WO2014073306A1 - Élément électroluminescent organique et dispositif électronique - Google Patents

Élément électroluminescent organique et dispositif électronique Download PDF

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WO2014073306A1
WO2014073306A1 PCT/JP2013/077224 JP2013077224W WO2014073306A1 WO 2014073306 A1 WO2014073306 A1 WO 2014073306A1 JP 2013077224 W JP2013077224 W JP 2013077224W WO 2014073306 A1 WO2014073306 A1 WO 2014073306A1
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carbon atoms
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池田　剛
裕勝 伊藤
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出光興産株式会社
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    • 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
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • 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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to an organic electroluminescence element and an electronic device.
  • organic electroluminescence devices using organic substances are promising for use as solid light-emitting, inexpensive, large-area full-color display devices, and many developments have been made. ing.
  • an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
  • organic EL elements have a higher driving voltage and lower luminance and luminous efficiency than inorganic light emitting diodes. Further, the characteristic deterioration has been remarkably not put into practical use. Although recent organic EL devices have been gradually improved, further higher light emission efficiency, longer life, improved color reproducibility, and the like are required.
  • Patent Document 1 describes an organic EL element including a light-emitting layer containing an aryl-substituted anthracene derivative as a host material and a fluoranthene derivative as a dopant material. Patent Document 1 describes that an organic EL element including the light emitting layer has a long lifetime, high light emission efficiency, and blue light emission.
  • the efficiency of the organic EL element described in Patent Document 1 is not sufficient, and further improvement in efficiency is required when the organic EL element is used as a light source of an electronic device such as a lighting device or a display device.
  • an object of the present invention is to provide an organic electroluminescence element that emits light with high efficiency and an electronic device equipped with the organic electroluminescence element.
  • An organic electroluminescence device includes an anode, a cathode provided to face the anode, a compound provided between the cathode and the anode, and represented by the following general formula (1) And a hole transport layer that is provided between the light emitting layer and the anode and contains a compound represented by the following general formula (21).
  • a, b and c each represents an integer of 1 to 4; Any one of R 101 to R 110 is a single bond and is used for bonding to L 1 ; R 101 to R 110 not used for bonding to L 1 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon number of 1 to 20 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring carbon atoms, and substituted or unsubstituted arylthio groups having 6 to 20 ring carbon atoms.
  • L 1 is selected from either a single bond or a linking group, and when L 1 is a linking group, L 1 is a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 50 ring carbon atoms ( a + 1) a residue formed by removing (a + 1) hydrogen atoms, a (a + 1) valence formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 50 ring atoms Or (a + 1) valences obtained by removing (a + 1) hydrogen atoms from the structure formed by bonding 2 to 4 of at least one of the above-mentioned aromatic hydrocarbon ring structure and the heterocyclic structure Residue.
  • L 1 is a linking group
  • R 101 ⁇ R 110 which is not used in binding to L 1 may also form a substituent and the ring L 1 or L 1.
  • L 1 may be the same or different.
  • Z 1 represents a structure represented by the following general formula (2).
  • a or c is an integer of 2 to 4
  • Z 1 may be the same or different.
  • R 111 ⁇ R 120 are used for binding to L 1 represents a single bond
  • R 111 ⁇ R 118 which is not used in binding to L 1 are each independently a bond between L 1 It is synonymous with R 101 to R 110 that are not used in the above.
  • R 119 to R 120 which are not used for bonding to L 1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trialkyl having 1 to 30 carbon atoms.
  • a silyl group, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 to 50 are selected from the group consisting of Further, at least one pair of adjacent two of the combinations of R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 115 and R 116 , R 116 and R 117 , and R 117 and R 118 Two substituents may form a ring structure represented by the following general formula (3). Also, R 111 ⁇ R 120 which is not used in binding to L 1 may also form a substituent and the ring L 1 or L 1. ]
  • y 1 and y 2 represent bonding positions with adjacent groups in R 111 to R 118 of the general formula (2).
  • R 121 to R 124 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group.
  • L 201 to L 203 are each independently selected from a single bond or a linking group, and the linking group includes two from a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 50 ring carbon atoms.
  • a divalent residue formed by removing a hydrogen atom a divalent residue formed by removing two hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 50 ring atoms, or the aromatic carbonization This is a divalent residue formed by removing two hydrogen atoms from a structure formed by bonding 2 to 4 hydrogen ring structures and / or at least one of the above heterocyclic structures.
  • Ar 201 to Ar 203 each independently represents a group represented by the following general formula (21a), a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring formation It is selected from heterocyclic groups having 5 to 50 atoms. However, at least one of Ar 201 to Ar 203 is a group represented by the following general formula (21a). ]
  • R 201 to R 208 are each independently a hydrogen atom, a substituted or unsubstituted aromatic heterocyclic group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. It is.
  • X is an oxygen atom, a sulfur atom, NR 209 or CR 210 R 211 .
  • R 209 to R 211 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 ring carbon atoms.
  • any one of R 201 to R 211 is a single bond used for bonding to any of L 201 to L 203 in the general formula (21). ]
  • An electronic apparatus includes the above-described organic electroluminescence element.
  • an organic electroluminescence element that emits light with high efficiency
  • an electronic device including the organic electroluminescence element
  • the organic EL device of the present invention includes an organic layer between a pair of electrodes. This organic layer has at least two layers composed of an organic compound.
