WO2014024880A1 - Élément électroluminescent organique et appareil électronique - Google Patents

Élément électroluminescent organique et appareil électronique Download PDF

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WO2014024880A1
WO2014024880A1 PCT/JP2013/071248 JP2013071248W WO2014024880A1 WO 2014024880 A1 WO2014024880 A1 WO 2014024880A1 JP 2013071248 W JP2013071248 W JP 2013071248W WO 2014024880 A1 WO2014024880 A1 WO 2014024880A1
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carbon atoms
general formula
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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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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • 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

Definitions

  • the present invention relates to an organic electroluminescence element and an electronic device.
  • an organic electroluminescence element (hereinafter sometimes referred to as an organic EL element)
  • holes from the anode and electrons from the cathode are injected into the light emitting layer.
  • the injected holes and electrons are recombined to form excitons.
  • singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
  • the fluorescence type uses light emission by singlet excitons.
  • the phosphorescent type since light emission by triplet excitons is used, it is known that the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.
  • Patent Document 1 attempts to provide a fluorescent organic EL element having high emission efficiency and a long lifetime by setting an anthracene derivative as a host material of the light emitting layer to a specific structure.
  • An object of the present invention is to provide an organic EL element with high luminous efficiency and long life. Another object of the present invention is to provide an electronic apparatus provided with the organic EL element of the present invention.
  • the organic electroluminescence device is The anode, A cathode provided opposite to the anode; An organic layer provided between the anode and the cathode, The organic layer includes a hole transport layer and a light emitting layer in this order from the anode side,
  • the hole transport layer includes a compound represented by the following general formula (1)
  • the light emitting layer includes a light emitting material, a compound represented by the following general formula (10), and a compound represented by the following general formula (11).
  • a 1 and A 2 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon 2 Represents 30 to 30 aromatic heterocyclic groups.
  • Y 1 to Y 16 each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
  • L 1 and L 2 each independently represent a single bond or a divalent linking group.
  • a 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted Benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, substituted or unsubstituted benzo [b ] Fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl group
  • R 101 to R 108 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 group.
  • Ar 31 to Ar 33 , R 109 , R 110 , and R 21 to R 28 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, or a substituted or unsubstituted carbon number.
  • Ar 31 to Ar 33 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms
  • Ar 31 when Ar 31 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, Ar 31 is substituted or unsubstituted. Substituted fluorenyl group.
  • Ar 31 , Ar 33 , R 109 , and R 110 are hydrogen atoms
  • Ar 32 is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms. is there. )
  • the organic electroluminescence element is The anode, A cathode provided opposite to the anode; An organic layer provided between the anode and the cathode, The organic layer includes a hole transport layer and a light emitting layer in this order from the anode side,
  • the hole transport layer includes a compound represented by the following general formula (30), and the light emitting layer includes a compound represented by the following general formula (2A) and a light emitting material.
  • a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5; Represents 30 to 30 aromatic heterocyclic groups. Any two adjacent R 41 to R 44 are bonded to a partial structure represented by the following general formula (31). Any two adjacent R 51 to R 54 may be bonded to a partial structure represented by the following general formula (31). )
  • R 41 to R 44 and R 51 to R 54 not bonded to the partial structure represented by the general formula (31) are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted A substituted amino group, 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 aryloxy group having 6 to 20 ring carbon atoms, Substituted or unsubstituted arylthio group having 6 to 20 carbon atoms, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted A substituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstit
  • * represents a bonding site with the ring structure represented by the general formula (30),
  • One of Z 1 and Z 2 is a single bond, and the other is —O—, —S—, —CR 65 R 66 —, or —NR 67 —;
  • R 61 to R 67 are each independently a hydrogen atom, 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 An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ⁇ 40 trialkylsilyl group, substituted or unsubstituted aryls
  • R 101 to R 108 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 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.
  • a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, Ar 1001 and Ar 101 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. .
  • Ar 100 may form a ring with R 101 or R 108, and Ar 101 may form a ring with R 104 or R 105 .
  • the configuration of (d) is preferably used. However, of course, it is not limited to these.
  • 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.
  • the “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “an electron injection layer and an electron transport layer”. "At least one of them”.
  • the positive hole injection layer is provided in the anode side.
  • the electron injection 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 includes a hole transport layer 5 and a light emitting layer 6 in this order from the anode 3 side. In the present embodiment, the hole transport layer 5 and the light emitting layer 6 are adjacent to each other. Further, the organic EL element 1 includes a hole injection layer 7 between the anode 3 and the hole transport layer 5, and includes an electron injection / transport layer 8 between the cathode 4 and the light emitting layer 6. .
  • the light emitting layer 6 includes a host material and a fluorescent dopant material as a fluorescent light emitting material. Further, an electron barrier layer may be provided on the phosphorescent light emitting layer 5 on the anode 3 side, and a hole barrier layer may be provided on the phosphorescent light emitting layer 5 on the cathode 4 side. With such a barrier layer, electrons and holes can be confined in the light emitting layer 6 and the exciton generation probability in the light emitting layer 6 can be increased.
  • the organic layer 10 may contain an inorganic compound.
  • 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 ⁇ / ⁇ ( ⁇ / sq. Ohm per 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 a method such as vapor deposition, for example, by forming a thin film on the electron transport layer or the electron injection layer.
