Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2002-10-14
2004-10-05
Truong, Duc (Department: 1711)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C313S504000, C313S507000, C528S086000
Reexamination Certificate
active
06800381
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel fluorene compound and polymers thereof having a polyphenylene group which can be used as an organic polymer semiconductor and optical electronic material, and especially an electro-luminescence (referred to as ‘EL’, hereinafter) material, and to an EL element comprising the same.
2. Description of the Background Art
Polyphenylenevinylene (referred to as ‘PPV’, hereinafter), polythiophene (referred to as ‘PTh’, hereinafter) and polyphenylene group polymers (
Synth. Met.,
50(1-3), p491 (1992);
Adv. Mater,
4, p36 (1992);
Adv Mater,
6, p190 (1994); and
Chem. Rev,
99, p1747 (1999)) have been widely and representatively known as organic polymer semiconductor and optical electronic materials (refer to
Semiconducting Polymers: Chemistry, Physics and Engineering
, Edited by G. Hadziioannou and P. F. van Hutten, WILEY-VCH (2000)) or as polymer light-emitting materials (
Angew, Chem, Int. Ed.,
37, p402 (1998);
Nature,
397, p121 (1999);
Prog. Polym. Sci.,
25, p1089 (2000); and
Adv Mater.,
12, p1737 (2000)).
Up to now, researches have been conducted on such polymer materials, but these materials have shortcomings that final products are not dissolved in an organic solvent.
PPV or PTh derivatives which emit various lights of blue, green and red having an improved processibility by introducing a suitable substituent thereto have been known (
Synth. Met.,
62, p35 (1994);
Adv. Mater.,
4, p36 (1992); and
Macromolecules,
28, p7525 (1995)), some of which exhibit an excellent processibility since they are easily dissolved in an organic solvent even though they have a large molecular weight (
Adv. Mater.,
10, p1340 (1998)).
In addition, fluorene group polymers have lately reported frequently as one of various light-emitting materials (refer to
Jpn. J. Appl. Phys.,
30, pL1941 (1991);
J. Polym. Sci. Polym. Chem. Ed.,
31, p2465 (1993);
J. Am. Chem. Soc.,
118, 7416 (1996);
Adv. Mater.,
9, p326 (1997);
Adv. Mater,
10, p993 (1998);
Macromolecules,
32, p1476 (1999);
Nature,
405, p661 (2000);
Syn. Met.,
111-112, p397 (2000);
Syn. Met.,
122, p79 (2001) and
J. Am. Chem. Soc.,
123, 946 (2001)).
Besides, there have been known U.S. Pat. Nos. 5,621,131, 5,708,130 and 5,900,327 which disclose fluorene group polymers having a single bond, and U.S. Pat. No. 5,807,974 which disclose a fluorene group alternate copolymer having a conjugate double bond as a light-emitting material for an EL element.
Polymers having an acetylene group have been presented as an organic polymer semiconductor and optical electronic material (refer to
Makromol. Chem.,
191, p857 (1990);
Macromolecules,
27, p562 (1994);
J. Chem. Soc., Chem. Commun
., p1433 (1995); and
Macromolecules,
29, p5157 (1996)), which are mostly related to a nonlinear optical material, a photo conductivity and photoluminescence (hereinafter referred to as ‘PL’), and
Syn. Met,
102, p933 (1999) discloses an example that they are used as an EL material. Researches into other applications have been also reported (refer to
Science,
297, p835 (1998)).
Polymers having a diacetylene group have been reported (refer to
Prog. Polym. Sci.,
20, p943 (1995);
CHEMTECH, October
, P32 (1993);
Macromolecules,
29, p2885 (1996);
Syn. Met.,
111-112, p429 (2000); and
Syn. Met,
119, p105 (2001)). These polymers are as sensitive to heat or light as the acetylene group polymers so that they can easily cross-link, and therefore stable cross-linked polymers can be obtained.
An application of such polymer having an acetylene or diacetylene group as an EL material has been patented to the same applicants of the present invention (U.S. Pat. No. 5,876,864 and Japanese Patent No. 3,046,814). This polymer can be also applied as a nonlinear optical material, a heat resistant polymer, polarized PL polymer, and electric or optical active polymer, as well as a light-emitting material.