  • the organic layer may contain an inorganic compound.
  • at least one of the organic layers is a light emitting layer, and at least one layer is a hole transport layer. Therefore, the organic layer may be composed of, for example, one light emitting layer and one hole transport layer, and further includes a hole injection layer, an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier. You may have the layer employ
  • Examples of the structure include anode / hole injection / transport layer / light emitting layer / barrier layer / electron injection / transport layer / cathode.
  • the configuration (c) is preferably used, but of course is not limited thereto.
  • the “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
  • hole injection / transport layer means “hole transport layer” or “hole injection layer and hole transport layer”, and “electron injection / transport layer” means “of electron injection layer and electron transport layer”. Means at least one of the following.
  • the positive hole injection layer is provided in the anode side.
  • the electron injection layer is provided in the cathode side.
  • the electron transport layer refers to an organic layer having the highest electron mobility among the organic layers in the electron transport region existing between the light emitting layer and the cathode.
  • the layer is an electron transport layer.
  • a barrier layer that does not necessarily have high electron mobility is used to prevent diffusion of excitation energy generated in the light emitting layer.
  • the organic layer adjacent to the light emitting layer does not necessarily correspond to the electron transport layer.
  • the organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 has a light emitting layer 5 containing a host material and a dopant material.
  • the organic layer 10 has a hole transport layer 6 between the light emitting layer 5 and the anode 3. Further, the organic layer 10 has an electron transport layer 7 between the light emitting layer 5 and the cathode 4.
  • a, b and c each represent an integer of 1 to 4. Any c number of R 101 ⁇ R 110 are used for binding to L 1 a single bond, R 101 ⁇ R 110 which is not used in binding to L 1 are each independently a hydrogen atom, a halogen atom , Hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and substituted or unsubstituted selected from the group consisting of heterocyclic group ring atoms 5 ⁇ 50, L 1 is selected
  • L 1 is a linking group
  • R 101 ⁇ R 110 which is not used in binding to L 1 may also form a substituent and the ring L 1 or L 1.
  • L 1 may be the same or different.
  • Z 1 represents a structure represented by the following general formula (2). When a or c is an integer of 2 to 4, Z 1 may be the same or different. ]
  • R 111 ⁇ R 120 are used for binding to L 1 represents a single bond
  • R 111 ⁇ R 118 which is not used in binding to L 1 is,
  • Each independently has the same meaning as R 101 to R 110 that are not used for bonding to L 1 .
  • R 119 to R 120 which are not used for bonding to L 1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trialkyl having 1 to 30 carbon atoms.
  • a silyl group, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 to 50 are selected from the group consisting of Further, at least one pair of adjacent two of the combinations of R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 115 and R 116 , R 116 and R 117 , and R 117 and R 118 Two substituents may form a ring structure represented by the following general formula (3). Also, R 111 ⁇ R 120 which is not used in binding to L 1 may also form a substituent and the ring L 1 or L 1. ]
  • y 1 and y 2 represent bonding positions with adjacent groups in R 111 to R 118 of the general formula (2).
  • R 121 to R 124 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group.
  • L 1 bonded to Z 1 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group-substituted or unsubstituted naphthylene group, and a substituted or unsubstituted group. It is preferably selected from the group consisting of fluorenylene groups. Among these, L 1 bonded to Z 1 is more preferably a single bond or a substituted or unsubstituted phenylene group.
  • L 1 bonded to Z 1 is selected from a single bond or a linking group, and when L 1 is a linking group, L 1 is represented by the following formula (111) to It is preferably selected from the group consisting of groups represented by (117).
  • L 1 in the general formula (1) is selected from either a single bond or a linking group, and when L 1 is a linking group, L 1 is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. It is preferably an (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from the group hydrocarbon ring structure. Further, L 1 is more preferably an (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from an unsubstituted aromatic hydrocarbon ring structure having 6 to 12 ring carbon atoms.
  • R 102 , R 103 , R 106 , R 107 , R 109 and R 110 is a single bond used for bonding to L 1.
  • R 109 and R 110 is a single bond used for bonding to L 1 .
  • R 109 is preferably a single bond used for bonding to L 1, and the general formula (1) is represented by the following general formula (1a). Is preferred.
  • R 110 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. And a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms is more preferable.
  • R 101 to R 108 are hydrogen atoms
  • R 109 is a single bond used for bonding to L 1
  • R 110 is a substituted or unsubstituted ring-forming carbon number of 6 to It is preferably a group selected from 50 aromatic hydrocarbon groups, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and particularly preferably represented by the following general formula (1b): .
  • L 1 and Z 1 have the same meanings as L 1, and Z 1 in the general formula (1).
  • R 110 is preferably represented by the following general formula (11). Therefore, it is preferable that the (1b) is represented by the following general formula (1c).
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. Indicates the group to be selected.
  • Each Ra has the same meaning as R 101 to R 110 that are not used for bonding with L 1 in the general formula (1).
  • d represents an integer of 1 to 4. When d is 2 to 4, a plurality of Ra are the same or different.
