Amine-based curing agents, and compositions, semiconductor packages, and electronic devices including the same

Patent metadata

Field	Value
Publication number	US-12404361-B2
Application number	US-202217935886-A
Country	US
Kind code	B2
Filing date	Sep 27, 2022
Priority date	Sep 28, 2021
Publication date	Sep 2, 2025
Grant date	Sep 2, 2025

Abstract

An amine-based curing agent including a compound represented by Chemical Formula 1, and a composition including the curing agent, and a semiconductor package, and an electronic device prepared with the composition.

The definition of Chemical Formula 1 is as described in the detailed description.

First claim

What is claimed is:

1. An amine-based curing agent, comprising a compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
R 11 , R 12 , R 21 , and R 22 are each independently hydrogen, a halogen, a C1 to C20 alkyl group, a C1 to C20 heteroalkyl group, a C1 to C20 haloalkyl group, a C1 to C20 alkoxy group, or a C6 to C10 aryl group,
A 1 is —CR a =CR b —, —N═CR c —, —N═N—, or —CR d =N—, wherein R a , R b , R c , and R d are each independently hydrogen, a C1 to C10 alkyl group, or a C1 to C10 haloalkyl group,
L 11 and L 12 are each independently —C(═O)O—, —OC(═O)—, —O—C(═O)O—, —C(═O)—, —CR e =CR f —C(═O)—, —S(═O)—, —CR g =N—, —NR h C(═O)O—, —C(═O)NR i —, or —OC(═O)NHS(═O)O—, wherein R e , R f , R g , R h , and R i are each independently hydrogen, a C1 to C10 alkyl group, or a C1 to C10 haloalkyl group,
Ar 11 and Ar 12 are each independently a substituted or unsubstituted C6 to C30 arylene group, C2 to C30 heteroarylene group, or a combination thereof, and
n1 and n2 are each independently an integer of greater than or equal to 2.

2. The amine-based curing agent of claim 1 , wherein
in Chemical Formula 1, Ar 11 and Ar 12 are each independently represented by Chemical Formulas 1A to 1I:

wherein, in Chemical Formulas 1A to 1I,
R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , and R 37 are each independently hydrogen or a C1 to C10 alkyl group,
X 1 and X 2 are each independently CR x , N, P, or As, wherein R x is hydrogen, a C1 to C10 alkyl group, or a C1 to C10 haloalkyl group,
Y 1 and Y 2 are each independently O, S, Se, or Te,
a1, a2 and a3 are each independently an integer of 0 to 4,
a4 and a5 are each independently an integer of 0 to 3, and
* is a linking point.

3. The amine-based curing agent of claim 1 , wherein
in Chemical Formula 1, Ar 11 and Ar 12 are the same or different aromatic moieties.

4. The amine-based curing agent of claim 1 , wherein
in Chemical Formula 1, an L 11 -Ar 11 bond and an Ar 11 -A 1 bond are in a meta position or a para position to each other, and independently, an L 12 -Ar 12 bond and an Ar 12 -A 1 bond are in a meta position or a para position to each other.

5. The amine-based curing agent of claim 1 , wherein
the compound represented by Chemical Formula 1 comprises a compound represented by Chemical Formula 2:

wherein, in Chemical Formula 2,
R 11 , R 12 , R 21 , R 22 , A 1 , L 11 , L 12 , n1, and n2 are the same as in Chemical Formula 1,
R 31 and R 32 are each independently hydrogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, or a C6 to C10 aryl group, and
a1 and a2 are each independently an integer of 0 to 4.

6. The amine-based curing agent of claim 1 , wherein
the compound represented by Chemical Formula 1 comprises a compound represented by Chemical Formula 3:

wherein, in Chemical Formula 3,
R 11 , R 12 , R 21 , R 22 , A 1 , L 11 , L 12 , n1 and n2 are the same as in Chemical Formula 1,
R 34 , R 35 , R′ 34 , and R′ 35 are each independently hydrogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, or a C6 to C10 aryl group, and
a4, a5, a4′ and a5′ are each independently an integer of 0 to 3.