  • 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 hole transport layer 5 of the present embodiment is adjacent to the light emitting layer 6 on the anode 3 side and includes a compound represented by the following general formula (1).
  • a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 Represents 30 to 30 aromatic heterocyclic groups.
  • Y 1 to Y 16 each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent, or a carbazole skeleton.
  • the compound represented by the general formula (1) includes a case where it has a carbazole skeleton and a case where it has an azalated carbazole skeleton.
  • L 1 and L 2 each independently represent a single bond or a divalent linking group.
  • at least one of A 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenant.
  • Renyl group substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, Substituted or unsubstituted benzo [b] fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl Group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted Conversion of phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubsti
  • Y 1 to Y 16 are all C (R), Y 6 and Y 11 are bonded by a single bond, L 1 and L 2 are a single bond, and A 1 Is a phenanthrenyl group, A 2 is not a phenanthrenyl group.
  • R when Y 1 to Y 16 are all C (R), Y 6 and Y 11 are bonded by a single bond, and L 1 and L 2 are a single bond, R Are not fluorenyl groups, and when A 1 is a fluorenyl group, A 2 is not a phenyl group, a naphthyl group, or a fluorenyl group.
  • At least one of Y 1 to Y 4 is C (R)
  • at least one of Y 5 to Y 8 is C (R)
  • Y 9 at least one of ⁇ Y 12 is a C (R)
  • at least one of Y 13 ⁇ Y 16 is C (R).
  • One of Y 5 to Y 8 is C (R) and one of Y 9 to Y 12 is C (R), and these Rs represent bonds that are bonded to each other.
  • R in the said General formula (1) may mutually be same or different.
  • the compound represented by the general formula (1) contained in the hole transport layer 5 is represented by the following general formula (1-2), the following general formula (1-3), or the following general formula (1-4). It is preferable.
  • At least one of A 1 and A 2 is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, substituted or Unsubstituted benzophenanthrenyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or An unsubstituted picenyl group, a substituted or unsubstituted benzo [b] fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group
  • a 1 and A 2 are each independently a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group.
  • Substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or substituted or unsubstituted A carbazolyl group is preferred.
  • a 1 and A 2 each independently represent a substituted or unsubstituted dibenzofuranyl group, Jibenzochio substituted or unsubstituted It is preferably a phenyl group or a substituted or unsubstituted carbazolyl group.
  • the structure of the portion represented by L 1 -A 1 and the structure of the portion represented by L 2 -A 2 are preferably different from each other.
  • substituents of A 1 and A 2 in this embodiment and the substituent represented by R include a halogen atom, a cyano group, a substituted or unsubstituted straight chain or branched chain having 1 to 20 carbon atoms.
  • halogen atom in this embodiment examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic, and examples of the linear or branched alkyl group include a methyl group, an ethyl group, and a propyl group.
  • 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.
  • Examples of the linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms in the present embodiment 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.
  • Examples of the linear, branched or cyclic alkylene group having 1 to 20 carbon atoms in the present embodiment include an ethylene group, a propylene group, and a butylene group.
  • Examples of the linear, branched or cyclic divalent unsaturated hydrocarbon group having 1 to 20 carbon atoms in the present embodiment include a 1,3-butadiene-1,4-diyl group.
  • the linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms in the present embodiment is represented as —OZ 1 .
  • Z 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.
  • the aryloxy group having 6 to 30 ring carbon atoms in the present embodiment is represented by —OZ 2 .
  • Z 2 include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.
  • the aryloxy group include a phenoxy group.
  • the arylthio group having 6 to 30 ring carbon atoms in the general formulas (1) and (1-2) to (1-4) is represented by —SZ 3 .
  • Z 3 include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.
  • Examples of the linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms in the present embodiment include those in which the alkoxy group having 1 to 20 carbon atoms is substituted with one or more halogen groups. It is done.
  • Examples of the linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms in the present embodiment include a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group, a dimethylethylsilyl group, a dimethylisopropylsilyl group, and dimethyl
  • Examples thereof include a propylsilyl group, a dimethylbutylsilyl group, a dimethyltertiarybutylsilyl group, and a diethylisopropylsilyl group.
  • Examples of the arylsilyl group having 6 to 30 carbon atoms in the present embodiment include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl tertiary butylsilyl group, and a triphenylsilyl group.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the present embodiment include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group. More specifically, a phenyl group, a naphthyl group, Phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl 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.
  • Examples of the aromatic heterocyclic group having 2 to 30 ring carbon atoms or the aromatic heterocyclic group having 5 to 30 ring atoms in the present embodiment include a non-condensed aromatic heterocyclic ring and a condensed aromatic heterocyclic ring, More specifically, pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl Group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, thienyl group, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring,
  • Examples of the divalent linking group represented by L 1 and L 2 in the present embodiment include a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent group. And an aromatic heterocyclic group having 2 to 10 ring carbon atoms.
  • Specific examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms include those having a divalent group as the aromatic hydrocarbon group having 6 to 30 ring carbon atoms described above. Can be mentioned.
  • specific examples of the divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms include those mentioned above as the aromatic heterocyclic group having 2 to 30 ring carbon atoms. Things.
  • Y 1 to Y 16 are preferably all C (R). That is, the compound represented by the general formula (1) contained in the hole transport layer 5 preferably has a structure in which two carbazole skeletons that are not azalated are connected. Furthermore, the compound represented by the general formula (1) preferably has two carbazole skeletons in the molecule.