  • L 1 and Z 1 have the same meanings as L 1, and Z 1 in the general formula (1). Further, in the general formula (1c), Ar 1, Ra, and d have the same meanings as Ar 1, Ra, and d in the general formula (11). ]
  • R 110 is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
  • the aromatic hydrocarbon group having 6 to 50 ring carbon atoms includes a phenyl group and a condensed aromatic hydrocarbon group having 10 to 50 ring carbon atoms. That is, in the general formula (1), R 110 is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 50 ring carbon atoms.
  • R 110 in the general formula (1) is preferably selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted fluorenyl group.
  • R 110 is preferably selected from the group consisting of groups represented by the following formulas (121) to (134).
  • R 112 to R 114 and R 115 to R 117 in the general formula (2) is preferably a single bond used for bonding to L 1, and among these, R 112 or R 117 is preferably selected from L 1 . It is more preferably a single bond used for bonding.
  • Z 1 is preferably selected from the group consisting of groups represented by the following formulas (141) to (146).
  • At least one of L 1 is a linking group
  • R 101 ⁇ R 110 which is not used in binding to L 1 forms a substituent and the ring of L 1 or L 1 and are, or, R 111 ⁇ R 120 which is not used in binding to L 1 is preferably also form a substituent and the ring of L 1 or L 1.
  • R 101 ⁇ R 110 which is not used in binding to L 1 is, as a structure forming a substituent and the ring of L 1 or L 1, for example, consider the structure R 101 was formed L 1 and the ring It is done.
  • L 1 is represented by the following general formula (L-1)
  • the compound represented by the general formula (1) is a compound having the following general formula (101a) or (101b) as a partial structure. May be.
  • L 101 is selected from a single bond or a linking group, and the linking group is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
  • a divalent residue formed by removing two hydrogen atoms from the structure a divalent residue formed by removing two hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 50 ring atoms, or It is a divalent residue formed by removing two hydrogen atoms from a structure formed by bonding 2 to 3 of at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure.
  • R L 101 is a hydrogen atom or a substituent.
  • R 102 ⁇ R 108 and R 110 have the same meanings as R 102 ⁇ R 108 and R 110 in formula (1).
  • L 101 has the same meaning as L 101 in formula (L-1).
  • R L 101 ⁇ R L 103 has the same meaning as R L 101 in formula (L-1). ]
  • L 1 is formula (L-1) Can be considered the following partial structures (102a) to (102f).
  • R 131 to R 138 and R 141 to R 146 have the same meanings as R 111 to R 120 in the general formula (2). However, one of R 141 to R 146 is a single bond bonded to L 101 in the general formula (L-1). ]
  • the general formula (2) is any of the following general formulas (2a) to (2c): It is preferably represented.
  • Ar 161 to Ar 162 in the general formula (2a), Ar 171 to Ar 172 in the general formula (2b), and Ar 181 to Ar 182 in the general formula (2c) each independently represent the general formula (2)
  • R 171 ⁇ R 180 in the formula (2b) is used for binding to L 1 represents a single bond
  • R 171 ⁇ R 180 which is not used in binding to L 1 are each independently Are the same as R 101 to R 110 that are not used for bonding to L 1
  • one of R 181 ⁇ R 190 in the formula (2c) is used for binding to L 1 represents a single bond
  • R 181 ⁇ R 190 which is not used in binding to L 1 are each independently Are the same as R 101 to R 110 that are not used for bonding to L 1 .
  • substituent described in the general formula (1) and the like include A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted amino group, A substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, A substituted or unsubstituted linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon
  • halogen atom in the general formula (1) examples include fluorine, chlorine, bromine, iodine and the like, and is preferably fluorine.
  • Examples of the substituted or unsubstituted amino group in the general formula (1) include an amino group substituted with each substituent, and an arylamino group substituted with an aromatic hydrocarbon group is preferable, and a phenyl group is substituted. More preferred is an amino group.
  • Examples of the aromatic hydrocarbon group substituted for the amino group include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the following aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms in the general formula (1) or the like may be linear, branched or cyclic, and examples of the linear or branched alkyl group include a 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, neopenty
  • cyclic alkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 4-methylcyclohexyl group, and 3,5-tetramethylcyclohexyl.
  • an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
  • a methyl group, an isopropyl group, a t-butyl group, and a cyclohexyl group are preferable.
  • linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms examples include those in which the alkyl group having 1 to 20 carbon atoms is substituted with one or more halogen atoms.
  • Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group.
  • the linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms in the general formula (1) or the like is represented by —OY 1 .
  • Y 1 include the alkyl group having 1 to 20 carbon atoms.
  • the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • an alkoxy group having 1 to 10 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms is more preferable.
  • Particularly preferred is an alkoxy group having 1 to 4 carbon atoms.
  • linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms in the general formula and the like include those in which the alkoxy group having 1 to 20 carbon atoms is substituted with one or more halogen groups. Can be mentioned.
  • the aryloxy group having 6 to 30 ring carbon atoms in the general formula (1) and the like is represented by —OZ 2 .
  • Examples of the Z 2 include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the following aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.
  • Examples of the aryloxy group include a phenoxy group.
  • the arylthio group having 6 to 30 ring carbon atoms in the above general formula and the like is represented by —SZ 3 .
  • Examples of the Z 3 include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the following aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.