7. The amine-based curing agent of claim 1 , wherein
in Chemical Formula 1, n is in the range of 2 to 12.

8. A composition comprising the amine-based curing agent of claim 1 and an epoxy compound.

9. The composition of claim 8 , wherein
the epoxy compound is a compound represented by Chemical Formula 4:

wherein, in Chemical Formula 4,
R 41 and R 42 are each independently hydrogen, a halogen, a C1 to C20 alkyl group, a C1 to C20 heteroalkyl group, a C1 to C20 haloalkyl group, a C1 to C20 alkoxy group, or a C6 to C10 aryl group,
A 11 and A 12 are —CR a =CR b —, —N═CR c —, —N═N—, or —CR d =N—, wherein R a , R b , R c and R d are each independently hydrogen, a C1 to C10 alkyl group, or a C1 to C10 haloalkyl group,
L 21 , L 22 , L 31 , and L 32 are each independently —C(═O)O—, —OC(═O)—, —O—C(═O)O—, —C(═O)—, —CR e =CR f —C(═O)—, —S(═O)—, —CR g =N—, —NR h C(═O)O—, —C(═O)NR hi —, or —OC(═O)NHS(═O)O—, wherein R e , R f , R g , R h , and R i are each independently hydrogen, a C1 to C10 alkyl group, or a C1 to C10 haloalkyl group,
Ar 21 , Ar 22 , Ar 31 , and Ar 32 are each independently a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C 2 to C30 heteroarylene group, or a combination thereof,
E 1 and E 2 are each independently an epoxy-containing group, and
n is each independently an integer of greater than or equal to 2.

10. The composition of claim 9 , wherein
in Chemical Formula 4, Ar 21 , Ar 22 , Ar 31 and Ar 32 are each independently represented by Chemical Formulas 1A to 1I:

wherein, in Chemical Formulas 1A to 1I,
R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , and R 37 are each independently hydrogen or a C1 to C10 alkyl group,
X 1 and X 2 are each independently CR x , N, P, or As, wherein R x is hydrogen, a C1 to C10 alkyl group, or a C1 to C10 haloalkyl group,
Y 1 and Y 2 are each independently O, S, Se, or Te,
a1, a2 and a3 are each independently an integer of 0 to 4,
a4 and a5 are each independently an integer of 0 to 3, and
* is a linking point.

11. The composition of claim 9 , wherein
in Chemical Formula 4, an L 31 -Ar 21 bond and an Ar 21 -A 11 bond; an A 11 -Ar 22 bond and an Ar 22 -L 21 bond; an L 22 -Ar 31 bond and an Ar 31 -A 12 bond; and an A 12 -Ar 33 bond and an Ar 33 -L 32 bond; are each independently in a meta position or a para position to each other.

12. The composition of claim 9 , wherein
in Chemical Formula 4, Ar 21 and Ar 22 and Ar 31 and Ar 32 are the same or different aromatic moieties.

13. The composition of claim 9 , wherein
in Chemical Formula 4, Ar 21 , Ar 22 , Ar 31 , and Ar 32 are a substituted or an unsubstituted phenylene.

14. The composition of claim 9 , wherein
in Chemical Formula 4, Ar 21 , Ar 22 , Ar 31 , and Ar 32 are a substituted or an unsubstituted naphthalene.

15. The composition of claim 9 , wherein
in Chemical Formula 4, Ar 21 and Ar 22 are a substituted or an unsubstituted phenylene, Ar 31 and Ar 32 are a substituted or an unsubstituted naphthalene, Ar 21 and Ar 22 are a substituted or an unsubstituted naphthalene, and Ar 31 and Ar 32 are a substituted or an unsubstituted phenylene.

16. The composition of claim 9 , wherein
the epoxy-containing groups, E 1 and E 2 , of Chemical Formula 4 are each independently represented by Chemical Formula 6:

wherein, in Chemical Formula 6,
D is —O—, —(CR p R q ) m —, —(CH(R p )CH(R q )O) l —, or a co

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Insu
• Kim In
• Pang Kyeon
• Seo Byung Hwa
• Lee Mooho
• Noh Changho
• Park Da-Hye

Classifications

• H10W74/473

  containing a filler · CPC title

• H10W90/291

  characterised by containers, encapsulations, or other housings for the stacked chips · CPC title

• H10W90/288

  characterised by arrangements for thermal management of the stacked chips · CPC title

• H10W90/297

  characterised by the through-semiconductor vias [TSVs] in the stacked chips · CPC title

• H10W90/724

  between a chip and a stacked insulating package substrate, interposer or RDL · CPC title