USRE49118E1 - Material for organic electroluminescence device and electroluminescence device employing the same - Google Patents

Material for organic electroluminescence device and electroluminescence device employing the same Download PDF

Info

Publication number
USRE49118E1
USRE49118E1 US16/804,850 US202016804850A USRE49118E US RE49118 E1 USRE49118 E1 US RE49118E1 US 202016804850 A US202016804850 A US 202016804850A US RE49118 E USRE49118 E US RE49118E
Authority
US
United States
Prior art keywords
group
substituents
carbon atoms
indolyl
phenanthrolin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
US16/804,850
Inventor
Yuki Nakano
Masahide Matsuura
Hidetsugu Ikeda
Toshihiro Iwakuma
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Priority to US16/804,850 priority Critical patent/USRE49118E1/en
Application granted granted Critical
Publication of USRE49118E1 publication Critical patent/USRE49118E1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • H01L51/5036—
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/0067—
    • H01L51/0072—
    • H01L51/0073—
    • H01L51/0074—
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H01L51/0061—
    • H01L51/0081—
    • H01L51/0085—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to a material for organic electroluminescence devices and an organic electroluminescence device using the material and, more particularly, to a material for organic electroluminescence devices providing an electroluminescence device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life and an organic electroluminescence device using the material.
  • An organic electroluminescence (“electroluminescence” will be referred to as “EL”, hereinafter) device is a spontaneous light emitting device which utilizes the principle that a fluorescent substance emits light by energy of recombination of holes injected from an anode and electrons injected from a cathode when an electric field is applied. Since an organic EL device of the laminate type driven under a low electric voltage was reported by C. W. Tang of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Volume 51, Pages 913, 1987), many studies have been conducted on organic EL devices using organic materials as the constituting materials. Tang et al.
  • the laminate structure using tris(8-quinolinolato)aluminum for the light emitting layer and a triphenyldiamine derivative for the hole transport layer.
  • Advantages of the laminate structure are that the efficiency of hole injection into the light emitting layer can be increased, that the efficiency of forming excitons by recombination can be increased by blocking electrons injected from the cathode, and that excitons formed can be enclosed within the light emitting layer.
  • a two-layered structure having a hole transport (injection) layer and an electron transport and light emitting layer and a three-layered structure having a hole transport (injection) layer, a light emitting layer and an electron transport (injection) layer are well known.
  • the structure of the device and the process for forming the device have been studied.
  • chelate complexes such as tris(8-quinolinolato)aluminum, coumarine derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives and oxadiazole derivatives are known. It is reported that light in the visible region ranging from blue light to red light can be obtained by using these light emitting materials, and development of a device exhibiting color images is expected (For example, Patent Reference 1, Patent Reference 2 and Patent Reference 3).
  • an organic phosphorescent material other than a fluorescent material is used in the light emitting layer of an organic EL device (for example, Non-Patent Reference 1 and Non-Patent Reference 2).
  • a great efficiency of light emission is achieved, as described above, by utilizing an organic phosphorescent material excited to the singlet state and the triplet state in the light emitting layer of an organic EL device. It is considered that singlet and triplet of the excited state are formed in relative amounts of 1:3 due to the difference in the multiplicity of spin when electrons and holes are recombined in an organic EL device. Therefore, it is expected that an efficiency of light emission 3 to 4 times as great as that of a device utilizing fluorescence alone can be achieved by utilizing a material emitting phosphorescent light.
  • a construction formed by successively laminating layers such as an anode, a hole transport layer, an organic light emitting layer, an electron transport layer (a hole blocking layer), an electron transport layer and a cathode is used so that the excited state of the triplet or the excitons of the triplet do not disappear, and a host compound and a phosphorescent compound are used for the organic light emitting layer (for example, Patent Reference 4 and Patent Reference 5).
  • a host compound and a phosphorescent compound are used for the organic light emitting layer (for example, Patent Reference 4 and Patent Reference 5).
  • 4,4-N,N-dicarbazole-biphenyl is used as the host compound. This compound has a glass transition temperature of 110° C.
  • Patent Reference 6 Devices having a fluorescent benzofuran compound or a fluorescent dibenzofuran compound are disclosed (Patent Reference 6). However, no specific descriptions are found on compounds having a substituent at the 7-position of benzofuran or at the 4-position or the 6-position of dibenzofuran, or no descriptions are found on exhibition of a unique property.
  • a compound having a 4-biphenylindol structure at the 4-position of benzofuran as the substituent is shown as an example of the host compound in a phosphorescent device, and an example using the compound as the host for an iridium complex which is a phosphorescent light emitting material emitting bluish green light is shown (Patent Reference 7).
  • Patent Reference 7 an example using the compound as the host for an iridium complex which is a phosphorescent light emitting material emitting bluish green light.
  • a compound having a skeleton structure of benzothiophene in which the skeleton structure of anthracene is essential is disclosed (Patent Reference 8). However, it is considered that application of this compound to a phosphorescence device is difficult since this compound has the skeleton structure of anthracene having a narrow triplet energy gap.
  • a furan-based compound in which the skeleton structure of anthracene is essential is disclosed (Patent Reference 9). However, no descriptions are found on compounds having a substituent at the 7-position of benzofuran or at the 4-position or 6-position of dibenzofuran, or no excellent properties of these compounds are found.
  • a benzofuran compound bonded to the skeleton structure of pyrene is disclosed (Patent Reference 10). However, it is considered that the application of the compound to the organic EL device of the phosphorescent type is difficult due to the narrow triplet state energy gap of the skeleton structure of pyrene. No examples using the compound are found.
  • Patent Reference 11 a dibenzofuran compound having the skeleton structure of benzotriazole is described. However, it is considered that that the application of the compound to the organic EL device of the phosphorescent type is difficult due to the narrow triplet state energy gap. No examples using the compound are found.
  • Patent Reference 1 Japanese Patent Application Laid-Open No. Heisei 8 (1996)-239655
  • Patent Reference 2 Japanese Patent Application Laid-Open No. Heisei 7 (1995)-138561
  • Patent Reference 5 International Patent Publication No. WO 2001/41512
  • Patent Reference 7 Japanese Patent Application Laid-Open No. 2004-214050
  • Patent Reference 8 Japanese Patent Application Laid-Open No. 2004-002351
  • Patent Reference 10 International Patent Publication No. WO 2004/096945
  • Patent Reference 11 International Patent Publication No. WO 2005/054212
  • Non-Patent Reference 1 D. F. O'Brien, M. A. Baldo et al., “Improved energy transfer in electrophosphorescent devices”, Vol. 74, No. 3, pp 442 to 444, Jan. 18, 1999
  • Non-Patent Reference 2 M. A. Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Applied Physics letters, Vol. 75, No. 1, pp 4-6, Jul. 5, 1999
  • the present invention has been made to overcome the above problems and has an object of providing a material for organic EL devices which provides an EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life and an organic EL device using the material.
  • the present invention provides a material for organic EL devices which comprises a compound represented by any one of the following general formulae (1) to (14):
  • R 1 ′, R 2 ′ and R 5 to R 7 each independently represent hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have sub stituents, an alkylsilyl group
  • R 1 ′ and R 2 ′, R 5 and R 6 or R 6 and R 7 may be bonded to each other to form a saturated or unsaturated cyclic structure
  • X represents sulfur atom, oxygen atom or a substituted silicon atom represented by SiRaRb, Ra and Rb each independently representing an alkyl group having 1 to 40 carbon atoms;
  • Y represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have sub stituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have sub stituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon
  • R 1 to R 7 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1), R 1 not representing a group having a skeleton structure of anthracene;
  • adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 may be bonded to each other to form a saturated or unsaturated cyclic structure
  • X is as defined for general formula (1).
  • Y′ represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have sub stituents, an aryl group having 6 to 60 carbon atoms and having no skeleton structure of pyrene which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have substituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an aryl si
  • R 1 to R 12 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1), at least one of R 8 to R 12 representing hydrogen atom;
  • adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 8 to R 12 may be bonded to each other to form a saturated or unsaturated cyclic structure;
  • X is as defined for general formula (1).
  • R 1 to R 10 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1);
  • adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 9 to R 10 in general formula (4), adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 and adjacent groups represented by R 9 and R 10 in general formula (5), and adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 and groups represented by R 7 and R 8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure;
  • X is as defined for general formula (1).
  • R 1 to R 11 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1);
  • adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 8 to R 11 in general formula (7), adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 , adjacent groups represented by R 8 and R 9 , adjacent groups represented by R 10 and R 11 and adjacent groups represented by R 7 and R 8 in general formula (5), and adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 9 to R 11 and groups represented by R 7 and R 8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and
  • X is defined for general formula (1).
  • R 1 to R 9 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1);
  • adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 may be bonded to each other to form a saturated or unsaturated cyclic structure
  • X is as defined for general formula (1).
  • R 1 to R 13 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1);
  • adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 , adjacent groups represented by R 8 and R 9 , adjacent groups represented by R 10 and R 11 and adjacent groups represented by R 12 and R 13 may be bonded to each other to form a saturated or unsaturated cyclic structure;
  • X is as defined for general formula (1).
  • R 1 to R 18 each independently represent a same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1);
  • adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 , among groups represented by R 12 to R 15 and among groups represented by R 16 to R 18 , adjacent groups represented by R 8 and R 7 and adjacent groups represented by R 10 and R 11 may be bonded to each other to form a saturated or unsaturated cyclic structure;
  • X is as defined for general formula (1).
  • the present invention further provides an organic electroluminescence device comprising a cathode, an anode and an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and is disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises the material for organic electroluminescence devices described above.
  • the organic EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life can be obtained by utilizing the material for organic EL devices which comprises the compound represented by general formula (1) and, therefore, the organic EL device of the present invention is very useful as the light source for various electronic instruments.
  • the material for organic EL devices of the present invention comprises a compound represented by any one of the following general formulae (1) to (14);
  • R 1 ′, R 2 ′ and R 5 to R 7 each independently represent hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have sub stituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have sub stituents, an alkyl
  • R 1 to R 7 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1), R 1 not representing a group having a skeleton structure of anthracene; adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 may be bonded to each other to form a saturated or unsaturated cyclic structure;
  • X is as defined for general formula (1); and Y′ represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms and having no skeleton structure of pyrene which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents
  • R 1 to R 12 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1), at least one of R 8 to R 12 representing hydrogen atom; adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 8 to R 12 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
  • R 1 to R 10 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1); adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 8 to R 10 in general formula (4), adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 and adjacent groups represented by R 9 and R 10 in general formula (5), and adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 and groups represented by R 7 and R 8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
  • R 1 to R 11 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1); adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 8 to R 11 in general formula (7), adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 , adjacent groups represented by R 8 and R 9 , adjacent groups represented by R 10 and R 11 and adjacent groups represented by R 7 and R 8 in general formula (5), and adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 and among groups represented by R 9 to R 11 and groups represented by R 7 and R 8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
  • R 1 to R 9 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1); adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
  • R 1 to R 13 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1); adjacent groups among groups represented by R 1 to R 4 and among groups represented by R 5 to R 7 , adjacent groups represented by R 8 and R 9 , adjacent groups represented by R 10 and R 11 and adjacent groups represented by R 12 and R 13 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
  • R 1 to R 18 each independently represent the same atom or group as that represented by R 1 ′, R 2 ′, R 5 , R 6 or R 7 in general formula (1); adjacent groups among groups represented by R 1 to R 4 , among groups represented by R 5 to R 7 , among groups represented by R 12 to R 15 and among groups represented by R 16 to R 18 , adjacent groups represented by R 8 and R 9 and adjacent groups represented by R 10 and R 11 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
  • Examples of the halogen atom represented by R 1 ′, R 2 ′ and R 1 to R 18 include fluorine atom, chlorine atom, bromine atom and iodine atom.
  • alkyl group having 1 to 40 carbon atoms and may have substituents which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopen
  • alkyl groups methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group
  • Examples of the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 1-imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridiny
  • the alkoxyl group having 1 to 40 carbon atoms which may have substituents which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, is a group represented by —OY.
  • Examples of the group represented by Y include the groups described above as the examples of the alkyl group.
  • Examples of the aryl group having 6 to 60 carbon atoms which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 andY include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphen
  • aryl groups phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group and 3,4-xylyl group are preferable.
  • Examples of the aryl group having 6 to 60 carbon atoms and having no skeleton structure of pyrene which may have substituents, which is represented by Y′, include the groups described above as the examples of the aryl group except the groups having the skeleton structure of pyrene.
  • the aryloxyl group having 6 to 60 carbon atoms which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, is a group represented by —OAr.
  • Examples of the group represented by Ar include the groups described above as the examples of the aryl group.
  • Preferable examples of the group represented by Ar include the groups described above as the preferable examples of the aryl group.
  • Examples of the aralkyl group having 7 to 60 carbon atoms which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -nap
  • benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group and 2-phenylisopropyl groups are preferable.
  • alkenyl group having 2 to 40 carbon atoms which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group and 3-phenyl-1-butenyl group.
  • alkenyl groups styryl group, 2,2-diphenylvinyl group and 1,2-diphenylvinyl groups
  • the alkylamino group having 1 to 40 carbon atoms which may have substituents and the aralkylamino group having 7 to 60 carbon atoms which may have substituents, which are represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, are represented by —NQ1Q2.
  • Examples of the groups represented by Q1 and Q2 include the groups described above as the examples of the alkyl group, the aryl group and the aralkyl group.
  • Preferable examples of the groups represented by Q1 and Q2 include the groups described above as the preferable examples of the alkyl group, the aryl group and the aralkyl group.
  • alkylsilyl group having 3 to 20 carbon atoms which may have substituents which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group and propyldimethylsilyl group.
  • Examples of the arylsilyl group having 8 to 40 carbon atoms which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include triphenylsilyl group, phenyldimethylsilyl group and t-butyldiphenylsilyl group.
  • Examples of the group represented by Ar 2 include the groups described above as the examples of the aryl group.
  • Preferable examples of the group represented by Ar include the groups described above as the preferable examples of the aryl group.
  • Examples of the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, which is represented by R 1 ′, R 2 ′, R 1 to R 18 , Y and Y′, include groups obtained by substituting at least one of hydrogen atoms in the groups described above as the examples of the alkyl group with a halogen atom.
  • Preferable examples of the halogenated alkyl group include groups obtained by substituting at least one of hydrogen atoms in the groups described above as the preferable examples of the alkyl group with a halogen atom.
  • Examples of the cyclic structure formed from a plurality of groups represented by R 1 ′, R 2 ′ and R 1 to R 18 include unsaturated six-membered rings such as benzene ring and saturated and unsaturated five-membered rings and seven-membered rings.
  • Examples of the alkyl group represented by Ra and Rb include the groups described above as the examples of the alkyl group. Methyl group, ethyl group, propyl group and butyl group are preferable.
  • the material for organic EL devices of the present invention is a host material comprised in the light emitting layer of an organic EL device.
  • the organic EL device of the present invention comprises a cathode, an anode and an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and is disposed between the cathode and the anode, wherein at least one layer in the organic thin film layer comprises the material for organic EL devices described above.
  • Examples of the structure of the organic EL device of the multi-layer type include multi-layer laminate structures such as an anode/a hole transport layer (a hole injection layer)/a light emitting layer/a cathode, an anode/a light emitting layer/an electron transport layer (an electron injection layer)/a cathode, an anode/a hole transport layer (a hole injection layer)/a light emitting layer/an electron transport layer (an electron injection layer)/a cathode and an anode/a hole transport layer (a hole injection layer)/a light emitting layer/a hole blocking layer/an electron transport layer (an electron injection layer)/a cathode.
  • multi-layer laminate structures such as an anode/a hole transport layer (a hole injection layer)/a light emitting layer/a cathode, an anode/a light emitting layer/an electron transport layer (an electron injection layer)/a cathode, an anode/a hole transport layer (a hole injection layer)/a light emitting layer/a hole blocking layer
  • the light emitting layer comprises a host material and a phosphorescent light emitting material
  • the host material comprises the material for organic EL devices described above.
  • the light emitting layer comprises a host material and a phosphorescent light emitting material, and light emitted from the phosphorescent light emitting material has a peak wavelength of 500 nm or shorter.
  • metal complexes such as iridium complexes, osmium complexes and platinum complexes are preferable, iridium complexes and platinum complexes are more preferable and ortho-metallated iridium complexes are most preferable since the quantum yield of phosphorescence is great and the external quantum efficiency of the light emitting device can be further increased.
  • ortho-metallated complex iridium complexes shown in the following are preferable.
  • the light emitting layer comprises a host material and a phosphorescent light emitting material
  • the phosphorescent light emitting material is a light emitting material having one or more carbene ligands coordinated to a metal center.
  • the material for organic EL devices is a host material comprised in the light emitting layer of the organic EL device.
  • the material for organic EL devices is a material comprised in a hole transport layer of the organic EL device.
  • the material for organic EL devices is a material comprised in an electron transport layer or a hole blocking layer of the organic EL device.
  • a reducing dopant is added into the interfacial region of the cathode and the organic thin film layer.
  • Examples of the reducing dopant include at least one substance selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes and rare earth metal compounds.
  • alkali metal examples include Na (the work function: 2.36 eV), K (the work function: 2.28 eV), Rb (the work function: 2.16 eV) and Cs (the work function: 1.95 eV).
  • Alkali metals having a work function of 2.9 eV or smaller are preferable.
  • K, Rb and Cs are more preferable, Rb and Cs are still more preferable, and Cs is most referable.
