WO2012033061A1 - Élément électroluminescent organique et matériau de transport de charges - Google Patents

Élément électroluminescent organique et matériau de transport de charges Download PDF

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WO2012033061A1
WO2012033061A1 PCT/JP2011/070189 JP2011070189W WO2012033061A1 WO 2012033061 A1 WO2012033061 A1 WO 2012033061A1 JP 2011070189 W JP2011070189 W JP 2011070189W WO 2012033061 A1 WO2012033061 A1 WO 2012033061A1
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group
ring
general formula
substituent
atom
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Japanese (ja)
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北村　哲
渡辺　康介
陽介 山本
伊勢　俊大
外山　弥
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富士フイルム株式会社
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Priority to KR1020137008356A priority Critical patent/KR101606244B1/ko
Priority to KR1020167007113A priority patent/KR101698148B1/ko
Publication of WO2012033061A1 publication Critical patent/WO2012033061A1/fr

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Definitions

  • the present invention relates to an organic electroluminescent element and a charge transport material.
  • Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they can emit light with high luminance when driven at a low voltage.
  • An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.
  • a doped element using a light emitting layer in which a light emitting material is doped in a host material is widely used.
  • Development of the charge transport material contained in the host material used for a light emitting layer and other organic layers is also performed actively.
  • a benzene ring substituted with triphenylene such as the compounds represented by ref-1, ref-2, and ref-3 below, consists of a benzene ring at the meta position with respect to the triphenylene.
  • An organic electroluminescent device comprising a triphenylene compound having a substituent is described.
  • Patent Document 2 describes an organic electroluminescence device containing a compound in which a fluorene ring is substituted on an anthracene ring substituted with triphenylene, such as a compound represented by ref-4 below.
  • Patent Documents 3 to 5 also describe organic electroluminescent elements containing a compound having a triphenylene structure and a fluorene structure.
  • the organic electroluminescence device using the compound having a triphenylene structure described in Patent Document 1 has a significantly reduced luminous efficiency after being stored at a high temperature.
  • the organic electroluminescent device using the compound having a triphenylene structure described in Patent Documents 2 to 5 is less prone to decrease in luminous efficiency after storage at high temperature, but the lowest excited triplet (T 1 ) energy. Therefore, it was found that when used in a phosphorescent element, the light emission was quenched, resulting in low efficiency.
  • An organic electroluminescent element that exhibits high efficiency even after high-temperature storage has been demanded for applications exposed to high temperatures such as outdoor applications and in-vehicle applications.
  • an aromatic 6-membered ring is present at a specific position of the triphenylene skeleton, and sp at the meta position with respect to triphenylene of the aromatic 6-membered ring.
  • a condensed ring in which a 5-membered or 6-membered ring containing 3 carbon atoms and at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocycle consisting of only a single ring are condensed It has been found that the above problems can be solved by a compound in which a monovalent group obtained by removing one hydrogen atom from a group having a substituted group (hereinafter also referred to as “sp 3 carbon-containing condensed ring group”) is substituted. That is, the present invention can be achieved by the following means.
  • An organic electroluminescent element comprising a substrate and a pair of electrodes comprising an anode and a cathode, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the organic layers has the following general formula ( The organic electroluminescent element containing the compound represented by 1).
  • R S1 represents a group represented by the following general formula (S1).
  • X 1 , X 2 , X 3 , and X 4 each independently represent a carbon atom or a nitrogen atom.
  • L 1 represents a single bond or a linking group composed of at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocycle consisting of only a single ring.
  • the linking group may have a substituent selected from the following substituent group W.
  • a 1 is a fused 5- or 6-membered ring containing sp 3 carbon atoms and at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocyclic ring consisting of only a single ring.
  • R A , R B , and R C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, a halogen atom, or the aforementioned
  • a 1 Represents a condensed ring group and a group obtained by combining these.
  • R A , R B and R C When a plurality of R A , R B and R C are present, they may be the same or different from each other, but R A and R B are not groups having the same structure as R S1 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • d1 represents an integer of 0 to 4.
  • the carbon atom that is not bonded to RD represents ⁇ CH—.
  • Substituent group W an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a fluorine atom, the condensed ring group represented by A 1 above, and Group obtained by combining these) [2]
  • the condensed ring in A 1 is represented by the following general formula (A-1), (A-2), (A-3), (A-4), or (A-5).
  • the organic electroluminescent element as described.
  • X a represents a X b, X c, X d , X e, X f, X g, and X h are each independently C (Rb 25) or a nitrogen atom.
  • Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each independently C (Ra 15 ) (Ra 16 ), oxygen atom, sulfur atom, N (Ra 17 ), Si (Ra 18 ) (Ra 19 ) , C ⁇ O, P ( ⁇ O) (Rb 26 ), or S ( ⁇ O) 2 .
  • Ra 1 ⁇ Ra 19 represents a substituent group selected from each independently a hydrogen atom or the following substituent group W A.
  • Rb 1 to Rb 26 each independently represents a hydrogen atom or a substituent selected from the following substituent group W. Two adjacent members out of Ra 1 to Ra 19 and Rb 1 to Rb 26 may combine to form a ring having sp 3 carbon atoms.
  • Substituent group W A alkyl group, an aryl group consisting of mono- alone, and group substituent group W substituent attached to these selected from Substituent Group W: alkyl group, an aryl group consisting of mono- alone, heteroaryl group consisting of monocyclic only, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by a 1, and groups obtained by combining these) [3]
  • X L represents C (Rb 27 ) or a nitrogen atom.
  • R L represents a substituent selected from the following substituent group W. When a plurality of R L are present, they may be the same as each other Rb 27 represents a hydrogen atom or a substituent selected from the following substituent group W. Rb 27 may be the same as or different from each other when there are a plurality of Rb 27.
  • L1 represents an integer of 0 to 4.
  • L2 represents an integer of 0 to 3.
  • the general formula (L-1) represents a single bond, and * represents a binding site.
  • Substituent group W alkyl group, cycloalkyl group, aryl group consisting of only a single ring, heteroaryl group consisting of only a single ring, silyl group, cyano group, fluorine atom, represented by A 1 in the general formula (1) Fused ring groups and groups obtained by combining them) [4]
  • the organic electroluminescence device according to any one of [1] to [3], wherein the compound represented by the general formula (1) is represented by the following general formula (2) or (3).
  • R S2 represents a group represented by the following general formula (S2).
  • R A , R B and R C each independently represents an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group or a halogen atom.
  • R A , R B , and R C may be the same or different from each other, but R A and R B are not groups having the same structure as R S2 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • R L represents a substituent selected from the following substituent group W. When a plurality of R L are present, they may be the same as or different from each other.
  • L1 represents an integer of 0 to 4.
  • L2 represents an integer of 0 to 3.
  • Ra 1 and Ra 2 each independently represents a hydrogen atom or a substituent selected from Substituent Group W A. When a plurality of Ra 1 and Ra 2 are present, they may be the same as or different from each other.
  • R b represents a substituent selected from the following substituent group W. When a plurality of R b are present, they may be the same as or different from each other.
  • b2 represents an integer of 0 to 4.
  • b3 represents an integer of 0 to 3.
  • n2 represents 1 or 2.
  • Two adjacent ones of Ra 1 , Ra 2 and R b may be combined to form a ring having sp 3 carbon atoms.
  • Substituent group W A alkyl group, a monocyclic only consists aryl group, and group substituent group substituent is bonded to these selected from the following substituent group W W: alkyl group, a cycloalkyl group, a monocyclic only comprising an aryl group, a heteroaryl group consisting of monocyclic only, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by a 1, and groups obtained by combining these)
  • R S3 represents a group represented by the following general formula (S3).
  • R A , R B and R C each independently represents an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group or a halogen atom.
  • R A , R B , and R C may be the same or different from each other, but R A and R B are not groups having the same structure as R S3 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • R L represents a substituent selected from the following substituent group W. When a plurality of R L are present, they may be the same as or different from each other.
  • L1 represents an integer of 0 to 4.
  • L2 represents an integer of 0 to 3.
  • Ra represents a substituent selected from a hydrogen atom or the following substituent group W A. Ra may be the same as or different from each other.
  • R b represents a substituent selected from the following substituent group W. When a plurality of R b are present, they may be the same as or different from each other.
  • b3 represents an integer of 0 to 3.
  • n3 represents 1 or 2. Two adjacent ones of Ra and Rb may be bonded to form a ring having sp 3 carbon atoms.
  • Substituent group W A An alkyl group, an aryl group consisting of only a single ring, and a group in which a substituent selected from the following substituent group W is bonded.
  • Substituent group W From an alkyl group, a cycloalkyl group, and a single ring only Aryl groups, heteroaryl groups consisting only of a single ring, silyl groups, cyano groups, fluorine atoms, fused ring groups represented by A 1 in the general formula (1), and groups obtained by combining these)
  • [5] The organic electroluminescence device according to any one of [1] to [4], wherein the light emitting layer contains at least one phosphorescent material.
  • [6] The organic electroluminescence device according to [5], wherein the phosphorescent material is represented by the following general formula (E-1).
  • Z 1 and Z 2 each independently represents a carbon atom or a nitrogen atom.
  • a 1 represents an atomic group that forms a 5- or 6-membered heterocycle with Z 1 and a nitrogen atom.
  • B 1 represents an atomic group that forms a 5- or 6-membered ring with Z 2 and a carbon atom.
  • (XY) represents a monoanionic bidentate ligand.
  • n E1 represents an integer of 1 to 3.
  • the organic electroluminescence device according to [6], wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2).
  • a E1 to A E8 each independently represents a nitrogen atom or C—R E.
  • R E represents a hydrogen atom or a substituent.
  • (XY) represents a monoanionic bidentate ligand.
  • n E2 represents an integer of 1 to 3.
  • the organic electroluminescence device according to any one of [1] to [9], wherein at least one organic layer is formed by film formation by a solution coating method.
  • the organic electroluminescence device according to any one of the above [1] to [10], wherein the organic layer containing the compound represented by the general formula (1) is formed by a solution coating method.
  • a light-emitting device using the organic electroluminescent element according to any one of [1] to [11].
  • the organic electroluminescent element which has the outstanding luminous efficiency and durability, and also has a low drive voltage and is excellent in heat resistance can be provided.
  • substituent groups A and B are defined as follows.
  • An alkyl group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.
  • alkenyl groups preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.
  • alkynyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentyny
  • Particularly preferably 0 to 10 carbon atoms such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.
  • an alkoxy group preferably having 1 to 30 carbon atoms, Preferably it has 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.
  • an aryloxy group preferably having 6 to 30 carbon atoms, More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms.
  • heterocyclic oxy group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • a heterocyclic oxy group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • an acyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms.
