The present invention relates to a compound suitable for use for a filter dye, a color conversion filter, a dye for a photographic material, a sensitizing dye, a dye for pulp-dyeing, a laser dye, a fluorescent medicine for a medical diagnosis, a material for a light emitting device (luminescence device), etc., and particularly relates to a light emitting device using thereof.
Prospects of an organic light emitting device in which organic materials are used are promising as a solid light emitting (luminescent) type inexpensive and large area full color display device and development has been tried variously. An organic light emitting device in general comprises a light emitting (luminescent) layer and a pair of counter electrodes with the light emitting layer between. When an electric field is impressed between both electrodes, electrons are injected from the cathode and positive holes are injected from the anode, and the electrons and the positive holes are recombined in the light emitting layer. A phenomenon of emitting energy as light when energy level is returned from conduction band to valence band is luminescence.
Organic light emitting devices so far been used require high driving voltage and emission luminance and luminous efficacy are low, but an organic EL device comprising lamination of thin layers containing an organic compound having high fluorescent quantum efficiency capable of emitting light with low voltage of 10 V or lower has been reported (Applied Physics Letters, Vol. 51, p. 913 (1987)) and attracting public attention in recent years. According to this technique, high luminance green light emission can be obtained by using a metal chelate complex as the electron-transporting layer, a fluorescent compound as the light emitting layer and an amine compound as the positive hole-transporting layer. Further, when taking into consideration the utilization of an organic light emitting device as a full color display and a light source, it is necessary to get three primary colors or a white color in practical use. A device capable of emitting a desired color by doping a fluorescent dye is reported (Journal of Applied Physics, Vol. 65, p. 3610 (1989)). This technique is particularly effective for red emission dyes in which extinction due to concentration is large and the emission of high efficacy is difficult when a fluorescent dye is used alone as the light emitting layer, and high color purity and high luminance have been attained due to the technique. However, when a device doped with a dye is produced by deposition, the operation is complicated and the performance of the device is liable to become uneven because a host material and a trace amount of a fluorescent dye are co-deposited. Therefore, from the viewpoint of the simplification of the producing step and the stability of the performance of a device, the development of light emitting materials of from orange to red capable of high luminance emission and excellent in durability even when a dye is used alone as the light emitting layer has so far been desired.
On the other hand, organic EL devices which have realized high luminance emission are laminated devices formed by vacuum deposition of organic materials, but from the viewpoint of simplification of producing step, process-ability, and realization of large area devices, it is desired to produce devices by a coating system. However, devices produced by a coating system so far been used are inferior to devices produced by a deposition system in the points of emission luminance and luminous efficacy, therefore, the realizations of high luminance and high efficacy luminescence have been left as the problems to be solved. In addition, with devices produced by coating an organic low molecular weight compound dispersed in an organic polymer medium, uniform planar emission for a long period of time is difficult due to the agglomeration of the organic low molecular weight compound.
Further, in recent years, various materials having fluorescence have been used for a filter dye, a color conversion filter, a dye for a photographic material, a sensitizing dye, a dye for pulp-dyeing, a laser dye, a fluorescent medicine for a medical diagnosis, a material for an organic light emitting device, etc., and demand for such materials has been increased. However, fluorescent dyes having high fluorescent strength and capable of long wave emission of from orange to red are less, therefore, the development of a novel material has been desired.
A first object of the present invention is to provide a material for a light emitting device of orange to red emission capable of emitting light with high luminance and high efficacy, excellent in stability at repeated use, and capable of uniform and planar emission with low voltage driving, and a light emitting device using the same.
A second object of the present invention is to provide a light emitting device showing no unevenness among devices and stable in performance, and a material capable of producing a light emitting device of red emission.
A third object of the present invention is to provide a material for a light emitting device capable of emitting light with high luminance and high efficacy even when a device is produced by coating system, and a light emitting device using the same.
A fourth object of the present invention is to provide a compound having fluorescence of from orange to red with high fluorescent strength.
The above objects of the present invention have been accomplished by the following means.