  • alkaline earth metal examples include Ca (the work function: 2.9 eV), Sr (the work function: 2.0 to 2.5 eV) and Ba (the work function: 2.52 eV). Alkaline earth metals having a work function of 2.9 eV or smaller are preferable.
  • rare earth metal examples include Sc, Y, Ce, Tb and Yb.
  • Rare earth metals having a work function of 2.9 eV or smaller are preferable.
  • the preferable metals among the above metals have great reducing ability, and the luminance of the emitted light and the life of the organic EL device can be increased by addition of a relatively small amount into the electron injection zone.
  • alkali metal compound described above examples include alkali metal oxides such as Li 2 O, Cs 2 O and K 2 O and alkali metal halides such as LiF, NaF, CsF and KF.
  • alkali metal oxides and alkali metal fluorides such as LiF, Li 2 O and NaF are preferable.
  • alkaline earth metal compound described above examples include BaO, SrO, CaO and mixtures thereof such as Ba x Sr 1-x O (0 ⁇ x ⁇ 1) and Ba x Ca 1-x O (0 ⁇ x ⁇ 1).
  • BaO, SrO and CaO are preferable.
  • Examples of the rare earth metal compound described above include YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 .
  • YbF 3 , ScF 3 and TbF 3 are preferable.
  • the alkali metal complex, the alkaline earth metal complex and the rare earth metal complex are not particularly limited as long as the complexes contain at least one of the alkali metal ions, the alkaline earth metal ions and rare earth metal ions, respectively, as the metal ion.
  • quinolinol benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazoles, hydroxydiarylthiadiazoles, hydroxyphenylpyridine, hydroxyphenyl-benzimidazole, hydroxybenzotriazole, hydroxyfulvorane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines and derivatives of these compounds are preferable.
  • the ligand is not limited to those described above.
  • the reducing dopant is added in a manner such that a layer or islands are formed in the interfacial region described above.
  • an organic material which is a light emitting material or an electron injection material forming the interfacial region is vapor deposited while the reducing dopant is simultaneously vapor deposited in accordance with the resistance heating method so that the reducing dopant is dispersed in the organic material.
  • concentration of the dispersion expressed as the ratio of the amounts by mole of the organic substance to the reducing dopant is in the range of 100:1 to 1:100 and preferably in the range of 5:1 to 1:5.
  • the reducing dopant When the reducing dopant is added to form a layer, the reducing dopant alone is vapor deposited in accordance with the resistance heating method to form a layer preferably having a thickness of 0.1 to 15 nm after a layer of an organic material such as the light emitting material and the electron injection material is formed as the interfacial region.
  • the reducing dopant When the reducing dopant is added to form islands, the reducing dopant alone is vapor deposited in accordance with the resistance heating method to form islands preferably having a thickness of 0.05 to 1 nm after islands of an organic material such as the light emitting material and the electron injection material are formed as the interfacial region.
  • the relative amounts by mole of the main component and the reducing dopant in the organic EL device of the present invention is in the range of 5:1 to 1:5 and more preferably in the range of 2:1 to 1:2.
  • an electron injection layer is disposed between the light emitting layer and the cathode, and the electron injection layer comprises a cyclic derivative having one or more nitrogen atoms as the main component.
  • aromatic heterocyclic compounds having one or more heteroatoms in the molecule are preferable, and cyclic derivatives having one or more nitrogen atoms are more preferable.
  • cyclic derivative having one or more nitrogen atoms for example, compounds represented by general formula (A) are preferable.
  • R 2 to R 7 each independently represent hydrogen atom, a halogen atom, an oxyl group, an amino group or a hydrocarbon group having 1 to 40 carbon atoms, and these groups may be substituted.
  • halogen atom examples include the halogen atoms described above.
  • amino group which may be substituted examples include the alkylamino groups, the arylamino groups and the aralkylamino groups described above.
  • Examples of the hydrocarbon group having 1 to 40 carbon atoms include alkyl groups, alkenyl groups, cycloalkyl groups, alkoxyl groups, aryl groups. heterocyclic groups, aralkyl groups, aryloxyl groups and alkoxylcarbonyl groups, which may be substituted or unsubstituted.
  • Examples of the alkyl group, the alkenyl group, the cycloalkyl group, the alkoxyl group, the aryl group, the heterocyclic group, the aralkyl group and the aryloxyl group include the groups described above as the examples of the corresponding groups.
  • the alkoxylcarbonyl group is represented by —COOY′, and examples of the group represented by Y′ include the groups described above as the examples of the alkyl group.
  • M aluminum (Al), gallium (Ga) or indium (In), and In is preferable.
  • L in general formula (A) represents a group represented by the following general formula (A′) or (A′′):
  • R 8 to R 12 each independently represent hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and adjacent groups may form a cyclic structure.
  • R 13 to R 27 each independently represent hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and adjacent groups may form a cyclic structure.
  • Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in general formulae (A′) and (A′′) include the groups described above as the examples of the groups represented by R 2 to R 7 .
  • Examples of the divalent group which is the cyclic group formed by bonding of the adjacent groups represented by R 8 to R 12 and R 13 to R 27 include tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethan-2,2′-diyl group, diphenylethan-3,3′-diyl group and diphenylpropan-4,4′-diyl group.
  • metal chelate complex having a ring having one or more nitrogen atoms represented by general formula (A) are shown in the following.
  • the metal chelate complex having a ring having one or more nitrogen atoms is not limited to the compounds shown as the examples.
  • the cyclic derivative having one or more nitrogen atoms of the main component of the electron injection layer five-membered derivatives having one or more nitrogen atoms are also preferable.
  • the five-membered ring include imidazole ring, triazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, oxatriazole ring and thiatriazole ring.
  • Examples of the five-membered cyclic derivative having one or more nitrogen atoms include derivatives having benzimidazole ring, derivatives having benzotriazole ring, derivatives having pyridinoimidazole ring, derivatives having pyrimidinoimidazole ring and derivatives having pyridazino-imidazole ring.
  • Derivatives represented by the following general formula (B) are preferable:
  • L B represents a linking atom or group having a valence of two or greater.
  • the linking atom and group preferably include carbon atom, silicon atom, nitrogen atom, boron atom, oxygen atom, sulfur atom, a metal atom such as barium atom and beryllium atom, aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups.
  • the linking atom or group is more preferably carbon atom, nitrogen atom, silicon atom, boron atom, oxygen atom, sulfur atom, an aryl group or an aromatic heterocyclic group, and most preferably carbon atom, silicon atom, an aryl group or an aromatic heterocyclic group.
  • the aryl group and the aromatic heterocyclic group represented by L B may have substituents.
  • substituents alkyl groups, alkenyl groups, alkynyl groups, aryl groups, amino groups, alkoxyl groups, aryloxyl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, acyloxyl groups, acylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio groups, arylthio groups, sulfonyl group, halogen atoms, cyano group and aromatic heterocyclic groups are preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups, halogen atoms, cyano group and aromatic heterocyclic groups are more preferable; alkyl groups, aryl groups, alkoxyl
  • Examples of the bonding atom and group represented by L B include atoms and groups shown in the following:
  • X B2 represents —O—, —S— or a group represented by ⁇ N.R B2 .
  • R B2 represents hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.
  • the aliphatic hydrocarbon group represented by R B2 is a linear, branched or cyclic alkyl group (an alkyl group preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms and most preferably having 1 to 8 carbon atoms, such as methyl group, ethyl group, isopropyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group and cyclohexyl group), alkenyl group (an alkenyl group preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms and most preferably having 2 to 8 carbon atoms, such as vinyl group, allyl group, 2-butenyl group and 3-pentenyl group) or alkynyl group (an alkynyl group preferably having 2 to 20 carbon atoms, more preferably
  • the aryl group represented by R B2 is an aryl group having a single ring or a condensed ring preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms and most preferably having 6 to 12 carbon atoms.
  • Examples of the aryl group include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-trifluoromethylphenyl group, pentafluoro-phenyl group, 1-naphthyl group and 2-naphthyl group.
  • the heterocyclic group represented by R B2 is a heterocyclic group having a single ring or a condensed ring and preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms and most preferably having 2 to 10 carbon atoms, and preferably an aromatic heterocyclic group having at least one of nitrogen atom, oxygen atom, sulfur atom and selenium atom.
  • heterocyclic group examples include groups derived from pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrol, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthylidine, quinoxaline, quinazoline, cinnoline, puteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetrazaindene, carbazole and azepine; preferably groups
  • the aliphatic hydrocarbon group, the aryl group and the heterocyclic group which are represented by R B2 may have substituents.
  • Examples of the sub stituent include the substituents described above as the examples of the substituent to the group represented by L B .
  • Preferable examples of the substituent include the substituents described above as the preferable examples of the substituent to the group represented by L B .
  • R B2 preferably represents an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, more preferably an aliphatic hydrocarbon group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms and most preferably 6 to 12 carbon atoms) or an aryl group and most preferably an aliphatic hydrocarbon group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms and most preferably 2 to 10 carbon atoms).
  • X B2 preferably represents —O— or a group represented by ⁇ N—R B2 , more preferably a group represented by ⁇ N—R B2 and most preferably a group represented by ⁇ N—R B2 .
  • Z B2 represents a group of atoms necessary for forming an aromatic ring.
  • the aromatic ring formed with the group of atoms represented by Z B2 may be any of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • Examples of the aromatic ring include benzene ring, pyridine ring, pyrazinc ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrol ring, furan ring, thiophene ring, selenophene ring, tellurophene ring, imidazole ring, thiazole ring, selenazole ring, tellurazole ring, thiadiazole ring, oxadiazole ring and pyrazole ring.
  • benzene ring, pyridine ring, pyrazine ring, pyrimidine ring and pyridazine ring are preferable, benzene ring, pyridine ring and pyrazine ring are more preferable, benzene ring and pyridine ring are still more preferable, and pyridine ring is most preferable.
  • the aromatic ring formed with the group of atoms represented by Z B2 may form a condensed ring in combination with other rings and may have substituents.
  • substituents include the substituents described above as the examples of the substituent to the groups represented by L B .
  • alkyl groups alkenyl groups, alkynyl groups, aryl groups, amino groups, alkoxyl groups, aryloxyl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, acyloxyl groups, acylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio groups, arylthio groups, sulfonyl group, halogen atoms, cyano group and heterocyclic groups are preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups, halogen atoms, cyano group and heterocyclic groups are more preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups and aromatic heterocyclic groups are still more preferable; and alkyl groups
  • n B2 represents an integer of 1 to 4 and preferably 2 or 3.
  • R B71 , R B72 and R B73 are each as defined for R B2 in general formula (B), and preferable groups are the same as those represented by R B2 .
  • Z B71 , Z B72 and Z B73 are each as defined for Z B2 in general formula (B), and preferable groups are the same as those represented by Z B2 .
  • L B71 , L B72 and L B73 each represent a linking group.
  • the group include divalent groups derived from the groups described as the examples of the group represented by L B in general formula (B).
  • the linking group is preferably the single bond, a divalent aromatic hydrocarbon cyclic group, a divalent aromatic heterocyclic group or a linking group obtained as a combination of these groups, and more preferably the single bond.
  • the groups represented by L B71 , L B72 and L B73 may have substituents. Examples of the substituent include the substituents described above as the examples of the sub stituent to the groups represented by L B in general formula (B). Preferable examples of the substituent include the substituents described above as the preferable examples of the sub stituent to the groups represented by L B in general formula (B).
  • Y represents nitrogen atom, 1,3,5-benzenetriyl group or 2,4,6-triazinetriyl group.
  • 1,3,5-Benzenetriyl group may have substituents at the 2-, 4- and 6-positions. Examples of the substituent include alkyl groups, aromatic hydrocarbon cyclic groups and halogen atoms.
  • Examples of the five-membered cyclic derivative having one or more nitrogen atoms which is represented by general formula (B) or (B′) are shown in the following. However, the five-membered cyclic derivative having one or more nitrogen atoms is not limited to the compounds shown as the examples.
  • an insulating material or a semiconductor of an inorganic compound is used as the substance constituting the electron injection layer for the substance other than the ring derivative having one or more nitrogen atoms.
  • the electron injection layer comprises the insulating material or the semiconductor, leak of the electric current can be effectively prevented, and the electron injection property can be improved.
  • the insulating material at least one metal compound selected from the group consisting of chalcogenides of alkali metals, chalcogenides of alkaline earth metals, halides of alkali metals and halides of alkaline earth metals is preferable.
  • the electron injection layer comprises the above metal compound since the electron injection property can be further improved.
  • the chalcogenide of an alkali metal include Li 2 O, K 2 O, Na 2 S, Na 2 Se and Na 2 O.
  • the chalcogenide of an alkaline earth metal include CaO, BaO, SrO, BeO, BaS and CaSe.
  • Preferable examples of the halide of an alkali metal include LiF, NaF, KF, LiCl, KCl and NaCl.
  • Preferable examples of the halide of an alkaline earth metal include fluoride such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 and halides other than the fluorides.
  • the semiconductor examples include oxides, nitrides and oxide nitrides comprising at least one element selected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn used singly or in combination of two or more. It is preferable that the inorganic compound constituting the electron injection layer forms crystallite or amorphous insulating thin film. When the electron injection layer is constituted with the insulating thin film described above, a more uniform thin film can be formed, and defects of pixels such as dark spots can be decreased.
  • the inorganic compound include chalcogenides of alkali metals, chalcogenides of alkaline earth metals, halides of alkali metals and halides of alkaline earth metals which are described above.
  • the electron injection layer in the present invention comprises the reducing dopant described above.
  • the anode of the organic EL device plays the role of injection holes into the hole transport layer or the light emitting layer. It is effective that the anode has a work function of 4.5 eV or greater.
  • the material of the anode used in the present invention include indium tin oxide alloys (ITO), tin oxides (NESA), gold, silver, platinum and copper.
  • ITO indium tin oxide alloys
  • NESA tin oxides
  • gold silver
  • platinum and copper copper
  • the cathode a material having a small work function is preferable so that electrons can be injected into the electron transport layer or the light emitting layer.
  • the material of the cathode is not particularly limited. Examples of the material of the cathode include indium, aluminum, magnesium, magnesium-indium alloys, magnesium-aluminum alloys, aluminum-lithium alloys, aluminum-scandium-lithium alloys and magnesium-silver alloys.
  • the process for forming the layers in the organic EL device of the present invention is not particularly limited.
  • a conventional process such as the vacuum vapor deposition process and the spin coating process can be used.
  • the organic thin film layer which comprises the compound represented by any one of general formulae (1) to (3) and used in the organic EL device of the present invention can be formed in accordance with the vacuum vapor deposition process or the molecular beam epitaxy process (the MBE process) or, using a solution prepared by dissolving the compound into a solvent, in accordance with a conventional coating process such as the dipping process, the spin coating process, the casting process, the bar coating process and the roll coating process.
  • each organic layer in the organic EL device of the present invention is not particularly limited.
  • an excessively thin layer tends to have defects such as pin holes, and an excessively thick layer requires a high applied voltage to decrease the efficiency.
  • a thickness in the range of several nanometers to 1 ⁇ m is preferable.
  • the obtained compound was purified by sublimation at 190° C.
  • the purity of the compound obtained after the purification by sublimation was 99.8%.
  • the obtained compound was purified by sublimation at 230° C.
  • the obtained compound was purified by sublimation at 260° C.
  • the purity of the compound obtained after the purification by sublimation was 99.4%.
  • the obtained compound was purified by sublimation at 210° C.
  • the purity of the compound obtained after the purification by sublimation was 99.4%.
  • the obtained compound was purified by sublimation at 210° C.
  • the purity of Compound E3 obtained after the purification by sublimation was 99.5%.
  • the obtained compound was purified by sublimation at 200° C.
  • the purity of Compound D3 obtained after the purification by sublimation was 99.7%.
  • the obtained compound was purified by sublimation at 350° C.
  • the purity of Compound E22 obtained after the purification by sublimation was 99.3%.
  • the obtained compound was purified by sublimation at 330° C.
  • the purity of Compound D22 obtained after the purification by sublimation was 99.5%.
  • the obtained substance was identified to be the object compound in accordance with 90 MHz 1 H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
  • the obtained compound was purified by sublimation at 200° C.
  • the purity of Compound G15 obtained after the purification by sublimation was 99.2%.
  • the obtained compound was purified by sublimation at 320° C.
  • the purity of Compound H2 obtained after the purification by sublimation was 99.0%.
  • the obtained compound was purified by sublimation at 315° C.
  • the purity of Compound H1 obtained after the purification by sublimation was 99.2%.
  • a glass substrate of 25 mm ⁇ 75 mm ⁇ 1.1 mm thickness having an ITO transparent electrode (manufactured by GEOMATEC Company) was cleaned by application of ultrasonic wave in isopropyl alcohol for 5 minutes and then by exposure to ozone generated by ultraviolet light for 30 minutes.
  • the cleaned glass substrate having the transparent electrode was attached to a substrate holder of a vacuum vapor deposition apparatus.
  • a film of HTM (the formula shown in the following) having a thickness of 100 nm was formed in a manner such that the formed film covered the transparent electrode.
  • the formed film of HTM worked as the hole injection and transport layer.
  • Compound D1 as the host compound and Complex P expressed by the formula shown in the following were vapor deposited simultaneously on the formed film of HTM in accordance with the resistance heating method so that a film having a thickness of 30 nm was formed.
  • the concentration of Complex P was 7% by weight.
  • the formed film of the host compound and Compound D1 worked as the light emitting layer.
  • a film having a thickness of 25 nm of ETM1 shown in the following was formed and, then, a film having a thickness of 5 nm of ETM2 shown in the following was formed on the formed film of ETM1.
  • the layers of ETM1 and ETM2 worked as the electron transport layer and the electron injection layer, respectively.
  • LiF was vapor deposited at a rate of 1 ⁇ /min to form a film having a thickness of 0.1 nm so that an electron injection electrode (the cathode) was formed.
  • metallic aluminum was vapor deposited to form a film having a thickness of 150 nm so that a metal cathode having a thickness of 150 nm was formed.
  • an organic EL device was prepared.
  • the luminance (L) was measured, and the efficiency of light emission (L/J) was obtained.
  • the results are shown in Table 1.
  • Organic EL devices were prepared in accordance with the same procedures as those conducted in Example 1 except that compounds described in the column of the host compound in Table 1 were used as the host compound in place of Compound D1. The efficiency of light emission of the obtained organic EL devices each was measured in accordance with the same procedure as that conducted in Example 1. The results are shown in Table 1.
  • Organic EL devices were prepared in accordance with the same procedures as those conducted in Example 1 except that compounds described in International Patent Publication No. WO 2004/096945, Japanese Patent Application Laid-Open No. Heisei 5 (1993)-109485 and Japanese Patent Application Laid-Open No. 2004-214050 were used as the host compound in Comparative Examples 1, 2 and 3, respectively, in place of Compound D1.
  • the formulae are shown in the following.
  • the efficiency of light emission of the obtained organic EL devices was measured in accordance with the same procedure as that conducted in Example 1. The results are shown in Table 1.
  • Table 1 show that the organic EL devices using the compound of the present invention in the light emitting layer exhibited greater efficiencies of light emission. It is shown that the compound of the present invention is useful for application to organic EL devices.
  • the organic EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life can be obtained when the material for organic EL devices of the present invention comprising the compound represented by any one of general formulae (1) to (14) is used and, therefore, the organic EL device of the present invention is very useful as the light source for various electronic instruments.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

