Classifications

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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
  • C07C15/20—Polycyclic condensed hydrocarbons
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  • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
  • C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
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  • C07C255/00—Carboxylic acid nitriles
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  • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
  • C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
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  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/56—Ring systems containing three or more rings
  • C07D209/80—[b, c]- or [b, d]-condensed
  • C07D209/82—Carbazoles; Hydrogenated carbazoles
  • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
  • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
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  • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
  • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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  • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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  • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
  • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
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  • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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  • Y10S428/917—Electroluminescent

Definitions

• the present invention relates to a novel organic compound and an organic electroluminescence (electroluminescence will be referred to as EL, hereinafter) device using the organic compound. More particularly, the present invention relates to an anthracene derivative used as a material constituting an organic EL device and an organic EL device which uses the anthracene derivative and exhibits a high efficiency of light emission and excellent heat resistance.
• Electroluminescence devices which utilize light emission in the electric field show high self-distinguishability because of the self-emission and are excellent in impact resistance because they are completely solid devices. Therefore, organic EL devices are used in the field of the back light of thin film display devices and liquid crystal displays and the planar light source.
• EL devices practically used at present are EL devices of the dispersion type. Since EL devices of the dispersion type require an alternating voltage of several tens volts or higher and 10 kiloHerz or higher, driving circuits of the EL devices are complicated.
• organic EL devices which can be driven at a voltage of 10 volts or lower and can achieve light emission of a high degree are actively studied.
• organic EL devices having a laminate structure of a transparent electrode/a hole injection layer/a light emitting layer/a back face electrode are proposed (Appl. Phys. Lett., Volume 51, Pages 913 to 915 (1987) and Japanese Patent Application Laid-Open No. Showa 63(1988)-264629).
• holes are efficiently injected into the light emitting layer through the hole injecting layer disposed in the organic EL devices.
• the light emitting layer used in the organic EL devices may be a single layer. However, an excellent balance between the electron transporting property and the hole transporting property cannot be achieved by the single layer structure. Improvement in the properties of the organic EL devices has been made by using a multi-layer laminate structure.
• Forming a laminate structure causes problems in that the process for producing the organic EL devices is complicated and the time required for the production increases and that restrictions such as the necessity for forming each layer into a sufficiently thin film arise. Moreover, in recent years, a lower driving voltage is required since information instruments are required to have a decrease size and to be portable. Therefore, development of a light emitting material and a hole transporting material which contribute to a decrease in the weight and a decrease in the driving voltage has been conducted. It is known that anthracene can be used as the light emitting material. However, forming a uniform thin film of anthracene is not easy. Therefore, introduction of various substituents into anthracene has been attempted.
• condensed multi-ring aromatic hydrocarbons are proposed for the light emitting material of organic EL devices (Japanese Patent Application Laid-Open Nos. Heisei 4(1992)-178488, Heisei 6(1994)-228544, Heisei 6(1994)-228545, Heisei 6(1994)-228546, Heisei 6(1994)-228547, Heisei 6(1994)-228548, Heisei 6(1994)-228549, Heisei 8(1996)-311442, Heisei 8(1996)-12600, Heisei 8(1996)-12969 and Heisei 10(1998)-72579).
• organic EL devices using the above compounds have a problem in that the efficiency of light emission and heat resistance are not sufficient.
• the present invention has been made under the above circumstances and has objects of providing a novel compound which exhibits a high efficiency of light emission and excellent heat resistance when the compound is used as a material constituting an organic EL device and an organic EL device using the compound.
• X and Y each independently represent a substituted or unsubstituted trifunctional aromatic ring group having 6 to 30 carbon atoms or a substituted or unsubstituted trifunctional heterocyclic group having 4 to 30 carbon atoms;
• a 1 to A 4 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms or
• a 1 represents hydrogen atom
• a 2 represents a styryl group in which a phenyl portion may be substituted and an ⁇ -position or a ⁇ -position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms
• a 3 represents hydrogen atom and
• a 4 represents a styryl group in which a phenyl portion may be substituted and an ⁇ -position or a ⁇ -position of a vinyl portion may be substituted with an alkyl group having
• a 1 to A 4 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms or (2) A 1 represents hydrogen atom, A 2 represents a styryl group in which a phenyl portion may be substituted and an ⁇ -position or a ⁇ -position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms, A 3 represents hydrogen atom and A 4 represents a styryl group in which a phenyl portion may be substituted and an ⁇ -position or a ⁇ -position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms; R 1 to R 16 each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl
• a 1 to A 4 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms or (2) A 1 represents hydrogen atom, A 2 represents a styryl group in which a phenyl portion may be substituted and an ⁇ -position or a ⁇ -position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms, A 3 represents hydrogen atom and A 4 represents a styryl group in which a phenyl portion may be substituted and an ⁇ -position or a ⁇ -position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms; R 1 to R 16 each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl
• X and Y each independently represent a substituted or unsubstituted trifunctional aromatic ring group having 6 to 30 carbon atoms or a substituted or unsubstituted trifunctional heterocyclic group having 4 to 30 carbon atoms;
• R 1 to R 20 each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group or a substituted or unsubstituted aryl group; adjacent groups represented by R 1 to R 20 may for rings by forming bonds between each other;
• Q represents a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon
• An organic electroluminescence device which comprises a light emitting area comprising an anthracene derivative described in any of [1] to [4].