(1) A material for a light emitting device which is a compound represented by the following formula (I): 
wherein Ar1 and Ar6, which may be the same or different, each represents a divalent aryl group or a divalent heterocyclic group; R2, R3, R7 and R8, which may be the same or different, each represents an aryl group, a heterocyclic group or an aliphatic hydrocarbon group; R4a, R5a, R9a and R10a, which may be the same or different, each represents a hydrogen atom or a monovalent group, and at least one of R4a, R5a, R9a and R10a represents an electron withdrawing group having a Hammett""s "sgr"p value of 0.2 or more; at least two of Ar1, R2, R3, R4a, and R5a may be linked to form a ring; at least two of R9a, R10a, Ar6, R7, and R8 may be linked to form a ring; at least two of R4a, R5a, R9a and R10a may be linked to form a ring; L1 represents (i) a divalent monocyclic or bicyclic aryl group, or a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, a Cxe2x95x90X group, a silyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom as the ring-constitutional atoms, or the combination of these groups; L1 and at least one of R4a and R5a may be linked to form a ring; L1 and at least one of R9a and R10a may be linked to form a ring; X represents an oxygen atom, a sulfur atom, Nxe2x80x94Rx1 or CRx2Rx3; and Rx1, Rx2 and Rx3, which may be the same or different, each represents a hydrogen atom or a substituent.
(2) The material for a light emitting device as described in the above item (1), wherein the compound represented by formula (I) is a compound represented by the following formula (II): 
wherein Ar1, Ar6 and L1 each has the same meaning as in formula (I); Ar2, Ar3, Ar7 and Ar8, which may be the same or different, each represents an aryl group or a heterocyclic group; R4b, R5b, R9b and R10b, which may be the same or different, each represents a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, provided that all of R4b, R5b, R9b and R10b do not represent hydrogen atoms at the same time; at least two of Ar1, Ar2, Ar3, R4b and R5b may be linked to form a ring; at least two of R9b, R10b, Ar6, Ar7, and Ar8 may be linked to form a ring; at least two of R4b, R5b, R9b and R10 may be linked to form a ring; L1 and at least one of R4b and R5b may be linked to form a ring; and L1 and at least one of R9b and R10b may be linked to form a ring.
(3) The material for a light emitting device as described in the above item (2), wherein the compound represented by formula (II) is a compound represented by the following formula (III): 
wherein Ar1, Ar2, Ar3, Ar6, Ar7, Ar8 and L1 each has the same meaning as in formula (II); at least two of Ar1, Ar2 and Ar3 may be linked to form a ring; at least two of Ar6, Ar7 and Ar8 may be linked to form a ring; and R4c and R9c, which may be the same or different, each represents a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group.
(4) An amine compound represented by the following formula (IV): 
wherein Ar2, Ar3, Ar7 and Ar8, which maybe the same or different, each represents an aryl group or a heterocyclic group; Rx and Ry each represents a substituent; m and n each represents an integer of 0 to 4, when m and n each represents 2, 3 or 4, a plurality of Rx and Ry may be the same with or different from each other; at least two of Ar2, Ar3 and Rx may be linked to form a ring; at least two of Ar7, Ar8 and Ry may be linked to form a ring; R4d and R9d, which may be the same or different, each represents a heterocyclic group, a cyano group, an oxycarbonyl group, a sulfonyl group, or an acyl group; and L2 represents (i) a divalent monocyclic orbicyclic aryl group, or a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom as the ring-constitutional atoms, or the combination of these groups.
(5) A light emitting device comprising a pair of electrodes and at least one organic thin layer between the electrodes, wherein the light emitting device comprises at least one compound represented by formula (I), (II), (III) or (IV) as described in the above item (1), (2), (3) or (4).
(6) A light emitting device comprising a pair of electrodes and at least one organic thin layer between the electrodes, wherein at least one layer is a layer containing at least one compound represented by formula (I), (II), (III) or (IV) as described in the above item (1), (2), (3) or (4) dispersed in a polymer.
In the first place, a compound represented by formula (I) will be described in detail below.
In formula (I), Ar1 and Ar6, which may be the same or different, each represents a divalent aryl group, or a divalent heterocyclic group. The divalent aryl group represented by Ar1 and Ar6 is preferably a monocyclic or bicyclic aryl group having from 6 to 30 carbon atoms (e.g., phenyl, naphthyl, biphenyl, fluorenyl), more preferably a phenyl or naphthyl group having from 6 to 20 carbon atoms, and still more preferably a phenyl or naphthyl group having from 6 to 14 carbon atoms.