A material for organic electroluminescence devices comprising a compound having a specific structure and an organic electroluminescence device comprising an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and disposed between a cathode and an anode, wherein at least one layer in the organic thin film layer comprises the material for organic electroluminescence devices, are provided. The material provides the organic electroluminescence device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life.

Description

REFERENCE TO RELATED APPLICATIONS
The present application is a reissue application of U.S. Pat. No. 7,846,560, which is a Continuation of U.S. application Ser. No. 11/300,368, filed Dec. 15, 2005 (now U.S. Pat. No. 7,651,791), the entire contents of which are incorporated herein by reference.
TECHNICAL FIELD
The present invention relates to a material for organic electroluminescence devices and an organic electroluminescence device using the material and, more particularly, to a material for organic electroluminescence devices providing an electroluminescence device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life and an organic electroluminescence device using the material.
BACKGROUND ART
An organic electroluminescence (“electroluminescence” will be referred to as “EL”, hereinafter) device is a spontaneous light emitting device which utilizes the principle that a fluorescent substance emits light by energy of recombination of holes injected from an anode and electrons injected from a cathode when an electric field is applied. Since an organic EL device of the laminate type driven under a low electric voltage was reported by C. W. Tang of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Volume 51, Pages 913, 1987), many studies have been conducted on organic EL devices using organic materials as the constituting materials. Tang et al. used a laminate structure using tris(8-quinolinolato)aluminum for the light emitting layer and a triphenyldiamine derivative for the hole transport layer. Advantages of the laminate structure are that the efficiency of hole injection into the light emitting layer can be increased, that the efficiency of forming excitons by recombination can be increased by blocking electrons injected from the cathode, and that excitons formed can be enclosed within the light emitting layer. As the structure of the organic EL device, a two-layered structure having a hole transport (injection) layer and an electron transport and light emitting layer and a three-layered structure having a hole transport (injection) layer, a light emitting layer and an electron transport (injection) layer are well known. To increase the efficiency of recombination of injected holes and electrons in the devices of the laminate type, the structure of the device and the process for forming the device have been studied.
As the light emitting material of the organic EL device, chelate complexes such as tris(8-quinolinolato)aluminum, coumarine derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives and oxadiazole derivatives are known. It is reported that light in the visible region ranging from blue light to red light can be obtained by using these light emitting materials, and development of a device exhibiting color images is expected (For example, Patent Reference 1, Patent Reference 2 and Patent Reference 3).
It is recently proposed that an organic phosphorescent material other than a fluorescent material is used in the light emitting layer of an organic EL device (for example, Non-Patent Reference 1 and Non-Patent Reference 2). A great efficiency of light emission is achieved, as described above, by utilizing an organic phosphorescent material excited to the singlet state and the triplet state in the light emitting layer of an organic EL device. It is considered that singlet and triplet of the excited state are formed in relative amounts of 1:3 due to the difference in the multiplicity of spin when electrons and holes are recombined in an organic EL device. Therefore, it is expected that an efficiency of light emission 3 to 4 times as great as that of a device utilizing fluorescence alone can be achieved by utilizing a material emitting phosphorescent light.
In the organic EL devices described above, a construction formed by successively laminating layers such as an anode, a hole transport layer, an organic light emitting layer, an electron transport layer (a hole blocking layer), an electron transport layer and a cathode is used so that the excited state of the triplet or the excitons of the triplet do not disappear, and a host compound and a phosphorescent compound are used for the organic light emitting layer (for example, Patent Reference 4 and Patent Reference 5). In these patent references, 4,4-N,N-dicarbazole-biphenyl is used as the host compound. This compound has a glass transition temperature of 110° C. or lower, and the symmetry is excessively excellent since the skeleton structure of biphenyl is bonded to the nitrogen atom on the central line of the skeleton structure of carbazole molecule. Therefore, problems arise in that this compound is easily crystallized and that short circuit takes place and defect pixels are formed in the test of heat resistance of the device.
It is also found that, when the compound is vapor deposited, growth of crystals takes place at portions where foreign substances or protrusions are present, and defects are formed at an early time before the test of heat resistance and continue to grow with time. Carbazole derivatives having the three-fold symmetry are also used as the host compound. However, since these compounds have structures exhibiting an excellent symmetry with respect to the nitrogen atom on the central line of the skeleton structure of carbazole in the molecule, it is inevitable that growth of crystals takes place in the vapor deposition at portions where foreign substances or protrusions are present, and defects are formed at an early time before the test of heat resistance and continue to grow with time.
Devices having a fluorescent benzofuran compound or a fluorescent dibenzofuran compound are disclosed (Patent Reference 6). However, no specific descriptions are found on compounds having a substituent at the 7-position of benzofuran or at the 4-position or the 6-position of dibenzofuran, or no descriptions are found on exhibition of a unique property.
A compound having a 4-biphenylindol structure at the 4-position of benzofuran as the substituent is shown as an example of the host compound in a phosphorescent device, and an example using the compound as the host for an iridium complex which is a phosphorescent light emitting material emitting bluish green light is shown (Patent Reference 7). However, since substituents are present at all positions of the benzene ring substituted at the 4-position of benzofuran, the compound is unstable due to the great steric hindrance, and there is the possibility that the obtained EL device has a short life. No compounds having bonding at the 4-position of benzothiophene are clearly disclosed.
A compound having a skeleton structure of benzothiophene in which the skeleton structure of anthracene is essential is disclosed (Patent Reference 8). However, it is considered that application of this compound to a phosphorescence device is difficult since this compound has the skeleton structure of anthracene having a narrow triplet energy gap. A furan-based compound in which the skeleton structure of anthracene is essential is disclosed (Patent Reference 9). However, no descriptions are found on compounds having a substituent at the 7-position of benzofuran or at the 4-position or 6-position of dibenzofuran, or no excellent properties of these compounds are found. A benzofuran compound bonded to the skeleton structure of pyrene is disclosed (Patent Reference 10). However, it is considered that the application of the compound to the organic EL device of the phosphorescent type is difficult due to the narrow triplet state energy gap of the skeleton structure of pyrene. No examples using the compound are found.
In Patent Reference 11, a dibenzofuran compound having the skeleton structure of benzotriazole is described. However, it is considered that that the application of the compound to the organic EL device of the phosphorescent type is difficult due to the narrow triplet state energy gap. No examples using the compound are found.
[Patent Reference 1] Japanese Patent Application Laid-Open No. Heisei 8 (1996)-239655
[Patent Reference 2] Japanese Patent Application Laid-Open No. Heisei 7 (1995)-138561
[Patent Reference 3] Japanese Patent Application Laid-Open No. Heisei 3 (1991)-200289
[Patent Reference 4] U.S. Pat. No. 6,097,147
[Patent Reference 5] International Patent Publication No. WO 2001/41512
[Patent Reference 6] Japanese Patent Application Laid-Open No. Heisei 5 (1993)-109485
[Patent Reference 7] Japanese Patent Application Laid-Open No. 2004-214050
[Patent Reference 8] Japanese Patent Application Laid-Open No. 2004-002351
[Patent Reference 9] Japanese Patent Application Laid-Open No. 2005-047868
[Patent Reference 10] International Patent Publication No. WO 2004/096945
[Patent Reference 11] International Patent Publication No. WO 2005/054212
[Non-Patent Reference 1] D. F. O'Brien, M. A. Baldo et al., “Improved energy transfer in electrophosphorescent devices”, Vol. 74, No. 3, pp 442 to 444, Jan. 18, 1999
[Non-Patent Reference 2] M. A. Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Applied Physics letters, Vol. 75, No. 1, pp 4-6, Jul. 5, 1999
DISCLOSURE OF THE INVENTION Problems to be Overcome by the Invention
The present invention has been made to overcome the above problems and has an object of providing a material for organic EL devices which provides an EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life and an organic EL device using the material.
Means for Overcoming the Problems
As the result of intensive studies by the present inventors to achieve the above object, it was found that an EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life could be obtained by using a compound represented by the following general formula (1) as the material of the organic EL device. The present invention has been completed based on this knowledge.
The present invention provides a material for organic EL devices which comprises a compound represented by any one of the following general formulae (1) to (14):
Figure USRE049118-20220628-C00001
In the above general formula (1), R1′, R2′ and R5 to R7 each independently represent hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have sub stituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon atoms which may have substituents, a ketoaryl group having 7 to 40 carbon atoms which may have substituents, a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents or cyano group;
a pair of groups represented by R1′ and R2′, R5 and R6 or R6 and R7 may be bonded to each other to form a saturated or unsaturated cyclic structure;
X represents sulfur atom, oxygen atom or a substituted silicon atom represented by SiRaRb, Ra and Rb each independently representing an alkyl group having 1 to 40 carbon atoms; and
Y represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have sub stituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have sub stituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon atoms which may have substituents or a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents.
Figure USRE049118-20220628-C00002
In the above general formula (2), R1 to R7 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1), R1 not representing a group having a skeleton structure of anthracene;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 may be bonded to each other to form a saturated or unsaturated cyclic structure;
X is as defined for general formula (1); and
Y′ represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have sub stituents, an aryl group having 6 to 60 carbon atoms and having no skeleton structure of pyrene which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have substituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an aryl silyl group having 8 to 40 carbon atoms which may have substituents or a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents.
Figure USRE049118-20220628-C00003
In the above general formula (3), R1 to R12 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1), at least one of R8 to R12 representing hydrogen atom;
adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R8 to R12 may be bonded to each other to form a saturated or unsaturated cyclic structure; and
X is as defined for general formula (1).
Figure USRE049118-20220628-C00004
In the above general formulae (4), (5) and (6), R1 to R10 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1);
adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R9 to R10 in general formula (4), adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 and adjacent groups represented by R9 and R10 in general formula (5), and adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 and groups represented by R7 and R8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and
X is as defined for general formula (1).
Figure USRE049118-20220628-C00005
In the above general formulae (7), (8) and (9), R1 to R11 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1);
adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R8 to R11 in general formula (7), adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7, adjacent groups represented by R8 and R9, adjacent groups represented by R10 and R11 and adjacent groups represented by R7 and R8 in general formula (5), and adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R9 to R11 and groups represented by R7 and R8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and
X is defined for general formula (1).
Figure USRE049118-20220628-C00006
In the above general formula (10), R1 to R9 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1);
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 may be bonded to each other to form a saturated or unsaturated cyclic structure; and
X is as defined for general formula (1).
Figure USRE049118-20220628-C00007
In the above general formulae (11) and (12) R1 to R13 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1);
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7, adjacent groups represented by R8 and R9, adjacent groups represented by R10 and R11 and adjacent groups represented by R12 and R13 may be bonded to each other to form a saturated or unsaturated cyclic structure; and
X is as defined for general formula (1).
Figure USRE049118-20220628-C00008
In the above general formulae (13) and (14), R1 to R18 each independently represent a same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1);
adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7, among groups represented by R12 to R15 and among groups represented by R16 to R18, adjacent groups represented by R8 and R7 and adjacent groups represented by R10 and R11 may be bonded to each other to form a saturated or unsaturated cyclic structure; and
X is as defined for general formula (1).
The present invention further provides an organic electroluminescence device comprising a cathode, an anode and an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and is disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises the material for organic electroluminescence devices described above.
The Effect of the Invention
To summarize the advantages of the present invention, the organic EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life can be obtained by utilizing the material for organic EL devices which comprises the compound represented by general formula (1) and, therefore, the organic EL device of the present invention is very useful as the light source for various electronic instruments.
THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
The material for organic EL devices of the present invention comprises a compound represented by any one of the following general formulae (1) to (14);
Figure USRE049118-20220628-C00009
In the above general formula (1), R1′, R2′ and R5 to R7 each independently represent hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have sub stituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have sub stituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon atoms which may have substituents, a ketoaryl group having 7 to 40 carbon atoms which may have substituents, a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents or cyano group; a pair of groups represented by R1′ and R2′, R5 and R6 or R6 and R7 may be bonded to each other to form a saturated or unsaturated cyclic structure; X represents sulfur atom, oxygen atom or a substituted silicon atom represented by SiRaRb, Ra and Rb each independently representing an alkyl group having 1 to 40 carbon atoms; and Y represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms which may have sub stituents, an aryloxyl group having 6 to 60 carbon atoms which may have sub stituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have substituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon atoms which may have substituents or a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents.
Figure USRE049118-20220628-C00010
In the above general formula (2), R1 to R7 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1), R1 not representing a group having a skeleton structure of anthracene; adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 may be bonded to each other to form a saturated or unsaturated cyclic structure; X is as defined for general formula (1); and Y′ represents an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, an alkoxyl group having 1 to 40 carbon atoms which may have substituents, an aryl group having 6 to 60 carbon atoms and having no skeleton structure of pyrene which may have substituents, an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have substituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon atoms which may have substituents or a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents.
Figure USRE049118-20220628-C00011
In the above general formula (3), R1 to R12 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1), at least one of R8 to R12 representing hydrogen atom; adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R8 to R12 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
Figure USRE049118-20220628-C00012
In the above general formulae (4) to (6), R1 to R10 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1); adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R8 to R10 in general formula (4), adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 and adjacent groups represented by R9 and R10 in general formula (5), and adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 and groups represented by R7 and R8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
Figure USRE049118-20220628-C00013
In the above general formulae (7) to (9), R1 to R11 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1); adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R8 to R11 in general formula (7), adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7, adjacent groups represented by R8 and R9, adjacent groups represented by R10 and R11 and adjacent groups represented by R7 and R8 in general formula (5), and adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7 and among groups represented by R9 to R11 and groups represented by R7 and R8 in general formula (6) may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
Figure USRE049118-20220628-C00014
In the above general formula (10), R1 to R9 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1); adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
Figure USRE049118-20220628-C00015
In the above general formulae (11) and (12), R1 to R13 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1); adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7, adjacent groups represented by R8 and R9, adjacent groups represented by R10 and R11 and adjacent groups represented by R12 and R13 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
Figure USRE049118-20220628-C00016
In the above general formulae (13) and (14), R1 to R18 each independently represent the same atom or group as that represented by R1′, R2′, R5, R6 or R7 in general formula (1); adjacent groups among groups represented by R1 to R4, among groups represented by R5 to R7, among groups represented by R12 to R15 and among groups represented by R16 to R18, adjacent groups represented by R8 and R9 and adjacent groups represented by R10 and R11 may be bonded to each other to form a saturated or unsaturated cyclic structure; and X is as defined for general formula (1).
Examples of the halogen atom represented by R1′, R2′ and R1 to R18 include fluorine atom, chlorine atom, bromine atom and iodine atom.
Examples of the alkyl group having 1 to 40 carbon atoms and may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxy-ethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 1,2-dinitroethyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group and 3,5-dimethylcyclohexyl group.
Among these alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group and 3,5-dimethylcyclohexyl group are preferable.
Examples of the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 1-imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxanyl group, 5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, β-carbolin-1-yl, β-carbolin-3-yl, β-carbolin-4-yl, β-carbolin-5-yl, β-carbolin-6-yl, β-carbolin-7-yl, β-carbolin-8-yl, β-carbolin-9-yl, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol5-yl group, 2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group, 4-t-butyl-3-indolyl group, 1-dibexofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group and 4-dibenzosilolyl group.
