Patent US6140456A successfully refreshed from Google Patents.
US6140456A
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US
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Chemicals and processes for making fluorinated poly(para-xylylenes)
Assignee: Canon USA Inc
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Filing: 1997-10-24
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Granted: 2000-10-31
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Expires: 2017-10-24
Abstract
Abstract New starting materials and chemical processes will be used to make fluorinated poly(para-xylylenes) (F-PPX) and fluorinated poly(para-fluoroxylylenes) (F-PPFX). The processes will use some very low cost and readily available starting materials, catalysts, chemical reactors, transport polymerization (TP) systems, and chemical vapor deposition (CVD) systems commonly used for making F-PPX. New TP and CVD deposition systems will also be used to make F-PPX and F-PPFX. These polymers are used for the manufacture of low dielectric films with high thermal stability and are sufficiently strong to withstand planarization and polishing for the manufacture of integrated circuits.
Inventors
- 👤 Chung J. Lee
- 👤 Hui Wang
- 👤 Giovanni Antonio Foggiato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:21
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/025; C08G2261/00; C08G2261/30; C08G2261/34; C08G2261/342; C08G2261/3424
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
97 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting as starting materials a fluorinating agent and a compound having the following structure: ##STR9## wherein Ar is a phenylene moiety comprising at least one fluorine atom comprising an sp 2 C--F bond; (b) processing the starting materials to produce a tetrafluoro precursor; (c) further processing the precursor with one of a TP and CVD process to produce a reactive intermediate compound; and (d) polymerizing the reactive intermediate compound into the fluorinated poly(para-xylylene), wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 2
Dependent Claim
97 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting as starting materials a fluorinating agent and a compound having the following structure: ##STR9## wherein Ar is a phenylene moiety comprising at least one fluorine atom comprising an sp 2 C--F bond; (b) processing the starting materials to produce a tetrafluoro precursor; (c) further processing the precursor with one of a TP and CVD process to produce a reactive intermediate compound; and (d) polymerizing the reactive intermediate compound into the fluorinated poly(para-xylylene), wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 3
Dependent Claim
20 words
The polymer of claim 1, wherein the precursor is YF 2 C--Ar--CF 2 Y, and Y is a leaving group.
Claim 4
Dependent Claim
43 words
The polymer of claim 1, wherein the fluorinating agent is SF 4 and the starting materials are reacted in a pressurized reactor at from about 1 MPas to about 20 MPas and at temperatures ranging from about 100° C. to about 200° C.
Claim 5
Dependent Claim
22 words
The polymer of claim 1, wherein the TP and CVD processes uses one of a resistive heating and an IR processing device.
Claim 6
Dependent Claim
29 words
The polymer of claim 1, wherein step (c) is selected from the group consisting of a thermal deposition process, a plasma enhanced deposition process, and photon assisted deposition processes.
Claim 7
Dependent Claim
28 words
The polymer of claim 2, wherein step (c) includes breaking the C--Y bonds while maintaining the sp 2 C--F bonds in order to produce the reactive intermediate compound.
Claim 8
Dependent Claim
22 words
The polymer of claim 1, wherein step (c) is a photolytic process using photons provided by one of UV and VUV sources.
Claim 9
Dependent Claim
17 words
The polymer of claim 5, wherein the photolytic process uses photon sources derived from incoherent excimer radiation.
Claim 10
Dependent Claim
16 words
The polymer of claim 8, wherein the incoherent excimer radiation is derived from dielectric barrier discharge.
Claim 11
Dependent Claim
25 words
The polymer of claim 8, wherein photons generated by dielectric discharge have an energy in the range of about 2 eV to about 15 eV.
Claim 12
Dependent Claim
23 words
The polymer of claim 8, wherein photons generated by dielectric discharge have an energy in the range of about 3 to 4 eV.
Claim 13
Dependent Claim
17 words
The polymer of claim 1, wherein step (c) includes a combination of both thermolytic and photolytic reactions.
Claim 14
Dependent Claim
14 words
The polymer of claim 1, wherein step (b) produces a tetrafluoro precursor in solution.
Claim 15
Dependent Claim
15 words
The polymer of claim 1, wherein step (c) employs a catalyst in a thermolytic process.
Claim 16
Dependent Claim
15 words
The polymer of claim 1, wherein step (c) is a thermolytic process using a furnace.
Claim 17
Dependent Claim
18 words
The polymer of claim 1, wherein step (c) is a thermolytic process using a rapid thermal processing system.