  • the number of substituents represented by R is 0 to 2 Preferably, it is 0 or 1, more preferably.
  • the compounds represented by the general formulas (1), (1-2) to (1-4) include a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group at a specific position.
  • Selected from the group consisting of a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group Are preferably bonded.
  • 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).
  • substituents include the aromatic hydrocarbon group, aromatic heterocyclic group, alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group). Group), 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 Groups.
  • an alkenyl group and an alkynyl group are also included.
  • an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable. Further, in the description of each substituent, Specific substituents that are preferred 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. In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.
  • the number of ring-forming carbon atoms refers to a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among atoms constituting the ring itself. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • the number of ring-forming atoms refers to the ring itself of a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of atoms to be played.
  • An atom that does not constitute a ring for example, a hydrogen atom that terminates the dangling bond of an atom that constitutes a ring
  • an atom contained in a substituent when the ring is substituted by a substituent is included in the number of ring-forming atoms Absent.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • 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.
  • examples of the compound contained in the hole transport layer 5 include the following compounds.
  • D represents deuterium.
  • the light emitting layer of the organic EL element has the following functions. That is, (1) injection function; a function capable of injecting holes from the anode or hole injection layer when an electric field is applied, and a function of injecting electrons from the cathode or electron injection layer; (2) Transport function; function to move injected charges (electrons and holes) by the force of electric field, (3) Luminescent function; a function to provide a field for recombination of electrons and holes and connect this to light emission, There is.
  • a known method such as an evaporation method, a spin coating method, or an LB method can be applied.
  • the light emitting layer is preferably a molecular deposited film.
  • the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state. Can be classified from a thin film (accumulated film) formed by the LB method according to a difference in an agglomerated structure and a higher-order structure and a functional difference resulting therefrom.
  • the light emitting layer can also be formed by dissolving a binder such as a resin and a material compound in a solvent to form a solution, and then thinning the solution by a spin coating method or the like.
  • the host material contained in the light emitting layer of this embodiment is a compound represented by following General formula (2).
  • R 101 to R 108 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 carbon group having 1 to 20 carbon atoms.
  • any one of R 109 to R 113 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom.
  • a heterocyclic group of formula 5 to 30, and other R 109 to R 113 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 group
  • Ar 101 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. .
  • the host material included in the light emitting layer is preferably either a compound represented by the following general formula (10) or a compound represented by the following general formula (11).
  • R 101 to R 108 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 group.
  • Ar 31 to Ar 33 , R 109 , R 110 , and R 21 to R 28 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, or a substituted or unsubstituted carbon number.
  • Ar 31 to Ar 33 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • Ar 31 is substituted or unsubstituted fluorenyl. It is a group.
  • Ar 32 is a substituted or unsubstituted aromatic group having 10 to 30 ring carbon atoms.
  • Group hydrocarbon group In this case, Ar 32 is preferably a substituted or unsubstituted naphthyl group.
  • R 31 and R 32 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R 33 to R 37 are each independently a hydrogen atom, 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 An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ⁇ 40 trialkylsilyl group, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50
  • the dopant material is selected from fluorescent materials that exhibit fluorescent emission.
  • Specific examples of the dopant material include naphthalene derivatives, anthracene derivatives, pyrene derivatives, chrysene derivatives, fluoranthene derivatives, indenoperylene derivatives, pyromethene boron complex compounds, compounds having a pyromethene skeleton or metal complexes thereof, diketopyrrolo Examples include pyrrole derivatives and perylene derivatives.
  • naphthalene derivatives include bisarylaminonaphthalene derivatives and aryl-substituted naphthalene derivatives
  • anthracene derivatives include bisarylaminoanthracene derivatives and aryl group-substituted anthracene derivatives
  • pyrene derivative examples include bisarylaminopyrene derivatives and aryl group-substituted pyrene derivatives.
  • chrysene derivatives include bisarylaminochrysene derivatives and aryl-substituted chrysene derivatives.
  • fluoranthene derivatives it is selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, fluorene derivatives, boron complexes, perylene derivatives, oxadiazole derivatives, anthracene derivatives, chrysene derivatives, and the like.
  • a fluoranthene derivative, a pyrene derivative, and a boron complex are used.
  • the emission color of the dopant material contained in the light emitting layer is not particularly limited, but is preferably a fluorescent light emitting dopant material that emits blue light having a main peak wavelength of 480 nm or less.
  • the main peak wavelength refers to the peak wavelength of the emission spectrum that maximizes the emission intensity in the emission spectrum measured in a toluene solution having a concentration of 10 ⁇ 5 mol / liter to 10 ⁇ 6 mol / liter.
  • a dopant material having such a main peak wavelength is doped into the host material represented by the general formula (2) to form a light emitting layer, and the hole transport layer adjacent to the anode side of the light emitting layer has the general formula
  • the organic EL device has high efficiency and long life.
  • 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 has a high hole mobility and a low ionization energy.
  • the hole injection / transport layer has at least a hole transport layer containing a compound represented by the general formula (2), and may have a hole injection layer in addition to this. Or may have another hole transport layer.
  • the hole injection / transport layer is formed from the anode side, the hole injection layer, the first hole transport layer, the second hole transport layer (a hole transport layer containing a compound represented by the general formula (2)) ) May be laminated in this order.