  • Examples of the aromatic hydrocarbon group having 6 to 50 ring carbon atoms in the general formula (1) and the like include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group, and more specifically, a phenyl group. , Naphthyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, pyrenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzo [ c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] phenanthrenyl group, naphtho [1,2-a] triphenylenyl group, dibenzo [a, c] triphenylenyl group, benzo [b] fluoranthenyl Group, and the like.
  • aromatic hydrocarbon groups an aromatic hydrocarbon group having 6 to 30 ring carbon atoms is preferable, an aromatic hydrocarbon group having 6 to 20 ring carbon atoms is more preferable, and an aromatic hydrocarbon group having 6 to 12 ring carbon atoms is more preferable.
  • Aromatic hydrocarbon groups are particularly preferred.
  • heterocyclic group having 5 to 50 ring atoms in the general formula (1) examples include a non-condensed heterocyclic ring and a condensed heterocyclic ring, and more specifically, a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group.
  • heterocyclic groups a heterocyclic group having 5 to 30 ring atoms is preferable, a heterocyclic group having 5 to 20 ring atoms is more preferable, and a heterocyclic group having 5 to 12 ring atoms is particularly preferable. .
  • R 101 to R 110 that are not used for bonding with L 1 are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
  • R 109 is a condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms, more preferably, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 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, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group and 4-methyl-1-anthryl group.
  • L 1 is a linking group
  • a substituted or unsubstituted (a + 1) -valent aromatic hydrocarbon group having 6 to 50 ring carbon atoms a substituted or unsubstituted (a + 1) -valent Or a divalent group formed by combining 2 to 4 of these aromatic hydrocarbon groups or heterocyclic groups.
  • Specific examples of the (a + 1) -valent aromatic hydrocarbon group having 6 to 50 ring carbon atoms include those listed above as the aromatic hydrocarbon group having 6 to 50 ring carbon atoms. Based on this.
  • (a + 1) -valent heterocyclic group having 5 to 50 ring atoms include the above-mentioned heterocyclic groups having 5 to 50 ring-forming atoms as the (a + 1) -valent group.
  • L 1 is an (a + 1) -valent aromatic hydrocarbon group having 6 to 50 ring carbon atoms
  • more preferred aromatic hydrocarbon groups are phenyl, biphenyl, naphthyl, 9,9-dimethylfurane. The thing which made the oleenyl group into bivalent group is mentioned.
  • L 1 is an (a + 1) -valent heterocyclic group having 6 to 50 ring atoms
  • more preferable heterocyclic group is a pyridyl group, pyrimidyl group, dibenzofuranyl group, or carbazolyl group as a divalent group. Things.
  • R 111 to R 118 that are not used for bonding with L 1 in the general formula (2) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
  • R 119 to R 120 in the general formula (2) are preferably alkyl groups, more preferably methyl groups, and even more preferably R 119 and R 120 are both methyl groups.
  • R 121 to R 124 in the general formula (3) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
  • Ar 1 is particularly preferably a phenyl group, a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, or a biphenyl group.
  • Ra is particularly preferably a hydrogen atom, an aryl group, or a heterocyclic group.
  • ring-forming carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • Ring-forming atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).
  • examples of the substituent include the aromatic hydrocarbon group, the heterocyclic group, and the alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group) as described above.
  • Alkoxy group, aryloxy group, aralkyl group, haloalkoxy group, alkylsilyl group, dialkylarylsilyl group, alkyldiarylsilyl group, triarylsilyl group, halogen atom, cyano group, hydroxyl group, nitro group, and carboxy group Can be mentioned.
  • an alkenyl group and an alkynyl group are also included.
  • an aromatic hydrocarbon group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and more preferable in the description of each substituent.
  • the specific substituents are preferred.
  • the term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
  • the “carbon number ab” in the expression “substituted or unsubstituted XX group having carbon number ab” represents the number of carbons when the XX group is unsubstituted. The number of carbon atoms of the substituent when the XX group is substituted is not included.
  • the case of “substituted or unsubstituted” is the same as described above.
  • Z 1 , L 1 , R 110 , Ar 1 and Ra do not contain a hetero atom. It is preferable to consist only of hydrocarbons. Accordingly, among the substituents described in the general formula (1) and the like, a group that does not contain a heteroatom is preferable, and a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring formation. An aromatic hydrocarbon group having 6 to 50 carbon atoms is more preferable.
  • the skeleton of the substituent preferably does not include a hetero atom and consists only of a hydrocarbon group.
  • the compounds represented by the general formulas (1) and (1a) to (1c) are hydrocarbon compounds composed only of hydrocarbons.
  • a dopant material used for the organic EL element of this invention a fluoranthene derivative, a chrysene derivative, and a pyrene derivative can be used, for example.
  • a fluoranthene derivative a compound represented by the following general formula (31) can be used.
  • R 301 , R 302 , R 305 , R 306 and R 308 to R 311 are each independently a hydrogen atom, hydroxyl group, cyano group, nitro group, carboxyl group, substituted or Substituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted Substituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted An arylamino group having 6 to 30 ring carbon atoms, a substituted
  • R 303 is selected from the second group constituted by removing hydrogen atoms from the first group shown for R 301 , R 302 , R 305 , R 306 and R 308 to R 311. It is.