  • Benzoyl, formyl, pivaloyl, etc. an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms such as methoxycarbonyl, ethoxy Carbonyl, etc.), an aryloxycarbonyl group (preferably having a carbon number)
  • the number of carbon atoms is 7 to 30, more preferably 7 to 20, and particularly preferably 7 to 12, and examples thereof include phenyloxycarbonyl.
  • An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy, etc.), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and alkoxycarbonylamino groups (preferably having 2-2 carbon atoms).
  • an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino).
  • an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino).
  • a sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), carbamoyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.), an arylthio group (preferably 6 to 30 carbon atoms).
  • Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carb
  • Is for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like.
  • a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl).
  • a aryloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.).
  • These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
  • the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
  • the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
  • alkyl group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.
  • alkenyl groups preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.
  • alkynyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.
  • aryl groups preferably having 6 to 30 carbon atoms, preferably 1
  • the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.
  • the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.
  • the organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on the substrate, the organic layer Of these, at least one layer contains a compound represented by the following general formula (1).
  • R S1 represents a group represented by the following general formula (S1).
  • X 1 , X 2 , X 3 , and X 4 each independently represent a carbon atom or a nitrogen atom.
  • L 1 represents a single bond or a linking group composed of at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocycle consisting of only a single ring.
  • the linking group may have a substituent selected from the following substituent group W.
  • a 1 is a fused 5- or 6-membered ring containing sp 3 carbon atoms and at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocyclic ring consisting of only a single ring.
  • R A , R B , and R C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, a halogen atom, or the aforementioned
  • a 1 Represents a condensed ring group and a group obtained by combining these.
  • R A , R B and R C When a plurality of R A , R B and R C are present, they may be the same or different from each other, but R A and R B are not groups having the same structure as R S1 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • d1 represents an integer of 0 to 4.
  • the carbon atom that is not bonded to RD represents ⁇ CH—.
  • Substituent group W an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a fluorine atom, the condensed ring group represented by A 1 above, and Group obtained by combining these)
  • the host material of the light emitting layer or the charge transport material of the organic layer between the light emitting layer and the cathode and adjacent to the light emitting layer has an energy gap in a thin film state than the light emitting material (if the light emitting material is a phosphorescent light emitting material, a thin film
  • the lowest excited triplet (T 1 ) energy in the state is large, quenching of light emission can be suppressed, which is advantageous for improving efficiency.
  • introduction of a condensed ring structure into a compound increases the molecular weight of the compound, increases Tg, and improves heat resistance.
  • a compound having a triphenylene skeleton is substituted with a condensed ring in which two or more aromatic hydrocarbon rings or aromatic heterocyclic rings such as a naphthalene ring, an anthracene ring, or a quinoline ring are condensed.
  • a condensed ring in which two or more aromatic hydrocarbon rings or aromatic heterocyclic rings such as a naphthalene ring, an anthracene ring, or a quinoline ring are condensed.
  • the triphenylene skeleton and the sp 3 carbon-containing fused ring group were linked at the meta position with an aromatic 6-membered ring, as in the compound represented by the general formula (1). It has been found that a compound having a different structure can improve the heat resistance without lowering the T 1 energy. This is considered that the T 1 energy does not decrease because the ⁇ -conjugated system is interrupted at the sp 3 carbon atom of the sp 3 carbon-containing fused ring group. Therefore, by using the compound represented by the general formula (1), it is possible to obtain an element that is excellent in all aspects of efficiency, driving voltage, driving durability, and heat resistance.
  • the T 1 energy in the film state of the compound represented by the general formula (1) is preferably 2.39 eV (55 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less and preferably 2.47 eV (57. 0 kcal / mol) to 3.04 eV (70 kcal / mol) is more preferable, and 2.52 eV (58.0 kcal / mol) to 2.82 eV (65 kcal / mol) is more preferable.
  • the T 1 energy is preferably in the above range.
  • R S1 represents a group represented by the following general formula (S1).
  • X 1 , X 2 , X 3 , and X 4 each independently represent a carbon atom or a nitrogen atom.
  • L 1 represents a single bond or a linking group composed of at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocycle consisting of only a single ring.
  • the linking group may have a substituent selected from the following substituent group W.
  • a 1 is a fused 5- or 6-membered ring containing sp 3 carbon atoms and at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocyclic ring consisting of only a single ring.
  • R A , R B , and R C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, a halogen atom, or the aforementioned
  • a 1 Represents a condensed ring group and a group obtained by combining these.
  • R A , R B and R C When a plurality of R A , R B and R C are present, they may be the same or different from each other, but R A and R B are not groups having the same structure as R S1 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • d1 represents an integer of 0 to 4.
  • the carbon atom that is not bonded to RD represents ⁇ CH—.
  • Substituent group W an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a fluorine atom, the condensed ring group represented by A 1 above, and Group obtained by combining these)
  • the compound represented by the general formula (1) can also be represented by the following general formula (1) ′.
  • an isotope such as deuterium atom
  • all hydrogen atoms in the compound may be replaced with isotopes, or a mixture in which a part is a compound containing an isotope may be used.
  • Substituent group W is an alkyl group, a cycloalkyl group, a monocyclic only consists aryl group, a heteroaryl group consisting of mono- alone, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by A 1 and, It consists of groups obtained by combining these.
  • the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms.
  • propyl group, a methyl group, an ethyl group, n- propyl group, n- butyl group, or t- butyl group is more preferable.
  • the cycloalkyl group is preferably a cycloalkyl group having 3 to 10 carbon atoms, more preferably 4 to 6 carbon atoms, and still more preferably 5 or 6 carbon atoms.
  • a cyclopentyl group and a cyclohexyl group are preferred.
  • aryl group consisting of only a single ring a phenyl group is preferable.
  • the heteroaryl group consisting only of a single ring is preferably a heteroaryl group consisting only of a nitrogen-containing or sulfur-containing monocycle, more preferably a pyridyl group, a pyrazyl group, a pyrimidyl group, or a thiophenyl group, and more preferably a pyridyl group.
  • Specific examples and preferred ranges of condensed ring group represented by A 1 is the same as A 1 to be described later.
  • Groups obtained by combining these include alkyl groups substituted with aryl groups, aryl groups substituted with alkyl groups, silyl groups substituted with alkyl groups or aryl groups (preferably trimethylsilyl groups or triphenylsilyl groups), fluoroalkyls Examples include a group (preferably a perfluoroalkyl group, more preferably a trifluoromethyl group), a group represented by the following general formula (Arx), and the like.
  • Ara to Ard each independently represent an aromatic hydrocarbon ring consisting of only a single ring, an aromatic heterocycle consisting of only a single ring, or a condensed ring represented by A 1 .
  • nb each independently represents 0 or 1
  • nc and nd represent 1.
  • Ara and Arb each represent a single bond
  • Ara to Ard each independently represents an alkyl group, only a single ring And may be substituted with an aryl group consisting of, a heteroaryl group consisting of only a single ring, a silyl group, a cyano group, a fluorine atom, or a condensed ring group represented by A 1.
  • * represents a bonding site.
  • the aromatic hydrocarbon ring consisting of only a single ring is preferably a benzene ring.
  • the aromatic heterocycle consisting of only a single ring is preferably a nitrogen-containing aromatic heterocycle or a sulfur-containing aromatic heterocycle, and more preferably a nitrogen-containing aromatic heterocycle.
  • a nitrogen-containing aromatic heterocyclic ring a pyridine ring, a pyrazine ring and a pyrimidine ring are preferable, and a pyridine ring is more preferable.
  • the sulfur-containing aromatic heterocycle is preferably a thiophene ring. Specific examples and preferred ranges of the condensed ring represented by A 1 are the same as those described later.
  • na and nb are preferably 0.
  • a 1 is selected from the group consisting of a 5-membered or 6-membered ring containing sp 3 carbon atoms, an aromatic hydrocarbon ring consisting of only a single ring, and an aromatic heterocycle consisting of only a single ring.
  • a monovalent group obtained by removing one hydrogen atom from a condensed ring condensed with at least one ring.
  • the monovalent group may have a substituent selected from the substituent group W.
  • a 1 in the general formula (1) of the present invention is a 5-membered or 6-membered ring containing sp 3 carbon atoms, an aromatic hydrocarbon ring consisting of only a single ring, and an aromatic consisting of only a single ring.
  • the ⁇ -conjugated system is interrupted at the sp 3 carbon atom, the T 1 energy does not decrease, and the heat resistance is improved.
  • the 5-membered or 6-membered ring containing sp 3 carbon atom in A 1 is preferably a saturated 5-membered or 6-membered ring, and a cyclopentane ring, cyclohexane ring, or a saturated 5-membered ring containing at least one heteroatom or A 6-membered ring is more preferable, a cyclopentane ring or a cyclohexane ring is further preferable, and a cyclopentane ring is particularly preferable.
  • an oxygen atom, a sulfur atom, a nitrogen atom, a silicon atom, or a phosphorus atom is preferable, an oxygen atom, a sulfur atom, or a nitrogen atom is more preferable, and an oxygen atom or a nitrogen atom is still more preferable.
  • the saturated 5-membered or 6-membered ring containing a nitrogen atom is preferably a pipediline ring, piperazine ring or pyrrolidine ring, more preferably a pipediline ring or piperazine ring, and still more preferably a pipediline ring.
  • the saturated 5-membered or 6-membered ring containing an oxygen atom a tetrahydropyran ring, a dioxane ring, a tetrahydrofuran ring, and a 1,3-dioxolane ring are preferable, and a dioxane ring and a 1,3-dioxolane ring are more preferable.
  • the saturated 5-membered or 6-membered ring containing a sulfur atom is preferably a 1,4-dithiane ring or a tetrahydrothiophene ring, and more preferably a 1,4-dithiane ring.
  • the 5-membered or 6-membered ring containing sp 3 carbon atom in A 1 may contain a carbonyl group, a sulfonyl group, or a phosphate group.
  • a 1 contains an aromatic hydrocarbon ring consisting of only a single ring
  • the aromatic hydrocarbon ring consisting of only this single ring is preferably a benzene ring.
  • the aromatic heterocycle consisting only of this monocycle is preferably a nitrogen-containing aromatic heterocycle or a sulfur-containing aromatic heterocycle, More preferred are group heterocycles.
  • the nitrogen-containing aromatic heterocycle a pyridine ring, a pyrazine ring, a pyrimidine ring and a triazine ring are preferable, and a pyridine ring is more preferable.
  • the sulfur-containing aromatic heterocycle is preferably a thiophene ring.
  • the condensed ring in A 1 is preferably a ring represented by the following general formula (A-1), (A-2), (A-3), (A-4), or (A-5).
  • X a represents a X b, X c, X d , X e, X f, X g, and X h are each independently C (Rb 25) or a nitrogen atom.
  • Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each independently C (Ra 15 ) (Ra 16 ), oxygen atom, sulfur atom, N (Ra 17 ), Si (Ra 18 ) (Ra 19 ) , C ⁇ O, P ( ⁇ O) (Rb 26 ), or S ( ⁇ O) 2 .
  • Ra 1 ⁇ Ra 19 represents a substituent group selected from each independently a hydrogen atom or the following substituent group W A.
  • Rb 1 to Rb 26 each independently represents a hydrogen atom or a substituent selected from the following substituent group W. Two adjacent members out of Ra 1 to Ra 19 and Rb 1 to Rb 26 may combine to form a ring having sp 3 carbon atoms.
  • Substituent group W A alkyl group, a monocyclic only consists aryl group, and group substituent group substituent is bonded to these selected from the following substituent group W W: alkyl group, a cycloalkyl group, a monocyclic only comprising an aryl group, a heteroaryl group consisting of monocyclic only, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by a 1, and groups obtained by combining these)
  • Ra 1 and Ra 2 represents a substituent, each being independently selected from a hydrogen atom or a substituent group W A.
  • Ra 1 and Ra 2 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting only of a single ring, and more preferably an alkyl group, from the viewpoint of charge transportability and chemical stability.
  • the alkyl group an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 5 carbon atoms is more preferable, a methyl group, an ethyl group, an n-propyl group, or an n-butyl group is further preferable, and a methyl group is preferable. Particularly preferred.
  • a phenyl group is preferred. It is also preferred that Ra 1 and Ra 2 are bonded to each other so that the ring represented by the general formula (A-1) forms a spirobifluorene ring.
  • Rb 1 to Rb 8 each independently represents a hydrogen atom or a substituent selected from substituent group W.
  • Rb 1 to Rb 8 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, more preferably a hydrogen atom or an alkyl group, and even more preferably a hydrogen atom, from the viewpoint of charge transportability and chemical stability.
  • the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and still more preferably a t-butyl group.
  • a phenyl group is preferred.
  • Ra 1 , Ra 2 and Rb 1 to Rb 8 may be bonded to form a ring having sp 3 carbon atoms.
  • the ring is preferably a cycloalkane ring, more preferably a cycloalkane ring having 3 to 10 carbon atoms, and still more preferably a cyclohexane ring.
  • Ra 2 and Rb 8 are preferably bonded to each other to form a ring having sp 3 carbon atoms.
  • at least one of Ra 1 , Ra 2 and Rb 1 to Rb 8 represents a hydrogen atom, and any one of the hydrogen atoms is removed.
  • Rb 1 to Rb 8 are particularly hydrogen atoms, and any one of the hydrogen atoms is removed and bonded to L 1 as A 1 in the general formula (1) It is preferable to do.
  • Ra 3 to Ra 6 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably a hydrogen atom, from the viewpoint of charge transport properties and chemical stability.
  • the preferable range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferable range when Ra 1 and Ra 2 are an alkyl group or an aryl group consisting of only a single ring.
  • Rb 9 to Rb 16 each independently represent a hydrogen atom or a substituent selected from substituent group W.
  • Rb 9 to Rb 16 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably a hydrogen atom, from the viewpoint of charge transportability and chemical stability.
  • the preferred range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferred range when Rb 1 to Rb 8 are an alkyl group or an aryl group consisting of only a single ring.
  • Two adjacent members out of Ra 3 to Ra 6 and Rb 9 to Rb 16 may be bonded to form a ring having sp 3 carbon atoms.
  • the ring is preferably a cycloalkane ring, more preferably a cycloalkane ring having 3 to 10 carbon atoms, and still more preferably a cyclohexane ring.
  • Rb 12 and Rb 13 are bonded to each other to form a ring having sp 3 carbon atoms.
  • at least one of Ra 3 to Ra 6 and Rb 9 to Rb 16 represents a hydrogen atom, and any one of the hydrogen atoms is removed. Then, it binds to L 1 as A 1 in the general formula (1).
  • Rb 9 to Rb 16 are particularly hydrogen atoms, and any one of the hydrogen atoms is removed and bonded to L 1 as A 1 in the general formula (1) It is preferable to do.
  • Ra 15 ⁇ Ra 19 represents a substituent, each being independently selected from a hydrogen atom or a substituent group W A.
  • Ra 15 and Ra 16 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably a hydrogen atom.
  • the preferable range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferable range when Ra 1 and Ra 2 are an alkyl group or an aryl group consisting of only a single ring.
  • Ra 17 is preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably an aryl group consisting of only a hydrogen atom or a single ring.
  • the preferable range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferable range when Ra 1 and Ra 2 are an alkyl group or an aryl group consisting of only a single ring.
  • Ra 18 and Ra 19 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably an alkyl group or an aryl group consisting of only a single ring.
  • the preferable range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferable range when Ra 1 and Ra 2 are an alkyl group or an aryl group consisting of only a single ring.
  • Rb 26 is preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably an aryl group consisting of only a single ring.
  • Y 1 and Y 2 are each independently C (Ra 15 ) (Ra 16 ), oxygen atom, sulfur atom, N (Ra 17 ), or Si (Ra 18 ) from the viewpoint of charge transportability and chemical stability. It preferably represents (Ra 19 ), preferably represents C (Ra 15 ) (Ra 16 ), an oxygen atom, or N (Ra 17 ), and represents C (Ra 15 ) (Ra 16 ) or an oxygen atom. It is more preferable that it represents C (Ra 15 ) (Ra 16 ).
  • Ra 7 ⁇ Ra 10 are each independently a hydrogen atom or a substituent group W A.
  • Ra 7 to Ra 10 are preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably a hydrogen atom, from the viewpoint of charge transport properties and chemical stability.
  • the preferable range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferable range when Ra 1 and Ra 2 are an alkyl group or an aryl group consisting of only a single ring.
  • X a , X b , X c , and X d each independently represent C (Rb 25 ) or a nitrogen atom.
  • X a represents a nitrogen atom
  • X b , X c , and X d each independently represent C (Rb 25 ) (Rb 26 )
  • X a , X b it is preferable if X c, and the X d represents a C (Rb 25) each independently, X a, X b, and more if X c, and the X d represents a C (Rb 25) independently are preferable.
  • Rb 25 each independently represents a hydrogen atom or a substituent selected from the substituent group W.
  • Rb 25 is preferably a hydrogen atom, an alkyl group, or an aryl group consisting only of a single ring, and more preferably a hydrogen atom, from the viewpoint of charge transportability and chemical stability.
  • the preferred range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferred range when Rb 1 to Rb 8 are an alkyl group or an aryl group consisting of only a single ring.
  • Two adjacent ones of Ra 7 to Ra 10 , Ra 15 to Ra 19 , Rb 25 and Rb 26 may be bonded to form a ring having sp 3 carbon atoms.
  • the ring is preferably a cycloalkane ring, more preferably a cycloalkane ring having 3 to 10 carbon atoms, and still more preferably a cyclohexane ring.
  • Ra 15 in Y 2 and Rb 25 in X d are bonded to each other to form a ring having sp 3 carbon atoms.
  • at least one of Ra 7 to Ra 10 , Ra 15 to Ra 19 , Rb 25 and Rb 26 represents a hydrogen atom, and among the hydrogen atoms, Any one of them is removed and bonded to L 1 as A 1 in the general formula (1).
  • Rb 25 or Rb 26 is a hydrogen atom, and any one of the hydrogen atoms is removed and bonded to L 1 as A 1 in the general formula (1) It is preferable to do.
  • Ra 15 ⁇ Ra 19 represents a substituent, each being independently selected from a hydrogen atom or a substituent group W A.
  • the preferred ranges of Ra 15 to Ra 19 and (Rb 26 ) are the same as those in the general formula (A-3).
  • the preferred range of Y 3 and Y 4 is the same as the preferred range of Y 1 and Y 2 in the general formula (A-3).
  • Ra 11 and Ra 12 are each independently a hydrogen atom or a substituent group W A.
  • the preferred ranges of Ra 11 and Ra 12 are the same as the preferred ranges of Ra 7 to Ra 10 in the general formula (A-3).
  • X e , X f , X g , and X h each independently represent C (Rb 25 ) or a nitrogen atom.
  • the preferred range of Rb 25 is the same as that in the general formula (A-3).
  • Preferred ranges of X e , X f , X g , and X h are the same as the preferred ranges of X a , X b , X c , and X d in the general formula (A-3).
  • Two adjacent members out of Ra 11 , Ra 12 , Ra 15 to Ra 19 , Rb 25 and Rb 26 may be bonded to form a ring having sp 3 carbon atoms.
  • the ring is preferably a cycloalkane ring, more preferably a cycloalkane ring having 3 to 10 carbon atoms, and still more preferably a cyclohexane ring.
  • Ra 15 in Y 4 and Rb 25 in X h are preferably bonded to each other to form a ring having sp 3 carbon atoms.
  • at least one of Ra 11 , Ra 12 , Ra 15 to Ra 19 , Rb 25 and Rb 26 represents a hydrogen atom, and the hydrogen atom Any one of them is removed and bonded to L 1 as A 1 in the general formula (1).
  • Rb 25 or Rb 26 is a hydrogen atom, and any one of the hydrogen atoms is removed and bonded to L 1 as A 1 in the general formula (1) It is preferable to do.
  • Ra 15 ⁇ Ra 19 represents a substituent, each being independently selected from a hydrogen atom or a substituent group W A.
  • the preferred ranges of Ra 15 to Ra 19 and (Rb 26 ) are the same as those in the general formula (A-3).
  • Y 5 preferably represents C (Ra 15 ) (Ra 16 ), an oxygen atom, or N (Ra 17 ), and more preferably represents C (Ra 15 ) (Ra 16 ), or N (Ra 17 ). , N (Ra 17 ) is more preferable.
  • Ra 13 and Ra 14 are each independently a hydrogen atom or a substituent group W A.
  • the preferred ranges of Ra 13 and Ra 14 are the same as the preferred ranges of Ra 7 to Ra 10 in the general formula (A-3).
  • Rb 17 to Rb 24 each independently represents a hydrogen atom or a substituent selected from substituent group W.
  • the preferred range of Rb 17 to Rb 24 is the same as Rb 1 to Rb 8 in the general formula (A-1).
  • Two adjacent members out of Ra 13 to Ra 19 and Rb 17 to Rb 26 may be bonded to form a ring having sp 3 carbon atoms.
  • the ring is preferably a cycloalkane ring, more preferably a cycloalkane ring having 3 to 10 carbon atoms, and still more preferably a cyclohexane ring.
  • Ra 13 and Ra 14 are preferably bonded to each other to form a ring having sp 3 carbon atoms.
