Chemistry of hydrocarbon compounds – Compound or reaction product mixture – Aromatic
Reexamination Certificate
2003-07-02
2004-09-28
Lambkin, Deborah C. (Department: 1626)
Chemistry of hydrocarbon compounds
Compound or reaction product mixture
Aromatic
C549S059000, C546S255000, C558S304000
Reexamination Certificate
active
06797848
ABSTRACT:
TECHNICAL FIELD
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.
BACKGROUND ART
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.
Therefore, 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. For example, 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). In these organic EL devices, 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. For example, 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).
However, organic EL devices using the above compounds have a problem in that the efficiency of light emission and heat resistance are not sufficient.
DISCLOSURE OF THE INVENTION
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.
As the result of extensive studies by the present inventors to achieve the above objects, it was found that the objects can be achieved by anthracene derivatives having specific structures. The present invention has been completed based on the knowledge.
The present invention can be summarized as follows.
[1] An anthracene derivative represented by general formula (I):
wherein 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; (1) 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 &agr;-position or a &bgr;-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 &agr;-position or a &bgr;-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 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
16
may form 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; and p represents a number selected from 0, 1 and 2.
[2] An anthracene derivative represented by general formula (II):
wherein (1) 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 styryl group in which a phenyl portion may be substituted and an &agr;-position or a &bgr;-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 &agr;-position or a &bgr;-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 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
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; and p represents a number selected from 0, 1 and 2.
[3] An anthracene derivative represented by general formula (II′):
wherein (1) 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 &agr;-position or a &bgr;-position of a vinyl portion may be substituted with an alkyl group having 1 to 30 carbon atoms, A
3
represents hydrogen ato
Funahashi Masakazu
Hosokawa Chishio
Ikeda Hidetsugu
Idemitsu Kosan, Ltd.
Lambkin Deborah C.
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