  • a material for forming the hole injection layer and the hole transport layer a material that transports holes to the light emitting layer with lower electric field strength is preferable.
  • an aromatic amine compound is preferably used.
  • a porphyrin compound, an aromatic tertiary amine compound or a styrylamine compound is preferably used. It is preferable to use it.
  • an aromatic amine compound for example, an aromatic amine derivative represented by the following general formula (A1) is preferably used.
  • Ar 1 to Ar 4 are each independently an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, an aromatic heterocyclic group having 2 to 40 ring carbon atoms, It represents a group in which the aromatic hydrocarbon group and the aromatic heterocyclic group are bonded, or a group in which the aromatic hydrocarbon group and the aromatic heterocyclic group are bonded.
  • the aromatic hydrocarbon group and aromatic heterocyclic group mentioned here may have a substituent.
  • L is a linking group, a divalent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a divalent aromatic heterocyclic ring having 5 to 50 ring carbon atoms.
  • the divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group mentioned here may have a substituent.
  • An aromatic amine represented by the following general formula (A2) is also preferably used for forming the hole injection / transport layer.
  • the electron injection / transport layer is a layer that assists injection of electrons into the light emitting layer, and has a high electron mobility.
  • the electron injection layer is provided to adjust the energy level, for example, to alleviate a sudden change in the energy level.
  • the electron injection / transport layer includes at least one of an electron injection layer and an electron transport layer.
  • This embodiment preferably has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer preferably contains a nitrogen-containing ring derivative as a main component.
  • the electron injection layer may be a layer that functions as an electron transport layer. “As a main component” means that the electron injection layer contains 50% by mass or more of a nitrogen-containing ring derivative.
  • an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • a nitrogen-containing ring derivative an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton is preferable.
  • this nitrogen-containing ring derivative for example, a nitrogen-containing ring metal chelate complex represented by the following general formula (B1) is preferable.
  • R 2 to R 7 in formula (B1) are independently a hydrogen atom, a halogen atom, an oxy group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, an alkoxy group, an aryloxy group, or an alkoxycarbonyl group. Or an aromatic heterocyclic group, which may have a substituent.
  • the halogen atom include fluorine, chlorine, bromine and iodine.
  • the optionally substituted amino group include an alkylamino group, an arylamino group, and an aralkylamino group.
  • the alkoxycarbonyl group is represented as —COOY ′, and examples of Y ′ include the same as the alkyl group.
  • the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 . Specific examples of Q 1 and Q 2 are independently the same as those described for the alkyl group and the aralkyl group, and preferred examples are also the same. One of Q 1 and Q 2 may be a hydrogen atom.
  • the aralkyl group is a group in which a hydrogen atom of the alkyl group is substituted with the aryl group.
  • the arylamino group is represented by —NAr 1 Ar 2, and specific examples of Ar 1 and Ar 2 are the same as those described for the non-condensed aromatic hydrocarbon group and the condensed aromatic hydrocarbon group, respectively.
  • One of Ar 1 and Ar 2 may be a hydrogen atom.
  • M is aluminum (Al), gallium (Ga) or indium (In), and is preferably In.
  • L in the general formula (B1) is a group represented by the following general formula (B2) or (B3).
  • R 8 to R 12 are independently a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure. .
  • This hydrocarbon group may have a substituent.
  • R 13 to R 27 are independently a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other form a cyclic structure. Also good.
  • This hydrocarbon group may have a substituent. 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 the general formula (B2) and the general formula (B3) include those in the general formula (B1).
  • examples of the divalent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, diphenylmethane- Examples include 2,2′-diyl group, diphenylethane-3,3′-diyl group, and diphenylpropane-4,4′-diyl group.
  • the electron transport layer preferably contains at least one of nitrogen-containing heterocyclic derivatives represented by the following general formulas (B4) to (B6).
  • R is a hydrogen atom, an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, or a condensed aromatic hydrocarbon having 6 to 60 ring carbon atoms.
  • n is an integer of 0 or more and 4 or less.
  • R 1 is an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.
  • R 2 and R 3 independently represent a hydrogen atom, an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, or 6 to 60 ring carbon atoms.
  • L represents an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, and pyridinylene.
  • Ar 1 represents an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridinylene group and a quinolinylene group;
  • Ar 2 is an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.
  • Ar 3 represents an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a group represented by “—Ar 1 —Ar 2 ” (Ar 1 and Ar 2 are The same).
  • 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
  • a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used.
  • 8-quinolinol or 8-hydroxyquinoline for example, tris (8-quinolinol
  • Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 are each an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, or a ring forming carbon number. 6 or more and 40 or less condensed aromatic hydrocarbon group. However, the aromatic hydrocarbon group and condensed aromatic hydrocarbon group mentioned here may have a substituent. Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same as or different from each other.
  • aromatic hydrocarbon group or condensed aromatic hydrocarbon group mentioned here examples include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group. And as a substituent to these, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyano group, etc. are mentioned.
  • Ar 20 , Ar 23, and Ar 24 are divalent aromatic hydrocarbon groups having 6 to 40 ring carbon atoms, or 2 having 6 to 40 ring carbon atoms.
  • Valent condensed aromatic hydrocarbon group may have a substituent.
  • Ar 23 and Ar 24 may be the same as or different from each other.
  • Examples of the divalent aromatic hydrocarbon group or the divalent condensed aromatic hydrocarbon group mentioned here include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
  • a substituent to these a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyano group, etc. are mentioned.