Meanwhile, through a Diels-Alder reaction of bis(acetylene), that is, a compound having two ethynyl groups with a compound having a bis(cyclopentadienone) group (refer to
J. Org. Chem.,
28, p2725 (1963);
Chem. Rev.,
65, p261 (1965);
J. Org. Chem.,
30, p3354 (1965); and U.S. Pat. No. 4,400,540), a polyphenylene group polymer in which a plurality of phenyl groups are substituted (refer to
J. Polym. Sci
., Part B, 4, p791 (1966);
J. Polym. Sci
., Part A-1, 5, p2721 (1967);
J. Polym
. Sci., Part B, 7, p519 (1969);
Macromolecules,
5, p49 (1972);
Macromolecules,
28, p124 (1995);
Macromolecules,
33, p3525 (2000)) can be obtained. This polymerization is a reaction that a molecular weight is increased while carbon monoxide is removed. This polymerization is carried out at 100-400° C. without a solvent, or with a solvent selected from among toluene, diphenyl ether, o-diclorobenzene and cyclohexylbenzene, by which a polymer is obtained with a high yield of more than 80%. Since several phenyl groups are substituted in the obtained polymer, the polymer is thermally stable and easily dissolved in an organic solvent while has a high molecular weight. Accordingly, such polymer can be applied as a photoreceptor (refer to U.S. Pat. No. 5,882,829), or a dielectric substance in microelectronics industry, and especially, in the field of integrated circuits (refer to U.S. Pat. No. 5,965,679).
In addition, a polyphenylene group polymer can be obtained through an Eidls-Alder polymerization with a bis(&agr;-pyrone) or bis(thiophene dioxide) instead of bis(cyclopentadienone) (refer to
J. Chem. Soc. Perkin Trans
1 p355 (1994); and U.S. Pat. Nos. 2,971,944 and 2,890,207).
However, in the case of the aforementioned monomers, that is, the bis(acetylene) compound or bis(cyclopentadienone) compound, preparation cost is high and preparation procedures are difficult, and therefore, various kinds of monomers have not been provided. Especially, in the case of the bis(cyclopentadienone), its kind is so limited that polyphenylene group polymers having various properties and structures can not be prepared.
The inventors of the present invention have made constant efforts to solve the aforementioned problems in the prior art and reached the present invention. That is, the present invention provides a fluorene compound having a polyphenylene group and polymers thereof, prepared from a variety of acetylene compounds and fluorene group bis(cyclopentadienone) monomers, and the use thereof as a light-emitting material.
SUMMARY OF THE INVENTION
Therefore, an object of the present invention is to provide a variety of acetylene compounds and fluorene compounds having one or more cyclopentadienone groups.
Another object of the present invention is to provide a variety of novel fluorene compounds having a polyphenylene group and polymers thereof, prepared from the above acetylene compounds and fluorene compounds having one or more cyclopentadienone groups, in which their structures can be identified, and which can be dissolved in an organic solvent and can be used as an EL material and other optical electronic materials.
Another object of the present invention is to provide an EL element using the fluorene compound or polymer thereof as a light-emitting material.
DETAILED DESCRIPTION OF THE INVENTION
A fluorene compound and polymers thereof according to the present invention can be represented by the following formula (1):
In formula (1), R
1
, R
2
, R
1
′ and R
2
′ are the same with each other or different from each other, and respectively represent a hydrogen atom, C
1
-C
22
aliphatic or cyclo-alkyl, or alkoxy group, or C
6
-C
18
aryl or aryloxy group. More specifically, they may be independently a hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, docodecyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, buthoxy, hexyloxy, methoxyethoxyethyl, methoxyethoxyethoxyethyl, cyanoethyl, carboxymethyl, phenyl, phenoxy, tolyl, benzyl, naphthyl or anthrancene, or a derivative t
Cho Hyun-Nam
Jung Sung Hyun
Kim Jong Bok
Son Sang Won
Darby & Darby
Korea Institute of Science and Technology
Truong Duc
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