The divalent heterocyclic group represented by Ar1 and Ar6 is a 3- to 10-membered saturated or unsaturated heterocyclic ring containing at least one N, O or S atom. The heterocyclic ring may be a monocyclic ring or may further form a condensed ring with other ring.
The heterocyclic group is preferably a 5- or 6-membered aromatic heterocyclic group, more preferably a 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom, and still more preferably a 5- or 6-membered aromatic heterocyclic group containing one or two of a nitrogen atom and a sulfur atom. Specific examples of the heterocyclic rings include, e.g., pyrrolidine, piperidine, piperazine, morpholine, thiophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, and tetraazaindene, preferred examples include thiophene, pyridine and quinoline.
The aryl group and the heterocyclic group represented by Ar1 and Ar6 may have substituents, and examples of the substituents include, for example, an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group (preferably an alkenyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., vinyl, allyl, 2-butenyl, 3-pentenyl), an alkynyl group (preferably an alkynyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., propargyl, 3-pentynyl), an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyl, p-methylphenyl, naphthyl), an amino group (preferably an amino group having from 0 to 20, more preferably from 0 to 10, and particularly preferably from 0 to 6, carbon atoms, e.g., amino, methylamino, dimethylamino, diethylamino, dibenzylamino), an alkoxyl group (preferably an alkoxyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methoxy, ethoxy, butoxy), an aryloxy group (preferably an aryloxy group having from 6 to 20, more preferably from 6 to 16, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyloxy, 2-naphthyloxy), an acyl group (preferably an acyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 10, carbon atoms, e.g., phenyloxycarbonyl), an acyloxy group (preferably an acyloxy group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 10, carbon atoms, e.g., acetoxy, benzoyloxy), an acylamino group (preferably an acylamino group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 10, carbon atoms, e.g., acetylamino, benzoylamino), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonylamino), an aryloxycarbonylamino group (preferably an aryloxy-carbonylamino group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 12, carbon atoms, e.g., phenyloxycarbonylamino), a sulfonylamino group (preferably a sulfonylamino group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfonylamino, benzene-sulfonylamino), a sulfamoyl group (preferably a sulfamoyl group having from 0 to 20, more preferably from 0 to 16, and particularly preferably from 0 to 12, carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl-sulfamoyl), a carbamoyl group (preferably a carbamoyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenyl-carbamoyl), an alkylthio group (preferably an alkylthio group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methylthio, ethylthio), an arylthio group (preferably an arylthio group having from 6 to 20, more preferably from 6 to 16, and particularly preferably from 6 to 12, carbon atoms, e.g., phenylthio), a sulfonyl group (preferably a sulfonyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., mesyl, tosyl), a sulfinyl group (preferably a sulfinyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfinyl, benzenesulfinyl), a ureido group (preferably a ureido group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., ureido, methylureido, phenylureido), a phosphoric acid amido group (preferably a phosphoric acid amido group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., diethylphosphoric acid amido, phenylphosphoric acid amido), a hydroxyl group, a mercapto group, a halogen atom (e.g., fluorine, chlorine, bromine, iodine), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (preferably a heterocyclic group having from 1 to 20, and more preferably from 1 to 12, carbon atoms; as hetero atoms, e.g., nitrogen, oxygen, sulfur, and specifically, e.g., pyrrolidine, piperidine, piperazine, morpholine, thiophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, and tetraazaindene can be exemplified), and a silyl group (preferably a silyl group having from 3 to 40, more preferably from 3 to 30, and particularly preferably from 3 to 24, carbon atoms, e.g., trimethylsilyl, triphenylsilyl). These substituents may further be substituted. When there are two or more substituents, they may be the same or different. Substituents may be linked to each other to form a ring, if possible.
Preferred examples of the substituents include an alkyl group, analkenyl group, anaralkyl group, anaryl group, an alkoxyl group, an amino group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, a hydroxyl group, and a heterocyclic group, more preferred examples include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxyl group, an amino group, anacylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, and a heterocyclic group, and still more preferred examples include an alkyl group, an alkenyl group, an aryl group, an alkoxyl group, and a substituted amino group.