  • electron transfer compounds those having good thin film forming properties are preferably used.
  • Specific examples of these electron transfer compounds include the following.
  • the nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following general formula, and includes a nitrogen-containing compound that is not a metal complex.
  • a 5-membered or 6-membered ring containing a skeleton represented by the following general formula (B7) and a structure represented by the following general formula (B8) can be given.
  • X represents a carbon atom or a nitrogen atom.
  • Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
  • the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, a skeleton obtained by combining the general formulas (B7) and (B8) or the general formula (B7) with the following general formula (B9) is used.
  • the nitrogen-containing aromatic polycyclic organic compound having is preferable.
  • the nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following general formula.
  • R represents an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and a ring forming carbon number.
  • n is an integer of 0 or more and 5 or less, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
  • preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following general formula (B10).
  • HAr-L 1 -Ar 1 -Ar 2 (B10)
  • HAr is a nitrogen-containing heterocyclic group having 1 to 40 ring carbon atoms.
  • L 1 represents a single bond, an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and a ring forming carbon number.
  • Ar 1 is a divalent aromatic hydrocarbon group having 6 to 40 ring carbon atoms.
  • Ar 2 represents an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and 2 to 40 ring carbon atoms.
  • the ring group and the condensed aromatic heterocyclic group may have a substituent.
  • HAr in the formula of the general formula (B10) is selected from the following group, for example.
  • L 1 in the formula (B10) is, for example, selected from the following group.
  • Ar 1 in the formula (B10) is, for example, selected from the following arylanthranyl groups.
  • R 1 to R 14 are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or ring-forming carbon.
  • Ar 3 represents an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and 2 or more ring carbon atoms.
  • the cyclic group may have a substituent.
  • any of R 1 to R 8 may be a nitrogen-containing heterocyclic derivative which is a hydrogen atom.
  • Ar 2 is selected from the following group, for example.
  • the nitrogen-containing aromatic polycyclic organic compound as the electron transfer compound, the following compounds (see JP-A-9-3448) are also preferably used.
  • R 1 to R 4 independently represent a hydrogen atom, an aliphatic group, an aliphatic cyclic group, a carbocyclic aromatic cyclic group, or a heterocyclic group.
  • the aliphatic group, aliphatic cyclic group, carbocyclic aromatic ring group, and heterocyclic group mentioned here may have a substituent.
  • X 1 and X 2 independently represent an oxygen atom, a sulfur atom, or a dicyanomethylene group.
  • R 1 , R 2 , R 3, and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following general formula.
  • R 5 , R 6 , R 7 , R 8 and R 9 are the same or different groups, and hydrogen atom or at least one of them is a saturated or unsaturated alkoxyl group, alkyl group, amino group A group or an alkylamino group.
  • the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
  • the thickness of the electron injection layer or the electron transport layer is not particularly limited, but is preferably 1 nm or more and 100 nm or less. Moreover, as a constituent component of the electron injection layer, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
  • alkali metal chalcogenides include, for example, lithium oxide (Li 2 O), potassium oxide (K 2 O), sodium sulfide (Na 2 S), sodium selenide (Na 2 Se), and sodium oxide (Na 2 O).
  • Preferred alkaline earth metal chalcogenides include, for example, calcium oxide (CaO), barium oxide (BaO), strontium oxide (SrO), beryllium oxide (BeO), barium sulfide (BaS), and calcium selenide (CaSe).
  • Examples of preferable alkali metal halides include lithium fluoride (LiF), sodium fluoride (NaF), potassium fluoride (KF), lithium chloride (LiCl), potassium chloride (KCl), and sodium chloride (NaCl). ) And the like.
  • Examples of preferable alkaline earth metal halides include calcium fluoride (CaF 2 ), barium fluoride (BaF 2 ), strontium fluoride (SrF 2 ), magnesium fluoride (MgF 2 ), and beryllium fluoride. Examples thereof include fluorides such as (BeF 2 ) and halides other than fluorides.
  • the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film.
  • the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, so that pixel defects such as dark spots can be reduced.
  • inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
  • the preferable thickness of the layer is about 0.1 nm to 15 nm.
  • the electron injection layer in this invention contains the above-mentioned reducing dopant material, it is preferable.
  • the organic EL device of the present invention preferably has at least one of an electron donating dopant and an organometallic complex in the interface region between the cathode and the organic layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
  • the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
  • alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • K, Rb and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.
  • alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
  • a work function of 2.9 eV or less is particularly preferable.
  • the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
  • alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
  • alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
  • the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), such as terbium fluoride (TbF 3) can be mentioned, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions as described above.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl thiadiazole, hydroxydiaryl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
  • the addition form of the electron donating dopant and the organometallic complex is preferably formed in a layered or island shape in the interface region.
  • a forming method while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material which is a light-emitting material or an electron injection material for forming an interface region is vapor-deposited at the same time.
  • a method of dispersing at least one of a donor dopant and an organometallic complex reducing dopant is preferable.
  • At least one of the electron donating dopant and the organometallic complex in a layered form, after forming the light emitting material or the electron injecting material as the organic layer at the interface in a layered form, at least one of the electron donating dopant and the organometallic complex is formed.