• An organic electroluminescence device which comprises an organic light emitting layer comprising an anthracene derivative described in any of [1] to [4].
• the organic compound of the present invention is a compound represented by general formula (I):
• X and Y each independently represent substituted or unsubstituted trivalent aromatic ring group having 6 to 30 carbon atoms or a substituted or unsubstituted trivalent heterocyclic group having 4 to 30 carbon atoms.
• Examples of the trivalent aromatic ring group having 6 to 30 carbon atoms include trivalent groups obtained by eliminating three hydrogen atoms from aromatic compounds such as benzene, naphthalene, biphenyl, terphenyl, triphenyl, chrysene, naphthacene, picene, perylene, pentacene, coronene, rubicene, anthracene, benzo[a]anthracene, benzo[a]pyrene, tetraphenylene and bisanthracene.
• aromatic compounds such as benzene, naphthalene, biphenyl, terphenyl, triphenyl, chrysene, naphthacene, picene, perylene, pentacene, coronene, rubicene, anthracene, benzo[a]anthracene, benzo[a]pyrene, tetraphenylene and bisanthracene.
• Examples of the trivalent heterocyclic group having 4 to 30 carbon atoms include trivalent groups obtained by eliminating three hydrogen atoms from heterocyclic compounds such as furan, thiophene, pyrrol, 2-hydroxypyrrol, benzofuran, isobenzofuran, 1-benzothiophene, 2-benzothiophene, indole, isoindole, indolidine, carbazole, 2-hydroxypyrane, 2-hydroxychromene, 1-hydroxy-2-benzopyrane, xanthene, 4-hydroxythiopyrane, pyridine, quinoline, isoquinoline, 4-hydroxyquinolidine, phenanthridine, acridine, oxazole, isoxazole, thiazole, isothiazole, furazane, imidazole, pyrazole, benzimidazole, 1-hydroxyimidazole, 1,8-naphthylidine, pyradine, pyrimidine, pyridazine
• a 1 to A 4 may each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 4 to 30 carbon atoms.
• the aryl group having 6 to 30 carbon atoms include phenyl group, naphthyl group, biphenyl group, anthranyl group, terphenyl group and styryl group.
• Examples of the monovalent heterocyclic group having 4 to 30 carbon atoms include monovalent groups corresponding to the trivalent heterocyclic groups described as the examples of the groups represented by X and Y.
• a 1 and A 3 may each represent hydrogen atom and A 2 and A 4 may each represent a styryl group.
• the phenyl portion of the styryl group may be substituted and the ⁇ -position or the ⁇ -position of the vinyl portion of the styryl group may be substituted with an alkyl group having 1 to 30 carbon atoms.
• the substituents may form a ring structure by forming a bond between each other.
• styryl group examples include phenylvinylene group, triphenylvinylene group, naphthylvinylene group, biphenylvinylene group, terphenylvinylene group and anthranylvinylene group.
• R 1 to R 16 each independently represent hydrogen atom, a halogen atom, cyano group, nitro group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 18 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 18 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted ester group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 5 to 16 carbon atoms.
• Examples of the alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, various types of pentyl groups and various types of hexyl groups.
• Examples of the alkoxy group having 1 to 6 carbon atoms include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, various types of pentyloxy groups and various types of hexyloxy groups.
• Examples of the aryloxy group having 5 to 18 carbon atoms include phenoxy group, tolyloxy group and naphthyloxy group.
• Examples of the aralkyloxy group having 7 to 18 carbon atoms include benzyloxy group, phenetyloxy group and naphthylmethoxy group.
• Examples of the alkylthio group having 1 to 20 carbon atoms and the arylthio group having 6 to 18 carbon atoms include methylthio group, ethylthio group, phenylthio group and tolylthio group.
