Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2000-09-07
2002-05-14
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S116000, C528S118000, C528S119000, C528S196000, C528S211000, C528S397000
Reexamination Certificate
active
06388044
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a thermosetting polyether resin and a polyether resin having low dielectric constant.
More particularly, the present invention relates to a thermosetting polyether resin used for insulation and coating in various electronic devices, a polyether resin having low dielectric constant used for insulation and coating of hypervelocity computing devices (MPU), a process for producing the same, and a coating solution for forming an insulation film containing said resin.
Further particularly, the present invention relates to a thermosetting polyether resin having low dielectric constant property, high heat resistance, chemical resistance and high film strength, a process for producing the same, and a coating solution for forming an insulation film containing said thermosetting polyether resin.
BACKGROUND OF THE INVENTION
High speed performance of LSI is attained by reduction in size of transistors constituting the LSI. Recently, the wiring distance has decreased by this reduction in size, and the signal propagation delay (wiring delay) and the crosstalk noise between adjacent wirings have become remarkable, providing important problems preventing the high performance of LSI itself. For solving these problems, lowering of the relative dielectric constant of an insulation film burying spaces between wirings is in investigation. Though a SOG (Spin on Glass) film conventionally used as an insulation film is an effective material since an insulation film can be formed easily on a device substrate by coating and baking, the dielectric constant thereof is from 3.0 to 3.9, being not sufficiently lower. When the distance between wirings is 0.25 &mgr;m or lower, an insulation film having a relative dielectric constant preferably less than 3.0 is required.
Use of a polyether resin for forming an insulation film is known. For example, Japanese Patent Application Laid-Open (JP-A) No. 9-246429 discloses an example using, as an insulation material, a polyphenylene ether resin obtained by oxidation polymerization. However, a polyether-based resin obtained by an oxidation polymerization is not admitted as satisfactory in the solubility into a solvent. For example, JP-A Nos. 9-202823 and 9-202824 disclose an application example of a polyether-based resin to a material having lower dielectric constant using a Ullmann's reaction.
Multilevel interconnect for high speed LSI needs low dielectric constant materials for inter-level layer dielectrics. Moreover, in the production process, the chemical resistance and mechanical strength of the insulation film are extremely important for inter-level dielectrics. Particularly when an insulation film is coated and sintered before patterning thereon by lithography, a process for contact with a developer (alkali aqueous solution, organic solvent) and a process for contact with a resist stripper containing an organic amine in releasing a resist are present, therefore, it is essential that the insulation film can endure these chemicals. Further, due to physical operations such as Chemical Mechanical Polishing (CMP) and the like, the insulation film is required to have certain mechanical strength, and strict adhesion is required to a material to be coated on which the insulation film is formed. However, when a known polyether-based resin for forming an insulation film, for example, a polyether polymer obtained by the above-mentioned Ullmann's reaction, is used, insufficient chemical resistance or film strength is problematical and improvement thereof is required.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a thermosetting polyether resin which can be used as an inter-layer insulation material which has excellent chemical resistance and film strength, or a polyether resin having a low dielectric constant having a low relative dielectric constant which can be applied to a hypervelocity computing device, a method for producing the same, and a coating solution which forms an insulation film having a low electric constant, and excellent in chemical resistance and film strength.
The present inventors have investigated various resins, and resultantly, found that a polyether having a specific structure shows excellent relative dielectric constant as an inter-layer insulation material and chemical resistance and film strength can be manifested by further introduction of a specific functional group, and have completed the present invention.
Namely, the present invention relates to [I] a thermosetting polyether resin obtained by polycondensing a dihalogen compound with a bisphenol compound to obtain a polyether resin having a repeating unit represented by the formula (1), and introducing a functional group which causes a cross-linking reaction by heating into the resulted polyether resin;
wherein each of R
1
to R
8
is independently selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, an alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group having 4 to 10 carbon atoms which may be substituted, a OR
9
group, a phenyl group which may be substituted; R
9
is selected from the group consisting of hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group having 4 to 10 carbon atoms which may be substituted, and a phenyl group which may be substituted; X is selected from any one or more groups described below; Y is selected from a single bond, a hydrocarbon group having 1 to 20 carbon atoms, or any one or more of —O—, —CO— and —SO
2
—;
each of Q
1
to Q
12
is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group having 4 to 10 carbon atoms which may be substituted and a phenyl group which may be substituted; m represents an integer from 0 to 4; n represents an integer from 0 to 3; Z is selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, a —OZ
1
group, and a —N(Z
2
)(Z
3
) group; each of Z
1
to Z
3
independently selected from the group consisting of hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, and a group carrying an ether group having 1 to 10 carbon atoms.
The present invention relates to [II] a polyether resin having a low dielectric constant represented by the formula (3):
wherein, R
1
to R
8
and Q
1
to Q
12
are as defined in the formula (1), however, at least one of R
1
to R
8
and Q
1
to Q
12
is selected from an alkyl group having 4 to 10 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms.
Further, the present invention relates to [III] a coating solution for forming an insulation film wherein the solution comprises the above-mentioned thermosetting polyether resin or polyether resin having a low dielectric constant.
DETAILED DESCRIPTION OF THE INVENTION
Then, the present invention will be illustrated in detail.
The polyether resin in the present invention comprises a repeating unit represented by the formula (1) obtained by condensing a dihalide compound represented by the formula (4) with a bisphenol compound represented by the formula (5), and may have two or more of different repeating units represented by the formula (1). In the formula, each of R
1
to R
8
is independently selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, an alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group having 4 to 10 carbon atoms which may be substituted, a OR
9
group, and a phenyl group which may be substituted. R
9
is selected from the group consisting of hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group having 4 to 10 carbon atoms which may be substituted, and a phenyl group which may be substituted,
A—X—A (4)
where
Choi Hyuncheol
Iwase Sadanobu
Yokota Akira
Yoshida Yuji
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