Among these heterocyclic groups, 2-pyridinyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group and 4-dibenzosilolyl group are preferable.
The alkoxyl group having 1 to 40 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, is a group represented by —OY. Examples of the group represented by Y include the groups described above as the examples of the alkyl group.
Examples of the aryl group having 6 to 60 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18 andY include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4″-t-butyl-p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group and mesityl group.
Among these aryl groups, phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group and 3,4-xylyl group are preferable.
Examples of the aryl group having 6 to 60 carbon atoms and having no skeleton structure of pyrene which may have substituents, which is represented by Y′, include the groups described above as the examples of the aryl group except the groups having the skeleton structure of pyrene.
The aryloxyl group having 6 to 60 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, is a group represented by —OAr. Examples of the group represented by Ar include the groups described above as the examples of the aryl group. Preferable examples of the group represented by Ar include the groups described above as the preferable examples of the aryl group.
Examples of the aralkyl group having 7 to 60 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group and 1-chloro-2-phenylisopropyl group.
Among these aralkyl groups, benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group and 2-phenylisopropyl groups are preferable.
Examples of the alkenyl group having 2 to 40 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group and 3-phenyl-1-butenyl group. Among these alkenyl groups, styryl group, 2,2-diphenylvinyl group and 1,2-diphenylvinyl groups are preferable.
The alkylamino group having 1 to 40 carbon atoms which may have substituents and the aralkylamino group having 7 to 60 carbon atoms which may have substituents, which are represented by R1′, R2′, R1 to R18, Y and Y′, are represented by —NQ1Q2. Examples of the groups represented by Q1 and Q2 include the groups described above as the examples of the alkyl group, the aryl group and the aralkyl group. Preferable examples of the groups represented by Q1 and Q2 include the groups described above as the preferable examples of the alkyl group, the aryl group and the aralkyl group.
Examples of the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group and propyldimethylsilyl group.
Examples of the arylsilyl group having 8 to 40 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include triphenylsilyl group, phenyldimethylsilyl group and t-butyldiphenylsilyl group.
The ketoaryl group having 7 to 40 carbon atoms which may have substituents, which is represented by R1′, R2′ and R1 to R18, is represented by —COAr2. Examples of the group represented by Ar2 include the groups described above as the examples of the aryl group. Preferable examples of the group represented by Ar include the groups described above as the preferable examples of the aryl group.
Examples of the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, which is represented by R1′, R2′, R1 to R18, Y and Y′, include groups obtained by substituting at least one of hydrogen atoms in the groups described above as the examples of the alkyl group with a halogen atom. Preferable examples of the halogenated alkyl group include groups obtained by substituting at least one of hydrogen atoms in the groups described above as the preferable examples of the alkyl group with a halogen atom.
Examples of the cyclic structure formed from a plurality of groups represented by R1′, R2′ and R1 to R18 include unsaturated six-membered rings such as benzene ring and saturated and unsaturated five-membered rings and seven-membered rings.
Examples of the alkyl group represented by Ra and Rb include the groups described above as the examples of the alkyl group. Methyl group, ethyl group, propyl group and butyl group are preferable.
Specific examples of the material for organic EL devices of the present invention which is represented by any one of general formulae (1) to (14) are shown in the following. However, the material for organic EL devices of the present invention is not limited to those shown as the examples.
Figure USRE049118-20220628-C00017
Figure USRE049118-20220628-C00018
Figure USRE049118-20220628-C00019
Figure USRE049118-20220628-C00020
Figure USRE049118-20220628-C00021
Figure USRE049118-20220628-C00022
Figure USRE049118-20220628-C00023
Figure USRE049118-20220628-C00024
Figure USRE049118-20220628-C00025
Figure USRE049118-20220628-C00026
Figure USRE049118-20220628-C00027
Figure USRE049118-20220628-C00028
Figure USRE049118-20220628-C00029
Figure USRE049118-20220628-C00030
Figure USRE049118-20220628-C00031
Figure USRE049118-20220628-C00032
Figure USRE049118-20220628-C00033
Figure USRE049118-20220628-C00034
Figure USRE049118-20220628-C00035
Figure USRE049118-20220628-C00036
Figure USRE049118-20220628-C00037
Figure USRE049118-20220628-C00038
Figure USRE049118-20220628-C00039
Figure USRE049118-20220628-C00040
Figure USRE049118-20220628-C00041
It is preferable that the material for organic EL devices of the present invention is a host material comprised in the light emitting layer of an organic EL device.
The organic EL device of the present invention will be described in the following.
The organic EL device of the present invention comprises a cathode, an anode and an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and is disposed between the cathode and the anode, wherein at least one layer in the organic thin film layer comprises the material for organic EL devices described above.
Examples of the structure of the organic EL device of the multi-layer type include multi-layer laminate structures such as an anode/a hole transport layer (a hole injection layer)/a light emitting layer/a cathode, an anode/a light emitting layer/an electron transport layer (an electron injection layer)/a cathode, an anode/a hole transport layer (a hole injection layer)/a light emitting layer/an electron transport layer (an electron injection layer)/a cathode and an anode/a hole transport layer (a hole injection layer)/a light emitting layer/a hole blocking layer/an electron transport layer (an electron injection layer)/a cathode.
It is preferable that the light emitting layer comprises a host material and a phosphorescent light emitting material, and the host material comprises the material for organic EL devices described above.
It is preferable that the light emitting layer comprises a host material and a phosphorescent light emitting material, and light emitted from the phosphorescent light emitting material has a peak wavelength of 500 nm or shorter.
As the phosphorescent light emitting material, metal complexes such as iridium complexes, osmium complexes and platinum complexes are preferable, iridium complexes and platinum complexes are more preferable and ortho-metallated iridium complexes are most preferable since the quantum yield of phosphorescence is great and the external quantum efficiency of the light emitting device can be further increased. As for the form of the ortho-metallated complex, iridium complexes shown in the following are preferable.
Figure USRE049118-20220628-C00042
Figure USRE049118-20220628-C00043
Figure USRE049118-20220628-C00044
Figure USRE049118-20220628-C00045
It is preferable that, in the organic EL device of the present invention, the light emitting layer comprises a host material and a phosphorescent light emitting material, and the phosphorescent light emitting material is a light emitting material having one or more carbene ligands coordinated to a metal center.
It is preferable that, in the organic EL device of the present invention, the material for organic EL devices is a host material comprised in the light emitting layer of the organic EL device.
It is preferable that, in the organic EL device of the present invention, the material for organic EL devices is a material comprised in a hole transport layer of the organic EL device.
It is preferable that, in the organic EL device of the present invention, the material for organic EL devices is a material comprised in an electron transport layer or a hole blocking layer of the organic EL device.
It is preferable that, in the organic EL device of the present invention, a reducing dopant is added into the interfacial region of the cathode and the organic thin film layer.
Examples of the reducing dopant include at least one substance selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes and rare earth metal compounds.
Examples of the alkali metal include Na (the work function: 2.36 eV), K (the work function: 2.28 eV), Rb (the work function: 2.16 eV) and Cs (the work function: 1.95 eV). Alkali metals having a work function of 2.9 eV or smaller are preferable. Among the above alkali metals, K, Rb and Cs are more preferable, Rb and Cs are still more preferable, and Cs is most referable.
Examples of the alkaline earth metal include Ca (the work function: 2.9 eV), Sr (the work function: 2.0 to 2.5 eV) and Ba (the work function: 2.52 eV). Alkaline earth metals having a work function of 2.9 eV or smaller are preferable.
Examples of the rare earth metal include Sc, Y, Ce, Tb and Yb. Rare earth metals having a work function of 2.9 eV or smaller are preferable.
The preferable metals among the above metals have great reducing ability, and the luminance of the emitted light and the life of the organic EL device can be increased by addition of a relatively small amount into the electron injection zone.
Examples of the alkali metal compound described above include alkali metal oxides such as Li2O, Cs2O and K2O and alkali metal halides such as LiF, NaF, CsF and KF. Among these compounds, alkali metal oxides and alkali metal fluorides such as LiF, Li2O and NaF are preferable.
Examples of the alkaline earth metal compound described above include BaO, SrO, CaO and mixtures thereof such as BaxSr1-xO (0<x<1) and BaxCa1-xO (0<x<1). Among these compounds, BaO, SrO and CaO are preferable.
Examples of the rare earth metal compound described above include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3 and TbF3. Among these compounds, YbF3, ScF3 and TbF3 are preferable.
The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex are not particularly limited as long as the complexes contain at least one of the alkali metal ions, the alkaline earth metal ions and rare earth metal ions, respectively, as the metal ion. As the ligand, quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazoles, hydroxydiarylthiadiazoles, hydroxyphenylpyridine, hydroxyphenyl-benzimidazole, hydroxybenzotriazole, hydroxyfulvorane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines and derivatives of these compounds are preferable. However, the ligand is not limited to those described above.
As for the form of the added reducing dopant, it is preferable that the reducing dopant is added in a manner such that a layer or islands are formed in the interfacial region described above. As the process for adding the reducing dopant, it is preferable that an organic material which is a light emitting material or an electron injection material forming the interfacial region is vapor deposited while the reducing dopant is simultaneously vapor deposited in accordance with the resistance heating method so that the reducing dopant is dispersed in the organic material. The concentration of the dispersion expressed as the ratio of the amounts by mole of the organic substance to the reducing dopant is in the range of 100:1 to 1:100 and preferably in the range of 5:1 to 1:5.
When the reducing dopant is added to form a layer, the reducing dopant alone is vapor deposited in accordance with the resistance heating method to form a layer preferably having a thickness of 0.1 to 15 nm after a layer of an organic material such as the light emitting material and the electron injection material is formed as the interfacial region.
When the reducing dopant is added to form islands, the reducing dopant alone is vapor deposited in accordance with the resistance heating method to form islands preferably having a thickness of 0.05 to 1 nm after islands of an organic material such as the light emitting material and the electron injection material are formed as the interfacial region.
It is preferable that the relative amounts by mole of the main component and the reducing dopant in the organic EL device of the present invention is in the range of 5:1 to 1:5 and more preferably in the range of 2:1 to 1:2.
It is preferable that, in the organic EL device of the present invention, an electron injection layer is disposed between the light emitting layer and the cathode, and the electron injection layer comprises a cyclic derivative having one or more nitrogen atoms as the main component.
As the electron transport material used for the above electron injection layer, aromatic heterocyclic compounds having one or more heteroatoms in the molecule are preferable, and cyclic derivatives having one or more nitrogen atoms are more preferable.
As the cyclic derivative having one or more nitrogen atoms, for example, compounds represented by general formula (A) are preferable.
Figure USRE049118-20220628-C00046
R2 to R7 each independently represent hydrogen atom, a halogen atom, an oxyl group, an amino group or a hydrocarbon group having 1 to 40 carbon atoms, and these groups may be substituted.
Examples of the halogen atom include the halogen atoms described above. Examples of the amino group which may be substituted include the alkylamino groups, the arylamino groups and the aralkylamino groups described above.
Examples of the hydrocarbon group having 1 to 40 carbon atoms include alkyl groups, alkenyl groups, cycloalkyl groups, alkoxyl groups, aryl groups. heterocyclic groups, aralkyl groups, aryloxyl groups and alkoxylcarbonyl groups, which may be substituted or unsubstituted. Examples of the alkyl group, the alkenyl group, the cycloalkyl group, the alkoxyl group, the aryl group, the heterocyclic group, the aralkyl group and the aryloxyl group include the groups described above as the examples of the corresponding groups. The alkoxylcarbonyl group is represented by —COOY′, and examples of the group represented by Y′ include the groups described above as the examples of the alkyl group.
M represents aluminum (Al), gallium (Ga) or indium (In), and In is preferable.
L in general formula (A) represents a group represented by the following general formula (A′) or (A″):
Figure USRE049118-20220628-C00047
In the above general formulae, R8 to R12 each independently represent hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and adjacent groups may form a cyclic structure. R13 to R27 each independently represent hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and adjacent groups may form a cyclic structure.
Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R8 to R12 and R13 to R27 in general formulae (A′) and (A″) include the groups described above as the examples of the groups represented by R2 to R7.
Examples of the divalent group which is the cyclic group formed by bonding of the adjacent groups represented by R8 to R12 and R13 to R27 include tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethan-2,2′-diyl group, diphenylethan-3,3′-diyl group and diphenylpropan-4,4′-diyl group.
Specific examples of the metal chelate complex having a ring having one or more nitrogen atoms represented by general formula (A) are shown in the following. However, the metal chelate complex having a ring having one or more nitrogen atoms is not limited to the compounds shown as the examples.
Figure USRE049118-20220628-C00048
Figure USRE049118-20220628-C00049
Figure USRE049118-20220628-C00050
Figure USRE049118-20220628-C00051
Figure USRE049118-20220628-C00052
Figure USRE049118-20220628-C00053
As the cyclic derivative having one or more nitrogen atoms of the main component of the electron injection layer, five-membered derivatives having one or more nitrogen atoms are also preferable. Examples of the five-membered ring include imidazole ring, triazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, oxatriazole ring and thiatriazole ring. Examples of the five-membered cyclic derivative having one or more nitrogen atoms include derivatives having benzimidazole ring, derivatives having benzotriazole ring, derivatives having pyridinoimidazole ring, derivatives having pyrimidinoimidazole ring and derivatives having pyridazino-imidazole ring. Derivatives represented by the following general formula (B) are preferable:
Figure USRE049118-20220628-C00054
In general formula (B), LB represents a linking atom or group having a valence of two or greater. Examples of the linking atom and group preferably include carbon atom, silicon atom, nitrogen atom, boron atom, oxygen atom, sulfur atom, a metal atom such as barium atom and beryllium atom, aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups. The linking atom or group is more preferably carbon atom, nitrogen atom, silicon atom, boron atom, oxygen atom, sulfur atom, an aryl group or an aromatic heterocyclic group, and most preferably carbon atom, silicon atom, an aryl group or an aromatic heterocyclic group.
The aryl group and the aromatic heterocyclic group represented by LB may have substituents. As the substituent, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, amino groups, alkoxyl groups, aryloxyl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, acyloxyl groups, acylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio groups, arylthio groups, sulfonyl group, halogen atoms, cyano group and aromatic heterocyclic groups are preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups, halogen atoms, cyano group and aromatic heterocyclic groups are more preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups and aromatic heterocyclic groups are still more preferable; and alkyl groups, aryl groups, alkoxyl groups and aromatic heterocyclic groups are most preferable.
Examples of the bonding atom and group represented by LB include atoms and groups shown in the following:
Figure USRE049118-20220628-C00055
Figure USRE049118-20220628-C00056
In formula (B), XB2 represents —O—, —S— or a group represented by ═N.RB2. RB2 represents hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.
The aliphatic hydrocarbon group represented by RB2 is a linear, branched or cyclic alkyl group (an alkyl group preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms and most preferably having 1 to 8 carbon atoms, such as methyl group, ethyl group, isopropyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group and cyclohexyl group), alkenyl group (an alkenyl group preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms and most preferably having 2 to 8 carbon atoms, such as vinyl group, allyl group, 2-butenyl group and 3-pentenyl group) or alkynyl group (an alkynyl group preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms and most preferably having 2 to 8 carbon atoms, such as propargyl group and 3-pentynyl group) and is preferably an alkyl group.
The aryl group represented by RB2 is an aryl group having a single ring or a condensed ring preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms and most preferably having 6 to 12 carbon atoms. Examples of the aryl group include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-trifluoromethylphenyl group, pentafluoro-phenyl group, 1-naphthyl group and 2-naphthyl group. The heterocyclic group represented by RB2 is a heterocyclic group having a single ring or a condensed ring and preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms and most preferably having 2 to 10 carbon atoms, and preferably an aromatic heterocyclic group having at least one of nitrogen atom, oxygen atom, sulfur atom and selenium atom. Examples of the heterocyclic group include groups derived from pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrol, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthylidine, quinoxaline, quinazoline, cinnoline, puteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetrazaindene, carbazole and azepine; preferably groups derived from furan, thiophene, pyridine, pyrazinc, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthylidine, quinoxaline or quinazoline; more preferably groups derived from furan, thiophene, pyridine or quinoline; and most preferably the group derived from quinoline.
The aliphatic hydrocarbon group, the aryl group and the heterocyclic group which are represented by RB2 may have substituents. Examples of the sub stituent include the substituents described above as the examples of the substituent to the group represented by LB. Preferable examples of the substituent include the substituents described above as the preferable examples of the substituent to the group represented by LB.
RB2 preferably represents an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, more preferably an aliphatic hydrocarbon group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms and most preferably 6 to 12 carbon atoms) or an aryl group and most preferably an aliphatic hydrocarbon group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms and most preferably 2 to 10 carbon atoms).
XB2 preferably represents —O— or a group represented by ═N—RB2, more preferably a group represented by ═N—RB2 and most preferably a group represented by ═N—RB2.