  • the condensed ring represented by the general formula (A-5) at least one of Ra 13 to Ra 19 and Rb 17 to Rb 26 represents a hydrogen atom, and any one of the hydrogen atoms is removed. Then, it binds to L 1 as A 1 in the general formula (1).
  • Ra 17 is a hydrogen atom, and the hydrogen atom is removed and bonded to L 1 as A 1 in the general formula (1).
  • Rb 17 to Rb 24 are particularly hydrogen atoms, and any one of the hydrogen atoms is removed to represent L 1 as A 1 in the general formula (1). It is preferable to bind to.
  • the condensed ring in A 1 is particularly preferably a ring represented by the general formula (A-1) or (A-4) from the viewpoints of charge transportability and chemical stability.
  • R represents a hydrogen atom, an alkyl group or an aryl group.
  • the preferred range of the alkyl group and aryl group is the same as in the substituent group W.
  • L 1 is a single bond or a linkage composed of at least one ring selected from the group consisting of an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocycle consisting of only a single ring. Represents a group.
  • a benzene ring is preferred as the aromatic hydrocarbon ring composed of only this single ring.
  • the aromatic heterocycle consisting of only this monocycle is preferably a nitrogen-containing heterocycle, more preferably a pyridine ring, a pyrazine ring, a pyrimidine ring or a triazine ring, and even more preferably pyridine.
  • L 1 is preferably represented by the following general formula (L-1).
  • X L represents C (Rb 27 ) represents a nitrogen atom.
  • R L represents a substituent selected from the following substituent group W. When a plurality of R L are present, they may be the same as each other.
  • Rb 27 represents a hydrogen atom or a substituent selected from the following substituent group W. Rb 27 may be the same as or different from each other when there are a plurality of Rb 27.
  • L1 represents an integer of 0 to 4.
  • L2 represents an integer of 0 to 3.
  • the general formula (L-1) represents a single bond, and * represents a binding site.
  • Substituent group W alkyl group, cycloalkyl group, aryl group consisting of only a single ring, heteroaryl group consisting of only a single ring, silyl group, cyano group, fluorine atom, represented by A 1 in the general formula (1) Fused ring groups and groups obtained by combining them)
  • X L represents C (Rb 27 ) or a nitrogen atom, and C (Rb 27 ) is preferable from the viewpoint of charge transportability and chemical stability.
  • Rb 27 represents a substituent selected from a hydrogen atom or the following substituent group W. When a plurality of Rb 27 are present, they may be the same as or different from each other.
  • Rb 27 is preferably a hydrogen atom, an alkyl group, or an aryl group consisting of only a single ring, and more preferably a hydrogen atom, from the viewpoint of charge transportability and chemical stability.
  • the preferred range of the alkyl group and the aryl group consisting of only a single ring is the same as the preferred range when Rb 1 to Rb 8 are an alkyl group or an aryl group consisting of only a single ring.
  • R L represents a substituent selected from the substituent group W.
  • R L is preferably an alkyl group, an aryl group consisting of only a single ring, a silyl group, a condensed ring group represented by A 1 and a group obtained by combining these from the viewpoint of charge transportability and chemical stability.
  • alkyl group an aryl group consisting of monocyclic only, monocyclic only consists aryl group fused ring group is substituted, represented by A 1, silyl group in which the alkyl group is substituted, fused ring group represented by A 1, alkyl A condensed ring group represented by A 1 substituted with a group is more preferred, and an alkyl group or a phenyl group substituted with a condensed ring group represented by A 1 is further preferred.
  • L1 represents an integer of 0 to 4, and is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0, from the viewpoint of charge transportability and chemical stability. .
  • L2 represents an integer of 0 to 3, and is preferably an integer of 0 to 2 from the viewpoint of charge transportability and chemical stability.
  • L 1 is preferably linked at the meta position or para position from the viewpoint of charge transportability, chemical stability, and T 1 energy.
  • L 1 Specific examples of L 1 are shown below, but are not limited thereto. In the following specific examples, RL is omitted.
  • R A , R B and R C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, a halogen atom represents the fused ring group represented by a 1, and groups obtained by combining these.
  • the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, and includes a methyl group, an ethyl group, an n-propyl group, and an n-butyl group. Group or t-butyl group is preferred.
  • the cycloalkyl group is preferably a cycloalkyl group having 3 to 10 carbon atoms, more preferably 4 to 6 carbon atoms, still more preferably 5 or 6 carbon atoms, and a cyclopentyl group or a cyclohexyl group is preferable.
  • a phenyl group is preferable.
  • the heteroaryl group consisting only of a single ring is preferably a heteroaryl group consisting only of a nitrogen-containing or sulfur-containing monocycle, more preferably a pyridyl group, a pyrazyl group, a pyrimidyl group, or a thiophenyl group, and more preferably a pyridyl group.
  • R A , R B and R C are preferably an alkyl group, an aryl group consisting only of a single ring, a silyl group and a cyano group, more preferably an alkyl group and an aryl group consisting only of a single ring, and more preferably Is an aryl group consisting of only a single ring.
  • a1 and b1 each independently represents an integer of 0 to 4.
  • a1 and b1 are preferably integers of 0 to 2, more preferably 0 or 1, and even more preferably 0.
  • c1 represents an integer of 0 to 3.
  • c1 is preferably an integer of 0 to 2, more preferably 0 or 1, and still more preferably 0.
  • X 1 , X 2 , X 3 , and X 4 each independently represent a carbon atom or a nitrogen atom.
  • X 2 is preferably a carbon atom, and more preferably X 1 , X 2 , X 3 , and X 4 are all carbon atoms.
  • R D represents a substituent selected from the substituent group W.
  • the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, from the viewpoint of charge transportability.
  • the alkyl group is also preferably an alkyl group substituted with a fluorine atom, more preferably a C 1-4 perfluoroalkyl group, still more preferably a trifluoromethyl group.
  • R D represents a cycloalkyl group
  • the cycloalkyl group is preferably a cycloalkyl group having 3 to 10 carbon atoms, more preferably 4 to 6 carbon atoms, still more preferably 5 or 6 carbon atoms, and cyclopentyl Group or a cyclohexyl group is preferred.
  • RD represents an aryl group consisting of only a single ring
  • the aryl group consisting of only a single ring is preferably a phenyl group.
  • fused ring group R D is represented by A 1 is a phenyl group substituted.
  • the preferred range of the condensed ring represented by A 1 is the same as that described above.
  • heteroaryl groups consisting only of monocyclic, pyridyl group, pyrazyl group, pyrimidyl group, preferably thiophenyl group, a pyridyl group are more preferable.
  • the silyl group is preferably an alkyl group or a silyl group substituted with a phenyl group, more preferably a C 1-4 alkyl group or a silyl group substituted with a phenyl group, A triphenylsilyl group is more preferable.
  • R D represents a fused ring group represented by A 1, as the condensed ring group represented by the A 1, fused ring group wherein the alkyl group represented by A 1 substituted is preferred, C 1 -
  • the condensed ring group represented by A 1 substituted with 4 alkyl groups is more preferred, and the condensed ring group represented by A 1 substituted with a t-butyl group is more preferred.
  • the preferred range of the condensed ring represented by A 1 is the same as that described above.
  • d1 represents an integer of 0 to 4, and is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0, from the viewpoint of charge transportability and easy synthesis. If d1 is 1, from the viewpoint of charge transporting property and durability, R D is preferably substituted with X 2.
  • the compound represented by the general formula (1) is preferably represented by the following general formula (2) or (3), and more preferably represented by the following general formula (2).
  • R S2 represents a group represented by the following General Formula (S2).
  • R A , R B and R C each independently represents an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group or a halogen atom.
  • R A , R B , and R C may be the same or different from each other, but R A and R B are not groups having the same structure as R S2 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • R L represents a substituent selected from the following substituent group W. When a plurality of R L are present, they may be the same as or different from each other.
  • L1 represents an integer of 0 to 4.
  • L2 represents an integer of 0 to 3.
  • Ra 1 and Ra 2 each independently represents a hydrogen atom or a substituent selected from Substituent Group W A. When a plurality of Ra 1 and Ra 2 are present, they may be the same as or different from each other.
  • R b represents a substituent selected from the following substituent group W. When a plurality of R b are present, they may be the same as or different from each other.
  • b2 represents an integer of 0 to 4.
  • b3 represents an integer of 0 to 3.
  • n2 represents 1 or 2.
  • Two adjacent ones of Ra 1 , Ra 2 and R b may be combined to form a ring having sp 3 carbon atoms.
  • Substituent group W A alkyl group, a monocyclic only consists aryl group, and group substituent group substituent is bonded to these selected from the following substituent group W W: alkyl group, a cycloalkyl group, a monocyclic only comprising an aryl group, a heteroaryl group consisting of monocyclic only, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by a 1, and groups obtained by combining these)
  • R A , R B , R C , R D , a1, b1, c1, d1, R L , L1, Ra 1 and Ra 2 are as defined above, and specific examples and The preferable range is also the same.
  • R b has the same meaning as Rb 5 to Rb 8 in formula (A-1) described above, and specific examples and preferred ranges thereof are also the same.
  • b2 represents an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and still more preferably 0.
  • b3 represents an integer of 0 to 3, preferably 0 or 1, more preferably 0.
  • L2 has the same meaning as L2 in formula (L-1) described above, and the preferred range is also the same.
  • n2 is preferably 1.
  • the compound represented by the general formula (2) can also be represented by the following general formula (2) ′.
  • R S3 represents a group represented by the following General Formula (S3).
  • R A , R B and R C each independently represents an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group or a halogen atom.
  • R A , R B , and R C may be the same or different from each other, but R A and R B are not groups having the same structure as R S3 .
  • a1 and b1 each independently represents an integer of 0 to 4.
  • c1 represents an integer of 0 to 3.
  • R D represents a substituent selected from the following substituent group W. If R D is more present, it may be the same or different from each other.
  • R L represents a substituent selected from the following substituent group W. When a plurality of R L are present, they may be the same as or different from each other.
  • L1 represents an integer of 0 to 4.
  • L2 represents an integer of 0 to 3.
  • Ra represents a substituent selected from a hydrogen atom or the following substituent group W A. Ra may be the same as or different from each other.
  • R b represents a substituent selected from the following substituent group W. When a plurality of R b are present, they may be the same as or different from each other.
  • b3 represents an integer of 0 to 3.
  • n3 represents 1 or 2. Two adjacent ones of Ra and Rb may be bonded to form a ring having sp 3 carbon atoms.
  • Substituent group W A An alkyl group, an aryl group consisting of only a single ring, and a group in which a substituent selected from the following substituent group W is bonded.