Here, the substituted amino group is a group represented by xe2x80x94Nra(Rb), wherein Ra and Rb may be the same or different, and specifically represents an alkyl group, an alkenyl group, an aralkyl group, an aryl group, or a heterocyclic group. As these alkyl, alkenyl, aryl and heterocyclic groups, the same groups described as the substituents of Ar1 can be exemplified. The aralkyl is an aralkyl group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 10, carbon atoms, e.g., a benzyl group and a phenethyl group can be exemplified.
R2, R3, R7 and R8, which may be the same or different, each represents an aryl group, a heterocyclic group or an aliphatic hydrocarbon group.
The aryl group represented by R2, R3, R7 and R8 is preferably a monocyclic, bicyclic, tricyclic or tetracyclic aryl group having from 6 to 26 carbon atoms (e.g., phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, indenyl), more preferably phenyl, naphthyl, anthryl, or phenanthryl each having from 6 to 20 carbon atoms, and still more preferably phenyl, naphthyl or anthryl each having from 6 to 14 carbon atoms.
The heterocyclic group represented by R2, R3, R7 and R8 is a 3- to 10-membered saturated or unsaturated heterocyclic ring containing at least one N, O or S atom. The heterocyclic ring may be a monocyclic ring or may further form a condensed ring with other ring.
The heterocyclic group is preferably a 5- or 6-membered aromatic heterocyclic group, more preferably a 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom, and still more preferably a 5- or 6-membered aromatic heterocyclic group containing one or two of a nitrogen atom and a sulfur atom. Specific examples of the heterocyclic rings include, e.g., pyrrolidine, piperidine, piperazine, morpholine, thiophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, and tetraazaindene, preferred examples include thiophene, pyridine and quinoline.
The aliphatic hydrocarbon group represented by R2, R3, R7 and R8 may be straight chain, branched or cyclic, e.g., an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group (preferably an alkenyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., vinyl, allyl, 2-butenyl, 3-pentenyl), or an alkynyl group (preferably an alkynyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., propargyl, 3-pentynyl). The aliphatic hydrocarbon group is preferably an alkyl group.
The aryl group, the heterocyclic group and the aliphatic hydrocarbon group represented by R2, R3, R7 and R8 may have substituents, and may further form a condensed ring. As the substituents, those described above as the substituents of Ar1 and Ar6 can be applied to.
Two or three of Ar1, R2 and R3 may be linked to form a ring, and the ring to be formed is preferably a 5 to 7-membered ring. At least two of Ar6, R7 and R8 may also be linked to form a ring, and the ring to be formed is preferably a 5 to 7-membered ring.
R4a, R5a, R9a and R10a, which may be the same or different, each represents a hydrogen atom or a substituent, and as the substituents, e.g., those described above as the substituents of Ar1 and Ar6 can be applied to. At least one of R4a, R5a, R9a and R10a represents an electron withdrawing group having a Hammett""s "sgr"p value of 0.2 or more. As the electron withdrawing group having a Hammett""s "sgr"p value of 0.2 or more, e.g., a halogen atom, a perhalogenoalkyl group (e.g., a perfluoroalkyl group, a perchloroalkyl group, a perbromoalkyl group), a cyano group, a formyl group, a carboxyl group, a carbamoyl group, a sulfonylmethyl group, an acyl group, an oxycarbonyl group (preferably an oxycarbonyl group substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; the aliphatic hydrocarbon group, the aryl group and the heterocyclic group have the same meaning as those described in R2) , a pentahalophenyl group, a carbonyloxy group, a sulfonyloxy group, a sulfonyl group, a sulfinyl group, a heterocyclic group and a sulfamoyl group can be exemplified. Preferred examples are a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group and an acyl group, and particularly preferred examples are benzoxazole, benzothiazole, benzimidazole, a cyano group, an oxycarbonyl group, a sulfonyl group, a sulfamoyl group and an acyl group.
At least two of Ar1, R2, R3, R4a, and R5a may be linked to form a ring. At least two of R9a, R10a, Ar6, R7, and R8 may be linked to form a ring. At least two of R4a, R5a, R9a and R10a may be linked to form a ring.
L1 and at least one of R4a and R5a may be linked to form a ring. L1 and at least one of R9a and R10a may be linked to form a ring.