• Examples of the amino group substituted with an aryl group having 5 to 16 carbon atoms include diphenylamino group, dinaphthylamino group and naphthylphenylamio group.
• Examples of the ester group having 1 to 6 carbon atoms include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group and isopropoxycarbonyl group.
• Examples of the halogen atom include fluorine atom, chlorine atom and bromine atom.
• Adjacent groups represented by R 1 to R 16 may for rings by forming bonds between each other.
• Q represents a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 4 to 30 carbon atoms.
• the cycloalkylene group having 5 to 30 carbon atoms include cyclopentylene group, cyclohexylene group and cycloheptylene group.
• Examples of the arylene group having 6 to 30 carbon atoms include phenylene group, naphthylene group, biphenylene group, anthranylene group and terphenylene group.
• Examples of the divalent heterocyclic group having 4 to 30 carbon atoms include divalent groups corresponding to the trivalent groups described as the examples of the groups represented by X and Y.
• p represents a number selected from 0, 1 and 2.
• p represents 0, groups at both sides are bonded through a single bond.
• substituents include the groups described as the examples of the groups represented by R 1 to R 16 .
• adjacent substituents may for rings by forming bonds between each other.
• the anthracene derivative represented by general formula (I) is a compound selected from the compounds having the structures described above. Among the above compounds, compounds having a glass transition temperature of 100° C. or higher are preferable and compounds having a glass transition temperature of 120° C. or higher are more preferable.
• anthracene derivative represented by general formula (I) include anthracene derivatives represented by the following general formulae (II) and (II′):
• anthracene derivative represented by general formula (I) further include anthracene derivatives represented by the following general formula (III):
• a 1 , A 2 and X are as defined above and Z represents a halogen atom, is reacted with an alkyllithium reagent and converted into a lithium compound.
• the obtained lithium compound is reacted with a bianthrone compound represented by general formula (1-b):
• R 1 to R 16 are as defined above, and a bisphenol derivative represented by general formula (1-c):
• the organic EL device is prepared on a substrate which transmits light.
• the substrate which transmits light is the substrate which supports the organic EL device. It is preferable that the substrate which transmits light has a transmittance of light of 50% or greater in the visible region of 400 to 700 nm. It is also preferable that a flat and smooth substrate is used.
• the cathode can be prepared by forming a thin film of the material described above in accordance with a process such as the vapor deposition process and the sputtering process.
• the light emitting layer in the organic EL of the present invention a layer having the combination of the following functions is preferably used.
• the injecting function the function of injecting holes from the anode or the hole injecting layer or injecting electrons from the cathode or the electron injecting layer when an electric field is applied.
• the transporting function the function of transporting injected charges (electrons and holes) by the force of the electric field.
• the light emitting function the function of providing the site for recombination of electrons and holes and emitting light generated by the recombination.
• the easiness of injection of holes may be different from the easiness of injection of electrons.
• the ability of transporting holes expressed by the mobility of holes may be different from the ability of transporting electrons expressed by the mobility of electrons. It is preferable that either holes or electrons are transported.
• the above anthracene derivative represented by any of general formulae (I), (II), (II′) and (III) satisfies the above three conditions and the light emitting layer can be formed by using the anthracene derivative as the main component.
• a substance forming a recombination site can be used as one of the materials constituting the light emitting layer of the organic EL device.
• the substance forming a recombination site is a substance which positively provides a site for recombination of electrons and holes injected from the both electrodes or a substance which provides a site where a recombination energy is transported and light is emitted although the recombination of electrons and holes does not take place. Therefore, when the substance forming a recombination site is used in combination, electrons and holes are recombined at portions more concentrated around the center of the light emitting layer and the luminance of light emission can be increased in comparison with the single use of the anthracene derivative.
• a substance having a higher quantum yield of fluorescence is used as the substance forming a recombination site in the light emitting layer of the organic EL device of the present invention.
• the substance has a quantum yield of fluorescence of 0.3 to 1.0.
• a compound selected from styrylamine compounds, quinacridone derivatives, rubrene derivatives, coumarine derivatives, perylene derivatives, pyrane derivatives and fluoranthene derivatives or a mixture of compounds selected from these compounds is used.
• substance forming a recombination site include conjugated macromolecular compounds such as polyarylenevinylene derivatives and polyarylene and vinylene derivatives substituted with alkyl groups and alkoxy groups having 1 to 50 carbon atoms.
• the substance forming a recombination site is selected in accordance with the color of light emitted from the light emitting layer.
• perylene, a styrylamine derivative or a distyrylarylene derivative substituted with an amino group is used.