  • Substituent group W From an alkyl group, a cycloalkyl group, and a single ring only Aryl groups, heteroaryl groups consisting only of a single ring, silyl groups, cyano groups, fluorine atoms, fused ring groups represented by A 1 in the general formula (1), and groups obtained by combining these)
  • R A , R B , R C , R D , a1, b1, c1, d1, R L , and L1 have the same meanings as described above, and specific examples and preferred ranges are also the same.
  • Ra has the same meaning as Ra 11 , Ra 12 , Ra 15 , and Ra 16 in formula (A-4), and specific examples and preferred ranges are also the same.
  • L2 has the same meaning as L2 in formula (L-1) described above, and the preferred range is also the same.
  • Specific examples and preferred ranges of R b are the same as Rb 25 in the general formula (A-3).
  • b3 represents an integer of 0 to 3, preferably 0 or 1, more preferably 0.
  • n3 preferably represents 1.
  • the compound represented by the general formula (3) can also be represented by the following general formula (3) ′.
  • R A , R B , R C , R D , a1, b1, c1, d1, R L , L1, L2, Ra, n3, R b , and b3 are the same as those in general formula (3). It is synonymous and the preferable range is also the same.
  • the molecular weight of the compound represented by the general formula (1) is preferably 400 or more and 1200 or less, more preferably 500 or more and 1000 or less, and more preferably 550 or more and 800 or less. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1000 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.
  • the compound represented by the general formula (1) is preferably contained in the hole blocking layer. If the T 1 energy as a light emitting material for an organic electroluminescent device is small green phosphorescent material than the blue phosphorescent material, or using a red phosphorescent material, a compound represented by the general formula (1), the light emitting layer or a positive It is preferably contained in the pore blocking layer.
  • the T 1 energy can be obtained from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is measured at F-7000 Hitachi Spectrofluorimeter (Hitachi High Technologies) under liquid nitrogen temperature. Use to measure.
  • the T 1 energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.
  • the glass transition temperature (Tg) of the compound represented by the general formula (1) is 80 ° C. or higher and 400 ° C. or lower from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device.
  • the temperature is 100 ° C. or higher and 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower.
  • the compound represented by the above general formula (1) is a method described in JP-A No. 2004-43349, JP-A No. 2004-83481, US 2006/0280965, WO 2009/021107, JP-A 2009-1114068, or the like. Further, it can be synthesized by combining other known reactions. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the compound represented by the general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescence device.
  • the compound represented by the general formula (1) is preferably contained in the organic layer adjacent to the light emitting layer or between the light emitting layer and the cathode and adjacent to the light emitting layer.
  • Examples of the organic layer that may contain the compound represented by the general formula (1) include a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer.
  • a hole blocking layer, an electron blocking layer, etc. can be mentioned, preferably a light emitting layer, an exciton blocking layer, a charge blocking layer, an electron transporting layer, or an electron injection layer, more preferably a light emitting layer.
  • the compound represented by the general formula (1) When the compound represented by the general formula (1) is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99% by weight, preferably 1 to 95% by weight, based on the total weight of the light emitting layer. More preferably, it is contained in an amount of 10 to 95% by mass.
  • the compound represented by the general formula (1) When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and 85 to 100% by mass, based on the total mass of the organic layer. More preferably.
  • the present invention also relates to a charge transport material represented by the general formula (1).
  • the compound represented by the general formula (1) and the charge transport material of the present invention are preferably used for organic electronic elements such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), and organic electroluminescence elements. It can be used and is particularly preferably used for an organic electroluminescent device.
  • the preferred range of the charge transport material represented by the general formula (1) is as described above.
  • the present invention also relates to a composition comprising a compound represented by the general formula (1).
  • the content of the compound represented by the general formula (1) is preferably 30 to 99% by mass, and preferably 50 to 97% by mass with respect to the total solid content in the composition. More preferred is 70 to 96% by mass.
  • Other components that may be contained in the composition of the present invention may be organic or inorganic, and as organic materials, materials described as host materials, fluorescent light emitting materials, phosphorescent light emitting materials, and hydrocarbon materials described later can be applied. A host material, a phosphorescent material, and a hydrocarbon material are preferable.
  • the composition can form an organic layer of an organic electroluminescent element by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.
  • the present invention also relates to a thin film containing the compound represented by the general formula (1).
  • the thin film can be formed using the composition by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.
  • the thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 ⁇ m, still more preferably 1 nm to 200 nm, and particularly preferably 1 nm to 100 nm. is there.
  • the organic electroluminescent element of the present invention is an organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on the substrate, the at least one layer In at least one of the organic layers, the compound represented by the general formula (1) of the present invention is included.
  • at least one of the pair of electrodes, the anode and the cathode is preferably transparent or translucent.
  • Examples of the organic layer include a hole injection layer, a hole transport layer, a block layer (such as a hole block layer and an exciton block layer), and an electron transport layer in addition to the light emitting layer.
  • a plurality of these organic layers may be provided, and when a plurality of layers are provided, they may be formed of the same material, or may be formed of different materials for each layer.
  • the organic electroluminescent element of the present invention preferably contains at least one phosphorescent material in the light emitting layer.
  • FIG. 1 an example of a structure of the organic electroluminescent element which concerns on this invention is shown.
  • a light emitting layer 6 between a pair of electrodes (anode 3 and cathode 9) on a substrate 2.
  • a hole injection layer 4 As the organic layer, a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7 and an electron transport layer 8 are laminated in this order from the anode side 3.
  • the substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer.
  • a substrate that does not scatter or attenuate light emitted from the organic layer In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
  • the anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.
  • the anode is usually provided as a transparent anode.
  • the cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element.
  • the electrode material can be selected as appropriate.
  • Organic layer in the present invention will be described.
  • each organic layer is preferably formed by any of dry film forming methods such as vapor deposition and sputtering, and solution coating methods such as transfer, printing, spin coating, and bar coating. Can be formed. It is preferable that at least one of the organic layers is formed by a solution coating method, and it is more preferable that a layer containing the compound represented by the general formula (1) is formed by a solution coating method.
  • the light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light.
  • the light emitting layer in the organic electroluminescent element of the present invention preferably contains at least one phosphorescent material.
  • Luminescent material in addition to at least one phosphorescent light-emitting material contained in the light-emitting layer, a fluorescent light-emitting material or a phosphorescent light-emitting material different from the phosphorescent light-emitting material contained in the light-emitting layer can be used as the light-emitting material. Details of these fluorescent materials and phosphorescent materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.
  • Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123684, JP-A No. 2002-170684, EP No. 121157, JP-A No. 2002 -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-1736 4.
  • Phosphorescent compounds and the like can be mentioned.
  • more preferable light emitting materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Examples thereof include phosphorescent metal complex compounds such as Gd complexes, Dy complexes, and Ce complexes.
  • an Ir complex, a Pt complex, or a Re complex among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.
  • an iridium complex represented by the following general formula (E-1) or a platinum complex represented by the following general formula (C-1) is used as the phosphorescent material contained in the light emitting layer in the present invention. It is preferable.
  • Z 1 and Z 2 each independently represent a carbon atom or a nitrogen atom.
  • a 1 represents an atomic group that forms a 5- or 6-membered heterocycle with Z 1 and a nitrogen atom.
  • B 1 represents an atomic group that forms a 5- or 6-membered ring with Z 2 and a carbon atom.
  • (XY) represents a monoanionic bidentate ligand.
  • n E1 represents an integer of 1 to 3.
  • n E1 represents an integer of 1 to 3, preferably 2 or 3.
  • Z 1 and Z 2 each independently represent a carbon atom or a nitrogen atom.
  • Z 1 and Z 2 are preferably carbon atoms.
  • a 1 represents an atomic group that forms a 5- or 6-membered heterocycle with Z 1 and a nitrogen atom.
  • the 5- or 6-membered heterocycle containing A 1 , Z 1 and a nitrogen atom includes a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
  • the 5- or 6-membered heterocycle formed by A 1 , Z 1 and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole.
  • the 5- or 6-membered heterocycle formed by the A 1 , Z 1 and the nitrogen atom may have a substituent, and as the substituent on the carbon atom, the substituent group A is on the nitrogen atom.
  • the substituent group B can be applied as the substituent.
  • Preferred substituents on carbon are alkyl groups, perfluoroalkyl groups, aryl groups, aromatic heterocyclic groups, dialkylamino groups, diarylamino groups, alkoxy groups, cyano groups, and fluorine atoms.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable.
  • an electron donating group, a fluorine atom, and an aromatic ring group are preferable.
  • an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected.
  • an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected.
  • the substituent on nitrogen is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
  • B 1 represents a 5- or 6-membered ring containing Z 2 and a carbon atom.
  • Examples of the 5- or 6-membered ring formed by B 1 , Z 2 and a carbon atom include a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
  • the benzene ring, pyridine ring, pyrazine ring, imidazole ring, pyrazole is preferable as the 5- or 6-membered ring formed by B 1 , Z 2 and carbon atom.
  • the 5- or 6-membered ring formed of B 1 , Z 2 and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as the substituent on the carbon atom.
  • the substituent group B can be applied.
  • Preferred substituents on carbon are alkyl groups, perfluoroalkyl groups, aryl groups, aromatic heterocyclic groups, dialkylamino groups, diarylamino groups, alkoxy groups, cyano groups, and fluorine atoms.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected.
  • an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.
  • the substituent on nitrogen is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
  • a 5- or 6-membered heterocyclic substituent formed by A 1 , Z 1 and a nitrogen atom and a 5- or 6-membered substituent formed by B 1 , Z 2 and a carbon atom are linked. Then, the same condensed ring as described above may be formed.
  • ligand represented by (XY) there are various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Included in ligands (eg, halogen ligands (preferably chlorine ligands), etc., published in 1987, published by Yersin, “Organometallic Chemistry-Fundamentals and Applications-” Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.), diketone ligands (for example, acetylacetone, etc.)
  • the ligand represented by (XY) is preferably a diketone or a picolinic acid. The derivative is most preferably acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency.
  • the ligands represented by (XY) are preferably the following general formulas (l-1) to (1-15), but the present invention is not limited to these.
  • Rx, Ry and Rz each independently represents a hydrogen atom or a substituent.
  • Rx, Ry, and Rz represent a substituent
  • substituents include a substituent selected from the substituent group A.
  • Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred.
  • Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom, or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are not considered to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect. Since complex synthesis is easy, (I-1), (I-4) and (I-5) are preferred, and (I-1) is most preferred.
  • Ligands having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, in the same manner as described in International Publication No. 2009-073245, page 46, it can be synthesized by the following method using commercially available difluoroacetylacetone.
  • a preferred embodiment of the Ir complex represented by the general formula (E-1) is an Ir complex represented by the general formula (E-2).
  • a E1 to A E8 each independently represent a nitrogen atom or C—R E.
  • R E represents a hydrogen atom or a substituent.
  • (XY) represents a monoanionic bidentate ligand.
  • n E2 represents an integer of 1 to 3.