L1 represents (i) a divalent monocyclic or bicyclic aryl group, or a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, a Cxe2x95x90X group, a silyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom as the ring-constitutional atoms, or the combination of these groups. Here, the divalent aryl group and the divalent heterocyclic group each has the same meaning as the divalent aryl group and the divalent heterocyclic group as defined in Ar1 and Ar6, and they may further contain a heterocyclic ring and may be condensed to form a 2- to 5-membered ring. The divalent aryl group is preferably a divalent monocyclic or bicyclic aryl group, or a divalent group a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed. More preferred examples of the heterocyclic groups include thiophene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, thiazole, thiadiazole, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, and benzotriazole. When L1 represents a group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group each connected by an aromatic heterocyclic group, the aromatic heterocyclic group is preferably a 6-membered aromatic heterocyclic group. X represents an oxygen atom, a sulfur atom, Nxe2x80x94Rx1 or CRx2Rx3; and Rx1, Rx2 and Rx3, which may be the same or different, each represents a hydrogen atom or a substituent. X preferably represents an oxygen atom, a sulfur atom, or CRx2Rx3. The substituents are the same as those described above as the substituents of Ar1 and Ar6. Rx1 preferably represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and Rx2 and Rx3 each preferably represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, provided that Rx2 and Rx3 do not represent hydrogen atoms at the same time. More preferably, the alkyl, aryl or heterocyclic group represented by Rx2, Rx2 and Rx3 each has the same meaning as the alkyl, aryl or heterocyclic group described above as the substituents represented by Ar1 and Ar6. The alkyl group represented by Rx2 and Rx3 is preferably a perfluoroalkyl group, i.e., a straight chain, branched or cyclic alkyl group having fluorine as a substituent (preferably having from 1 to 30, more preferably from 1 to 20, and still more preferably from 1 to 12 carbon atoms, e.g., a trifluoromethyl group, a pentafluoromethyl group).
The oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, or acyl group represented by Rx2 and Rx3 is preferably an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, and each group has the same meaning as the oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, or acyl group represented by R4, R5a, R9a and R10a, and the preferred range is also the same.
Rx2 and Rx3 may be linked to form a ring.
As the examples of L1, the following compounds can be exemplified, for instance. 
A compound represented by formula (II) will be described in detail below.
Ar1, Ar6 and L1 each has the same meaning as in formula (I) and each preferred range is also the same. Ar2, Ar3, Ar7 and Ar8, which may be the same or different, each represents an aryl group or a heterocyclic group, and has the same meaning as the aryl group or the heterocyclic group represented by R2, R3, R7 and R8 in formula (I), and each preferred range is also the same. R4b, R5b, R9b and R10b beach represents a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, provided that all of R4b, R5b, R9b and R10b do not represent hydrogen atoms at the same time.
Preferably, the heterocyclic group represented by R4b, R5b , R9b and R10b has the same meaning as the heterocyclic group represented by R2, R3, R7 and R8 The heterocyclic group represented by R4b, R5b, R9b and R10b is more preferably benzoxazole, benzothiazole or benzimidazole.
The oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, or acyl group represented by R4b, R5b, R9b and R10b is preferably an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.
In this case, the aliphatic hydrocarbon group has the same meaning as the aliphatic hydrocarbon group represented by R2, R3, R7 and R8, preferably the aliphatic hydrocarbon group is an alkyl group or an alkenyl group, and more preferably a methyl group, an ethyl group, a propyl group, a butyl group, a trifluoromethyl group, or an allyl group.
The aryl group preferably has the same meaning as the aryl group represented by R2, R3, R7 and R8. The heterocyclic group preferably has the same meaning as the heterocyclic group represented by R2, R3, R7 and R8. They may be monocyclic or may form a condensed ring with other rings.
R4b, R4b, R9b and R10b each more preferably represents a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a sulfonyl group, or an acyl group.
A compound represented by formula (III) will be described in detail below.
Ar1, Ar2, Ar3, Ar6, Ar7, Ar8 and L1 each has the same meaning as in formula (II) and each preferred range is also the same. R4c and R9c, which may be the same or different, each represents a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, and each group has the same meaning as each group represented by R4b, R5b, R9b and R10b and the preferred range of each group is also the same.
A compound represented by formula (IV) will be described in detail below.