• a quinacridone derivative or a coumarine derivative is used.
• a rubrene derivative is used.
• emission of orange light or reddish orange light it is preferable that a dicyanomethylpyrane derivative is used.
• anthracene derivative represented by any of general formulae (I), (II), (II) and (III) of the present invention is used as the substance forming a recombination site.
• the amount of the substance forming a recombination site used in the device is decided in accordance with the luminance of light emission and the color of emitted light of the light emitting layer. It is preferable that the amount is in the range of 0.1 to 20 parts by mass per 100 parts by mass of the organic compound described above.
• the amount of the substance forming a recombination site is less than 0.1 parts by mass, the luminance of light emission tends to decrease.
• the amount exceeds 20 parts by mass heat resistance tends to decrease.
• the amount is 0.5 to 20 parts by mass and more preferably 1.0 to 10 parts by mass per 100 parts by mass of the organic compound described above.
• X represents a divalent group represented by the following general formula:
• a representing an integer of 2 to 5
• Y represents an aryl group expressed by the following formula:
• phenyl group, phenylene group and naphthyl group may have a single or a plurality of substituents selected from alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, hydroxyl group, sulfonyl group, carbonyl group, amino group, dimethylamino group and diphenylamino group.
• substituents selected from alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, hydroxyl group, sulfonyl group, carbonyl group, amino group, dimethylamino group and diphenylamino group.
• the bond is formed at the para-position of phenyl group, phenylene group and naphthyl group since the bonding is rigid and a smooth film is formed by vapor deposition without chemical decomposition.
• Specific examples of the compound represented by general formula (IV) include the compounds expressed by the following formulae.
• Me represents methyl group
• t-Bu represents tertiary-butyl group
• Ph represents phenyl group
• a fluorescent whitening agent of benzothiazole, benzimidazole or benzoxazole, a metal chelate compound of an oxinoid compound or a styrylbenzene compound can be used.
• examples of the above compounds include compounds disclosed in Japanese Patent Application Laid-Open No. Showa 59(1984)-194393. Further examples of the compound useful as the above compounds include compounds listed in Chemistry of Synthetic Dies, 1971, pages 628 to 637 and 640.
• metal chelate compound of an oxinoid compound for example, compounds disclosed in Japanese Patent Application Laid-Open No. Showa 63(1988)-295695 can be used.
• Typical examples of the above compound include metal complexes of 8-hydroxyquinolines such as tris(8-quinolinol)aluminum and dilithium-epintridione.
• styrylbenzene compound for example, compounds disclosed in European Patent Nos. 0319881 and 0373582 can be used. Distyrylpyrazine derivatives disclosed in Japanese Patent Application Laid-Open No. Heisei 2(1990)-252793 can also be used as the material of the light emitting layer. Polyphenyl compounds disclosed in European Patent No. 0387715 can also be used as the material of the light emitting layer.
• Compounds other than the fluorescent whitening agents, metal chelate compounds of oxinoid compounds and styrylbenzene compounds can be used as the material of the light emitting layer.
• Examples of such compounds include the following compounds: 12-phthaloperinone (J. Appl. Phys., Volume 27, L713 (1988)); 1,4-diphenyl-1,3-butadiene and 1,1,4,4-tetraphenyl-1,3-butadiene (Appl. Phys, Lett., Volume 56, L799 (1990)); naphthalimide derivatives (Japanese Patent Application Laid-Open No.
• aromatic dimethylidine compounds disclosed in European Patent No. 0388768 and Japanese Patent Application Laid-Open No. Heisei 3 (1991)-231970 are used as the material of the light emitting layer.
• aromatic dimethylidine compounds disclosed in European Patent No. 0388768 and Japanese Patent Application Laid-Open No. Heisei 3 (1991)-231970 are used as the material of the light emitting layer.
• the above compounds include 4,4′-bis(2,2-di-t-butylphenylvinyl)biphenyl, 4,4′-bis(2,2-diphenylvinyl)biphenyl and derivatives of these compounds.
• L represents a hydrocarbon group having 6 to 24 carbon atoms which comprises a phenyl portion
• O—L represents a phenolate ligand
• Q represents a 8-quilinolate ligand
• Rs represents a substituent to the 8-quinolinolate ring which is selected so as to inhibit coordination of more than two 8-quinolinolate ligands to the aluminum atom.
• the above compound include bis(2-methyl-8-quinolinolato)(para-phenylphenolato)aluminum(III) and bis (2-methyl-8-quinolinolato)(1-naphtholato)aluminum(III).