  • a E1 to A E8 each independently represents a nitrogen atom or C—R E.
  • R E represents a hydrogen atom or a substituent, and R E may be connected to each other to form a ring.
  • Examples of the ring formed include the same ring as the condensed ring described in the general formula (E-1).
  • Examples of the substituent represented by R E we are the same as those mentioned above substituent group A.
  • a E1 ⁇ A E4 is C-R E, if A E1 ⁇ A E4 is C-R E, preferably a hydrogen atom R E of A E3, alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom.
  • R E of A E1 , A E2 and A E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom, An alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.
  • a E5 to A E8 are preferably C—R E , and when A E5 to A E8 are C—R E , R E is preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, aromatic A heterocyclic group, a dialkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, more preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, Or a fluorine atom, and more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom.
  • a E6 is preferably a nitrogen atom.
  • (X-Y) and n E2 of the general formula in (E1) (X-Y) , and has the same meaning as n E1 preferable ranges are also the same.
  • a more preferred form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).
  • R T1 , R T2 , R T3 , R T4 , R T5 , R T6 and R T7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, Represents —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R, —C (O) R, —N (R) 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group; Furthermore, you may have the substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • A represents CR ′ or a nitrogen atom
  • R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R, —C (O ) Represents R, —N (R) 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R T1 to R T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl.
  • the condensed 4- to 7-membered ring may further have a substituent Z.
  • a case where a ring is condensed with R T1 and R T7 , or R T5 and R T6 to form a benzene ring is preferable, and a case where a ring is condensed with R T5 and R T6 to form a benzene ring is particularly preferable.
  • the substituents Z are each independently a halogen atom, —R ′′, —OR ′′, —N (R ′′) 2 , —SR ′′, —C (O) R ′′, —C (O) OR ′′, —C ( O) represents N (R ′′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′′, —SO 2 R ′′, or —SO 3 R ′′, and each R ′′ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a monoanionic bidentate ligand.
  • n E3 represents an integer of 1 to 3.
  • the alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the alkyl group represented by R T1 to R T7 and R ′ is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl Group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like.
  • the cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the cycloalkyl group represented by R T1 to R T7 and R ′ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, A cyclopentyl group, a cyclohexyl group, etc. are mentioned.
  • the alkenyl group represented by R T1 to R T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • vinyl, allyl Examples include 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
  • the alkynyl group represented by R T1 to R T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • R T1 to R T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • Examples of the perfluoroalkyl group represented by R T1 to R T7 and R ′ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.
  • the aryl group represented by R T1 to R T7 and R ′ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, or a naphthyl group.
  • the heteroaryl group represented by R T1 to R T7 and R ′ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group.
  • Groups such as pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofuryl , Thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzis
  • R T1 to R T7 and R ′ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group or a heteroaryl group, more preferably A hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are more preferable.
  • substituent Z an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.
  • R T1 to R T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl;
  • the condensed 4- to 7-membered ring may further have a substituent Z.
  • the definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R T1 to R T7 and R ′.
  • A represents CR ′, and among R T1 to R T7 and R ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms, and R T1 to R T7 , And R ′ are particularly preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.
  • n E3 is preferably 2 or 3.
  • the type of ligand in the complex is preferably composed of 1 to 2 types, more preferably 1 type.
  • the ligand consists of two types from the viewpoint of ease of synthesis.
  • (XY) has the same meaning as (XY) in formula (E-1), and the preferred range is also the same.
  • One preferred form of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).
  • R T1 to R T4 , A, (XY) and n E4 in the general formula (E-4) are R T1 to R T4 , A, (XY) and n E3 in the general formula (E-3).
  • the preferred range is also the same.
  • R 1 ′ to R 5 ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO 2 R, —C (O) R , —N (R) 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, and optionally having a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. Any one of R 1 ′ to R 5 ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent Z.
  • the substituents Z are each independently a halogen atom, —R ′′, —OR ′′, —N (R ′′) 2 , —SR ′′, —C (O) R ′′, —C (O) OR ′′, —C ( O) represents N (R ′′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′′, —SO 2 R ′′, or —SO 3 R ′′, and each R ′′ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R 1 ′ to R 5 ′ are the same as R T1 to R T7 and R ′ in formula (E-3).
  • A represents CR ′, and 0 to 2 of R T1 to R T4 , R ′, and R 1 ′ to R 5 ′ are alkyl groups or phenyl groups, and the rest are all hydrogen atoms.
  • R T1 to R T4 , R ′, and R 1 ′ to R 5 ′ are more preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.
  • Another preferred embodiment of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-5).
  • R T2 to R T6 , A, (XY) and n E5 in the general formula (E-5) are R T2 to R T6 , A, (XY) and n E3 in the general formula (E-3).
  • the preferred range is also the same.
  • R 6 ′ to R 8 ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO 2 R, —C (O) R , —N (R) 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, and optionally having a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R T5 , R T6 , R 6 ′ to R 8 ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or It is a heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent Z.
  • the substituents Z are each independently a halogen atom, —R ′′, —OR ′′, —N (R ′′) 2 , —SR ′′, —C (O) R ′′, —C (O) OR ′′, —C ( O) represents N (R ′′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′′, —SO 2 R ′′, or —SO 3 R ′′, and each R ′′ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • R 6 ′ to R 8 ′ are the same as R T1 to R T7 and R ′ in formula (E-3).
  • A represents CR ′, and among R T2 to R T6 , R ′, and R 6 ′ to R 8 ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms.
  • R T2 to R T6 , R ′, and R 6 ′ to R 8 ′ are more preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.
  • the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer. More preferably, it is contained in the light emitting layer.
  • Another preferred embodiment of the compound represented by the general formula (E-1) is a case represented by the following general formula (E-6).
  • R 1a to R 1k each independently represent a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO 2 R, —C (O) R, —N (R) 2 , —NO 2 , —OR, a halogen atom, an aryl group, or a heteroaryl group may be represented, and may further have a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. Any two of R 1a to R 1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The 7-membered ring may further have a substituent Z.
  • the substituents Z are each independently a halogen atom, —R ′′, —OR ′′, —N (R ′′) 2 , —SR ′′, —C (O) R ′′, —C (O) OR ′′, —C ( O) represents N (R ′′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′′, —SO 2 R ′′, or —SO 3 R ′′, and each R ′′ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a monoanionic bidentate ligand.
  • n E6 represents an integer of 1 to 3.
  • R 1a to R 1k are the same as those in R T1 to R T7 and R ′ in the general formula (E-3). Further, it is particularly preferred that 0 to 2 of R 1a to R 1k are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and 0 to 2 of R 1a to R 1k are alkyl groups and the rest are all hydrogen atoms. More preferably, it is an atom. The case where R 1j and R 1k are linked to form a single bond is particularly preferable.
  • the preferred range of (XY) and n E6 is the same as (XY) and n E3 in general formula (E-3).
  • a more preferable form of the compound represented by the general formula (E-6) is a case represented by the following general formula (E-7).
  • R 1a to R 1i each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R, —C (O) R, —N (R) 2 , —NO 2 , —OR, a halogen atom, an aryl group, or a heteroaryl group may be represented, and may further have a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. Any one of R 1a to R 1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is a cycloalkyl group, an aryl group, or a heteroaryl group; The condensed 4- to 7-membered ring may further have a substituent Z.
  • the substituents Z are each independently a halogen atom, —R ′′, —OR ′′, —N (R ′′) 2 , —SR ′′, —C (O) R ′′, —C (O) OR ′′, —C ( O) represents N (R ′′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′′, —SO 2 R ′′, or —SO 3 R ′′, and each R ′′ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a monoanionic bidentate ligand.
  • n E7 represents an integer of 1 to 3.
  • R 1a ⁇ R 1i definition and preferable ranges of R 1a ⁇ R 1i are the same as R 1a ⁇ R 1i in the formula (E-6). Further, it is particularly preferable that 0 to 2 of R 1a to R 1i are alkyl groups or aryl groups and the rest are all hydrogen atoms.
  • the definitions and preferred ranges of (XY) and n E7 are the same as (XY) and n E3 in general formula (E-3).
  • the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer. .
  • the compounds exemplified as the compound represented by the general formula (E-1) can be synthesized by the method described in JP2009-99783A, various methods described in US Pat. No. 7,279,232 and the like. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the compound represented by the general formula (E-1) is preferably contained in the light emitting layer, but its use is not limited, and may be further contained in any layer in the organic layer. .
  • the compound represented by the general formula (E-1) in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. From the viewpoint of durability and external quantum efficiency, the content is preferably 1% by mass to 50% by mass, and more preferably 2% by mass to 40% by mass.
  • the platinum complex that can be used as the phosphorescent material is preferably a platinum complex represented by the following general formula (C-1).
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represent a ligand coordinated to Pt.
  • L 1 , L 2 and L 3 are each independently a single bond or a divalent linking group. Represents.
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represent a ligand coordinated to Pt.
  • the bond between Q 1 , Q 2 , Q 3 and Q 4 and Pt may be any of a covalent bond, an ionic bond, a coordinate bond, and the like.
  • a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q ⁇ 1 >, Q ⁇ 2 >, Q ⁇ 3 > and Q ⁇ 4 >
  • a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q ⁇ 1 >, Q ⁇ 2 >, Q ⁇ 3 > and Q ⁇ 4 >
  • at least one is preferably a carbon atom, more preferably two are carbon atoms, particularly preferably two are carbon atoms and two are nitrogen atoms.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand etc.), heterocyclic ligand (eg furan ligand, thiophene ligand, pyridine) Ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole And a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.).
  • the groups represented by Q 1 , Q 2 , Q 3, and Q 4 may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other (when Q 3 and Q 4 are connected, a Pt complex of a cyclic tetradentate ligand is formed).
  • the group represented by Q 1 , Q 2 , Q 3 and Q 4 is preferably an aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, and an aromatic heterocyclic ligand bonded to Pt with a carbon atom.
  • L 1 , L 2 and L 3 represent a single bond or a divalent linking group.
  • the divalent linking group represented by L 1 , L 2 and L 3 include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR—) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (such as phenylphosphinidene group), silylene group (—SiRR′—) (dimethylsilylene group, diphenylsilylene group, etc.), or a combination thereof.
  • alkylene groups methylene, ethylene, propylene, etc.
  • arylene groups phenylene, naphthalenediyl
  • heteroarylene groups pyridined
  • R and R ′ each independently include an alkyl group, an aryl group, and the like. These linking groups may further have a substituent.
  • L 1 , L 2 and L 3 are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group or a silylene group. More preferably a single bond, an alkylene group, an arylene group or an imino group, still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably.
  • Single bond, disubstituted methylene group more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, A lopentanediyl group, a fluorenediyl group, and a fluoromethylmethylene group.