  • These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
  • the electron donating dopant and the organometallic complex is formed in an island shape
  • the electron donating dopant and the organometallic complex At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
  • each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
  • the organic layer used in the organic EL device of the present invention is formed by a vacuum deposition method, a molecular beam deposition method (MBE method, MBE; Molecular Beam Epitaxy), a solution dipping method in a solvent, a spin coating method, a casting method, or a bar coating method. It can be formed by a known method using a coating method such as a roll coating method.
  • 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 compound contained in the hole transport layer is different from the above-described first embodiment, and the compound contained in the light-emitting layer has more types than the above-described first embodiment.
  • the other points are the same as in the first embodiment.
  • the same materials, compounds, device configurations, and definitions as those described in the first embodiment can be applied unless otherwise specified.
  • the hole transport layer of the organic EL device according to this embodiment contains a compound represented by the following general formula (30).
  • a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 5 ring atoms.
  • 30 aromatic heterocyclic groups are represented. Any two adjacent R 41 to R 44 are bonded to a partial structure represented by the following general formula (31). Any two adjacent R 51 to R 54 may be bonded to a partial structure represented by the following general formula (31).
  • R 41 to R 44 and R 51 to R 54 not bonded to the partial structure represented by the general formula (31) are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, substituted or unsubstituted.
  • L 1 and L 2 each independently represents a single bond or a divalent linking group.
  • * represents a binding site with the ring structure represented by the general formula (30).
  • One of Z 1 and Z 2 is a single bond, and the other is —O—, —S—, —CR 65 R 66 —, or —NR 67 —.
  • it is preferable that one of Z 1 and Z 2 is a single bond, and the other is —O— or —CR 65 R 66 —.
  • either one of Z 1 and Z 2 is preferably a single bond, and the other is preferably —S— or —NR 67 —.
  • R 61 to R 67 are each independently a hydrogen atom, 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 An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ⁇ 40 trialkylsilyl group, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring formation It is a heterocyclic group having 5 to 50 atoms.
  • the compound represented by the general formula (30) is preferably represented by the following general formula (32).
  • the compound represented by the general formula (30) is preferably represented by the following general formula (33) or the following general formula (34).
  • R 67 is as defined in the general formulas (30) and (31).
  • the compound represented by the general formula (30) is preferably represented by any one of the following general formula (35), general formula (36), and general formula (37).
  • a 1 , A 2 , L 1 , L 2 , R 41 to R 45 , R 51 to R 55 , p, q, Z 1 and Z 2 , R 61 to R 67 in the general formulas (35) to (37). are synonymous with those in the general formulas (30) and (31), respectively.
  • Z 1 in the general formulas (35) to (37) is —O— or —CR 65 R 66 —, and Z 2 is a single bond.
  • Z 1 in the general formulas (35) to (37) is a single bond, and Z 2 is —O— or —CR 65 R 66 —.
  • Z 1 in the general formulas (35) to (37) is —CR 65 R 66 — and Z 2 is a single bond.
  • Z 1 in the general formulas (35) to (37) is —S— or —NR 67 —
  • Z 2 is a single bond
  • Z 1 in the general formulas (35) to (37) is a single bond
  • Z 2 is —S— or —NR 67 —.
  • a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • the A 2 is preferably a substituted or unsubstituted phenyl group.
  • a 2 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
  • the A 2 is more preferably a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group. More preferably.
  • a 2 is more preferably a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 2-dibenzofuranyl group, or a substituted or unsubstituted 4-dibenzofuranyl group. More preferably.
  • L 2 is preferably a substituted or unsubstituted phenylene group, more preferably a substituted or unsubstituted m-phenylene group, or a substituted or unsubstituted p-phenylene group. It is more preferably a substituted or unsubstituted m-phenylene group.
  • the A 2 is a substituted or unsubstituted 2-dibenzothiophenyl group or a substituted or unsubstituted 4-dibenzothiophenyl group
  • the L 2 is a substituted or unsubstituted m-phenylene group.
  • a 2 is a substituted or unsubstituted 4-dibenzothiophenyl group
  • L 2 is a substituted or unsubstituted m-phenylene group.
  • L 2 is preferably a single bond.
  • a 2 is a substituted or unsubstituted 2-dibenzothiophenyl group or a substituted or unsubstituted 4-dibenzothiophenyl group, and L 2 is a single bond. More preferably, A 2 is a substituted or unsubstituted 4-dibenzothiophenyl group, and L 2 is a single bond.
  • Examples of the compound contained in the hole transport layer of the present embodiment include the following compounds, but the present invention is not limited to this specific example.
  • the light emitting layer of the present embodiment includes a compound represented by the following general formula (2A) and a light emitting material.
  • R 101 to R 108 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 carbon group having 1 to 20 carbon atoms.
  • Ar 101 and Ar 101 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. .
  • the compound described in the first embodiment can also be used in the light emitting layer of the present embodiment.
  • the host material is preferably a compound represented by the following general formula (3), the following general formula (4), or the following general formula (5).
  • Ar 111 and Ar 112 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 30 heterocyclic groups.
  • R 121 to R 132 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 carbon group having 1 to 20 carbon atoms.
  • the Ar 111 and the Ar 112 in the general formula (3) are preferably naphthyl groups.
  • the Ar 111 and the Ar 112 are 2-naphthyl groups, or the Ar 111 is a 1-naphthyl group, and the Ar 112 is a 2-naphthyl group. More preferred.
  • Ar 121 and Ar 122 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 30 heterocyclic groups.