  • R 304 is constituted by removing an aromatic hydrocarbon group and a heterocyclic group from the first group shown for R 301 , R 302 , R 305 , R 306 and R 308 to R 311. Selected from the third group.
  • R 307 and R 312 are each independently a hydrogen atom or a hydroxyl group from the first group shown for R 301 , R 302 , R 305 , R 306 and R 308 to R 311.
  • R 301 and R 302 , R 302 and R 303 , R 305 and R 306 , R 306 and R 307 , R 307 and R 308 , R 308 and R 309 , R 309 and R 310 , R 310 and R 311 , and R 311 and R 312 may combine with each other to form a saturated or unsaturated ring, or may not form a saturated or unsaturated ring, Substituted or unsubstituted. ]
  • the second group is a group formed by removing a hydrogen atom from the first group, that is, the second group includes a hydroxyl group, a cyano group, a nitro group, and a silyl group.
  • the third group is a group constituted by removing the aromatic hydrocarbon group and the heterocyclic group from the first group, that is, the third group includes a hydrogen atom, a hydroxyl group. , Cyano group, nitro group, silyl group, carboxyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Or an unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted And an alkoxycarbonyl group having 2 to 50 carbon atoms and a substituted or unsubstituted aryla
  • the fourth group is a group configured by removing a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, and a silyl group from the first group, that is, the fourth group.
  • the group includes a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted group.
  • R 304 in the general formula (31) is preferably a hydrogen atom.
  • R 307 and R 312 in the general formula (31) are preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms. Further, R 307 and R 312 in the general formula (31) are preferably substituted or unsubstituted phenyl groups.
  • R 301 to R 302 , R 304 to R 306 and R 308 to R 311 in the general formula (31) are hydrogen atoms, and R 303 , R 307 and R 312 in the general formula (31) are substituted.
  • it is preferably an unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
  • R 301 to R 302 , R 304 to R 306 and R 308 to R 311 in the general formula (31) are hydrogen atoms, and R 307 and R 312 in the general formula (31) are substituted or unsubstituted ring formation.
  • An aromatic hydrocarbon group having 6 to 50 ring carbon atoms is preferable.
  • Ar 31 or Ar 32 is an aromatic hydrocarbon group having a cyano group as a substituent.
  • R 301 to R 302 , R 304 to R 306 and R 308 to R 311 in the general formula (31) are hydrogen atoms, and R 307 and R 312 in the general formula (31) are substituted or not.
  • a substituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, R 303 in the general formula (31) is —Ar 31 —Ar 32 —Ar 33 , and Ar 31 , Ar 32 and Ar 33 are Independently, it is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
  • Ar 31 , Ar 32 or Ar 33 is preferably an aromatic hydrocarbon group having a cyano group as a substituent.
  • the aralkyl group having 7 to 30 carbon atoms is represented by —R X —R Y.
  • R X include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms.
  • R Y include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the above aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.
  • the aromatic hydrocarbon group moiety has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
  • the alkyl group moiety has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 6 carbon atoms.
  • Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -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- ⁇ -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-bromine Benzyl group, m
  • silyl group examples include an unsubstituted silyl group, an alkylsilyl group having 1 to 30 carbon atoms, and an arylsilyl group having 6 to 60 carbon atoms.
  • alkylsilyl group having 1 to 30 carbon atoms examples include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, specifically, a trimethylsilyl group, a triethylsilyl group, a tri-n group.
  • arylsilyl group having 6 to 60 ring carbon atoms examples include arylsilyl group, alkylarylsilyl group, dialkylarylsilyl group, diarylsilyl group, alkyldiarylsilyl group, and triarylsilyl group.
  • a plurality of aryl groups or alkyl groups may be the same or different.
  • the dialkylarylsilyl group has, for example, two alkyl groups exemplified as the alkyl group having 1 to 20 carbon atoms, and among the aromatic hydrocarbon groups having 6 to 50 ring carbon atoms, the ring forming carbon number is 6 And a dialkylarylsilyl group having 1 to 30 aromatic hydrocarbon groups.
  • the carbon number of the dialkylarylsilyl group is preferably 8-30.
  • the two alkyl groups may be the same or different.
  • the alkyldiarylsilyl group has, for example, one alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, and among the aromatic hydrocarbon groups having 6 to 50 ring carbon atoms, the ring forming carbon number is 6 And alkyldiarylsilyl groups having 2 to 30 aromatic hydrocarbon groups.
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • the two aryl groups may be the same or different.
  • Examples of the triarylsilyl group include a triarylsilyl group having three aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the above aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.
  • the carbon number of the triarylsilyl group is preferably 18-30.
  • the three aryl groups may be the same or different from each other. Examples of such an arylsilyl group include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl-t-butylsilyl group, and a triphenylsilyl group.
  • the alkoxycarbonyl group is represented as —COOY ′, and examples of Y ′ include the same as the alkyl group.
  • the arylamino group is represented by —NAr 1 Ar 2, and specific examples of Ar 1 and Ar 2 include, independently of each other, an aromatic hydrocarbon group having 6 to 50 ring carbon atoms and 6 to 6 ring forming carbon atoms. This is the same as the group explained for the 30 aromatic hydrocarbon group.
  • One of Ar 1 and Ar 2 may be a hydrogen atom.
  • a chrysene derivative represented by the following general formula (41) can also be used.
