Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
1999-04-28
2001-04-03
Acquah, Samuel A. (Department: 1711)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S461000, C428S500000, C428S917000, C252S500000, C252S511000, C252S301160, C252S301350, C313S504000, C313S506000, C564S315000
Reexamination Certificate
active
06210817
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to a conjugated compound, a process of the production thereof and an organic luminous element (particularly, an electroluminescence (EL) element) containing the same.
BACKGROUND OF THE INVENTION
In these days, researches and developments have been energetically made on various display elements using organic fluorescent materials (organic luminous elements). Among all, organic EL elements have attracted public attention as display elements with a potential capability of achieving luminescence with a high luminance at a low voltage. For example, it is reported to construct an EL element by forming an organic thin layer through deposition of organic compounds (Applied Physics Letters, vol. 51, p. 913, 1987). The organic EL elements disclosed in this report have a laminated structure of an electron-transporting material and a hole-transporting material and thus show highly improved electroluminescence characteristics compared with the conventional elements of the single-layer type.
Because of being formed by the deposition method, however, the above-mentioned EL elements suffer from difficulties in the area-enlargement and productivity. Taking these points into consideration, it has been required to establish a process for producing EL elements by the advantageous coating method. Known examples of EL element materials which can be used in producing EL elements by the coating method include paraphenylene vinylene polymers (Advanced Materials, p. 4, 1992). Although EL elements containing these conjugated polymers can achieve luminescence with a high luminance, the polymer compounds disclosed in the above literature can exclusively give green to red luminescence. To supply full-color EL elements and achieve white luminescence, it has been therefore required to develop conjugated polymer compounds capable of giving blue luminescence.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide a compound excellent in blue luminescence.
Another object of the present invention is to provide a process of the producing the compound.
A still other object of the present invention is to provide an organic luminous element using the compound.
Other objects and effects of the present invention will become apparent from the following description.
The above-described objects of the present invention have been achieved by providing the following compounds, organic luminous elements and process.
1) A compound containing at least two units of a structure represented by the following general formula (1):
wherein R
1
, R
2
, R
3
and R
4
each represents a hydrogen atom or a substituent; R
5
represents a substituent; l is an integer of 0 to 2; and Ar
1
and Ar
2
each represents an aryl group or a heteroaryl group.
2) The compound according to the above 1), further containing at least two units of a structure represented by the following general formula (2):
wherein R
6
represents a substituent; and m is an integer of from 0 to 4.
3) The compound according to the above 1), further containing at least two units of a structure represented by the following general formula (3):
wherein R
7
, R
8
, R
10
and R
11
each represents a hydrogen atom or a substituent; R
9
represents a substituent; and n is an integer of 0 to 4.
4) The compound according to the above 1), further containing at least two units of a structure represented by following general formula (4):
wherein R
12
and R
13
each represents a hydrogen atom or a substituent; R
14
and R
15
each represents a substituent; and n1 and n2 each is an integer of from 0 to 3.
5) The compound according to any one of the above 1), 2), 3) or 4), having soluble substituents on Ar
1
and Ar
2
.
6) The compound according to any one of the above 1), 2), 3), 4) or 5) having a maximum luminescent wavelength (&lgr;max) of the fluorescence emission spectrum of not more than 500 nm.
7) The compound according to any one of the above 1), 2), 3), 4), 5) or 6), having a weight-average molecular weight of from 1,000 to 1,000,000.
8) An organic luminous element having an organic layer which comprises at least one compound selected from:
compounds according to any one of the above 1), 2), 3), 4), 5), 6) or 7); and
compounds containing at least two units of a structure represented by the following general formula (a):
wherein R
1
, R
2
, R
3
and R
4
each represents a hydrogen atom or a substituent; and Ar, Ar
1
and Ar
2
each represents an aryl group or a heteroaryl group.
9) The organic luminous element according to the above 8), wherein the organic layer has a laminated structure.
10) A process for producing a styryl compound, which comprises a step of forming a carbon—carbon bond in the presence of a palladium catalyst, to thereby prepare a compound according to any one of the above 1), 2), 3), 4), 5), 6) or 7).
DETAILED DESCIRPTION OF THE INVENTION
Now, general formulae (a), (1), (2) and (3) are described below.
Ar represents a substituted or unsubstituted (provided that Ar has substituents shown in formula (a)) aryl group (preferably having from 6 to 40 carbon atoms, still preferably from 6 to 30 carbon atoms and particularly preferably from 6 to 20 carbon atoms (for example, phenyl, naphthyl, pyrenyl, diphenylamino)) or heteroaryl group (preferably containing an oxygen atom, a sulfur atom or a nitrogen atom and preferably having from 1 to 30 carbon atoms, still preferably from 2 to 12 carbon atoms (for example, pyridyl, thienyl, oxadiazolyl, triazolyl, carbazolyl)). Preferred examples thereof include substituted or unsubstituted phenyl, pyridyl and oxadiazolyl groups. Of these, substituted or unsubstituted phenyl and pyridyl groups are still preferred and a substituted or unsubstituted phenyl group is particularly preferred.
R
1
, R
2
, R
3
, R
4
, R
7
, R
8
, R
10
and R
11
each represents a hydrogen atom or a substituent. Examples of the substituent represented by these symbols include alkyl groups (preferably having from 1 to 20 carbon atoms, still preferably from 1 to 12 carbon atoms and particularly preferably from 1 to 8 carbon atoms (for example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl)), alkenyl groups (preferably having from 2 to 20 carbon atoms, still preferably from 2 to 12 carbon atoms and particularly preferably from 2 to 8 carbon atoms (for example, vinyl, allyl, 2-butenyl, 3-pentenyl)), alkynyl groups (preferably having from 2 to 20 carbon atoms, still preferably from 2 to 12 carbon atoms and particularly preferably from 2 to 8 carbon atoms (for example, propargyl, 3-pentynyl)), aryl groups (preferably having from 6 to 40 carbon atoms, still preferably from 6 to 30 carbon atoms and particularly preferably from 6 to 20 carbon atoms (for example, phenyl, p-methylphenyl, naphthyl)), substituted carbonyl groups (preferably having from 1 to 20 carbon atoms, still preferably from 1 to 16 carbon atoms and particularly preferably from 1 to 12 carbon atoms (for example, acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl)), amino groups (preferably having from 0 to 20 carbon atoms, still preferably from 1 to 16 carbon atoms and particularly preferably from 1 to 12 carbon atoms (for example, dimethylamino, methylcarbamoyl, ethylsulfonylamino, dimethylaminocarbonylamino, phthalimido)), sulfonyl groups (preferably having from 1 to 20 carbon atoms, still preferably from 1 to 16 carbon atoms and particularly preferably from 1 to 12 carbon atoms (for example, mesyl, tosyl)), a sulfo group, a carboxyl group, heterocycles (preferably containing an oxygen atom, a sulfur atom or a nitrogen atom and preferably having from 1 to 30 carbon atoms, still preferably from 1 to 16 carbon atoms and particularly preferably from 2 to 12 carbon atoms (for example, imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl)), a hydroxyl group, alkoxy groups (preferably having from 1 to 20 carbon atoms, still preferably from 1 to 16 carbon atoms and particularly preferably
Acquah Samuel A.
Fuji Photo Film Co. , Ltd.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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