  • R 141 to R 152 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 carbon group having 1 to 20 carbon atoms.
  • Ar 131 is a substituted or unsubstituted phenyl group
  • Ar 132 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted group.
  • the number of ring-forming atoms is 5-30.
  • R 161 to R 172 are each independently a hydrogen atom, 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 An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 A trialkylsilyl group of ⁇ 40, or a substituted or unsubstituted arylsilyl group of 8 to 50 carbon atoms.
  • Ar 131 and Ar 132 in the general formula (5) are naphthyl groups.
  • the Ar 131 is a 2-naphthyl group and the Ar 132 is a 1-naphthyl group, or the Ar 131 is a 2-naphthyl group, and the Ar 132 is 1-naphthyl group. More preferably, it is a group.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the compound included in the light emitting layer of this embodiment include the aromatic hydrocarbon groups exemplified in the above embodiment.
  • a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthryl group are particularly preferable, and more specifically, a phenyl group, 2- A biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.
  • heterocyclic group having 5 to 30 ring atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the aromatic heterocyclic groups exemplified in the above embodiment.
  • Examples of the alkyl group having 1 to 20 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the alkyl groups exemplified in the above embodiment.
  • the linear or branched alkyl group in the compound represented by the general formula (2A) contained in the light emitting layer of the present embodiment preferably has 1 to 10 carbon atoms, and preferably 1 to 6 carbon atoms. Further preferred.
  • the linear or branched 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 Is preferred.
  • the number of ring-forming carbon atoms of the cycloalkyl group in the compound represented by the general formula (2A) contained in the light emitting layer of the present embodiment is preferably 3 to 10, and more preferably 5 to 8.
  • a cyclopentyl group and a cyclohexyl group are preferable.
  • Examples of the alkoxy group having 1 to 20 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the alkoxy groups exemplified in the above embodiment.
  • Examples of the aryloxy group having 6 to 30 ring carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the aryloxy groups exemplified in the above embodiment.
  • Examples of the arylthio group having 6 to 30 ring carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the arylthio groups exemplified in the above embodiment.
  • Examples of the trialkylsilyl group having 3 to 40 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the trialkylsilyl groups exemplified in the above embodiment.
  • Examples of the arylsilyl group having 8 to 60 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. It is done.
  • Examples of the dialkylarylsilyl group having 8 to 50 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include, for example, the alkyl groups exemplified as the alkyl group having 1 to 20 carbon atoms. And a dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 20 ring carbon atoms.
  • the carbon number of the dialkylarylsilyl group is preferably 8-30.
  • the two alkyl groups in the dialkylarylsilyl group may be the same or different.
  • Examples of the alkyldiarylsilyl group having 13 to 50 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include, for example, the alkyl groups exemplified as the alkyl group having 1 to 20 carbon atoms.
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • the two aryl groups may be the same or different from each other.
  • the triarylsilyl group having 18 to 60 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include, for example, the aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • a triarylsilyl group having three groups The carbon number of the triarylsilyl group is preferably 18-30.
  • the three aromatic hydrocarbon groups may be the same or different.
  • Specific examples of the compound represented by the general formula (2A) contained in the light emitting layer of the present embodiment include the following compounds in addition to the compounds described in the first embodiment.
  • the light emitting material described in the first embodiment can be used as the light emitting material.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • at least one light emitting layer may be a combination of the compound contained in the hole transport layer described in the above embodiment and the compound contained in the light emitting layer.
  • the light emitting layer may be a fluorescent light emitting layer or a phosphorescent light emitting layer.
  • 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 agent to the light emitting layer hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.
  • a general hole injection / transport material or the like can be used as the charge injection auxiliary agent.
  • 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.
  • the organic EL element of the present invention can be suitably used as an electronic device such as a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicular lamp.
  • a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicular lamp.
  • 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 the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and the following compound (HI-1) is first formed so as to cover the transparent electrode on the surface where the ITO transparent electrode line is formed. ) was deposited to form a 5 nm thick HI-1 film, and a hole injection layer was formed.
  • the following compound HT-1 was deposited as a first hole transporting material to form an HT-1 film having a thickness of 80 nm to form a first hole transporting layer.
  • the following compound HT-2 (compound 1 obtained in Synthesis Example 1) is deposited to form a 15 nm-thick HT-2 film, and the second hole transport A layer was formed.
  • Compound BH-1 was vapor-deposited on this HT-2 film to form a light emitting layer having a thickness of 25 nm.
  • the following compound (BD1) was co-deposited as a fluorescent material.
  • the concentration of Compound BD1 was 5.0% by mass. This co-deposited film functions as a light emitting layer.
  • the following compound ET-1 was deposited to form an ET-1 film having a thickness of 20 nm to form a first electron transport layer.
  • the following compound ET-2 was vapor-deposited on this ET-1 film to form an ET-2 film having a thickness of 5 nm, thereby forming a second electron transport layer.
  • LiF was deposited on the ET-2 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 3 The organic EL devices of Examples 2 to 3 were produced in the same manner as in Example 1 except that the compounds in the second hole transport layer and the light emitting layer in Example 1 were changed to the compounds shown in Table 1. .
  • Comparative examples 1 to 3 In the organic EL elements of Comparative Examples 1 to 3, except that at least one of the compound HT-2 of the second hole transport layer and the compound BH-1 of the light emitting layer in Example 1 was changed to the compounds shown in Table 1. Was prepared in the same manner as in Example 1.