  • R 400 to R 409 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring forming carbon number.
  • 6 to 50 aromatic hydrocarbon groups are shown.
  • Ar 401 to Ar 404 each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • Ar 401 to Ar 404 have an alkyl group as a substituent, each of them has at least two alkyl groups.
  • R 400 to R 409 are preferably hydrogen atoms.
  • each of Ar 401 to Ar 404 preferably has two or more substituents.
  • a 1 to A 4 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • Group substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted Alternatively, it is selected from the first group consisting of an unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • p, q, r and s are each independently an integer of 0 to 3, and when p, q, r and s are each 2 or more, A 1 to A 4 are the same or different.
  • a 5 to A 12 are each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or unsubstituted It is selected from a substituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • a 5 and A 6 , A 7 and A 8 , A 9 and A 10 , A 11 and A 12 may be connected to each other to form a saturated or unsaturated ring.
  • a 5 to A 12 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • the halogen atom, alkyl group, alkoxy group, aryloxy group, aralkyl group, amino group, silyl group, aromatic hydrocarbon group, and heterocyclic group may be the above general formula (1).
  • Etc. and the groups described in the general formula (31).
  • a pyrene derivative represented by the following general formula (51) can also be used.
  • R 501 to R 508 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring forming carbon number.
  • Ar 501 to Ar 504 each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number.
  • 5 to 50 heterocyclic groups are shown. However, at least one of Ar 501 to Ar 504 is a heterocyclic group represented by the following formula (52). ]
  • R 511 to R 517 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted An alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 50 ring atoms.
  • the heterocyclic group of is shown.
  • R 511 and R 512 , R 512 and R 513 , R 513 and R 514 , R 515 and R 516 , and R 516 and R 517 may be bonded to each other to form a saturated or unsaturated ring. These rings may be substituted.
  • X 51 is selected from either an oxygen atom or a sulfur atom.
  • y 51 is a single bond bonded to the nitrogen atom of the general formula (51). ]
  • Ar 51 and Ar 53 are preferably a heterocyclic group represented by the general formula (52).
  • R 501 to R 508 are preferably hydrogen atoms.
  • R 502 and R 506 in the general formula (51) are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, R 501 , R 503 , R 504 , R 505 , R 507 , and R 508 are more preferably hydrogen atoms.
  • the X 51 in formula (52) is an oxygen atom.
  • Ar 51 to Ar 54 are represented by the general formula (52), and X 51 is an oxygen atom.
  • the halogen atom, aromatic hydrocarbon group, heterocyclic group, alkyl group, alkoxy group, aryloxy group, arylthio group, arylamino group, and silyl group may be the above general formula ( Examples thereof include groups described in 1) and the like and the general formula (31).
  • the alkenyl group having 2 to 20 carbon atoms in the general formula (52) may be linear, branched or cyclic, such as vinyl, propenyl, butenyl, oleyl, eicosapentaenyl, docosahexa Examples include enyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl, 2-phenyl-2-propenyl and the like.
  • a vinyl group is preferable.
  • the alkynyl group having 2 to 20 carbon atoms in the general formula (52) may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like. Of the alkynyl groups described above, an ethynyl group is preferred.
  • the saturated or unsaturated ring formed by combining R 511 and R 512 , R 512 and R 513 , R 513 and R 514 , R 515 and R 516 , and R 516 and R 517 together includes cyclobutane, cyclo Cycloalkanes having 4 to 12 ring carbon atoms such as pentane, cyclohexane, adamantane and norbornane, cycloalkens having 4 to 12 ring carbon atoms such as cycloalkane, cyclobutene, cyclopentene, cyclohexene, cycloheptene and cyclootaten, cyclohexadiene, etc.
  • Aromatic rings having 6 to 50 ring carbon atoms such as cyclohexabutadiene, cyclooctane and the like having 6 to 12 ring carbon atoms, benzene, naphthalene, phenanthrene, anthracene, pyrene, taricene, acenaphthylene, etc. Can be mentioned.
  • examples of the substituent are the same as those described above.
  • the hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and a compound having a high hole mobility and a low ionization energy is used.
  • a material for forming the hole injecting / transporting layer a material for transporting holes to the light emitting layer with lower electric field strength is preferable.
  • a compound represented by the following general formula (21) is used. Is preferred.
  • L 201 to L 203 are each independently selected from a single bond or a linking group, and the linking group has a substituted or unsubstituted ring structure having 6 to 30 carbon atoms.
  • Divalent residue formed by removing two hydrogen atoms from an aromatic hydrocarbon ring structure Divalent formed by removing two hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 30 ring atoms
  • Ar 201 to Ar 203 each independently represents a group represented by the following general formula (21a), a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring formation It is selected from heterocyclic groups having 5 to 50 atoms. However, at least one of Ar 201 to Ar 203 is a group represented by the following general formula (21a). ]
  • each of R 201 to R 208 independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring formation. It is a heterocyclic group having 5 to 50 atoms.
  • X represents an oxygen atom, a sulfur atom, N—R 209 or CR 210 R 211 .
  • R 209 to R 211 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 ring carbon atoms.
  • any one of R 201 to R 211 is a single bond used for bonding to any of L 201 to L 203 in the general formula (21). ]
  • those other than the group represented by the general formula (21a) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted group. It is preferably selected from the group consisting of a naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted terphenyl group.