  • L 1 is particularly preferably a dimethylmethylene group, a diphenylmethylene group, or a cyclohexanediyl group, and most preferably a dimethylmethylene group.
  • L 2 and L 3 are most preferably a single bond.
  • platinum complexes represented by the general formula (C-1) a platinum complex represented by the following general formula (C-2) is more preferable.
  • L 21 represents a single bond or a divalent linking group.
  • a 21 and A 22 each independently represents a carbon atom or a nitrogen atom.
  • Z 21 and Z 22 each independently represent a nitrogen-containing aromatic heterocyclic ring.
  • Z 23 and Z 24 each independently represents a benzene ring or an aromatic heterocycle.
  • L 21 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • a 21 and A 22 each independently represent a carbon atom or a nitrogen atom. Of A 21, A 22, Preferably, at least one is a carbon atom, it A 21, A 22 are both carbon atoms are preferred from the standpoint of emission quantum yield stability aspects and complexes of the complex .
  • Z 21 and Z 22 each independently represent a nitrogen-containing aromatic heterocycle.
  • the nitrogen-containing aromatic heterocycle represented by Z 21 and Z 22 include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, Examples include thiadiazole rings.
  • the ring represented by Z 21 and Z 22 is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably a pyridine ring.
  • Z 23 and Z 24 each independently represent a benzene ring or an aromatic heterocycle.
  • the nitrogen-containing aromatic heterocycle represented by Z 23 and Z 24 include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadi Examples include an azole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
  • the ring represented by Z 23 and Z 24 is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring, More preferred are a benzene ring, a pyridine ring and a pyrazole ring, and still more preferred are a benzene ring and a pyridine ring.
  • platinum complexes represented by the general formula (C-2) one of the more preferred embodiments is a platinum complex represented by the following general formula (C-4).
  • a 401 to A 414 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • L 41 represents a single bond or a divalent linking group.
  • a 401 to A 414 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • substituent represented by R those exemplified as the substituent group A can be applied.
  • a 401 to A 406 are preferably C—R, and Rs may be connected to each other to form a ring.
  • R in A 402 and A 405 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group.
  • R in A 401 , A 403 , A 404 and A 406 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or an amino group.
  • L 41 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • the number of N is preferably 0 to 2, and more preferably 0 to 1.
  • a 408 or A 412 is preferably a nitrogen atom, and both A 408 and A 412 are more preferably nitrogen atoms.
  • platinum complexes represented by the general formula (C-2) one of the more preferred embodiments is a platinum complex represented by the following general formula (C-5).
  • a 501 to A 512 each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, and L 51 represents a single bond or a divalent linkage. Represents a group.
  • a 501 to A 506 and L 51 have the same meanings as A 401 to A 406 and L 41 in formula (C-4), and preferred ranges are also the same.
  • R represents a hydrogen atom or a substituent.
  • substituent represented by R those exemplified as the substituent group A can be applied.
  • platinum complexes represented by the general formula (C-1) another more preferable embodiment is a platinum complex represented by the following general formula (C-6).
  • L 61 represents a single bond or a divalent linking group.
  • a 61 independently represents a carbon atom or a nitrogen atom.
  • Z 61 and Z 62 each independently represent a nitrogen-containing aromatic heterocyclic ring.
  • Z 63 independently represents a benzene ring or an aromatic heterocycle, and Y is an anionic acyclic ligand bonded to Pt.
  • L 61 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • a 61 represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A 61 is preferably a carbon atom.
  • Z 61 and Z 62 are synonymous with Z 21 and Z 22 in the general formula (C-2), respectively, and preferred ranges thereof are also the same.
  • Z 63 has the same meaning as Z 23 in formula (C-2), and the preferred range is also the same.
  • Y is an anionic acyclic ligand that binds to Pt.
  • An acyclic ligand is one in which atoms bonded to Pt do not form a ring in the form of a ligand.
  • a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
  • a vinyl ligand is mentioned as Y couple
  • Examples of Y bonded to Pt with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphate ligand, Examples thereof include sulfonic acid ligands.
  • Examples of Y bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.
  • the ligand represented by Y may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.
  • the ligand represented by Y is preferably a ligand bonded to Pt with an oxygen atom, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand. , A silyloxy ligand, and more preferably an acyloxy ligand.
  • platinum complexes represented by the general formula (C-6) one of more preferred embodiments is a platinum complex represented by the following general formula (C-7).
  • a 701 to A 710 each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, L 71 represents a single bond or a divalent linking group, Y represents An anionic acyclic ligand that binds to Pt.
  • L 71 has the same meaning as L 61 in formula (C-6), and the preferred range is also the same.
  • a 701 to A 710 have the same meanings as A 401 to A 410 in formula (C-4), and preferred ranges are also the same.
  • Y has the same meaning as Y in formula (C-6), and the preferred range is also the same.
  • platinum complex represented by the general formula (C-1) include [0143] to [0152], [0157] to [0158], and [0162] to [0168] of JP-A-2005-310733.
  • Examples of the platinum complex compound represented by the general formula (C-1) include Journal of Organic Chemistry 53,786, (1988), G.S. R. Newkome et al. ), Page 789, method described in left column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26 to 35, and the like.
  • a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent,
  • a solvent for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent
  • a base inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.
  • a base inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.
  • the content of the compound represented by formula (C-1) in the light emitting layer of the present invention is preferably 1 to 30% by mass, more preferably 3 to 25% by mass in the light emitting layer. More preferably, it is 20 mass%.
  • the thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm, and more preferably 10 nm to 100 nm, from the viewpoint of external quantum efficiency. More preferably.
  • the light emitting layer in the element of the present invention may be composed of only a light emitting material, or may be a mixed layer of a host material and a light emitting material.
  • the kind of the light emitting material may be one kind or two or more kinds.
  • the host material is preferably a charge transport material.
  • the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
  • the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
  • the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.
  • the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light.
  • “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
  • a compound represented by the general formula (1) can be used as the host material.
  • Examples of other host materials that can be used in the present invention include the following compounds. Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amines, amino-substituted chalcones, styrylanthracenes, fluorenones, hydrazones, stilbenes, silazanes, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, condensed aromatic hydrocarbon compounds (fluorene, naphthalene, phenanthrene, triphenylene, etc.) , Polysilane compound, poly (N-
  • the host material that can be used in combination may be a hole transporting host material or an electron transporting host material.
  • the triplet lowest excitation energy (T 1 energy) in the film state of the host material is preferably higher than the T 1 energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable T 1 is greater 0.1eV higher than the T 1 of the phosphorescent material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large. T 1 of the a film state of the host material is a large T 1 is obtained from the phosphorescent material to the host material for thereby quench T 1 is less than the light emission of the phosphorescent material.
  • the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass to 95% by mass with respect to the total compound mass forming the light emitting layer. Preferably there is.
  • the light emitting layer contains a plurality of types of host compounds including the compound represented by the general formula (1)
  • the compound represented by the general formula (1) is 50% by mass or more and 99% by mass or less in all the host compounds. It is preferable.
  • the charge transport layer is a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element.
  • Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer is preferable. If the charge transport layer formed by the coating method is a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
  • the charge transport layer is more preferably a hole injection layer, a hole transport layer, or an electron block layer.
  • the hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
  • the hole injection layer and the hole transport layer the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention.
  • the hole injection layer preferably contains an electron accepting dopant.
  • an electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations.
  • TCNQ tetracyanoquinodimethane
  • F 4 -TCNQ tetrafluorotetracyanoquinodimethane
  • molybdenum oxide and the like.
  • the electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the hole injection layer. %, More preferably 0.2% by mass to 30% by mass.
  • the electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
  • the electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
  • an electron transport material the compound represented by General formula (1) of this invention can be used.
  • Other materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, imidazopyridine derivatives, fluorenone.
  • anthraquinodimethane derivatives anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives , 8-quinolinol derivative metal complexes and metal phthalocyanines, benzoxazole and benzothiazole metal complexes It is preferable to select from various metal complexes typified by organic compounds, organosilane derivatives typified by siloles, condensed ring hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, triphenylene, pyrene, etc., pyridine derivatives, benzimidazole derivatives, imidazo It is more preferably any of a pyridine
  • the thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
  • the thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
  • the electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the electron injection layer preferably contains an electron donating dopant.
  • an electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions.
  • TTF tetrathiafulvalene
  • TTT dithiaimidazole compounds
  • TTT tetrathianaphthacene
  • bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl] lithium, cesium and the like.
  • the electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.
  • the hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side.
  • a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
  • organic compounds constituting the hole blocking layer include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7-diphenyl-1,10-) phenanthroline derivatives such as phenanthroline (abbreviated as BCP)) and the like.
  • BCP phenanthroline
  • the thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, still more preferably 5 nm to 50 nm.
  • the hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
  • Materials used in the hole blocking layer, the phosphorescent material is color purity higher than the T 1 energy of the luminous efficiency, in view of driving durability.
  • Holes T 1 of the at film state of the material used in the blocking layer is preferably greater 0.1eV higher than the T 1 of the phosphorescent material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV greater .
  • the electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side.
  • an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
  • the organic compound constituting the electron blocking layer for example, those mentioned as the hole transport material described above can be applied.
  • the thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and even more preferably 5 nm to 50 nm.
  • the electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the material used for the electron blocking layer is preferably higher than the T 1 energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable T 1 is greater than 0.1eV than T 1 of the phosphorescent material in the film state of the material used for the electron blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
  • the entire organic EL element may be protected by a protective layer.
  • the protective layer the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.
  • the element of this invention may seal the whole element using a sealing container.
  • the sealing container the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
  • the organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.
  • a direct current which may include an alternating current component as necessary
  • the driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
  • the driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
  • the external quantum efficiency of the organic electroluminescent element of the present invention is preferably 7% or more, more preferably 10% or more, and further preferably 12% or more.
  • the value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency around 300 to 400 cd / m 2 when the device is driven at 20 ° C. Can do.
  • the internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more.
  • the internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%.
  • the element of the present invention can be suitably used for a display element, a display, a backlight, electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.
  • a device driven in a region having a high light emission luminance such as a lighting device or a display device.
  • FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
  • the light emitting device 20 in FIG. 2 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.
  • the organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2.
  • a protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween.
  • a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate
  • the adhesive layer 14 a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.
  • the use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.
  • FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention.
  • the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
  • the light scattering member 30 is not particularly limited as long as it can scatter light.
  • the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31.
  • the transparent substrate 31 for example, a glass substrate can be preferably cited.
  • transparent resin fine particles can be preferably exemplified.
  • the glass substrate and the transparent resin fine particles known ones can be used.
  • the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.