Ar2, Ar3, Ar7 and Ar8 each has the same meaning as in formula (III) and each preferred range is also the same. Rx and Ry each represents a substituent (those exemplified as the substituents of Ar1 can be applied to). m and n each represents an integer of 0 to 4, when m and n each represents 2, 3 or 4, a plurality of Rx and Ry may be the same with or different from each other. At least two of Ar2, Ar3 and Rx may be formed to form a ring, and/or at least two of Ar7, Ar8 and Ry may be linked to form a ring, and the ring to be formed is preferably a 5- to 7-membered ring. R4d and R9d, which may be the same or different, each represents a heterocyclic group, a cyano group, an oxycarbonyl group, a sulfonyl group, or an acyl group, and each group has the same meaning as each group represented by R4b, R5b, R9b and R10b in formula (II) and the preferred range of each group is also the same. L2 represents (i) a divalent monocyclic or bicyclic aryl group, or a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom, or the combination of these groups. The aryl group or the heterocyclic group represented by L2 each preferably has the same meaning as the aryl group or the heterocyclic group represented Ar1 and Ar6 in formula (I). More preferably L2 represents a monocyclic, bicyclic or tricyclic aryl group, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, or a bicyclic or tricyclic heterocyclic group comprising any of these groups condensed with a benzene ring.
m and n each preferably represents 0.
L2 particularly preferably represents a monocyclic or condensed bicyclic or tricyclic aryl group or heterocyclic group.
The compounds represented by formulae (I) to (IV) may be low molecular weight compounds, may be high molecular weight compounds (preferably having a weight average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and particularly preferably from 10,000 to 1,000,000) having the residual monomers of the compounds represented by formulae (I) to (IV) bonded to the polymer main chains, or may be high molecular weight compounds (preferably having a weight average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and particularly preferably from 10,000 to 1,000,000) having the skeletons of the compounds represented by formulae (I) to (IV) at the main chains. The high molecular weight compounds may be homopolymers or copolymers with other monomers.
The compounds represented by formulae (I) to (IV) are preferably low molecular weight compounds. Further, formulae (I) to (IV) take limiting structures for convenience sake but the compounds may be tautomers thereof.
With respect to the compound represented by formula (I), preferred combinations of the substituents will be described below. Ar1 and Ar6 each represents a divalent monocyclic or bicyclic aryl group having from 6 to 20 carbon atoms, or a divalent 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom and having from 1 to 20 carbon atoms. R2, R3, R7 and R8, which may be the same or different, each represents a monocyclic, bicyclic, tricyclic or tetracyclic aryl group having from 6 to 30 carbon atoms, a 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom and having from 1 to 20 carbon atoms, or an alkyl group having from 1 to 20 carbon atoms. Ar1, Ar6, R2, R3, R7 and R8 each may have a substituent. Examples of the substituents include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxyl group, an amino group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, a hydroxyl group, and a heterocyclic group, and these groups may further be substituted. At least two of Ar1, R2 and R3 may be linked to form a ring, and/or at least two of Ar6, R7 and R8 may be linked to form a ring, and the ring to be formed is preferably a 5- to 7-membered ring.
R4a, R5a, R9a and R10a, which may be the same or different, each represents a hydrogen atom or a monovalent group, and at least one of R4a, R5a, R9a and R10a represents an electron withdrawing group having a Hammett""s "sgr"p value of 0.2 or more. Examples of the substituents (monovalent groups) include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxyl group, an amino group, an acyl group, an oxycarbonyl group, a carbonylamino group, a sulfonylamino group, a sulfonyl group, a sulfamoyl group, a carbamoyl group, a cyano group and a heterocyclic group. At least two of Ar1, R2, R3, R4a, and R5a may be linked to form a ring. At least two of R9a, R10a, Ar6, R7, and R8 may be linked to form a ring. At least two of R4a, R5a, R9a and R10a may be linked to form a ring.