• a light emitting material having a distyrylarylene skeleton structure and preferably 4,4′-bis(2,2-diphenylvinyl)biphenyl is used as the host and a perylene derivative and preferably, for example, a distyrylarylene derivative is used as the dopant.
• the light emitting layer for obtaining emission of white light is not particularly limited.
• the following light emitting layers may be used:
• a light emitting layer having a two-layer structure Japanese Patent Application Laid-Open Nos. Heisei 2(1990)-220390 and Heisei 2(1990)-216790.
• a light emitting layer divided into a plurality of layers each of which is composed of a material having a different wavelength of emitted light Japanese Patent Application Laid-Open No. Heisei 4(1992)-51491.
• a light emitting layer in which a light emitting layer emitting blue light contains a fluorescent die emitting blue light, a light emitting layer emitting green light has an area containing a fluorescent die emitting red light and a fluorescent material emitting green light is further contained Japanese Patent Application Laid-Open No. Heisei 7(1995)-142169).
• the light emitting layer having structure (5) is preferably used.
• Me represents methyl group
• iPr represents isopropyl group
• Et represents ethyl group.
• the process for forming the light emitting layer using the above materials for example, a conventional process such as the vapor deposition process, the spin coating process and the Langmuir-Blodgett process (the LB process) can be used.
• the light emitting layer is a molecular deposition film.
• the molecular deposition film is a film formed by deposition of a material compound in the gas phase or a film formed by solidification of a material compound in a solution or in the liquid state.
• the molecular deposition film can be distinguished from a thin film formed by the LB process (a molecular accumulation film) based on differences in the aggregation structure and the higher order structures and functional differences due to these structural differences.
• the light emitting layer can also be formed by dissolving a binding material such as a resin and a material compound into a solvent to prepare a solution, followed by forming a thin film in accordance with the spin coating process.
• the thickness of the light emitting layer thus formed is not particularly limited and can be suitably selected in accordance with the situation. It is preferable that the thickness is in the range of 5 nm to 5 ⁇ m.
• the light emitting layer may be constituted with a single layer comprising one or more materials selected from the above materials or may be a laminate of the above light emitting layer with a light emitting layer comprising a compound different from the compound comprised in the above light emitting layer.
• the hole injecting and transporting layer is a layer which helps injection of holes into the light emitting layer and transports holes to the light emitting area. This layer has a great mobility of holes and the ionization energy is, in general, as small as 5.5 eV or smaller.
• a material transporting holes to the light emitting layer under a small electric field strength is preferable. It is preferable that the mobility of holes is, for example, at least 10 ⁇ 6 cm 2 /V ⁇ sec when an electric field of 104 to 106 V/cm is applied.
• the material which is mixed with the distyrylarylene derivative of the present invention and forms the hole injecting and transporting layer is not particularly limited as long as the material has the desirable properties described above.
• a material can be suitably selected from materials conventionally used as the hole transporting material in optically conductive materials and materials conventionally used for a hole injecting layer in EL devices.
• Examples of the material forming the hole injecting and transporting layer are as follows: triazole derivatives (U.S. Pat. No. 3,112,197); oxadiazole derivatives (U.S. Pat. No. 3,189,447); imidazole derivatives (Japanese Patent Application Publication No. Showa 37(1962)-16096); polyarylalkane derivatives (U.S. Pat. Nos. 3,615,402, 3,820,989 and 3,542,544, Japanese Patent Application Publication Nos. Showa 45(1970)-555 and Showa 51(1976) -10983 and Japanese Patent Application Laid-Open Nos.
• Heisei 2(1990)-204996 aniline copolymers (Japanese Patent Application Laid-Open No. Heisei 2(1990)-282263); and electrically conductive macromolecular oligomers, in particular, thiophene oligomers (Japanese Patent Application Laid-Open No. Heisei 1(1989)-211399).
• the above materials can be used.
• the following materials can also be used as the material of the hole injecting layer: porphyrin compounds (Japanese Patent Application Laid-Open No. Showa 63(1988)-295695); aromatic tertiary-amine compounds and styrylamine compounds (U.S. Pat. No. 4,127,412 and Japanese Patent Application Laid-Open Nos.
• Further examples include compounds having two condensed aromatic rings in the molecule which are disclosed in U.S. Pat. No. 5,061,569, such as 4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl and compounds having three triphenylamine units bonded in the star burst form, which are disclosed in Japanese Patent Application Laid-Open No. Heisei 4(1992)-308688, such as 4,4′,4′′-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine.
• Aromatic dimethylidine compounds described above as the material of the light emitting layer and inorganic compounds such as the p-type Si and the p-type SiC can also be used as the material of the hole injecting layer.