ZB2 represents a group of atoms necessary for forming an aromatic ring. The aromatic ring formed with the group of atoms represented by ZB2 may be any of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. Examples of the aromatic ring include benzene ring, pyridine ring, pyrazinc ring, pyrimidine ring, pyridazine ring, triazine ring, pyrrol ring, furan ring, thiophene ring, selenophene ring, tellurophene ring, imidazole ring, thiazole ring, selenazole ring, tellurazole ring, thiadiazole ring, oxadiazole ring and pyrazole ring. Among these rings, benzene ring, pyridine ring, pyrazine ring, pyrimidine ring and pyridazine ring are preferable, benzene ring, pyridine ring and pyrazine ring are more preferable, benzene ring and pyridine ring are still more preferable, and pyridine ring is most preferable.
The aromatic ring formed with the group of atoms represented by ZB2 may form a condensed ring in combination with other rings and may have substituents. Examples of the substituent include the substituents described above as the examples of the substituent to the groups represented by LB. As the substituent, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, amino groups, alkoxyl groups, aryloxyl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, acyloxyl groups, acylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio groups, arylthio groups, sulfonyl group, halogen atoms, cyano group and heterocyclic groups are preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups, halogen atoms, cyano group and heterocyclic groups are more preferable; alkyl groups, aryl groups, alkoxyl groups, aryloxyl groups and aromatic heterocyclic groups are still more preferable; and alkyl groups, aryl groups, alkoxyl groups and aromatic heterocyclic groups are most preferable.
nB2 represents an integer of 1 to 4 and preferably 2 or 3.
Among the five-membered derivative having one or more nitrogen atoms represented by the above general formula (B), compounds represented by the following general formula (B′) are preferable.
Figure USRE049118-20220628-C00057
In general formula (B′), RB71, RB72 and RB73 are each as defined for RB2 in general formula (B), and preferable groups are the same as those represented by RB2.
ZB71, ZB72 and ZB73 are each as defined for ZB2 in general formula (B), and preferable groups are the same as those represented by ZB2.
LB71, LB72 and LB73 each represent a linking group. Examples of the group include divalent groups derived from the groups described as the examples of the group represented by LB in general formula (B). The linking group is preferably the single bond, a divalent aromatic hydrocarbon cyclic group, a divalent aromatic heterocyclic group or a linking group obtained as a combination of these groups, and more preferably the single bond. The groups represented by LB71, LB72 and LB73 may have substituents. Examples of the substituent include the substituents described above as the examples of the sub stituent to the groups represented by LB in general formula (B). Preferable examples of the substituent include the substituents described above as the preferable examples of the sub stituent to the groups represented by LB in general formula (B).
Y represents nitrogen atom, 1,3,5-benzenetriyl group or 2,4,6-triazinetriyl group. 1,3,5-Benzenetriyl group may have substituents at the 2-, 4- and 6-positions. Examples of the substituent include alkyl groups, aromatic hydrocarbon cyclic groups and halogen atoms.
Examples of the five-membered cyclic derivative having one or more nitrogen atoms which is represented by general formula (B) or (B′) are shown in the following. However, the five-membered cyclic derivative having one or more nitrogen atoms is not limited to the compounds shown as the examples.
Figure USRE049118-20220628-C00058
Figure USRE049118-20220628-C00059
Figure USRE049118-20220628-C00060
Figure USRE049118-20220628-C00061
It is preferable that an insulating material or a semiconductor of an inorganic compound is used as the substance constituting the electron injection layer for the substance other than the ring derivative having one or more nitrogen atoms. When the electron injection layer comprises the insulating material or the semiconductor, leak of the electric current can be effectively prevented, and the electron injection property can be improved.
As the insulating material, at least one metal compound selected from the group consisting of chalcogenides of alkali metals, chalcogenides of alkaline earth metals, halides of alkali metals and halides of alkaline earth metals is preferable. It is preferable that the electron injection layer comprises the above metal compound since the electron injection property can be further improved. Preferable examples of the chalcogenide of an alkali metal include Li2O, K2O, Na2S, Na2Se and Na2O. Preferable examples of the chalcogenide of an alkaline earth metal include CaO, BaO, SrO, BeO, BaS and CaSe. Preferable examples of the halide of an alkali metal include LiF, NaF, KF, LiCl, KCl and NaCl. Preferable examples of the halide of an alkaline earth metal include fluoride such as CaF2, BaF2, SrF2, MgF2 and BeF2 and halides other than the fluorides.
Examples of the semiconductor include oxides, nitrides and oxide nitrides comprising at least one element selected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn used singly or in combination of two or more. It is preferable that the inorganic compound constituting the electron injection layer forms crystallite or amorphous insulating thin film. When the electron injection layer is constituted with the insulating thin film described above, a more uniform thin film can be formed, and defects of pixels such as dark spots can be decreased. Examples of the inorganic compound include chalcogenides of alkali metals, chalcogenides of alkaline earth metals, halides of alkali metals and halides of alkaline earth metals which are described above.
It is also preferable that the electron injection layer in the present invention comprises the reducing dopant described above.
The anode of the organic EL device plays the role of injection holes into the hole transport layer or the light emitting layer. It is effective that the anode has a work function of 4.5 eV or greater. Examples of the material of the anode used in the present invention include indium tin oxide alloys (ITO), tin oxides (NESA), gold, silver, platinum and copper. As the cathode, a material having a small work function is preferable so that electrons can be injected into the electron transport layer or the light emitting layer. The material of the cathode is not particularly limited. Examples of the material of the cathode include indium, aluminum, magnesium, magnesium-indium alloys, magnesium-aluminum alloys, aluminum-lithium alloys, aluminum-scandium-lithium alloys and magnesium-silver alloys.
The process for forming the layers in the organic EL device of the present invention is not particularly limited. A conventional process such as the vacuum vapor deposition process and the spin coating process can be used. The organic thin film layer which comprises the compound represented by any one of general formulae (1) to (3) and used in the organic EL device of the present invention can be formed in accordance with the vacuum vapor deposition process or the molecular beam epitaxy process (the MBE process) or, using a solution prepared by dissolving the compound into a solvent, in accordance with a conventional coating process such as the dipping process, the spin coating process, the casting process, the bar coating process and the roll coating process.
The thickness of each organic layer in the organic EL device of the present invention is not particularly limited. In general, an excessively thin layer tends to have defects such as pin holes, and an excessively thick layer requires a high applied voltage to decrease the efficiency. In general, a thickness in the range of several nanometers to 1 μm is preferable.
EXAMPLES
The present invention will be described more specifically with reference to examples in the following.
Synthesis Example 1 Synthesis of D1
Figure USRE049118-20220628-C00062
Into a 300 ml three-necked flask, 3.75 g (17.7 mmole) of 4-dibenzofuranboric acid and 1.02 g (0.885 mmole) of tetrakis-(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 53.1 ml of 1,2-dimethoxyethane, 0.810 ml (6.73 mmole) of 1,4-dibromobenzene and 26.6 ml of a 2.0 M aqueous solution of sodium carbonate (53.1 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 2.72 g (6.63 mmole; the yield: 98%) of Compound D1 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C30H18O2=410; found: m/z=410 (M+, 100)
The obtained compound was purified by sublimation at 190° C. The purity of the compound obtained after the purification by sublimation was 99.8%.
Synthesis Example 2 Synthesis of E1
Figure USRE049118-20220628-C00063
Into a 300 ml three-necked flask, 3.42 g (15.0 mmole) of 4-dibenzothiopheneboric acid and 0.867 g (0.750 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 45.0 ml of 1,2-dimethoxyethane, 0.688 ml (5.70 mmole) of 1,4-dibromo-benzene and 22.5 ml of a 2.0 M aqueous solution of sodium carbonate (45.0 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 1.64 g (3.71 mmole; the yield: 54%) of Compound E1 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C30H18S2=442; found: m/z=442 (M+, 100)
The obtained compound was purified by sublimation at 230° C.
The purity of Compound 2 obtained after the purification by sublimation was 99.7%.
Synthesis Example 3 Synthesis of Compound E4
The route of synthesis of Compound E4 is shown in the following.
Figure USRE049118-20220628-C00064
Into a 300 ml three-necked flask, 6.04 g (26.5 mmole) of 4-dibenzothiopheneboric acid, 2.25 g (7.14 mmole) of 1,3,5tribromo-benzene and 2.30 g (1.99 mmole) of tetrakis(triphenylphosphine)-palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 79.5 ml of 1,2-dimethoxy-ethane and 39.8 ml of a 2.0 M aqueous solution of sodium carbonate (79.5 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 1.78 g (2.85 mmole; the yield: 40%) of Compound E4 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS; calcd. for C42H24S3=624; found: m/z=624 (M+, 100)
The obtained compound was purified by sublimation at 260° C. The purity of the compound obtained after the purification by sublimation was 99.4%.
Synthesis Example 4
Synthesis of Compound E2
The route of syntheis of Compound E2 is shown in the following.
Figure USRE049118-20220628-C00065
Into a 300 ml three-necked flask, 4.04 g (17.7 mmole) of 4-dibenzothiopheneboric acid and 1.02 g (0.885 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 53.1 ml of 1,2-dimethoxyethane, 0.800 ml (6.73 mmole) of 1,2-dibromo-benzene and 26.6 ml of a 2.0 M aqueous solution of sodium carbonate (53.1 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.92 g (4.34 mmole; the yield: 64%) of Compound E2 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C30H18S2=442; found: m/z=442 (M+, 100)
The obtained compound was purified by sublimation at 210° C.
The purity of the compound obtained after the purification by sublimation was 99.4%.
Synthesis Example 5 Synthesis of Compound E3
The route of synthesis of Compound E3 is shown in the following.
Figure USRE049118-20220628-C00066
Into a 300 ml three-necked flask, 1.41 g (6.17 mmole) of 4-dibenzothiopheneboric acid, 1.20 g (2.59 mmole) of aryl dibromide and 0.356 g (0.309 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 18.5 ml of 1,2-dimethoxyethane and 9.25 ml of a 2.0 M aqueous solution of sodium carbonate (18.5 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. To the reaction fluid, 100 ml of water and 100 ml of methylene chloride were added, and the organic layer was separated and dried with anhydrous magnesium sulfate. After the dried solution was concentrated under a reduced pressure using an evaporator, the formed solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.30 g (1.94 mmole; the yield: 75%) of Compound E3 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C48H30S2=670; found: m/z=670 (M+, 100)
The obtained compound was purified by sublimation at 210° C. The purity of Compound E3 obtained after the purification by sublimation was 99.5%.
Synthesis Example 6 Synthesis of Compound D3
The route of synthesis of Compound D3 is shown in the following.
Figure USRE049118-20220628-C00067
Into a 300 ml three-necked flask, 2.31 g (10.9 mmole) of 4-dibenzofuranboric acid, 2.12 g (4.57 mmole) of aryl dibromide and 0.630 g (0.545 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 32.7 ml of 1,2-dimethoxyethane and 16.4 ml of a 2.0 M aqueous solution of sodium carbonate (32.7 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. To the reaction fluid, 100 ml of water and 100 ml of methylene chloride were added, and the organic layer was separated and dried with anhydrous magnesium sulfate. After the dried solution was concentrated under a reduced pressure using an evaporator, the formed solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.90 g (2.97 mmole; the yield: 65%) of Compound D3 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C48H30O2=638; found: m/z=638 (M+, 100)
The obtained compound was purified by sublimation at 200° C. The purity of Compound D3 obtained after the purification by sublimation was 99.7%.
Synthesis Example 7 Synthesis of Compound E22
The route of synthesis of Compound E22 is shown in the following.
Figure USRE049118-20220628-C00068
Into a 300 ml three-necked flask, 4.33 g (19.0 mmole) of 4-dibenzothiopheneboric acid, 3.75 g (8.00 mmole) of an aryl dibromide and 1.10 g (0.950 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 57.0 ml of 1,2-dimethoxyethane and 28.5 ml of a 2.0 M aqueous solution of sodium carbonate (57.0 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 1.70 g (2.53 mmole: the yield: 32%) of Compound E22 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C46H28N2S2=672; found: m/z=672 (M+, 100)
The obtained compound was purified by sublimation at 350° C. The purity of Compound E22 obtained after the purification by sublimation was 99.3%.
Synthesis Example 8 Synthesis of Compound D22
The route of synthesis of Compound D22 is shown in the following.
Figure USRE049118-20220628-C00069
Into a 300 ml three-necked flask, 4.87 g (22.9 mmole) of 4-dibenzofuranboric acid, 4.50 g (9.65 mmole) of aryl dibromide and 1.32 g (1.15 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 68.7 ml of 1,2-dimethoxyethane and 34.4 ml of a 2.0 M aqueous solution of sodium carbonate (68.7 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 2.78 g (4.34 mmole; the yield: 45%) of Compound D22 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C46H28N2O2=640; found: m/z=640 (M+, 100)
The obtained compound was purified by sublimation at 330° C. The purity of Compound D22 obtained after the purification by sublimation was 99.5%.
Synthesis Example 9 Synthesis of Compound G15
The route of synthesis of Compound G15 is shown in the following.
Figure USRE049118-20220628-C00070
Into a 300 ml three-necked flask, 2.31 g (10.9 mmole) of 4-dibenzofuranboric acid, 2.48 g (10.9 mmole) 4-dibenzothiopheneboric acid, 4.21 g (9.07 mmole) of aryl dibromide and 1.26 g (1.09 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 65.4 ml of 1,2-dimethoxyethane and 32.7 ml of a 2.0 M aqueous solution of sodium carbonate (65.4 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. To the reaction fluid, 100 ml of water and 100 ml of methylene chloride were added, and the organic layer was separated and dried with anhydrous magnesium sulfate. After the dried solution was concentrated under a reduced pressure using an evaporator, the formed solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.49 g (2.27 mmole; the yield: 25%) of Compound G15 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C48H30OS=654; found: m/z=654 (Mt, 100)
The obtained compound was purified by sublimation at 200° C. The purity of Compound G15 obtained after the purification by sublimation was 99.2%.
Syntheis Example 10 Synthesis of Coupound H2
The route of synthesis of Compound H2 is shown in the following.
Figure USRE049118-20220628-C00071
Into a 300 ml three-necked flask, 4.44 g (19.5 mmole) of 4-dibenzothiopheneboric acid, 2.78 g (8.18 mmole) of 4,4′-dibromo-benzophenone and 1.13 g (0.975 mmole) of tetrakis (triphenylphosphine)-palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 58.5 ml of 1,2-dimethoxyethane and 29.3 ml of a 2.0 M aqueous solution of sodium carbonate (58.5 mmole) were added. and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and toluene, and 3.31 g (6.05 mmole; the yield: 74%) of Compound H2 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C37H22OS2=546; found: m/z=546 (M+, 100)
The obtained compound was purified by sublimation at 320° C. The purity of Compound H2 obtained after the purification by sublimation was 99.0%.
Synthesis Example 11 Synthesis of Compound H1
The route of synthesis of Compound H1 is shown in the following.
Figure USRE049118-20220628-C00072
Into a 300 ml three-necked flask, 4.59 g (21.6 mmole) of 4-dibenzofuranboric acid, 3.09 g (9.09 mmole) of 4,4′-dibromo-benzophenone and 1.25 g (1.08 mmole) of tetrakis (triphenylphosphine)-palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 64.8 ml of 1,2-dimethoxy-ethane and 32.4 ml of a 2.0 M aqueous solution of sodium carbonate (64.8 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and toluene, and 2.67 g (5.18 mmole; the yield: 57%) of Compound H1 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz 1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.
FD-MS: calcd. for C37H22O3=514; found: m/z=514 (M+, 100)
The obtained compound was purified by sublimation at 315° C. The purity of Compound H1 obtained after the purification by sublimation was 99.2%.
Example 1 Preparation of an Organic EL Device
A glass substrate of 25 mm×75 mm×1.1 mm thickness having an ITO transparent electrode (manufactured by GEOMATEC Company) was cleaned by application of ultrasonic wave in isopropyl alcohol for 5 minutes and then by exposure to ozone generated by ultraviolet light for 30 minutes. The cleaned glass substrate having the transparent electrode was attached to a substrate holder of a vacuum vapor deposition apparatus. On the surface of the cleaned substrate at the side having the transparent electrode, a film of HTM (the formula shown in the following) having a thickness of 100 nm was formed in a manner such that the formed film covered the transparent electrode. The formed film of HTM worked as the hole injection and transport layer. Following the formation of the hole injection and transport layer, Compound D1 as the host compound and Complex P expressed by the formula shown in the following were vapor deposited simultaneously on the formed film of HTM in accordance with the resistance heating method so that a film having a thickness of 30 nm was formed. The concentration of Complex P was 7% by weight. The formed film of the host compound and Compound D1 worked as the light emitting layer. Following the formation of the light emitting layer, a film having a thickness of 25 nm of ETM1 shown in the following was formed and, then, a film having a thickness of 5 nm of ETM2 shown in the following was formed on the formed film of ETM1. The layers of ETM1 and ETM2 worked as the electron transport layer and the electron injection layer, respectively. Then, LiF was vapor deposited at a rate of 1 Å/min to form a film having a thickness of 0.1 nm so that an electron injection electrode (the cathode) was formed. On the formed LiF layer, metallic aluminum was vapor deposited to form a film having a thickness of 150 nm so that a metal cathode having a thickness of 150 nm was formed. Thus, an organic EL device was prepared.
(Evaluation of the Light Emitting Property of the Organic EL Device)
The organic EL device prepared as described above was driven under a direct current (the current density J=1 mA/cm2) to emit light. The luminance (L) was measured, and the efficiency of light emission (L/J) was obtained. The results are shown in Table 1.
Figure USRE049118-20220628-C00073
Examples 2 to 9
Organic EL devices were prepared in accordance with the same procedures as those conducted in Example 1 except that compounds described in the column of the host compound in Table 1 were used as the host compound in place of Compound D1. The efficiency of light emission of the obtained organic EL devices each was measured in accordance with the same procedure as that conducted in Example 1. The results are shown in Table 1.
Comparative Examples 1 to 3
Organic EL devices were prepared in accordance with the same procedures as those conducted in Example 1 except that compounds described in International Patent Publication No. WO 2004/096945, Japanese Patent Application Laid-Open No. Heisei 5 (1993)-109485 and Japanese Patent Application Laid-Open No. 2004-214050 were used as the host compound in Comparative Examples 1, 2 and 3, respectively, in place of Compound D1. The formulae are shown in the following. The efficiency of light emission of the obtained organic EL devices was measured in accordance with the same procedure as that conducted in Example 1. The results are shown in Table 1.
Figure USRE049118-20220628-C00074
TABLE 1
J (mA/ L (cd/ L/J
Host compound cm2) m2) (cd/A)
D1 1.0 400 40
E1 1.0 284 28
E4 1.0 310 31
E2 1.0 295 30
E3 1.0 456 46
D3 1.0 482 48
D22 1.0 405 41
E22 1.0 325 33
G15 1.0 358 36
H1 1.0 328 33
H2 1.0 444 44
Comparative 1.0  20 2.0
Example 1
Comparative 1.0  32 3.2
Example 2
Comparative 1.0 139 14
Example 3
The results in Table 1 show that the organic EL devices using the compound of the present invention in the light emitting layer exhibited greater efficiencies of light emission. It is shown that the compound of the present invention is useful for application to organic EL devices.
INDUSTRIAL APPLICABILITY
As described specifically in the above, the organic EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life can be obtained when the material for organic EL devices of the present invention comprising the compound represented by any one of general formulae (1) to (14) is used and, therefore, the organic EL device of the present invention is very useful as the light source for various electronic instruments.