Claim 18
Dependent Claim
14 words
The polymer of claim 16, wherein the rapid thermal processing system utilizes infrared radiation.
Claim 19
Dependent Claim
13 words
The polymer of claim 1, wherein step (c) employs a free radical initiator.
Claim 20
Dependent Claim
13 words
The polymer of claim 18, wherein the free radical initiator is a halogen.
Claim 21
Dependent Claim
23 words
The polymer of claim 18, wherein the free radical initiator is selected from the group consisting of Br 2 and I 2 .
Claim 22
Dependent Claim
9 words
The polymer of claim 1, wherein Y is H.
Claim 23
Dependent Claim
75 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a tetrafluoro compound as precursor, wherein the tetrafluoro compound comprises a phenylene moiety and contains at least one fluorine atom comprising an sp 2 C--F bond; (b) processing the precursor with one of a TP and a CVD process; and (c) polymerizing the reactive intermediate compound into the fluorinated poly(para-xylylene), wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 24
Dependent Claim
75 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a tetrafluoro compound as precursor, wherein the tetrafluoro compound comprises a phenylene moiety and contains at least one fluorine atom comprising an sp 2 C--F bond; (b) processing the precursor with one of a TP and a CVD process; and (c) polymerizing the reactive intermediate compound into the fluorinated poly(para-xylylene), wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 25
Dependent Claim
18 words
The polymer of claim 22, wherein step (b) includes splitting the precursor to form a reactive intermediate compound.
Claim 26
Dependent Claim
82 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting as a precursor, a tetrafluoro derivative of a phenylene moiety comprising at least one fluorine atom comprising an sp 2 C--F bond; (b) processing the tetrafluoro derivative with one of a thermolytic process, a plasma enhanced process, or a photolytic process to produce a reactive intermediate compound; and (c) polymerizing the reactive intermediate compound into a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 27
Dependent Claim
82 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting as a precursor, a tetrafluoro derivative of a phenylene moiety comprising at least one fluorine atom comprising an sp 2 C--F bond; (b) processing the tetrafluoro derivative with one of a thermolytic process, a plasma enhanced process, or a photolytic process to produce a reactive intermediate compound; and (c) polymerizing the reactive intermediate compound into a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 28
Dependent Claim
128 words
A cross-linked polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a precursor with the chemical structure: ##STR10## wherein Ar is a phenylene moiety containing at least one fluorine atom comprising at least one sp 2 C--F bond, wherein Y, Y', Y", and Y'" are leaving groups independently selected from the group consisting of --H, --SR, --NR 3 , --SR 3 , --CR 3 , --OR, --SO 2 R, --Cl, --Br, and --I and wherein R groups are selected from the group consisting of H, alkyl, and aromatic moieties; (b) processing the precursor to produce at least a tri-functional reactive intermediate compound; and (c) polymerizing the tri-functional reactive intermediate compound into a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 29
Dependent Claim
128 words
A cross-linked polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a precursor with the chemical structure: ##STR10## wherein Ar is a phenylene moiety containing at least one fluorine atom comprising at least one sp 2 C--F bond, wherein Y, Y', Y", and Y'" are leaving groups independently selected from the group consisting of --H, --SR, --NR 3 , --SR 3 , --CR 3 , --OR, --SO 2 R, --Cl, --Br, and --I and wherein R groups are selected from the group consisting of H, alkyl, and aromatic moieties; (b) processing the precursor to produce at least a tri-functional reactive intermediate compound; and (c) polymerizing the tri-functional reactive intermediate compound into a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 30
Dependent Claim
15 words
The polymer of claim 25, wherein step (b) comprises a TP and a CVD process.
Claim 31
Dependent Claim
27 words
The polymer of claim 26, wherein the TP and CVD processes comprise one of a thermolytic deposition process, a plasma enhanced process, and a photolytic deposition process.
