Polyarylene and method for production thereof

Details Polyarylene and method for production thereof Polyarylene and method for production thereof

2002-01-15

2003-07-01

Truong, Duc (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From phenol, phenol ether, or inorganic phenolate

C528S166000, C525S328100, C525S534000

Reexamination Certificate

active

06586554

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a polyarylene, a teraryl and a teraryl precursor, as well as to a method for producing a polyarylene. More particularly, the invention relates to a polyarylene having terarylene recurring units on the backbone and a method for production thereof.
BACKGROUND ART
Polyarylenes are of interest because the arylene group as a recurring unit has excellent thermal and chemical stability. Also, polyarylenes have been attracting considerable attention to their peculiar physical properties because of the advanced &pgr;-electron conjugated system.
A variety of applications as, e.g., conductive polymers are anticipated for polyarylenes. Polyphenylene s may also be either oxidized or reduced so that anions or cations are doped to form p type or n type semiconductors. Utilizing the property, it is also expected to apply poly(p-phenylene) to electrode materials or apply as display elements using a change in absorbance upon oxidation or reduction.
Moreover, polyarylenes are expected to be applicable to macro molecule light emitting elements. In this field, elements called macro molecule light emitting electrochemical elements (LEC) have been proposed lately and drawn attention in view of their high luminous efficiency. The structure includes two electrodes, between which a electrically conductive polymer material and a polymer membrane comprising polyethylene oxide having ionic conductivity and a substrate salt are inserted. It is assumed that the principle of working mechanism is based on the input of positive and negative charges from the electrodes and the transfer of both positive and negative ions of the substrate salt as a dopant, whereby a p-n junction would be formed in the membrane. If an ionic conductivity is further imparted to conductive polymer substances having an electronic conductivity, such light emitting elements will be manufactured using a sole material, not with the composite membrane mentioned above, resulting in a great advantage in manufacturing steps.
Processes for manufacturing polyarylenes such as polyphenylene have been hitherto limited. For manufacturing polyphenylenes, for example, oxidative cation polymerization called the Kovacic process, which is polycondensation using benzene as a monomer, is known. As is described in P. Kovacic, et al., Chem. Rev., 1987, 87, 357-379, an oxidizing agent such as cupric chloride and a Lewis acid catalyst such as aluminum chloride are employed to form insoluble polyphenylene of uncertain structure. It is reported that polyphenylene formed by oxidation of benzene is branched polyphenylene with a low molecular weight.
Further processes are proposed for manufacturing polyarylenes, which include electrochemical oxidative polymerization (a process using a cupric chloride-lithium aluminum hexafluoride-based electrolyte and applying a voltage between electrodes to produce a polymer on the electrodes); as polycondensation of substituted benzene derivatives, Wurtz-Fittig reaction (a process involving condensation of a dihalogenobenzene with an alkali metal) Ullmann reaction (a process involving condensation of diiodobenzene with a metal copper), Grignard reaction called Yamamoto method (a process involving condensation of a dihalogenobenzene Grignard derivative with a nickel chloride-bipyridyl complex), diazonium coupling (a process involving condensation of a diazonium derivative with sodium nitrite/hydrochloric acid followed by treatment with copper chloride); as processes via precursors, dehydration of cyclohexadiene polymer, a bio-engineering method (which comprises oxidizing benzene with bacteria to synthesize 5,6-dihydroxycyclohexane-1,3-diene, subjecting the carbonic acid ester of the diene to radical polymerization and then heating the resulting intermediate polymer to effect synthesis); and so on.
DISCLOSURE OF THE INVENTION
However, polyarylenes having terarylene recurring units are extremely rarely known. In these polyarylenes, it has been sought to introduce substituents freely into the central arylene of the terarylene unit and modify the terarylene in various ways.
For example, Japanese Patent Unexamined Publication (Laid-open) No. 9-309945 discloses polyphenylene copolymers. According to this patent publication, polyphenylene copolymers are synthesized using various types of monoarylenes as recurring units.
Now, an object of the present invention is to provide polyarylenes containing a terarylene as the recurring unit.
In a first aspect of the present invention, there are provided polyarylenes comprising a recurring unit represented by formula (I) or (II) below:
(wherein:
Ar
1
and Ar
2
which may be the same or different, each represents independently an arylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
R
1
and R
2
, which may be the same or different, each represents independently a C
1
-C
20
hydrocarbon group which may optionally be substituted, a C
1
-C
20
alkoxy group which may optionally be substituted, a C
6
-C
20
aryloxy group which may optionally be substituted, an amine group, hydroxy group or a group shown by formula: —Si(R
3
)(R
4
)(R
5
) (wherein R
3
, R
4
and R
5
, which may be the same or different, each represents independently a C
1
-C
20
alkyl group, a C
6
-C
20
arylalkyl group, a C
1
-C
20
alkoxy group or a C
6
-C
20
arylalkyloxy group)
provided that, in the recurring unit of formula (I), R
1
and R
2
may form together a C
4
-C
20
saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
A
1
and A
2
, which may be the same or different, each represents hydrogen atom; a C
1
-C
20
hydrocarbon group which may optionally be substituted; a C
1
-C
20
alkoxy group which may optionally be substituted; a C
6
-C
20
aryloxy group which may optionally be substituted; a C
6
-C
20
alkylaryloxy group which may optionally be substituted; a C
1
-C
20
alkoxycarbonyl group which may optionally be substituted; a C
6
-C
20
aryloxycarbonyl group which may optionally be substituted; cyano group (—CN); carbamoyl group (—C(═O)NH
2
); a haloformyl group (—C(═O)—X, wherein X is a halogen atom); or formyl group (—C(═O)—H); and,
n is an integer of 2 or more).
In the present invention, preferably, A
1
and A
2
, which may be the same or different, each represents independently a phenylene group which may optionally be substituted.
Also, the recurring unit is preferably a recurring unit shown by formula (I) described above, wherein R
1
and R
2
may form together a C
4
-C
20
saturated or unsaturated ring which may be intervened by an oxygen atom and may optionally be substituted.
Furthermore, the C
1
-C
20
hydrocarbon group is preferably a linear or branched C
1
-C
20
alkyl group, a linear or branched C
2
-C
20
alkenyl group, a linear or branched C
2
-C
20
alkynyl group, a linear or branched C
3
-C
20
allyl group, a linear or branched C
4
-C
20
alkadienyl group, a linear or branched C
4
-C
20
polyenyl group, a C
6
-C
18
aryl group, a C
6
-C
20
alkylaryl group, a C
6
-C
20
arylalkyl group, a C
4
-C
20
cycloalkyl group, or a C
4
-C
20
cycloalkenyl group.
In a further aspect of the invention, there is provided a polyarylene comprising a recurring unit represented by the formula (I) below:
(wherein:
Ar
1
and Ar
2
, which may be the same or different, each represents independently a paraarylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
R
1
and R
2
, which may be the same or different, each represents independently a C
1
-C
20
hydrocarbon group which may be substituted, a C
1
-C
20
alkoxy group which may be substituted, a C
6
-C
20
aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula: —Si(R
3
)(R
4
)(R
5
) (wherein R
3
, R
4
and R
5
, which may be the same or different, each represents independently a C
1
-C
20
alkyl group, a C
6
-C
20
arylalkyl group, a C
1
-C
20
alkoxy group or a C
6
-C
20
arylalkyloxy group);
provided that, in the recurring uni

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