one of Formulae 9a 9o:
6. The epoxy compound of claim 1 , wherein a melting point of the epoxy compounds represented by one of Formulae 4a to 4f is about 200° C. or lower.
7. An epoxy resin composition comprising:
the epoxy compound of claim 1 ; and
a curing agent.
8. The epoxy resin composition of claim 7 , wherein a metal ion content of the resin composition is about 10 parts per million or less.
9. The epoxy resin composition of claim 7 further comprising a filler, wherein the filler is an inorganic filler, an organic filler, or a combination thereof.
10. The epoxy resin composition of claim 9 , wherein an amount of the filler is in a range of about 20 weight % to about 99 weight % based on the total weight of the epoxy resin composition.
11. A semiconductor device comprising
a substrate;
a semiconductor; and
a cured product of the epoxy resin composition of claim 7 ,
wherein the cured product is a sealing portion, a substrate portion, a reinforcement portion, or an adhesive portion, of the semiconductor device.
12. The semiconductor device of claim 11 , wherein a thermal conductivity of the cured product is about 0.25 Watts per meter-Kelvin or more.
13. An electronic device comprising:
a substrate;
an electronic component; and
a cured product of the epoxy resin composition of claim 7 ,
wherein the cured product is a sealing portion, a substrate portion, a reinforcement portion, or an adhesive portion, of the semiconductor device.
14. The electronic device of claim 13 , wherein a thermal conductivity of the cured product is about 0.25 Watts per meter-Kelvin or more.
15. An article comprising
a substrate; and
a cured product of the epoxy resin composition of claim 7 ,
wherein the cured product is a sealing portion, a substrate portion, a reinforcement portion, or an adhesive portion, of the article.
16. The article of claim 15 , wherein a thermal conductivity of the cured product is about 0.25 Watts per meter-Kelvin or more.