Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2003-02-21
2004-08-24
Pezzuto, Helen L. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S256000, C526S257000, C526S259000, C526S260000, C526S261000, C526S265000, C526S270000
Reexamination Certificate
active
06780950
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to pyrrole compounds, polymers thereof which can be used as a material for an organic polymer semiconductor and optical electronic material, and in particular, as a core material for an organic and polymeric electroluminescence (referred to as “EL”, hereinafter) element, and to an EL element using the same.
2. Description of the Background Art
Poly(phenylenevinylene) (referred to as “PPV”, hereinafter), polythiophene (referred to as “PTh”, hereinafter) and polyphenylene group polymers (d 2F
Nature
, 4 7, p549 (1990),
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 (See
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)). However, such polymer materials in which researches have been conducted into up to now have shortcomings that final products are not dissolved in an organic solvent.
There have been known PPV or PTh derivatives which emit lights of blue, green and red, and have an improved processibility by introducing a suitable substituent thereto (
Synth. Met
., 62, p35 (1994);
Adv. Mater
., 4, p36 (1992); and
Macromolecules
, 28, p7525 (1995)), and some of which exhibit an excellent processibility since they can be easily dissolved in an organic solvent even though they have a large molecular weight (
Adv. Mater
., 10, p1340 (1998)).
Recently, fluorene group polymers have been reported frequently as light-emitting materials (See
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);
Synth. Met
., 111-112, p397 (2000);
Synth. Met
., 122, p79 (2001) and
J. Am. Chem. Soc
., 123, 946 (2001)).
In addition, there are 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 discloses 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 (See
Makromol. Chem
., 191, p857 (1990);
Macromolecules
, 27, p562 (1994);
J. Chem. Soc., Chem. Commun
., p1433 (1995); and
Macromolecules
, 29, p5157 (1996)), which mostly relate to a nonlinear optical material, a photoconductivity and photoluminescence (hereinafter referred to as “PL”) material. Among them,
Synth. Met
., 102, p933 (1999) discloses an example used as an EL material, and researches into other applications have been also reported (See
Science
, 297, p835 (1998)). Polymers having a diacetylene group have been also reported (See
Prog. Polym. Sci
., 20, p943 (1995);
CHEMTECH
, October P32 (1993);
Macromolecules
, 29, p2885 (1996);
Synth. Met
., 111-112, p429 (2000); and
Synth. Met
., 119, p105 (2001)). These polymers are so sensitive to heat or light, like the above acetylene group polymers, that they can be easily cross-linked, so as to enable to obtain stable cross-linked polymers. Applications of polymers having an acetylene or diacetylene group as EL materials have been patented to the applicant of the present invention (U.S. Pat. Nos. 5,876,864 and 6,344,286).
However, until now, organic light-emitting diodes using organic complex such as Alq3 or Ir(Ppy)3, rather than polymers, have been commercialized as organic EL materials (U.S. Pat. Nos. 4,356, 429 and 5,061,569
; Appl. Phys. Lett
., 51, p913 (1987);
SID Digest
, 27, p849 (1996);
Nature
, 395, p161 (1998); and
Nature
, 403, p750 (2000)).
There have not been reported any blue light emitting polymers, including a fluorene group polymer, which shows good enough performances in efficiency and life of element to be commercialized, except for some green and orange color emitting PPV group polymers exhibiting excellent characteristics (
Adv. Mater
., 10, p1340 (1998)). Therefore, it is still expected a novel organic and polymer EL material, which can ensure highest efficiency and maximize stable life of an element, to be presented.
Polyaniline, polypyrrole and derivatives thereof which have been known as conducting materials (
Handbook of Conducting Polymers
, Edited by T. A. Skotheim, Marcel Dekker (1986)) are only subjected to researches for using antistatic, electrode and chromic materials, and their applications as light emitting materials can be rarely found.
SUMMARY OF THE INVENTION
Therefore, an object of the present invention is to provide novel pyrrole compounds and polymers thereof, in which their structure can be identified, and which can be well dissolved in an organic solvent and can be applied as EL and other optical electronic materials.
Another object of the present invention is to provide an EL element using the above pyrrole compounds and/or polymers thereof as a core material.
The foregoing and other features, aspects and advantages of the present invention will become more apparent from the following detailed description of the present invention when taken in conjunction with the accompanying drawings.
DETAILED DESCRIPTION OF THE INVENTION
A pyrrole compound and polymers thereof according to the present invention are represented by the following chemical formula (1):
wherein, m is 0 or an integer of above 1, and n is an integer of above 1;
R
1
and R
2
are substituents which are the same with or different from each other, and includes hydrogen, C
1
-C
22
aliphatic alkyl, C
1
-C
22
alicyclic alkyl, C
1
-C
22
acyl and C
1
-C
22
alkoxy, C
6
-C
30
aryl or aryloxy, a halogen containing substituent, silicon containing substituents, organic acid and ester of organic acid, but not limited thereto, and in more detail, R
1
and R
2
can be independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, docodecyl, cyclopropyl, cyclopentyl, cyclohexyl, acetyl, octanoyl, benzoyl, methoxy, ethoxy, etylenedioxy, buthoxy, hexyloxy, methoxyethoxyethyl, methoxyethoxyethoxyethyl, cyanoethyl, carboxymethyl, phenyl, phenoxy, tolyl, benzyl, naphthyl, anthracenyl, terphenyl, pyrenyl, diphenylanthracenyl, pentacenyl and derivatives thereof, chloride, bromide, iodide, bromomethyl, trimethylsilyl, dimethyloctylsilyl, and butylsulfonic acid, propionic acid and methyl esters thereof;
Ar
1
, Ar
2
and Ar
3
are the same or different aromatic group, respectively selected from the group consisting of C
6
-C
30
aromatic group, or halogen, metal or hetero atom-containing C
6
-C
30
aryl group, and examples include phenyl, tolyl, naphthyl, stilbenyl, fluorenyl, anthracenyl, terphenyl, pyrenyl, diphenylanthracenyl, dinaphthylanthracenyl, pentacenyl and derivatives thereof, bromophenyl, hydroxyphenyl, thienyl, pyridyl, azobenzenyl, ferrocenyl, carbazoyl, porphyrinyl and derivatives thereof; and
Ar′ is an aromatic or heterocyclic group such as phenyl, naphthyl, anthracenyl, fluorenyl, thiopenyl, pyrrolyl, pyridinyl, aryloxadiazolyl, triazolyl, carbazolyl, arylamino, arylsilano or derivatives thereof, but not limited thereto, and especially preferable examples include the groups represented by the following chemical formulae:
wherein, R1 and R2 are the same substituents as described in the above chemical formula (1).
The pyrrole compounds and polymers thereof of the present invention include a reaction or polymerization product between the same or different pyrrole compounds of the present invention, and a reaction or p
Cho Hyun-Nam
Jung Sung Hyun
Son Sang Won
Won Jae Hong
Darby & Darby
Korea Institute of Science and Technology
Pezzuto Helen L.
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