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 5a to 5e:
E3-A2-L5-M5-L6-M6-L7-M7-L8-A3-E4 Formula 5a
E3-M5-L6-M6-L7-M7-L8-A3-E4 Formula 5b
E3-A2-L5-M5-L6-M6-L7-M7-E4 Formula 5c
E3-A2-L6-M6-L7-M7-L8-A3-E4 Formula 5d
E3-A2-L5-M5-L6-M6-L7-A3-E4. Formula 5e
wherein in Formulae 5a to 5e,
M5 and M7 are each independently an arylene group represented by Formulae 3a to 3j,
M6 is a naphthalene group represented by Formulae 3g, 3i, and 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;
A2 and A3 are each independently ethylene, propylene, 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;
L5, L6, L7, and L8 are each independently —C(═O)O— or —OC(═O)—, and
E3 and E4 are each independently an epoxy-containing group.
2 . The epoxy compound of claim 1 , wherein A2 and A3 are each independently 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, and
L5, L6, L7, and L8 are each independently —C(═O)O— or —OC(═O)—.
3 . The epoxy compound of claim 1 , wherein E3 and E4 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
M5 and M7 are each independently an arylene group represented by Formula 7a to 7j,
M6 is a naphthalene group represented by Formula 7h to 7j, and
E3 and E4 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 a melting point of the epoxy compound represented by Formulae 5a to 5e is about 200° C. or lower.
6 . An epoxy resin composition comprising:
the epoxy compound of claim 1 ; and
a curing agent.
7 . The epoxy resin composition of claim 6 , wherein a metal ion content of the resin composition is about 10 parts per million or less.
8 . The epoxy resin composition of claim 6 further comprising a filler, wherein the filler is an inorganic filler, an organic filler, or a combination thereof.
9 . The epoxy resin composition of claim 8 , 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.
10 . A semiconductor device comprising
a substrate;
a semiconductor; and
a cured product of the epoxy resin composition of claim 6 .
11 . The semiconductor device of claim 10 , wherein a thermal conductivity of the cured products of the epoxy resin compositions is about 0.25 Watts per meter-Kelvin or more.
12 . An electronic device comprising:
a substrate;
an electronic component; and
a cured product of the epoxy resin composition of claim 10 .
13 . The electronic device of claim 12 , wherein a thermal conductivity of the cured products of the epoxy resin compositions is about 0.25 Watts per meter-Kelvin or more.
14 . An article comprising
a substrate; and
a cured product of the epoxy resin composition of claim 6 disposed on the substrate.
15 . The article of claim 14 , wherein a thermal conductivity of the cured products of the epoxy resin compositions is about 0.25 Watts per meter-Kelvin or more.
16 . An epoxy compound represented by one of Formulae 10e to 10h and 10m to 10p
17 . An epoxy resin composition comprising:
the epoxy compound of claim 16 ; and
a curing agent.
18 . A semiconductor device comprising
a substrate;
a semiconductor; and
a cured product of an epoxy resin composition of claim 17 .
19 . An electronic device comprising:
a substrate;
an electronic component; and
a cured product of an epoxy resin composition of claim 17 .
20 . An article comprising
a substrate; and
a cured product of an epoxy resin composition of claim 17 .