L1 represents (i) a divalent monocyclic or bicyclic aryl group, or a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, a Cxe2x95x90X group, a silyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom, or the combination of these groups. Here, the divalent aryl group or the divalent heterocyclic group is a divalent monocyclic or bicyclic aryl group having from 6 to 20 carbon atoms, or a divalent 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom and having from 1 to 20 carbon atoms. The heterocyclic group and a condensed ring may be further condensed to formed a 2- to 5-membered ring. More preferred examples of the heterocyclic groups include thiophene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole, thiazole, thiadiazole, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, and benzotriazole. X represents an oxygen atom, a sulfur atom, Nxe2x80x94Rx1 or CRx2Rx3 and Rx1, Rx2 and Rx3, which may be the same or different, each represents a hydrogen atom or a substituent. X more preferably represents an oxygen atom, a sulfur atom, or CRx2Rx3. Rx1 preferably represents a hydrogen atom, analkyl group, an aryl group, or a heterocyclic group, and Rx2 and Rx3 each preferably represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, provided that Rx2 and Rx3 do not represent hydrogen atoms at the same time. More preferably, the alkyl, aryl or heterocyclic group represented by Rx1, Rx2 and Rx3 each has the same meaning as the alkyl, aryl or heterocyclic group described above as the substituents represented by Ar1 and Ar6.
The alkyl group represented by Rx2 and Rx3 is preferably a perfluoroalkyl group, i.e., a straight chain, branched or cyclic alkyl group having fluorine as a substituent (preferably having from 1 to 30, more preferably from 1 to 20, and still more preferably from 1 to 12 carbon atoms, e.g., a trifluoromethyl group, a pentafluoromethyl group).
The oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, or acyl group represented by Rx2 and Rx3 is preferably an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, and each group has the same meaning as the oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, or acyl group represented by R4a, R5a, R9a and R10a.
The more preferred combination of the substituents of the compound represented by formula (I) is represented by formula (II).
Ar1, Ar6 and L1 each has the same meaning as the combination in formula (I). Ar2, Ar3, Ar7 and Ar8 each preferably represents an aryl group having from 6 to 26 carbon atoms e.g., a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, or a pyrenyl group, or a 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom and having from 1 to 20 carbon atoms, and more preferably a 5- or 6-membered aromatic heterocyclic group containing one or two sulfur atoms. R4b, R5b, R9b and R10b, which may be the same or different, each represents a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group, provided that all of R4b, R5b, R9b and R10b do not represent hydrogen atoms at the same time.
The heterocyclic group represented by R4b, R5b, R9b and R10b is a 5- or 6-membered aromatic heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom and having from 1 to 20 carbon atoms. The oxycarbonyl group, carbamoyl group, sulfonyl group, sulfamoyl group, or acyl group represented by R4b, R5b, R9b and R10b is preferably an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group substituted with an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.
In this case, the aliphatic hydrocarbon group has the same meaning as the aliphatic hydrocarbon group represented by R2, R3, R7 and R8, preferably the aliphatic hydrocarbon group is an alkyl group or an alkenyl group, and more preferably a methyl group, an ethyl group, a propyl group, a butyl group, a trifluoromethyl group, or an allyl group.
The aryl group preferably has the same meaning as the aryl group represented by R2, R3, R7 and R8 The heterocyclic group preferably has the same meaning as the heterocyclic group represented by R2, R3, R7 and R8. They may be monocyclic or may form a condensed ring with other rings.
The more preferred combination of the substituents of the compound represented by formula (II) is represented by formula (III). Ar1, Ar2, Ar3, Ar6, Ar7, Ar8 and L1 each has the same meaning as the combination in formula (II). R4c and R9c, which may be the same or different, each represents a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, or an acyl group.
The more preferred combination of the substituents of the compound represented by formula (III) is represented by formula (IV). Ar2, Ar3, Ar7 and Ar8 each has the same meaning as the combination in formula (III). R4d and R9d, which may be the same or different, each represents a heterocyclic group, a cyano group, an oxycarbonyl group, a sulfonyl group, or an acyl group. L2 represents (i) a divalent monocyclic or bicyclic aryl group, or a divalent monocyclic orbicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom, or the combination of these groups. The aryl group or the heterocyclic group represented by L2 each preferably has the same meaning as the aryl group or the heterocyclic group represented Ar1 and Ar6 in formula (I). More preferably, L2 represents a monocyclic, bicyclic or tricyclic aryl group, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, or a bicyclic or tricyclic heterocyclic group comprising any of these groups condensed with a benzene ring. L2 particularly preferably represents a monocyclic or condensed bicyclic or tricyclic aryl group or heterocyclic group. m and n each represents 0.
USPTO Backgrounds
USPTO Backgrounds