Polyhexahydrotriazine dielectrics

Patent metadata

Field	Value
Publication number	US-9650471-B2
Application number	US-201514680181-A
Country	US
Kind code	B2
Filing date	Apr 7, 2015
Priority date	Apr 7, 2015
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

Low dielectric constant (low-k) polyhemiaminal (PHA) and polyhexahydrotriazine (PHT) materials with cyclic aliphatic ring structures are described. The materials are formed by a method that includes heating a mixture comprising amines and paraformaldehyde. The reaction mixtures may be used to form low-k PHT prepregs, composites and dielectrics used in integrated circuits.

First claim

What is claimed is:

1. A polyhexahydrotriazine (PHT), comprising:
a plurality of trivalent hexahydrotriazine groups having the structure

and
a plurality of carbon groups having the structure

wherein each wavy bond site of a given hexahydrotriazine group is covalently linked at a respective wavy bond site of a carbon group, and each wavy bond site of a given carbon group is covalently linked at a respective wavy bond site of a hexahydrotriazine group, and wherein at least one of 1, 2, and 3 comprises a chemical group that is a cyclic carbon chemical group, or 1 and 2 are part of a polycyclic hydrocarbon chemical group, or 2 and 3 are part of a polycyclic hydrocarbon chemical group, or 1 and 3 are part of a polycyclic hydrocarbon chemical group.

2. The PHT of claim 1 , wherein at least one of 1, 2, and 3 is a covalently bonded carbon substituent.

3. The PHT of claim 2 , wherein at least one of 1, 2, and 3 comprises a covalently bonded cyclic aliphatic chemical group.

4. The PHT of claim 3 , wherein at least one cyclic aliphatic chemical group comprises at least one cyclic carbon ring.

5. The PHT of claim 4 , wherein at least one cyclic carbon ring is fused to at least one other cyclic carbon ring.

6. The PHT of claim 1 , wherein at least one of 1, 2, and 3 covalently bonds at least one hexahydrotriazine group to another hexahydrotriazine group.

7. A polyhexahydrotriazine (PHT), comprising:
a plurality of trivalent hexahydrotriazine groups having the structure

and
a plurality of carbon groups having the structure

wherein each wavy bond site of a given hexahydrotriazine group is covalently linked at a respective wavy bond site of a carbon group, and each wavy bond site of a given carbon group is covalently linked at a respective wavy bond site of a hexahydrotriazine group, and wherein at least one of 1, 2, and 3 comprises a chemical group that is a cyclic carbon chemical group, or 1 and 2 are part of a cyclic carbon chemical group, or 2 and 3 are part of a cyclic carbon chemical group, or 1 and 3 are part of a cyclic carbon chemical group, and the PHT further comprises at least 50% by mole aliphatic carbon-carbon chemical bonds based on polymer.

8. The PHT of claim 7 , comprising at least 50% by mole cyclic aliphatic carbon-carbon chemical bonds based on polymer.

9. The PHT of claim 8 , comprising less than 50% by mole aromatic carbon-carbon chemical bonds based on polymer.

10. A polyhexahydrotriazine (PHT), comprising:
a plurality of trivalent hexahydrotriazine groups having the structure

and
a plurality of carbon groups having the structure

wherein each wavy bond site of a given hexahydrotriazine group is covalently linked at a respective wavy bond site of a carbon group, and each wavy bond site of a given carbon group is covalently linked at a respective wavy bond site of a hexahydrotriazine group, and wherein at least one of 1, 2, and 3 comprises a chemical group that is a cyclic carbon chemical group, or 1 and 2 are part of a cyclic carbon chemical group, or 2 and 3 are part of a cyclic carbon chemical group, or 1 and 3 are part of a cyclic carbon chemical group, and the PHT further comprises covalently bonded fluorine atoms.

11. The PHT of claim 10 , comprising cyclic chemical groups that contain covalently bonded fluorine atoms.

12. The PHT of claim 1 , wherein the PHT has a dielectric constant less than 5.

13. The PHT of claim 12 , wherein the PHT has a dielectric constant of at least 1.8.

14. The PHT of claim 1 , wherein 1 and 2 are part of a polycyclic hydrocarbon chemical group, or 2 and 3 are part of a polycyclic hydrocarbon chemical group, or 1 and 3 are part of a polycyclic hydrocarbon chemical group, and at least one polycyclic hydrocarbon chemical group includes a fused ring structure.

15. The PHT of claim 14 , wherein at least one polycyclic hydrocarbon chemical group includes a cyclic aliphatic chemical group.

16. The PHT of claim 14 , wherein at least one polycyclic hydrocarbon chemical group includes a cyclic aromatic chemical group.

17. The PHT of claim 14 , comprising covalently bonded fluorine atoms.

18. The PHT of claim 17 , wherein at least one polycyclic hydrocarbon chemical group contains covalently bonded fluorine atoms.

19. The PHT of claim 14 , wherein the PHT has a dielectric constant less than 5.

20. The PHT of claim 19 , wherein the PHT has a dielectric constant that is at least 1.8.

Assignees

• IBM

Inventors

• Boday Dylan J
• Garcia Jeannette M
• Hedrick James L
• Wojtecki Rudy J

Classifications

• H10W20/42

  Vias, e.g. via plugs · CPC title

• H05K2201/0137

  Materials · CPC title

• C08J2379/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• H01L23/5226

  Electricity · mapped topic

• D06M15/37

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title