Claims (30)

The invention claimed is:
1. A material for organic electroluminescence devices, which comprises a compound represented by following general formula (3):
Figure USRE049118-20220628-C00075
wherein:
R1 to R12 each independently represent
hydrogen atom,
a halogen atom,
an alkyl group having 1 to 40 carbon atoms which may have substituents,
a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, provided that the heterocyclic group is selected from the group consisting of 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 1-imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxanyl group, 5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, β-carbolin-1-yl, β-carbolin-3-yl, 62 -carbolin-4-yl, β-carbolin-5-yl, β-carbolin-6-yl, β-carbolin-7-yl, β-carbolin-8-yl, β-carbolin-9-yl, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthfidinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl)pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group, 4-t-butyl-3-indolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, and 4-dibenzosilolyl group; an alkoxyl group having 1 to 40 carbon atoms which may have substituents,
an aryl group having 6 to 60 carbon atoms which may have substituents, provided the aryl group is selected from the group consisting of phenyl group, 1-naphthyl group, 2-naphthyl group, phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4′-methylbiphenylyl group, 4″-t-butyl-p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, and mesityl group;
an aryloxyl group having 6 to 60 carbon atoms which may have substituents,
an aralkyl group having 7 to 60 carbon atoms which may have substituents,
an alkenyl group having 2 to 40 carbon atoms which may have substituents,
an alkylamino group having 1 to 40 carbon atoms which may have substituents,
an aralkylamino group having 7 to 60 carbon atoms which may have substituents,
an alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
an arylsilyl group having 8 to 40 carbon atoms which may have substituents,
a ketoaryl group having 7 to 40 carbon atoms which may have substituents,
a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or cyano group,
provided that each R8 to R12 do not represent
an alkyl group having 1 to 40 carbon atoms which may have substituents,
an aralkyl group having 7 to 60 carbon atoms which may have substituents,
an alkenyl group having 2 to 40 carbon atoms which may have substituents,
or a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or
a halogen atom;
provided that each R1 to R7 do not represent 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group;
at least one of R8 to R12 representing hydrogen atom represents the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group; and
the rest of R8 to R12 represent hydrogen atom, the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group;
adjacent groups among groups represented by R1 to R4, and among groups represented by R5 to R7 and among groups represented by R8 to R12 may be bonded to each other to form a saturated or unsaturated cyclic structure, and adjacent groups among groups represented by R8 to R12 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
X represents sulfur atom, oxygen atom or a substituted silicon atom represented by SiRaRb, Ra and Rb each independently representing an alkyl group having 1 to 40 carbon atoms,
provided that the compound excludes 1,3,5-tris(4-dibenzothiophenyl)benzene.
2. An organic electroluminescence device comprising a cathode, an anode and an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and is disposed between the cathode and the anode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described in claim 1.
3. An organic electroluminescence device according to claim 2, wherein the light emitting layer comprises a host material and a phosphorescent light emitting material, and the host material comprises a material for organic electroluminescence devices described in claim 1.
4. An organic electroluminescence device according to claim 3, wherein light emitted from the phosphorescent light emitting material has a peak wavelength of 500 nm or shorter.
5. An organic electroluminescence device according to claim 3, wherein the phosphorescent light emitting material is a compound having a metal selected from Er, Os and Pt.
6. An organic electroluminescence device according to claim 3, wherein the phosphorescent light emitting material is a light emitting material having one or more carbene ligands coordinated to a metal center.
7. An organic electroluminescence device according to claim 2, wherein the material for organic electroluminescence devices is a host material comprised in the light emitting layer of the organic electroluminescence device.
8. An organic electroluminescence device according to claim 2, wherein the material for organic electroluminescence devices is a material comprised in a hole transport layer of the organic electroluminescence device.
9. An organic electroluminescence device according to claim 2, wherein the material for organic electroluminescence devices is a material comprised in an electron transport layer or a hole blocking layer of the organic electroluminescence device.
10. An organic electroluminescence device according to claim 2, wherein a reducing dopant is added into an interfacial region of the cathode and the organic thin film layer.
11. An organic electroluminescence device according to claim 2, wherein an electron injection layer is disposed between the light emitting layer and the cathode, and the electron injection layer comprises a cyclic derivative having one or more nitrogen atoms as a main component.
12. An organic electroluminescence device according to claim 2, wherein R1 to R12 each independently represent hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
13. An organic electroluminescence device according to claim 2, wherein:
the alkyl group represented by R1 to R12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group;
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; and
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group.
14. An organic electroluminescence device according to claim 2, wherein X represents oxygen atom.
15. An organic electroluminescence device according to claim 2, wherein X represents sulfur atom.
16. An organic electroluminescence device according to claim 2, wherein adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure.
17. An organic electroluminescence device according to claim 2, wherein all of R1 to R12 which may have substituents do not have substituents.
18. An organic electroluminescence device according to claim 2, wherein:
one of R1 to R7 is
the halogen atom,
the alkyl group having 1 to 40 carbon atoms which may have substituents,
the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents,
the aryl group having 6 to 60 carbon atoms which may have substituents,
the aryloxyl group having 6 to 60 carbon atoms which may have substituents,
the aralkyl group having 7 to 60 carbon atoms which may have substituents,
the alkenyl group having 2 to 40 carbon atoms which may have substituents,
the alkylamino group having 1 to 40 carbon atoms which may have substituents,
the aralkylamino group having 7 to 60 carbon atoms which may have substituents,
the alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
the arylsilyl group having 8 to 40 carbon atoms which may have substituents,
the ketoaryl group having 7 to 40 carbon atoms which may have substituents,
the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or
cyano group, and
the rest of R1 to R7 are hydrogen atom.
19. An organic electroluminescence device according to claim 2, wherein all of R1 to R7 are hydrogen atom.
20. An organic electroluminescence device according to claim 2, wherein:
one of R8 to R12 is
the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents,
the aryl group having 6 to 60 carbon atoms which may have substituents,
the aryloxyl group having 6 to 60 carbon atoms which may have substituents,
the alkylamino group having 1 to 40 carbon atoms which may have substituents,
the aralkylamino group having 7 to 60 carbon atoms which may have substituents,
the alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
the arylsilyl group having 8 to 40 carbon atoms which may have substituents,
the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or
cyano group, and
the rest of RR to R12 are hydrogen atom.
21. An organic electroluminescence device according to claim 2, wherein:
R1 to R12 each independently represent hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; and
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure.
22. An organic electroluminescence device according to claim 2, wherein:
R1 to R12 each independently represent hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
all of R1 to R12 which may have substituents do not have substituents.
23. An organic electroluminescence device according to claim 2, wherein:
R1 to R12 each independently represent hydrogen atom, an aryl group, or a heterocyclic group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
one of R1 to R7 is
the halogen atom,
the alkyl group having 1 to 40 carbon atoms which may have substituents,
the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents,
the aryl group having 6 to 60 carbon atoms which may have substituents,
the aryloxyl group having 6 to 60 carbon atoms which may have substituents,
the aralkyl group having 7 to 60 carbon atoms which may have substituents,
the alkenyl group having 2 to 40 carbon atoms which may have substituents,
the alkylamino group having 1 to 40 carbon atoms which may have substituents,
the aralkylamino group having 7 to 60 carbon atoms which may have substituents,
the alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
the arylsilyl group having 8 to 40 carbon atoms which may have substituents,
the ketoaryl group having 7 to 40 carbon atoms which may have substituents,
the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or
cyano group, and
the rest of R1 to R7 are hydrogen atom.
24. An organic electroluminescence device according to claim 2, wherein:
R1 to R12 each independently represent hydrogen atom, an aryl group, or a heterocyclic group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
all of R1 to R7 are hydrogen atom.
25. An organic electroluminescence device according to claim 2, wherein:
the alkyl group represented by R1 to R12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group;
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group;
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; and
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure.
26. An organic electroluminescence device according to claim 2, wherein:
the alkyl group represented by R1 to R12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group;
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group;
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
all of R1 to R12 which may have substituents do not have substituents.
27. An organic electroluminescence device according to claim 2, wherein:
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group;
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
one of R1 to R7 is
the halogen atom,
the alkyl group having 1 to 40 carbon atoms which may have substituents,
the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents,
the aryl group having 6 to 60 carbon atoms which may have substituents,
the aryloxyl group having 6 to 60 carbon atoms which may have substituents,
the aralkyl group having 7 to 60 carbon atoms which may have substituents,
the alkenyl group having 2 to 40 carbon atoms which may have substituents,
the alkylamino group having 1 to 40 carbon atoms which may have substituents,
the aralkylamino group having 7 to 60 carbon atoms which may have substituents,
the alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
the arylsilyl group having 8 to 40 carbon atoms which may have substituents,
the ketoaryl group having 7 to 40 carbon atoms which may have substituents,
the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or
cyano group, and
the rest of R1 to R7 are hydrogen atom.
28. An organic electroluminescence device according to claim 2, wherein:
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group;
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and
all of R1 to R7 are hydrogen atom.
29. An organic electroluminescence device according to claim 2, wherein:
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group;
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure;
all of R1 to R7 are hydrogen atom; and
one of R8 to R12 is
the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents,
the aryl group having 6 to 60 carbon atoms which may have substituents,
the aryloxyl group having 6 to 60 carbon atoms which may have substituents,
the alkylamino group having 1 to 40 carbon atoms which may have substituents,
the aralkylamino group having 7 to 60 carbon atoms which may have substituents,
the alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
the arylsilyl group having 8 to 40 carbon atoms which may have substituents,
the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or
cyano group, and
the rest of R8 to R12 are hydrogen atom.
30. An organic electroluminescence device according to claim 2, wherein:
the alkyl group represented by R1 to R12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group;
the aryl group represented by R1 to R12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group;
the heterocyclic group represented by R1 to R12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group;
adjacent groups among groups represented by R1 to R4 and among groups represented by R5 to R7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure;
all of R1 to R7 are hydrogen atom;
one of R8 to R12 is
the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents,
the aryl group having 6 to 60 carbon atoms which may have substituents,
the aryloxyl group having 6 to 60 carbon atoms which may have substituents,
the alkylamino group having 1 to 40 carbon atoms which may have substituents,
the aralkylamino group having 7 to 60 carbon atoms which may have substituents,
the alkylsilyl group having 3 to 20 carbon atoms which may have substituents,
the arylsilyl group having 8 to 40 carbon atoms which may have substituents,
the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or
cyano group, and
the rest of R8 to R12 are hydrogen atom; and
X represents oxygen atom.
US16/804,850 2005-12-15 2020-02-28 Material for organic electroluminescence device and electroluminescence device employing the same Active USRE49118E1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US16/804,850 USRE49118E1 (en) 2005-12-15 2020-02-28 Material for organic electroluminescence device and electroluminescence device employing the same