• the hole injecting and transporting layer a thin film of the above compound is formed in accordance with a conventional process such as the vacuum vapor deposition process, the spin coating process, the casting process and the LB process.
• the thickness of the hole injecting and transporting layer is not particularly limited. The thickness is, in general, 5 nm to 5 ⁇ m.
• the hole injecting and transporting layer may be composed of a single layer comprising one or more materials selected from the materials described above or may be a laminate of the above hole injecting and transporting layer with a hole injecting and transporting layer comprising a compounds different from the compound comprised in the above hole injecting and transporting layer.
• the layer of an organic semiconductor is a layer for helping injection of holes or electrons into the light emitting layer. It is preferable that this layer has an electric conductivity of 10 ⁇ 10 S/cm or greater.
• electrically conductive oligomers such as oligomers containing thiophene, oligomers containing arylamines disclosed in Japanese Patent Application Laid-Open No. Heisei 8(1996)-193191 and electrically conductive dendrimers such as dendrimers containing arylamines can be used.
• the electron injecting layer is a layer for helping injection of electrons into the light emitting layer and has a great mobility of electrons.
• the layer for improving adhesion is the electron injecting layer made of a material exhibiting excellent adhesion with the cathode.
• metal complexes of 8-hydroxyquinoline and derivatives thereof are preferably used.
• the metal complexes of 8-hydroxyquinoline and derivatives thereof which can be used as the material for electron injecting layer include metal chelate compounds of oxinoid compounds including chelate compounds of oxine (in general, 8-quinolinol or 8-hydroxyquinoline) such as tris(8-quinolinol) aluminum.
• Examples of the oxadiazole derivative include electron transferring compounds represented by the following general formulae (V) to (VII):
• Ar 1 , Ar 2 , Ar 3 , Ar 5 , Ar 6 and Ar 9 each represent an aryl group which may have substituents
• Ar 1 and Ar 2 , Ar 3 and Ar 5 , and Ar 6 and Ar 9 may represent the same group or different groups
• Ar 4 , Ar 7 and Ar 8 each represent an arylene group which may have substituents and Ar 7 and Ar 8 may represent the same group or different groups.
• Examples of the aryl group in the above general formulae (V) to (VII) include phenyl group, biphenyl group, anthranyl group, perylenyl group and pyrenyl group.
• Examples of the arylene group include phenylene group, naphthylene group, biphenylene group, anthranylene group, perylenylene group and pyrenylene group.
• Examples of the substituent to the above groups include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms and cyano group.
• As the electron transferring compound compounds having the excellent property to form a thin layer are used.
• the electron transferring compound include the compounds expressed by the following formulae.
• Me represents methyl group and t-Bu represents tertiary-butyl group.
• the organic EL device can be prepared by forming the anode, the light emitting layer and, where necessary, the hole injecting layer and the electron injecting layer using the above materials in accordance with the above process, followed by forming the cathode.
• the organic EL device may be prepared in the reverse order, i.e., by preparing the cathode first and the anode last.
• the anode is formed first.
• a thin film of an anode material is formed on the substrate transmitting light in accordance with a process such as the vapor deposition process or the sputtering process so that the formed thin film has a thickness of 1 ⁇ m or smaller and preferably in the range of 10 to 200 nm.
• the hole injecting layer is then formed on the anode.
• the hole injecting layer may be formed in accordance with a process such as the vacuum vapor deposition process, the spin coating process, the casting process and the LB process.
• the vacuum vapor deposition process is preferable since a uniform film can be obtained and the formation of pin holes can be suppressed.
• the conditions of the vacuum vapor deposition process are different depending on the compound used (the material of the hole injecting layer) and the crystal structure and the recombination structure of the hole injecting layer to be formed.
• the temperature of the source of the vapor deposition is selected in the range of 50 to 450° C.
• the degree of vacuum is selected in the range of 10 ⁇ 7 to 10 ⁇ 3 torr
• the rate of vapor deposition is selected in the range of 0.01 to 50 nm/second
• the temperature of the substrate plate is selected in the range of ⁇ 50 to 300° C.
• the thickness of the film is selected in the range of 5 nm to 5 ⁇ m.
• the light emitting layer is formed on the hole injecting layer.
• a thin film of the organic light emitting material is formed in accordance with a process such as the vacuum vapor deposition process, the sputtering process, the spin coating process and the casting process.
• the vacuum vapor deposition process is preferable since a uniform film can be obtained and the formation of pin holes can be suppressed.
• the conditions of the vacuum vapor deposition process is different depending on the compound used. In general, the conditions can be selected in the same ranges as those described above in the formation of the hole injecting layer.