  • Ar 201 to Ar 203 in the general formula (21) are all groups represented by the general formula (21a)
  • at least Ar 201 out of Ar 201 to Ar 203 is Ar 202 or Ar 203.
  • at least L 201 out of L 201 to L 203 is preferably a group different from L 202 or L 203 . That is, in the compound represented by the general formula (21), it is preferable that -L 201 -Ar 201 , -L 202 -Ar 202 , and -L 203 -Ar 203 are not all the same at the same time.
  • one of -L 201 -Ar 201 , -L 202 -Ar 202 , and -L 203 -Ar 203 is preferably different from the other two.
  • the “different group” means not only the same as the skeleton of the substituent but also the bonding position with the adjacent group.
  • a group having a carbazole skeleton a group having a 3-carbazole skeleton and a group having a 4-carbazole skeleton are different groups.
  • X in the general formula (21a) is preferably any one of an oxygen atom, a sulfur atom, and N—R 209 . Further, X in the general formula (21a) is preferably an oxygen atom or N—R 209 .
  • At least one of Ar 201 to Ar 203 is preferably selected from the group consisting of groups represented by the following formulas (211) to (241).
  • L 201 to L 203 in the general formula (21) are each independently a divalent ring formed by removing two hydrogen atoms from a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 13 ring carbon atoms. It is preferably a residue.
  • the aromatic hydrocarbon ring having 6 to 13 ring carbon atoms includes a benzene ring and a condensed aromatic hydrocarbon ring having 10 to 13 ring carbon atoms.
  • L 201 to L 203 in the general formula (21) are each independently 2 from a substituted or unsubstituted phenylene group or a substituted or unsubstituted condensed aromatic hydrocarbon ring having 10 to 13 ring carbon atoms.
  • L 201 to L 203 in the general formula (21) are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted group. It is preferably selected from the group consisting of:
  • Ar 201 to Ar 203 are represented by the general formula (21a), and X in the general formula (21a) is an oxygen atom, a sulfur atom, or N—R 209 .
  • L 201 to L 203 bonded to Ar 201 to Ar 203 are preferably a linking group, and examples of the linking group include substituted or unsubstituted aromatic hydrocarbons having 6 to 13 ring carbon atoms. A divalent residue formed by removing two hydrogen atoms from the ring structure is preferred.
  • any of R 203 , R 206 , and R 209 is more preferably a single bond used for bonding to any of L 201 to L 203 in the general formula (21). That is, when the general formula (21a) is a carbazolyl group, it is more preferable that the third or ninth position of the carbazolyl group is bonded to any one of L 201 to L 203 . Particularly preferably, R 209 , that is, the 9-position of the carbazolyl group is bonded to any one of L 201 to L 203 .
  • any one of R 201 to R 203 or R 206 to R 208 is any of L 201 to L 203 in the general formula (21). It is preferably a single bond used for bonding. Furthermore, it is more preferable that any one of R 201 , R 203 , R 206 , and R 208 is a single bond used for bonding to any one of L 201 to L 203 in the general formula (21), and R 201 , It is particularly preferable that any one of R 208 is a single bond used for bonding to any one of L 201 to L 203 in the general formula (21).
  • the general formula (21a) is a dibenzofuranyl group or a dibenzothiophenyl group
  • the 4-position of the dibenzofuranyl group and the dibenzothiophenyl group is preferably bonded to any one of L 201 to L 203 .
  • L 201 to L 203 are any one selected from the group consisting of groups represented by the following formulas (L-211) to (L-226).
  • Luminescence element In the general formula (21), L 201 to L 203 are any one selected from the group consisting of groups represented by the following formulas (L-211) to (L-226). Luminescence element.
  • examples of the alkyl group, the aromatic hydrocarbon group, and the heterocyclic group include the groups described in the general formula (1) and the like.
  • the compound represented by the general formula (21) is preferably a compound having one amino group, and L 201 to L 203 , Ar 201 to Ar 203 , and R 201 to R 208 have a substituent. In this case, the substituent is preferably not an amino group.
  • Examples of the compound represented by the general formula (21) include the following compounds.
  • the hole injection / transport layer containing the compound represented by the general formula (21) is preferably provided adjacent to the light emitting layer.
  • a plurality of hole injection / transport layers may be provided, and in that case, the hole injection / transport layer containing the compound represented by the general formula (21) is provided adjacent to the light emitting layer. It is preferred that
  • the electron injection / transport layer is a layer that assists injection of electrons into the light emitting layer and transports it to the light emitting region, and a compound having a high electron mobility is used.
  • a compound used in the electron injecting / transporting layer for example, an aromatic heterocyclic compound containing one or more hetero atoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • a nitrogen-containing ring derivative a heterocyclic compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton is preferable.
  • an organic compound other than the light emitting layer can be used by selecting any compound from the materials used in the conventional organic EL device in addition to the compounds exemplified above.
  • the organic EL element of the present invention is produced on a light-transmitting substrate.
  • the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • the anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
  • Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
  • the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the light transmittance in the visible region of the anode be greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ (ohm / square) or less.
  • the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the cathode a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer, the electron transport layer, or the light emitting layer.
  • the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering.
  • the aspect which takes out light emission from a cathode side is also employable.
  • the aspect which takes out light emission from a light emitting layer from a cathode side is also employable.
  • the light transmittance in the visible region of the cathode be greater than 10%.
  • the sheet resistance of the cathode is preferably several hundred ⁇ / ⁇ or less.
  • the layer thickness of the cathode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 50 nm to 200 nm.
  • the organic layer is applied by a vacuum deposition method, a molecular beam deposition method (MBE method, MBE; Molecular Beam Epitaxy) or a solution dipping method in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method, etc. Can be formed by a known method.
  • MBE method molecular beam deposition method
  • MBE molecular Beam Epitaxy
  • the thickness of the light emitting layer is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm.
  • the film thickness of each of the other organic layers is not particularly limited, but is usually preferably in the range of several nm to 1 ⁇ m.
  • the organic EL element of the present invention can be suitably used by being mounted on an electronic device such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicle lamp.
  • an electronic device such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicle lamp.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer contains the compound represented by the general formula (1), and the other light emitting layers are fluorescent light emitting layers.
  • a phosphorescent light emitting layer may be used.
  • these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.
  • the light emitting layer contains a charge injection auxiliary material.
  • a light emitting layer is formed using a host material having a wide energy gap, the difference between the ionization potential (Ip) of the host material and Ip of the hole injection / transport layer, etc. increases, and holes are injected into the light emitting layer. This may make it difficult to increase the driving voltage for obtaining sufficient luminance.
  • by adding a hole injection / transport charge injection auxiliary material to the light emitting layer hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.
  • charge injection auxiliary material for example, a general hole injection / transport material or the like can be used.
  • specific examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, fluorenone derivatives, hydrazone derivatives, stilbenes.
  • Derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), and the like can be given.
  • hole-injecting material examples include those described above, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds are preferred.
  • NPD 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter abbreviated as NPD) having two condensed aromatic rings in the molecule, or triphenylamine 4,4 ′, 4 ′′ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA), etc., in which three units are connected in a starburst type. it can.
  • a hexaazatriphenylene derivative or the like can also be suitably used as the hole injecting material.
  • inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.
  • Example 1 A glass substrate with an ITO transparent electrode of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
  • the glass substrate with the ITO transparent electrode line after washing is attached to the substrate holder of the vacuum evaporation apparatus, and the following compound (HA) is first coated so as to cover the transparent electrode on the surface on which the ITO transparent electrode line is formed.
  • a HA film having a thickness of 5 nm was formed by vapor deposition to form a hole injection layer.
  • the following compound HT1 was deposited as a first hole transport material on this HA film to form an HT1 film having a thickness of 80 nm, thereby forming a first hole transport layer.
  • the following compound HT2 was deposited as a second hole transport material to form an HT2 film having a thickness of 15 nm, thereby forming a second hole transport layer.
  • a compound BH2 was vapor-deposited on the HT2 film to form a light emitting layer having a thickness of 25 nm.
  • the following compound BD was co-deposited as a fluorescent material.
  • the concentration of Compound BD was 5.0% by mass. This co-deposited film functions as a light emitting layer.
  • the following compound ET1 was vapor-deposited and the ET1 film
  • the following compound ET2 was vapor-deposited on the ET1 film to form an ET2 film having a thickness of 5 nm, thereby forming a second electron transport layer.
  • LiF was deposited on the ET2 film at a deposition rate of 0.1 angstrom / min to form a 1 nm-thick LiF film to form an electron injecting electrode (cathode).
  • metal Al was vapor-deposited on this LiF film
  • Examples 2 to 5 and Comparative Examples 1 to 4 In the organic EL devices of Examples 2 to 5 and Comparative Examples 1 to 4, at least one of the host material of the light emitting layer and the second hole transport material of the second hole transport layer in Example 1 is shown in Table 1. This was prepared in the same manner as in Example 1 except that the compound was changed to.
  • Main peak wavelength ⁇ p was determined from the obtained spectral radiance spectrum.
  • the organic EL elements of Examples 1 to 5 were found to be organic EL elements having higher luminous efficiency than the organic EL elements of Comparative Examples 1 to 4.
  • the organic EL device of Example 3 has an external quantum efficiency EQE of about 1.4 times, that is, about 40%, compared with the organic EL device of Comparative Example 1.

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Abstract

L'invention concerne un élément électroluminescent organique qui est caractérisé par la fourniture d'une anode, d'une cathode qui est disposée de façon à faire face à l'anode, d'une couche électroluminescente qui est disposée entre l'anode et la cathode et qui contient le composé représenté par la formule (1), et d'une couche de transport de trous positive qui est disposée entre la couche électroluminescente et l'anode et qui contient le composé représenté par la formule (21).
PCT/JP2013/077224 2012-11-07 2013-10-07 Élément électroluminescent organique et dispositif électronique WO2014073306A1 (fr)

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EP3653619A1 (fr) 2018-11-16 2020-05-20 Novaled GmbH Composé, dispositif électronique organique le comprenant, dispositif d'affichage et dispositif d'éclairage le comprenant

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JPWO2017010438A1 (ja) * 2015-07-10 2018-02-22 出光興産株式会社 有機エレクトロルミネッセンス素子および電子機器
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