  • Main peak wavelength ⁇ p (unit: nm) was determined from the obtained spectral radiance spectrum.
  • External quantum efficiency EQE (unit:%) was calculated from the obtained spectral radiance spectrum on the assumption that Lambtian radiation was performed.
  • the organic EL element of Example 1 was higher in luminous efficiency and longer in life than the organic EL elements of Comparative Examples 1 to 3.
  • the organic EL element of Example 1 has an external quantum efficiency EQE of 2.3 times, a lifetime LT80 of 1.3 times, a high luminous efficiency, and a long lifetime compared to the organic EL element of Comparative Example 1. It turns out that.
  • the organic EL elements of Examples 2 and 3 were higher in luminous efficiency and longer in life than the organic EL elements of Comparative Examples 1 to 3. .
  • the organic EL element of the present invention has high luminous efficiency and can be used for electronic devices such as lighting devices and display devices as long-life organic EL elements.

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Abstract

L'invention concerne un élément électroluminescent présentant les caractéristiques suivantes : l'élément électroluminescent est muni d'une électrode positive, d'une électrode négative agencée en face de l'électrode positive, et d'une couche organique placée entre l'électrode positive et l'électrode négative ; la couche organique est munie dans l'ordre indiqué à partir du côté de l'électrode positive d'une couche de transport de trous et d'une couche électroluminescente ; la couche de transport de trous contient un composé représenté par la formule générale (1) ; et la couche électroluminescente contient soit un composé représenté par la formule générale (10), soit un composé représenté par la formule générale (11).
PCT/JP2013/071248 2012-08-10 2013-08-06 Élément électroluminescent organique et appareil électronique WO2014024880A1 (fr)

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JP2017178832A (ja) * 2016-03-30 2017-10-05 Jnc株式会社 自己組織化し得る多環式芳香族化合物およびそれを用いた有機ｅｌ素子
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WO2019088281A1 (fr) * 2017-11-06 2019-05-09 保土谷化学工業株式会社 Composé à structure cyclique indénocarbazole, et élément électroluminescent organique
CN109796450A (zh) * 2017-11-16 2019-05-24 江苏三月光电科技有限公司 一种以吡啶并吲哚为核心的化合物及其在电致发光器件上的应用
TWI688137B (zh) * 2015-03-24 2020-03-11 學校法人關西學院 有機電場發光元件、顯示裝置以及照明裝置
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US11581487B2 (en) 2017-04-26 2023-02-14 Oti Lumionics Inc. Patterned conductive coating for surface of an opto-electronic device
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US11730012B2 (en) 2019-03-07 2023-08-15 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11985841B2 (en) 2020-12-07 2024-05-14 Oti Lumionics Inc. Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating

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US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
JP5520423B1 (ja) * 2012-09-03 2014-06-11 保土谷化学工業株式会社 インデノアクリダン環構造を有する化合物および有機エレクトロルミネッセンス素子
TWI688137B (zh) * 2015-03-24 2020-03-11 學校法人關西學院 有機電場發光元件、顯示裝置以及照明裝置
JP7206319B2 (ja) 2015-08-21 2023-01-17 三星ディスプレイ株式會社 有機発光素子
US11968890B2 (en) 2015-08-21 2024-04-23 Samsung Display Co., Ltd. Organic light-emitting device
US11672173B2 (en) 2015-08-21 2023-06-06 Samsung Display Co., Ltd. Organic light-emitting device
JP2021132221A (ja) * 2015-08-21 2021-09-09 三星ディスプレイ株式會社Samsung Display Co., Ltd. 有機発光素子
JP2017178832A (ja) * 2016-03-30 2017-10-05 Jnc株式会社 自己組織化し得る多環式芳香族化合物およびそれを用いた有機ｅｌ素子
US11594700B2 (en) 2016-11-16 2023-02-28 Hodogaya Chemical Co., Ltd. Organic electroluminescent device
US11581487B2 (en) 2017-04-26 2023-02-14 Oti Lumionics Inc. Patterned conductive coating for surface of an opto-electronic device
JP7213820B2 (ja) 2017-11-06 2023-01-27 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
JPWO2019088281A1 (ja) * 2017-11-06 2020-11-26 保土谷化学工業株式会社 インデノカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子
CN111316462B (zh) * 2017-11-06 2023-04-18 保土谷化学工业株式会社 具有茚并咔唑环结构的化合物及有机电致发光元件
CN111316462A (zh) * 2017-11-06 2020-06-19 保土谷化学工业株式会社 具有茚并咔唑环结构的化合物及有机电致发光元件
WO2019088281A1 (fr) * 2017-11-06 2019-05-09 保土谷化学工業株式会社 Composé à structure cyclique indénocarbazole, et élément électroluminescent organique
CN109796450B (zh) * 2017-11-16 2022-08-30 江苏三月科技股份有限公司 一种以吡啶并吲哚为核心的化合物及其在电致发光器件上的应用
CN109796450A (zh) * 2017-11-16 2019-05-24 江苏三月光电科技有限公司 一种以吡啶并吲哚为核心的化合物及其在电致发光器件上的应用
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11730012B2 (en) 2019-03-07 2023-08-15 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11985841B2 (en) 2020-12-07 2024-05-14 Oti Lumionics Inc. Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating

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