Claim 32
Dependent Claim
197 words
A cross-linked polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a first precursor comprising: FYY'C--Ar--CY"Y'"F wherein Ar is a phenylene moiety comprising at least one fluorine atom having an sp 2 C--F bond; wherein Y, Y', Y" and Y'" are leaving groups selected independently from the group consisting of --H, --SR, --NR 3 , --SO 2 R, --SiR 3 , --CR 3 , --OR, --Cl, --Br, and --I, and wherein R groups are selected from the group consisting of H, alkyl, and aromatic moieties; (b) selecting a second precursor comprising: YH 2-n F n --C--Ar--CYH 2-m F m , wherein Ar is a phenylene moiety comprising at least one fluorine atom having an sp 2 C--F bond; Y is a leaving group and n and m are 0, 1, or 2; (c) mixing desired amounts of the first and second precursors; the desired amounts selected to optimize the amount of cross-linking between polymers; (d) processing the precursors to produce reactive intermediate compounds with one of a TP and a CVD process; and (e) polymerizing the reactive intermediate compounds into a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 33
Dependent Claim
197 words
A cross-linked polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a first precursor comprising: FYY'C--Ar--CY"Y'"F wherein Ar is a phenylene moiety comprising at least one fluorine atom having an sp 2 C--F bond; wherein Y, Y', Y" and Y'" are leaving groups selected independently from the group consisting of --H, --SR, --NR 3 , --SO 2 R, --SiR 3 , --CR 3 , --OR, --Cl, --Br, and --I, and wherein R groups are selected from the group consisting of H, alkyl, and aromatic moieties; (b) selecting a second precursor comprising: YH 2-n F n --C--Ar--CYH 2-m F m , wherein Ar is a phenylene moiety comprising at least one fluorine atom having an sp 2 C--F bond; Y is a leaving group and n and m are 0, 1, or 2; (c) mixing desired amounts of the first and second precursors; the desired amounts selected to optimize the amount of cross-linking between polymers; (d) processing the precursors to produce reactive intermediate compounds with one of a TP and a CVD process; and (e) polymerizing the reactive intermediate compounds into a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond.
Claim 34
Dependent Claim
32 words
The polymer of claim 28 wherein the TP and CVD processes are selected from the group consisting of a thermal deposition process, a plasma enhanced deposition process, and a photolytic deposition process.
Claim 35
Dependent Claim
129 words
A cross-linked polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting as starting materials a fluorinating agent and a compound having the following structure: ##STR11## wherein A is a phenylene moiety comprising at least one fluorine atom having an sp 2 C--F bond; (b) processing the starting materials to produce a tetrafluoro compound precursor; (c) further processing the precursor with one of a TP and CVD process to produce a reactive intermediate compound; (d) polymerizing the reactive intermediate compound to form a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond; (e) exposing he polymer to an energy source sufficient to produce reactive intermediate groups within the polymer; and (f) permitting the reactive intermediates of adjacent polymers to bond with each other.
Claim 36
Dependent Claim
129 words
A cross-linked polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting as starting materials a fluorinating agent and a compound having the following structure: ##STR11## wherein A is a phenylene moiety comprising at least one fluorine atom having an sp 2 C--F bond; (b) processing the starting materials to produce a tetrafluoro compound precursor; (c) further processing the precursor with one of a TP and CVD process to produce a reactive intermediate compound; (d) polymerizing the reactive intermediate compound to form a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond; (e) exposing he polymer to an energy source sufficient to produce reactive intermediate groups within the polymer; and (f) permitting the reactive intermediates of adjacent polymers to bond with each other.
Claim 37
Dependent Claim
39 words
The cross-linked polymer of claim 30, wherein the TP and CVD processes are selected from the group consisting of a thermolytic deposition process, a plasma enhanced deposition process, and a photolytic deposition process to produce a reactive intermediate compound.
Claim 38
Dependent Claim
116 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a precursor for a poly(para-xylylene), said precursor comprising a phenylene moiety having at least one fluorine atom having an sp 2 C--F bond; (b) injecting the precursor into one of a TP and a CVD apparatus; (c) cracking the precursor to form a reactive intermediate; (d) depositing the reactive intermediate on a substrate; (e) permitting the reactive intermediate to polymerize on the substrate to form a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond; (f) exposing the polymer to an energy source sufficient to generate reactive intermediates within the polymer; and (g) permitting the reactive intermediates to re-polymerize.
Claim 39
Dependent Claim
116 words
A polymer comprising a poly(para-xylylene) made according to the steps of: (a) selecting a precursor for a poly(para-xylylene), said precursor comprising a phenylene moiety having at least one fluorine atom having an sp 2 C--F bond; (b) injecting the precursor into one of a TP and a CVD apparatus; (c) cracking the precursor to form a reactive intermediate; (d) depositing the reactive intermediate on a substrate; (e) permitting the reactive intermediate to polymerize on the substrate to form a polymer, wherein said phenylene moiety comprises at least one sp 2 C--F bond; (f) exposing the polymer to an energy source sufficient to generate reactive intermediates within the polymer; and (g) permitting the reactive intermediates to re-polymerize.
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