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/300,368 US7651791B2 (en) 2005-12-15 2005-12-15 Material for organic electroluminescence device and electroluminescence device employing the same
US12/632,988 US7846560B2 (en) 2005-12-15 2009-12-08 Material for organic electroluminescence device and electroluminescence device employing the same
US16/804,850 USRE49118E1 (en) 2005-12-15 2020-02-28 Material for organic electroluminescence device and electroluminescence device employing the same

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US12/632,988 Reissue US7846560B2 (en) 2005-12-15 2009-12-08 Material for organic electroluminescence device and electroluminescence device employing the same

Publications (1)

Publication Number Publication Date
USRE49118E1 true USRE49118E1 (en) 2022-06-28

Family

ID=38173961

Family Applications (3)

Application Number Title Priority Date Filing Date
US11/300,368 Active 2027-02-16 US7651791B2 (en) 2005-12-15 2005-12-15 Material for organic electroluminescence device and electroluminescence device employing the same
US12/632,988 Ceased US7846560B2 (en) 2005-12-15 2009-12-08 Material for organic electroluminescence device and electroluminescence device employing the same
US16/804,850 Active USRE49118E1 (en) 2005-12-15 2020-02-28 Material for organic electroluminescence device and electroluminescence device employing the same

Family Applications Before (2)

Application Number Title Priority Date Filing Date
US11/300,368 Active 2027-02-16 US7651791B2 (en) 2005-12-15 2005-12-15 Material for organic electroluminescence device and electroluminescence device employing the same
US12/632,988 Ceased US7846560B2 (en) 2005-12-15 2009-12-08 Material for organic electroluminescence device and electroluminescence device employing the same

Country Status (1)

Country Link
US (3) US7651791B2 (en)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7651791B2 (en) * 2005-12-15 2010-01-26 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and electroluminescence device employing the same
WO2007097149A1 (en) * 2006-02-20 2007-08-30 Konica Minolta Holdings, Inc. Organic electroluminescence element, white light emitting element, display device and illuminating device
EP1998387B1 (en) * 2006-03-17 2015-04-22 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
EP2034538B1 (en) * 2006-06-02 2013-10-09 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence element, and organic electroluminescence element using the material
EP2437326A3 (en) * 2006-12-13 2013-11-13 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
US8080658B2 (en) 2007-07-10 2011-12-20 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent element and organic electroluminescent element employing the same
EP2166584B1 (en) * 2007-07-10 2016-06-08 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence element, and organic electroluminescence element prepared by using the material
EP3159333B1 (en) * 2007-08-08 2020-04-22 Universal Display Corporation Benzo-fused thiophene or furan compounds comprising a triphenylene group
WO2009085344A2 (en) 2007-12-28 2009-07-09 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
KR101638991B1 (en) * 2008-05-07 2016-07-12 바이엘 인텔렉쳐 프로퍼티 게엠베하 Synergistic active ingredient combinations
KR20120052231A (en) 2009-10-16 2012-05-23 이데미쓰 고산 가부시키가이샤 Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same
JP5507381B2 (en) * 2010-07-30 2014-05-28 ユー・ディー・シー アイルランド リミテッド Organic electroluminescent device and compound
WO2012046560A1 (en) * 2010-10-04 2012-04-12 Semiconductor Energy Laboratory Co., Ltd. Composite material, light-emitting element, light-emitting device, electronic device, and lighting device
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
KR101950363B1 (en) * 2010-10-29 2019-02-20 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Phenanthrene compound, light-emitting element, light-emitting device, electronic device, and lighting device
CN103228647B (en) 2010-11-24 2017-02-15 默克专利有限公司 Materials for organic electroluminescent devices
KR20130130788A (en) * 2010-12-20 2013-12-02 이 아이 듀폰 디 네모아 앤드 캄파니 Triazine derivatives for electronic applications
JP5973762B2 (en) * 2011-03-31 2016-08-23 ユー・ディー・シー アイルランド リミテッド Charge transport material, organic electroluminescent element, and light emitting device, display device or illumination device using the element
JP5804797B2 (en) * 2011-06-28 2015-11-04 キヤノン株式会社 Benzotriphenylenofuran compound and organic light emitting device having the same
TWI613195B (en) 2011-08-25 2018-02-01 半導體能源研究所股份有限公司 Light-emitting elements, light-emitting devices, electronic devices, lighting devices, and novel organic compounds
KR102046775B1 (en) * 2011-11-22 2019-11-20 이데미쓰 고산 가부시키가이샤 Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
JP2013133278A (en) * 2011-12-23 2013-07-08 Semiconductor Energy Lab Co Ltd Method for synthesizing material for light-emitting element
US9059411B2 (en) 2012-02-29 2015-06-16 Semiconductor Energy Laboratory Co., Ltd. Fluorene compound, light-emitting element, light-emitting device, electronic device, and lighting device
JP6312960B2 (en) * 2012-08-03 2018-04-18 株式会社半導体エネルギー研究所 Light emitting element, light emitting device, electronic device, lighting device, and heterocyclic compound
KR101423067B1 (en) 2012-10-04 2014-07-29 롬엔드하스전자재료코리아유한회사 Novel organic electroluminescence compounds and organic electroluminescence device comprising the same
JP6335428B2 (en) * 2012-12-21 2018-05-30 出光興産株式会社 Organic electroluminescence device and electronic device
US9496503B2 (en) 2013-03-25 2016-11-15 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
TWI633100B (en) 2013-07-19 2018-08-21 半導體能源研究所股份有限公司 Organic compound, light-emitting element, display module, lighting module, light-emitting device, display device, lighting device and electronic device
KR102140018B1 (en) 2013-12-17 2020-07-31 삼성전자주식회사 Condensed cyclic compound and organic light emitting device including the same
US10985329B2 (en) 2013-12-17 2021-04-20 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
KR101788094B1 (en) 2014-01-09 2017-10-19 제일모직 주식회사 Organic compound and organic optoelectric device and display device
KR20150105584A (en) * 2014-03-07 2015-09-17 삼성디스플레이 주식회사 Compound and organic light emitting device comprising same
JP6537877B2 (en) * 2014-05-02 2019-07-03 株式会社半導体エネルギー研究所 Organometallic complex, light emitting element, light emitting device, electronic device and lighting device
KR102457008B1 (en) 2014-05-23 2022-10-19 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
KR102308117B1 (en) * 2014-10-17 2021-10-01 삼성전자주식회사 Carbazole-based compound and organic light emitting device including the same
JP2019521995A (en) 2016-06-22 2019-08-08 出光興産株式会社 Benzofuro- or benzothienoquinoline substituted at specific positions for organic light-emitting diodes
KR102027961B1 (en) 2016-06-29 2019-10-02 삼성에스디아이 주식회사 Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
KR102054276B1 (en) 2016-06-29 2019-12-10 삼성에스디아이 주식회사 Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
KR102050000B1 (en) 2016-07-12 2019-11-28 삼성에스디아이 주식회사 Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
JP2016185984A (en) * 2016-07-19 2016-10-27 株式会社半導体エネルギー研究所 Method for synthesizing material for light-emitting element
CN106467458B (en) * 2016-07-27 2019-05-24 江苏三月光电科技有限公司 A kind of compound based on diaryl ketone and its application on organic electroluminescence device
KR102054277B1 (en) 2016-07-29 2019-12-10 삼성에스디아이 주식회사 Composition for organic optoelectronic device and organic optoelectronic device and display device
US11279709B2 (en) * 2016-09-05 2022-03-22 Idemitsu Kosan Co., Ltd. Specifically substituted aza-dibenzofurans and aza-dibenzothiophenes for organic electronic devices
KR20180038834A (en) 2016-10-07 2018-04-17 삼성에스디아이 주식회사 Composition for organic optoelectronic device and organic optoelectronic device and display device
KR101970000B1 (en) 2016-10-12 2019-04-17 삼성에스디아이 주식회사 Compound for organic optoelectronic device and organic optoelectronic device and display device
CN110139913B (en) * 2016-11-04 2023-07-28 三星显示有限公司 Electroluminescent device comprising host compound
US11158817B2 (en) 2017-01-05 2021-10-26 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
CN107412852A (en) * 2017-07-26 2017-12-01 山东冠龙医疗用品有限公司 Bone cement compositions and its set group
KR102146792B1 (en) 2017-08-01 2020-08-21 삼성에스디아이 주식회사 Compound for organic optoelectronic device, and organic optoelectronic device and display device
JP2018027977A (en) * 2017-10-30 2018-02-22 株式会社半導体エネルギー研究所 Method for producing material for light emitting element
EP3527557A1 (en) * 2018-02-16 2019-08-21 Novaled GmbH N-heteroarylene compounds
WO2021033724A1 (en) 2019-08-19 2021-02-25 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
WO2022149476A1 (en) 2021-01-08 2022-07-14 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic appliance

Citations (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3657281A (en) 1969-12-31 1972-04-18 Parke Davis & Co 4-aryl-1-dibenzofuran-alkanoic acids and salts thereof
US3673219A (en) 1970-06-23 1972-06-27 Gen Electric 4-phenyl 2-(2{40 -hydroxy-meta-terphenyl-5{40 -yl)-dibenzofuran and 4,4{40 -diphenyl-2,2{40 -bidibenzofuran
JPH03200889A (en) 1989-06-30 1991-09-02 Ricoh Co Ltd Electroluminescent element
JPH03200289A (en) 1989-12-28 1991-09-02 Casio Comput Co Ltd Automatic player
JPH05109485A (en) 1991-10-15 1993-04-30 Ricoh Co Ltd Electroluminescence element
JPH0753950A (en) 1993-08-10 1995-02-28 Toyo Ink Mfg Co Ltd Organic electroluminescence device material and organic electroluminescence device using the same
JPH07138561A (en) 1993-11-17 1995-05-30 Idemitsu Kosan Co Ltd Organic electroluminescent device
JPH08239655A (en) 1995-03-06 1996-09-17 Idemitsu Kosan Co Ltd Organic electroluminescent device
US6097147A (en) 1998-09-14 2000-08-01 The Trustees Of Princeton University Structure for high efficiency electroluminescent device
JP2001043979A (en) 2000-01-01 2001-02-16 Toyo Ink Mfg Co Ltd Hole transport materials for organic electroluminescence devices
US6229012B1 (en) 1998-10-01 2001-05-08 Xerox Corporation Triazine compositions
WO2001041512A1 (en) 1999-12-01 2001-06-07 The Trustees Of Princeton University Complexes of form l2mx as phosphorescent dopants for organic leds
JP2001196182A (en) 2000-01-14 2001-07-19 Toray Ind Inc Luminous element
US20030068535A1 (en) 2001-03-08 2003-04-10 Takao Takiguchi Metal coordination compound, luminescence device and display apparatus
JP2004002351A (en) 2002-03-27 2004-01-08 Tdk Corp Organic el device
WO2004009645A2 (en) 2002-07-19 2004-01-29 CID Centro de Investigación y Desarrollo Tecnológico, S.A. de C.V. Block copolymers containing functional groups
CN1474639A (en) 2002-06-20 2004-02-11 ����Sdi��ʽ���� Organic electroluminescent device using phosphorescent material as luminescent substance
WO2004013080A1 (en) 2002-08-01 2004-02-12 Covion Organic Semiconductors Gmbh Spirobifluorene derivatives, their preparation and uses thereof
US20040076853A1 (en) 2002-04-24 2004-04-22 Eastman Kodak Company Organic light-emitting diode devices with improved operational stability
US20040086745A1 (en) 2002-03-22 2004-05-06 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence devices and organic electroluminescence device using the material
US20040115476A1 (en) 2002-11-26 2004-06-17 Tomohiro Oshiyama Organic electroluminescent element, and display and illuminator
JP2004214050A (en) 2003-01-06 2004-07-29 Konica Minolta Holdings Inc Organic electroluminescent element and display device
CN1535483A (en) 2001-03-14 2004-10-06 ����˹�ٴ�ѧ���»� Materials and Devices for Blue Phosphorescent-Based Organic Light-Emitting Diodes
CN1541035A (en) 2003-03-27 2004-10-27 ������������ʽ���� Organic electroluminesscence element
JP2004311404A (en) 2003-03-26 2004-11-04 Konica Minolta Holdings Inc Organic electroluminescent element, illumination device and display device
JP2004311405A (en) 2003-03-27 2004-11-04 Konica Minolta Holdings Inc Organic electroluminescent element, display device, and lighting system
WO2004096945A1 (en) 2003-05-01 2004-11-11 Fujitsu Limited 1,3,6,8-tetrasubstituted pyrene compounds, organic el device and organic el display
CN1578557A (en) 2003-06-26 2005-02-09 三星Sdi株式会社 Organometallic complex and organic electroluminescent device employing the same
JP2005047868A (en) 2003-07-30 2005-02-24 Mitsui Chemicals Inc Anthracene compound and organic electroluminescent element containing the anthracene compound
CN1589307A (en) 2001-10-17 2005-03-02 通用显示公司 Phosphorescent compounds and devices comprising the same
CN1599527A (en) 2003-09-15 2005-03-23 三星Sdi株式会社 Full color organic electroluminescent device and method for fabricating the same
JP2005082702A (en) 2003-09-09 2005-03-31 Toyo Ink Mfg Co Ltd Organic electroluminescent device material and organic electroluminescent device using the same
WO2005047868A1 (en) 2003-11-14 2005-05-26 Hamamatsu Photonics K.K. Fluorescence measuring device
JP2005154396A (en) 2003-10-30 2005-06-16 Mitsubishi Chemicals Corp Organometallic complex and organic electroluminescence device using the same
WO2005054212A2 (en) 2003-12-05 2005-06-16 Ciba Specialty Chemicals Holding Inc. Electroluminescent device
TW200534745A (en) 2004-03-02 2005-10-16 Idemitsu Kosan Co Organic electroluminescent device
WO2005101912A1 (en) 2004-04-14 2005-10-27 Konica Minolta Holdings, Inc. Organic electroluminescence device, display unit and lighting apparatus
CN1692680A (en) 2002-09-20 2005-11-02 出光兴产株式会社 organic electroluminescent element
JP2005314239A (en) 2004-04-27 2005-11-10 Mitsui Chemicals Inc Anthracene compound and organic electroluminescent element containing the anthracene compound
US20050260441A1 (en) 2004-05-18 2005-11-24 Thompson Mark E Luminescent compounds with carbene ligands
WO2005113531A1 (en) 2004-05-21 2005-12-01 Toray Industries, Inc. Light-emitting device material and light-emitting device
US20060134538A1 (en) 2004-12-16 2006-06-22 Radu Nora S Aromatic chalcogen compounds and their use
US20060141284A1 (en) 2002-10-21 2006-06-29 Seiji Tomita Material for organic electroluminescence element, and organic electroluminescence element using the same
US20060180806A1 (en) 2003-01-24 2006-08-17 Takashi Arakane Organic electroluminescence device
US7128982B2 (en) 2002-04-12 2006-10-31 Konica Corporation Organic electroluminescence element
US20060257684A1 (en) 2002-10-09 2006-11-16 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2006128800A1 (en) 2005-05-30 2006-12-07 Ciba Specialty Chemicals Holding Inc. Electroluminescent device
US20070052346A1 (en) 2005-09-08 2007-03-08 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2007029798A1 (en) 2005-09-08 2007-03-15 Toray Industries, Inc. Light-emitting device material and light-emitting device
US20070069638A1 (en) 2005-09-05 2007-03-29 Idemitsu Kosan Co., Ltd. Blue organic electroluminescent device
US20070093548A1 (en) * 2005-10-25 2007-04-26 Wyeth Use of progesterone receptor modulators
US20070090753A1 (en) 2004-03-25 2007-04-26 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
JP2007126403A (en) 2005-11-04 2007-05-24 Sanyo Electric Co Ltd Dibenzothiophene derivative and organic electroluminescent device using the same
US20070141387A1 (en) * 2005-12-15 2007-06-21 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and electroluminescence device employing the same
US20070159083A1 (en) 2004-02-13 2007-07-12 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US20070188083A1 (en) 2004-04-02 2007-08-16 Idemitsu Kosan Co., Ltd. Organic electroluminescence element having two electroluminescent layers through electron barrier layer
US20070190355A1 (en) 2004-03-08 2007-08-16 Idemitsu Kosan Co., Ltd Material for organic electroluminescence device and organic electroluminescence device utilizing the same
US20070194701A1 (en) 2004-03-19 2007-08-23 Idemitsu Kosan Co., Ltd., Organic electroluminescent device
US20070224446A1 (en) 2006-03-24 2007-09-27 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US20070224448A1 (en) 2004-05-14 2007-09-27 Idemitsu Kosan Co., Ltd. Organic Electroluminescent Device
US20070257600A1 (en) 2004-02-09 2007-11-08 Idemitsu Kosan Co., Ltd. Organic Electroluminescent Device
US20070296328A1 (en) 2004-02-06 2007-12-27 Idemitsu Kosan Co., Ltd. Organic Electroluminescent Device
EP1894923A1 (en) 2005-06-24 2008-03-05 Idemitsu Kosan Co., Ltd. Benzothiophene derivative and organic electroluminescence device making use of the same
US7345301B2 (en) 2003-04-15 2008-03-18 Merck Patent Gmbh Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures
CN101171239A (en) 2005-04-28 2008-04-30 西巴特殊化学品控股有限公司 Electroluminescent device
US20080206597A1 (en) 2005-09-09 2008-08-28 Idemitsu Kosan Co., Ltd. Azaaromatic compounds having azafluoranthene skeletons and organic electroluminescent devices made by using the same
US20090066223A1 (en) 2005-02-21 2009-03-12 Mitsubishi Chemical Corporation Organic electric field light emitting element and production therefor
US20090134779A1 (en) 2005-05-24 2009-05-28 Shin Kawami Organic electroluminescence element
US20090224658A1 (en) 2006-06-02 2009-09-10 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence element, and organic electroluminescence element using the material