• the electron injecting layer is formed on the light emitting layer formed above. Similarly to the formation of the hole injecting layer and the light emitting layer, it is preferable that the vacuum vapor deposition process is used since the formation of a uniform film is necessary. The conditions of the vacuum vapor deposition process can be selected in the same ranges as those described in the formation of the hole injecting layer and the light emitting layer.
• the process for adding the anthracene derivative of the present invention is different depending on the layer in which the anthracene derivative is comprised.
• the anthracene derivative can be vacuum vapor deposited simultaneously with other materials.
• the spin coating process is used, the anthracene derivative can be used as a mixture with other materials.
• the cathode is laminated in the final step and the organic EL device can be obtained.
• the cathode is constituted with a metal and the vacuum vapor deposition process or the sputtering process can be used for the formation.
• the vacuum vapor deposition process is preferable since formation of damages in the organic layers formed in previous steps during the formation of the cathode can be prevented.
• the steps for preparing the organic EL device from the formation of the anode to the formation of the cathode are conducted after the pressure in the apparatus for the preparation is reduced and while the pressure is maintained at the reduced pressure.
• the light emission can be observed when the anode is connected to the positive electrode (+) and the cathode is connected to the negative electrode ( ⁇ ) and a voltage of 3 to 40 V is applied.
• the anode is connected to the negative electrode ( ⁇ ) and the cathode is connected to the positive electrode (+)
• the light emission is not observed at all.
• an alternating voltage is applied, a uniform emission of light is observed only when the anode is connected to the positive electrode (+) and the cathode is connected to the negative electrode ( ⁇ ).
• the wave form of the applied alternating voltage is not limited.
• reaction product was quenched by adding 50 ml of a saturated aqueous solution of ammonium chloride.
• the formed solid substance was separated by filtration and washed with water, methanol and acetone and 4.8 g (the yield: 67%) of a diol compound was obtained as a white solid.
• 4.8 g (4.6 mmol) of the diol compound obtained above was suspended in 50 ml of acetic acid.
• a 57% hydroiodic acid (6 ml; 46 mmol; 10 eq) was added and the resultant mixture was stirred at 80° C. for 8 hours.
• the reaction product was quenched by adding 30 ml of a 50% hypophosphorous acid.
• the formed solid substance was separated by filtration and washed with water, methanol and acetone and 3.8 g (the yield: 81%) of a white solid was obtained.
• the results of measurements with the obtained product in accordance with the elemental analysis and the field desorption mass spectroscopy (FD-MS) were as follows:
• reaction product was quenched by adding 50 ml of a saturated aqueous solution of ammonium chloride.
• the formed solid substance was separated by filtration and washed with water, methanol and acetone and 4.9 g (the yield: 71%) of a diol compound was obtained as a white solid.
• 4.9 g (4.8 mmol) of the diol compound obtained above was suspended in 50 ml of acetic acid.
• a 57% hydroiodic acid (6 ml; 48 mmol; 10 eq) was added and the resultant mixture was stirred at 80° C. for 8 hours.
• the reaction product was quenched by adding, 30 ml of a 50% hypophosphorous acid.
• the formed solid substance was separated by filtration and washed with water, methanol and acetone and 4.4 g (the yield: 92%) of a white solid was obtained.
• the results of measurements with the obtained product in accordance with the elemental analysis and the field desorption mass spectroscopy (FD-MS) were as follows:
• reaction product was quenched by adding 50 ml of a saturated aqueous solution of ammonium chloride.
• the formed solid substance was separated by filtration and washed with water, methanol and acetone and 5.1 g (the yield: 76%) of a diol compound was obtained as a white solid.
• 5.1 g (5.5 mmol) of the diol compound obtained above was suspended in 50 ml of acetic acid.
• a 57% hydroiodic acid (6 ml; 48 mmol; 10 eq) was added and the resultant mixture was stirred at 80° C. for 8 hours.
• the reaction product was quenched by adding 30 ml of a 50% hypophosphorous acid.
• the formed solid substance was separated by filtration and washed with water, methanol and acetone and 4.5 g (the yield: 92%) of a white solid was obtained.
• the results of measurements with the obtained product in accordance with the elemental analysis and the field desorption mass spectroscopy (FD-MS) were as follows:
• a glass substrate of a size of 25 mm ⁇ 75 mm ⁇ 1.1 mm having a transparent electrode of indium tin oxide was cleaned in isopropyl alcohol by ultrasonic vibration for 5 minutes and then with ozone for 30 minutes under irradiation by ultraviolet light and attached to a substrate holder of a vacuum vapor deposition apparatus.
• TPD232 film On the surface of the substrate at the side having the transparent electrode line, a film of N,N′-bis(N,N′-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenyl (referred to as a TPD232 film, hereinafter) having a thickness of 60 nm was formed.
• the formed TPD232 film worked as the hole injecting layer.
• NPD film 4,4′-bis[N-(1-naphthyl)-N-phenyl]biphenyl (referred to as an NPD film, hereinafter) having a thickness of 20 nm was formed.
• the formed NPD film worked as the hole transporting film.
• a film of compound E1 having a thickness of 40 nm was formed on the formed NPD film.
• the formed film worked as the light emitting layer.
• Alq film a film of tris(8-quinolinol)aluminum having a thickness of 20 nm was formed.
• the Alq film worked as the electron injecting film.
• Alq film Li (manufactured by SAES GETTERS Company) and Alq were binary vacuum vapor deposited and an Alq:Li film was formed as the electron injecting layer (an anode).
• a device was prepared in accordance with the same procedures as those conducted in Example 5 except that the light emitting layer was prepared by using compound E4 in place of compound E1. Using the prepared device, the properties of light emission were confirmed and the test of heat resistance was conducted. The results are shown in Table 1.
• the luminance of the prepared device was measured and the obtained value was used as the initial luminance (I 0 ). Then, the device was kept in a vessel thermostatted at 85° C. for 500 hours. Then, the device was taken out of the vessel and left standing until the temperature reached the room temperature. The luminance (I 500 ) after being kept for 500 hours under the above condition was measured. The decrease in the luminance (%) was obtained in accordance with the following equation and used for evaluating the heat resistance.
• a device was prepared in accordance with the same procedures as those conducted in Example 5 except that the light emitting layer was prepared by using compound E9 in place of compound E1. Using the prepared device, the properties of light emission were confirmed and the test of heat resistance was conducted. The results are shown in Table 1.
• a device was prepared in accordance with the same procedures as those conducted in Example 5 except that the light emitting layer was prepared by using compound E14 in place of compound E1. Using the prepared device, the properties of light emission were confirmed and the test of heat resistance was conducted. The results are shown in Table 1.
• a device was prepared in accordance with the same procedures as those conducted in Example 5 except that the light emitting layer was prepared by using compound E17 in place of compound E1. Using the prepared device, the properties of light emission were confirmed and the test of heat resistance was conducted. The results are shown in Table 1.
• a device was prepared in accordance with the same procedures as those conducted in Example 5 except that the light emitting layer was prepared by using an anthracene compound H1 expressed by the following formula in place of compound E1. Using the prepared device, the properties of light emission were confirmed and the test of heat resistance was conducted. The results are shown in Table 1.
• the reaction solution was cooled with ice water.
• the formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone, successively, and 3.5 g of a yellow powder was obtained.
• the yellow powder was identified to be compound E32 by measurements in accordance with NMR, IR and FD-MS (the yield: 50%).
• the reaction solution was cooled with ice water.
• the formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone, successively, and 1.4 g of a yellow powder was obtained.
• the yellow powder was identified to be compound E33 by measurements in accordance with NMR, IR and FD-MS (the yield: 20%).
• the reaction solution was cooled with ice water.
• the formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone, successively, and 5.7 g of a yellow powder was obtained.
• the yellow powder was identified to be compound E35 by measurements in accordance with NMR, IR and FD-MS (the yield: 80%).
• the reaction solution was cooled with ice water.
• the formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone, successively, and 4.4 g of a yellow powder was obtained.
• the yellow powder was identified to be compound E42 by measurements in accordance with NMR, IR and FD-MS (the yield: 60%).
• the reaction solution was cooled with ice water.
• the formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone, successively, and 5.8 g of a yellow powder was obtained.
• the yellow powder was identified to be compound E44 by measurements in accordance with NMR, IR and FD-MS (the yield: 79%).
• Tg of compound H1 used in Comparative Example 1 was measured in accordance with DSC and found to be as low as 96° C.
• a device was prepared in accordance with the same procedures as those conducted in Example 5 except that the light emitting layer was formed by using compound E43 in place of compound E1. Using the prepared device, the properties of light emission were confirmed and the chromaticity coordinates were obtained. The results are shown in Table 1.
• the organic EL devices of Comparative Examples 1, 3 and 4 exhibited low efficiencies of light emission. Moreover, the organic EL devices of Comparative Examples 1 and 4 exhibited strongly greenish light and could not be used as a device emitting blue light.

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• 2001
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