  • Example 1 A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomatic Co., Ltd., surface resistance 10 ⁇ / ⁇ (also referred to as ⁇ / sq.)) Is placed in a cleaning container and ultrasonically cleaned in 2-propanol. After that, UV-ozone treatment was performed for 30 minutes. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
  • ITO film transparent anode
  • First layer HAT-CN: film thickness 10 nm
  • Second layer NPD: film thickness 30 nm
  • Third layer host material described in Table 1 and GD-1 (mass ratio 90:10): film thickness 30 nm
  • Fourth layer HBL material described in Table 1: film thickness 5 nm
  • Fifth layer Alq: film thickness 45 nm
  • 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
  • the obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used.
  • (B) Driving voltage Each element is caused to emit light by applying a DC voltage so that the luminance becomes 1000 cd / m 2 .
  • the applied voltage at this time was used as an index for driving voltage evaluation.
  • the driving voltage is preferably as small as possible.
  • (C) a durable each element brightness continues to emit light by applying a DC voltage to be 5000 cd / m 2, luminance is used as an index of durability time taken until 4000 cd / m 2.
  • Table 1 the value of the element 1-1, in Table 2, the value of the element 2-1, in Table 3, the value of the element 3-1, in Table 4, the value of the element 4-1, In Table 6, the value of element 5-1, the value of element 6-1 in Table 6, the value of element 7-1 in Table 7, and 1.0 are shown as relative values in each table. The larger the number, the better the durability.
  • Example 2 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and performing the same evaluation as in Example 1.
  • First layer 2-TNATA and F 4 -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
  • Example 3 shows the results obtained by fabricating the device in the same manner as in Example 1 except that the layer configuration is changed to the following, and performing the same evaluation as in Example 1.
  • First layer CuPc: film thickness 10 nm
  • Second layer NPD: film thickness 30 nm
  • Third layer Host material described in Table 3 and RD-1 (mass ratio 95: 5): film thickness 30 nm
  • Fourth layer ET-3: film thickness 50 nm
  • Example 4 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
  • Example 5 Table 5 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
  • First layer HAT-CN: film thickness 10 nm
  • Second layer NPD: film thickness 115 nm
  • Third layer HT-3: film thickness 5 nm
  • Fourth layer H-2 and Firepic (mass ratio 90:10): film thickness 30 nm
  • Fifth layer HBL material described in Table 5: film thickness 5 nm 6th layer: ET-5: film thickness 25 nm
  • Example 6 shows the results obtained by fabricating the device in the same manner as in Example 1 except that the layer configuration is changed to the following, and performing the same evaluation as in Example 1.
  • First layer 2-TNATA and F 4 -TCNQ (mass ratio 99.7: 0.3): film thickness 120 nm
  • Example 7 A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomatic Co., Ltd., surface resistance 10 ⁇ / ⁇ (also referred to as ⁇ / sq.)) Is placed in a cleaning container and ultrasonically cleaned in 2-propanol. After that, UV-ozone treatment was performed for 30 minutes. On this transparent anode (ITO film), PEDOT (poly (3,4-ethylenedioxythiophene)) / PSS (polystyrene sulfonic acid) aqueous solution (BaytronP (standard product)) was spin-coated (4000 rpm, 60 seconds), 120 By drying at a temperature of 10 ° C.
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS polystyrene sulfonic acid
  • a hole injecting and transporting layer having a thickness of about 50 nm was formed.
  • a toluene solution containing 1% by mass of the host material described in Table 7 and 0.05% by mass of GD-1 is spin-coated on the previous buffer layer (hole injection transport layer) (1000 rpm, 60 seconds).
  • a light emitting layer having a thickness of about 50 nm was formed.
  • ET-4 having a film thickness of about 45 nm was formed on this light emitting layer by a vacuum evaporation method to form an electron injecting and transporting layer.
  • 0.1 nm of lithium fluoride and 100 nm of metal aluminum were evaporated in this order to form a cathode.
  • This laminated body is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Then, organic electroluminescent elements 7-1 to 7-3 and comparative elements 7-1 to 7-2 were obtained.
  • XNR5516HV ultraviolet curable adhesive
  • the device using the compound represented by the general formula (1) of the present invention has high efficiency, low driving voltage, excellent durability, and high efficiency after high-temperature storage.
  • the organic electroluminescent element which has the outstanding luminous efficiency and durability, and also has a low drive voltage and is excellent in heat resistance can be provided.

Abstract

L'invention porte sur un élément électroluminescent organique ayant une efficacité lumineuse et une durabilité supérieures ainsi qu'une faible tension de commande et une résistance thermique supérieure. L'élément électroluminescent organique comprend une paire d'électrodes formée sur un substrat à partir d'une électrode positive et d'une électrode négative et au moins une couche organique contenant une couche électroluminescente entre ces électrodes. L'élément électroluminescent organique comprend un noyau aromatique à six chaînons en une position spécifique sur un squelette triphénylène comme dans la formule dans au moins l'une des couches organiques et contient un composé dans lequel un groupe cyclique condensé contenant un carbone sp3 est substitué en position méta du triphénylène par le noyau aromatique à six chaînons.
PCT/JP2011/070189 2010-09-08 2011-09-05 Élément électroluminescent organique et matériau de transport de charges WO2012033061A1 (fr)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104203920A (zh) * 2012-04-10 2014-12-10 保土谷化学工业株式会社 具有9,10-二氢吖啶环结构的化合物以及有机电致发光器件
US20150318487A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device
CN105315219A (zh) * 2014-05-27 2016-02-10 环球展览公司 有机电致发光材料及其用途
US20160126472A1 (en) * 2013-09-06 2016-05-05 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device, and display device
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
CN107540620A (zh) * 2016-06-23 2018-01-05 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US11925106B2 (en) 2018-12-28 2024-03-05 Samsung Electronics Co., Ltd. Condensed cyclic compound, composition including the same, and organic light-emitting device including the condensed cyclic compound

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103503187B (zh) 2011-05-05 2016-11-02 默克专利有限公司 用于电子器件的化合物
KR101618683B1 (ko) 2013-05-16 2016-05-09 제일모직 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR20140135525A (ko) 2013-05-16 2014-11-26 제일모직주식회사 유기 광전자 소자용 발광 재료, 유기 광전자 소자 및 표시 장치
DE102013106949A1 (de) * 2013-07-02 2015-01-08 Osram Opto Semiconductors Gmbh Optoelektronisches Bauelement, organische funktionelle Schicht und Verfahren zur Herstellung eines optoelektronischen Bauelements
KR101627761B1 (ko) 2013-07-10 2016-06-07 제일모직 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR102293727B1 (ko) * 2014-05-02 2021-08-27 삼성디스플레이 주식회사 유기 발광 소자
KR102288347B1 (ko) * 2014-05-02 2021-08-11 삼성디스플레이 주식회사 유기 발광 소자
KR102244071B1 (ko) * 2014-05-02 2021-04-26 삼성디스플레이 주식회사 유기 발광 소자
KR101818581B1 (ko) * 2014-10-31 2018-01-15 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR102578856B1 (ko) * 2021-04-13 2023-09-18 삼성디스플레이 주식회사 유기 발광 소자

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021126A2 (fr) * 2007-08-08 2009-02-12 Universal Display Corporation Matériaux hybrides à base de thiophène/triphénylène benzo-fusionnés
WO2010074087A1 (fr) * 2008-12-26 2010-07-01 出光興産株式会社 Matériau pour élément électroluminescent organique, et élément électroluminescent organique
US20100187984A1 (en) * 2009-01-16 2010-07-29 Universal Display Corporation Materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
JP4751954B1 (ja) * 2010-07-09 2011-08-17 富士フイルム株式会社 有機電界発光素子

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4338367B2 (ja) 2002-07-11 2009-10-07 三井化学株式会社 化合物、有機電界発光素子用材料および有機電界発光素子
JP3902993B2 (ja) 2002-08-27 2007-04-11 キヤノン株式会社 フルオレン化合物及びそれを用いた有機発光素子
KR20160104752A (ko) 2007-08-08 2016-09-05 유니버셜 디스플레이 코포레이션 인광성 발광 다이오드의 단일 트리페닐렌 발색단
JP2009114068A (ja) 2007-11-01 2009-05-28 Canon Inc トリフェニレン化合物及びこれを用いた有機発光素子
WO2009066809A1 (fr) 2007-11-22 2009-05-28 Gracel Display Inc. Composés électroluminescents bleus à haut rendement et dispositif d'affichage utilisant ces composés
KR101170220B1 (ko) * 2009-12-30 2012-07-31 주식회사 두산 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자
JP2011231033A (ja) 2010-04-26 2011-11-17 Canon Inc 新規１０，１０−ジアルキルアントロン化合物及びこれを有する有機発光素子
KR101324784B1 (ko) * 2011-04-13 2013-10-31 (주)씨에스엘쏠라 유기발광 화합물 및 이를 이용한 유기 광소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021126A2 (fr) * 2007-08-08 2009-02-12 Universal Display Corporation Matériaux hybrides à base de thiophène/triphénylène benzo-fusionnés
WO2010074087A1 (fr) * 2008-12-26 2010-07-01 出光興産株式会社 Matériau pour élément électroluminescent organique, et élément électroluminescent organique
US20100187984A1 (en) * 2009-01-16 2010-07-29 Universal Display Corporation Materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
JP4751954B1 (ja) * 2010-07-09 2011-08-17 富士フイルム株式会社 有機電界発光素子

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104203920A (zh) * 2012-04-10 2014-12-10 保土谷化学工业株式会社 具有9,10-二氢吖啶环结构的化合物以及有机电致发光器件
US20160126472A1 (en) * 2013-09-06 2016-05-05 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device, and display device
US10431766B2 (en) * 2014-05-02 2019-10-01 Samsung Display Co., Ltd. Organic light-emitting device
US11882714B2 (en) 2014-05-02 2024-01-23 Samsung Display Co., Ltd. Organic light-emitting device
US20150318487A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device
US11316124B2 (en) 2014-05-02 2022-04-26 Samsung Display Co., Ltd. Organic light-emitting device
CN105315219A (zh) * 2014-05-27 2016-02-10 环球展览公司 有机电致发光材料及其用途
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11456423B2 (en) 2014-07-09 2022-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US11957047B2 (en) 2014-07-09 2024-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US11024811B2 (en) 2014-07-09 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US11641774B2 (en) 2014-09-29 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US11342510B2 (en) 2014-10-06 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
CN107540620A (zh) * 2016-06-23 2018-01-05 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
CN107540620B (zh) * 2016-06-23 2022-10-18 三星Sdi株式会社 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
US10672990B2 (en) 2016-06-23 2020-06-02 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
US11925106B2 (en) 2018-12-28 2024-03-05 Samsung Electronics Co., Ltd. Condensed cyclic compound, composition including the same, and organic light-emitting device including the condensed cyclic compound

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