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3200889B2 (en) 1991-10-23 2001-08-20 ソニー株式会社 Image vibration correction device

Patent Citations (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3657281A (en) 1969-12-31 1972-04-18 Parke Davis & Co 4-aryl-1-dibenzofuran-alkanoic acids and salts thereof
US3673219A (en) 1970-06-23 1972-06-27 Gen Electric 4-phenyl 2-(2{40 -hydroxy-meta-terphenyl-5{40 -yl)-dibenzofuran and 4,4{40 -diphenyl-2,2{40 -bidibenzofuran
JPH03200889A (en) 1989-06-30 1991-09-02 Ricoh Co Ltd Electroluminescent element
JPH03200289A (en) 1989-12-28 1991-09-02 Casio Comput Co Ltd Automatic player
JPH05109485A (en) 1991-10-15 1993-04-30 Ricoh Co Ltd Electroluminescence element
JPH0753950A (en) 1993-08-10 1995-02-28 Toyo Ink Mfg Co Ltd Organic electroluminescence device material and organic electroluminescence device using the same
JPH07138561A (en) 1993-11-17 1995-05-30 Idemitsu Kosan Co Ltd Organic electroluminescent device
JPH08239655A (en) 1995-03-06 1996-09-17 Idemitsu Kosan Co Ltd Organic electroluminescent device
US6097147A (en) 1998-09-14 2000-08-01 The Trustees Of Princeton University Structure for high efficiency electroluminescent device
US6229012B1 (en) 1998-10-01 2001-05-08 Xerox Corporation Triazine compositions
WO2001041512A1 (en) 1999-12-01 2001-06-07 The Trustees Of Princeton University Complexes of form l2mx as phosphorescent dopants for organic leds
CN1413426A (en) 1999-12-01 2003-04-23 普林斯顿大学理事会 Complexes in the form of phosphorescent dopants L2MX as organic light-emitting devices
JP2001043979A (en) 2000-01-01 2001-02-16 Toyo Ink Mfg Co Ltd Hole transport materials for organic electroluminescence devices
JP2001196182A (en) 2000-01-14 2001-07-19 Toray Ind Inc Luminous element
US20030068535A1 (en) 2001-03-08 2003-04-10 Takao Takiguchi Metal coordination compound, luminescence device and display apparatus
CN1535483A (en) 2001-03-14 2004-10-06 ����˹�ٴ�ѧ���»� Materials and Devices for Blue Phosphorescent-Based Organic Light-Emitting Diodes
CN1589307A (en) 2001-10-17 2005-03-02 通用显示公司 Phosphorescent compounds and devices comprising the same
US20040086745A1 (en) 2002-03-22 2004-05-06 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence devices and organic electroluminescence device using the material
JP2004002351A (en) 2002-03-27 2004-01-08 Tdk Corp Organic el device
US7128982B2 (en) 2002-04-12 2006-10-31 Konica Corporation Organic electroluminescence element
US20040076853A1 (en) 2002-04-24 2004-04-22 Eastman Kodak Company Organic light-emitting diode devices with improved operational stability
CN1474639A (en) 2002-06-20 2004-02-11 ����Sdi��ʽ���� Organic electroluminescent device using phosphorescent material as luminescent substance
WO2004009645A2 (en) 2002-07-19 2004-01-29 CID Centro de Investigación y Desarrollo Tecnológico, S.A. de C.V. Block copolymers containing functional groups
WO2004013080A1 (en) 2002-08-01 2004-02-12 Covion Organic Semiconductors Gmbh Spirobifluorene derivatives, their preparation and uses thereof
CN1692680A (en) 2002-09-20 2005-11-02 出光兴产株式会社 organic electroluminescent element
US20060257684A1 (en) 2002-10-09 2006-11-16 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US20060141284A1 (en) 2002-10-21 2006-06-29 Seiji Tomita Material for organic electroluminescence element, and organic electroluminescence element using the same
US20040115476A1 (en) 2002-11-26 2004-06-17 Tomohiro Oshiyama Organic electroluminescent element, and display and illuminator
JP2004214050A (en) 2003-01-06 2004-07-29 Konica Minolta Holdings Inc Organic electroluminescent element and display device
US20060180806A1 (en) 2003-01-24 2006-08-17 Takashi Arakane Organic electroluminescence device
JP2004311404A (en) 2003-03-26 2004-11-04 Konica Minolta Holdings Inc Organic electroluminescent element, illumination device and display device
CN1541035A (en) 2003-03-27 2004-10-27 ������������ʽ���� Organic electroluminesscence element
JP2004311405A (en) 2003-03-27 2004-11-04 Konica Minolta Holdings Inc Organic electroluminescent element, display device, and lighting system
US7345301B2 (en) 2003-04-15 2008-03-18 Merck Patent Gmbh Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures
US20050238920A1 (en) 2003-05-01 2005-10-27 Fujitsu Limited 1,3,6,8-Tetrasubstituted pyrene compound, organic electroluminescent element, and organic electroluminescent display
WO2004096945A1 (en) 2003-05-01 2004-11-11 Fujitsu Limited 1,3,6,8-tetrasubstituted pyrene compounds, organic el device and organic el display
CN1578557A (en) 2003-06-26 2005-02-09 三星Sdi株式会社 Organometallic complex and organic electroluminescent device employing the same
JP2005047868A (en) 2003-07-30 2005-02-24 Mitsui Chemicals Inc Anthracene compound and organic electroluminescent element containing the anthracene compound
JP2005082702A (en) 2003-09-09 2005-03-31 Toyo Ink Mfg Co Ltd Organic electroluminescent device material and organic electroluminescent device using the same
CN1599527A (en) 2003-09-15 2005-03-23 三星Sdi株式会社 Full color organic electroluminescent device and method for fabricating the same
JP2005154396A (en) 2003-10-30 2005-06-16 Mitsubishi Chemicals Corp Organometallic complex and organic electroluminescence device using the same
WO2005047868A1 (en) 2003-11-14 2005-05-26 Hamamatsu Photonics K.K. Fluorescence measuring device
WO2005054212A3 (en) 2003-12-05 2005-11-03 Ciba Sc Holding Ag Electroluminescent device
WO2005054212A2 (en) 2003-12-05 2005-06-16 Ciba Specialty Chemicals Holding Inc. Electroluminescent device
US20070296328A1 (en) 2004-02-06 2007-12-27 Idemitsu Kosan Co., Ltd. Organic Electroluminescent Device
US20070257600A1 (en) 2004-02-09 2007-11-08 Idemitsu Kosan Co., Ltd. Organic Electroluminescent Device
US20070159083A1 (en) 2004-02-13 2007-07-12 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
TW200534745A (en) 2004-03-02 2005-10-16 Idemitsu Kosan Co Organic electroluminescent device
US20070172698A1 (en) 2004-03-02 2007-07-26 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US20070190355A1 (en) 2004-03-08 2007-08-16 Idemitsu Kosan Co., Ltd Material for organic electroluminescence device and organic electroluminescence device utilizing the same
US20070194701A1 (en) 2004-03-19 2007-08-23 Idemitsu Kosan Co., Ltd., Organic electroluminescent device
US20070090753A1 (en) 2004-03-25 2007-04-26 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US20070188083A1 (en) 2004-04-02 2007-08-16 Idemitsu Kosan Co., Ltd. Organic electroluminescence element having two electroluminescent layers through electron barrier layer
WO2005101912A1 (en) 2004-04-14 2005-10-27 Konica Minolta Holdings, Inc. Organic electroluminescence device, display unit and lighting apparatus
JP2005314239A (en) 2004-04-27 2005-11-10 Mitsui Chemicals Inc Anthracene compound and organic electroluminescent element containing the anthracene compound
US20070224448A1 (en) 2004-05-14 2007-09-27 Idemitsu Kosan Co., Ltd. Organic Electroluminescent Device
US20050260441A1 (en) 2004-05-18 2005-11-24 Thompson Mark E Luminescent compounds with carbene ligands
WO2005113531A1 (en) 2004-05-21 2005-12-01 Toray Industries, Inc. Light-emitting device material and light-emitting device
US20060134538A1 (en) 2004-12-16 2006-06-22 Radu Nora S Aromatic chalcogen compounds and their use
US20090066223A1 (en) 2005-02-21 2009-03-12 Mitsubishi Chemical Corporation Organic electric field light emitting element and production therefor
CN101171239A (en) 2005-04-28 2008-04-30 西巴特殊化学品控股有限公司 Electroluminescent device
JP2008539192A (en) 2005-04-28 2008-11-13 チバ ホールディング インコーポレーテッド Electroluminescent device
US20090134779A1 (en) 2005-05-24 2009-05-28 Shin Kawami Organic electroluminescence element
CN101184822A (en) 2005-05-30 2008-05-21 西巴特殊化学品控股有限公司 Electroluminescent device
TW200712171A (en) 2005-05-30 2007-04-01 Ciba Sc Holding Ag Electroluminescent device
JP2008545729A (en) 2005-05-30 2008-12-18 チバ ホールディング インコーポレーテッド Electroluminescent device
WO2006128800A1 (en) 2005-05-30 2006-12-07 Ciba Specialty Chemicals Holding Inc. Electroluminescent device
EP1885818A1 (en) 2005-05-30 2008-02-13 Ciba Specialty Chemicals Holding Inc. Electroluminescent device
EP1894923A1 (en) 2005-06-24 2008-03-05 Idemitsu Kosan Co., Ltd. Benzothiophene derivative and organic electroluminescence device making use of the same
US20070069638A1 (en) 2005-09-05 2007-03-29 Idemitsu Kosan Co., Ltd. Blue organic electroluminescent device
CN101258221A (en) 2005-09-08 2008-09-03 东丽株式会社 Light-emitting element material and light-emitting element
WO2007029798A1 (en) 2005-09-08 2007-03-15 Toray Industries, Inc. Light-emitting device material and light-emitting device
US20070052346A1 (en) 2005-09-08 2007-03-08 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US20080206597A1 (en) 2005-09-09 2008-08-28 Idemitsu Kosan Co., Ltd. Azaaromatic compounds having azafluoranthene skeletons and organic electroluminescent devices made by using the same
US20070093548A1 (en) * 2005-10-25 2007-04-26 Wyeth Use of progesterone receptor modulators
JP2007126403A (en) 2005-11-04 2007-05-24 Sanyo Electric Co Ltd Dibenzothiophene derivative and organic electroluminescent device using the same
US20070141387A1 (en) * 2005-12-15 2007-06-21 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and electroluminescence device employing the same
US20070224446A1 (en) 2006-03-24 2007-09-27 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US20090224658A1 (en) 2006-06-02 2009-09-10 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence element, and organic electroluminescence element using the material

Non-Patent Citations (14)

* Cited by examiner, † Cited by third party
Title
B. Carlson, et al., "Tuned Emission From Organic Light Emitting Devices Based Upon Divalent Osmium Complexes", Organic light-Emitting Materials and Devices VII., vol. 5214, pp. 328-336, 2004.
C.W. Tang, et al., "Organice Electroluminescent Diodes", Appl. Phys. Lett., vol. 51, No. 12, Sep. 21, 1987, pp. 913-915.
Extended European Search Report dated Jan. 22, 2010, in Patent Application No. 06834437.3.
F.D. O'Brien, et al., "Improved Energy Transfer in Electrophosphorescent Devices", Appl. Phys. Lett., vol. 74, No. 3, Jan. 18, 1999, pp. 442-444.
International Search Report dated Feb. 20, 2007, in Patent Application No. PCT/JP2006/324682.
Invalidation Procedure dated Dec. 20, 2018, in Chinese Patent Application No. 200680047266.5.
M.A. Baldo, et al., "Very High-Efficiency Green Organic Light-Emitting Devices Based on Electrophosphorescence", Appl. Phys. Lett., vol. 75, No. 1, Jul. 5, 1999, pp. 4-7.
Machine Translation of JP 2004-311404.
Office Action dated Apr. 29, 2013, in Taiwanese Patent Application No. 95146379.
Office Action dated Dec. 20, 2011, in Japanese Patent Application No. 2007-550166 w/English Translation.
Office Action dated Jan. 31, 2013, in Patent Application No. 06834437.3.
Office Action dated May 27, 2013, in Korean Patent Application No. 2008-7014171 w/English Translation.
Office Action dated Sep. 11, 2009, in Patent Application No. 200680047266.5.
Office Action dated Sep. 11, 2012, in Japanese Patent Application No. 2007-550166 w/English Translation.

Also Published As

Publication number Publication date
US7846560B2 (en) 2010-12-07
US20070141387A1 (en) 2007-06-21
US20100084971A1 (en) 2010-04-08
US7651791B2 (en) 2010-01-26

Similar Documents

Publication Publication Date Title
USRE49118E1 (en) Material for organic electroluminescence device and electroluminescence device employing the same
US11895917B2 (en) Material for organic electroluminescence device and organic electroluminescence device using the same
US8563145B2 (en) Material containing two or three dibenzofuran groups, dibenzothiophene groups, or a combination thereof, which is operable for organic electroluminescence elements, and organic electroluminescence elements using the material
JP5290581B2 (en) Material for organic electroluminescence device and organic electroluminescence device using the same
US7939183B2 (en) Material for organic electroluminescent device and organic electroluminescent device using same
US8057919B2 (en) Material for organic electroluminescence device and organic electroluminescence device using the same
JP4490923B2 (en) Material for organic electroluminescence device and organic electroluminescence device using the same
US8895966B2 (en) Material for organic electroluminescence element, and organic electroluminescence element using same
US20060035109A1 (en) Organic electroluminescent element
US7501521B2 (en) Metal-complex compound and organic electroluminescence device using the compound
US7462719B2 (en) Metal-complex compound and organic electroluminescence device using the compound
JPWO2007086505A1 (en) Transition metal complex compound and organic electroluminescence device using the same
JP2008266163A (en) Transition metal complex compound and organic electroluminescence device using the same
US7781960B2 (en) Metal complex compound and organic electroluminescent element using the same
US7446197B2 (en) Metal-complex compound and organic electroluminescence device using the compound
JP2006131561A (en) Metal complex compound

Legal Events

Date Code Title Description
FEPP Fee payment procedure

Free format text: ENTITY STATUS SET TO UNDISCOUNTED (ORIGINAL EVENT CODE: BIG.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY