WO2019066054A1 - Matériau de transport de charge, élément électroluminescent organique et composé - Google Patents

Matériau de transport de charge, élément électroluminescent organique et composé Download PDF

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WO2019066054A1
WO2019066054A1 PCT/JP2018/036533 JP2018036533W WO2019066054A1 WO 2019066054 A1 WO2019066054 A1 WO 2019066054A1 JP 2018036533 W JP2018036533 W JP 2018036533W WO 2019066054 A1 WO2019066054 A1 WO 2019066054A1
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substituted
group
general formula
unsubstituted
light emitting
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PCT/JP2018/036533
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Japanese (ja)
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圭朗 那須
飛鳥 吉▲崎▼
礼隆 遠藤
洸子 野村
ユソク ヤン
直人 能塚
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株式会社Ｋｙｕｌｕｘ
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T90/00—Enabling technologies or technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02T90/10—Technologies relating to charging of electric vehicles
    • Y02T90/16—Information or communication technologies improving the operation of electric vehicles
    • Y02T90/167—Systems integrating technologies related to power network operation and communication or information technologies for supporting the interoperability of electric or hybrid vehicles, i.e. smartgrids as interface for battery charging of electric vehicles [EV] or hybrid vehicles [HEV]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y04—INFORMATION OR COMMUNICATION TECHNOLOGIES HAVING AN IMPACT ON OTHER TECHNOLOGY AREAS
    • Y04S—SYSTEMS INTEGRATING TECHNOLOGIES RELATED TO POWER NETWORK OPERATION, COMMUNICATION OR INFORMATION TECHNOLOGIES FOR IMPROVING THE ELECTRICAL POWER GENERATION, TRANSMISSION, DISTRIBUTION, MANAGEMENT OR USAGE, i.e. SMART GRIDS
    • Y04S30/00—Systems supporting specific end-user applications in the sector of transportation
    • Y04S30/10—Systems supporting the interoperability of electric or hybrid vehicles
    • Y04S30/12—Remote or cooperative charging

Definitions

  • the present invention relates to a compound useful as a charge transport material and an organic light emitting device using the same.
  • organic light emitting devices such as organic electroluminescent devices (organic EL devices)
  • organic electroluminescent devices organic electroluminescent devices
  • various charge transports used in combination with a light emitting material such as an electron transport material, a hole transport material, an electron blocking material, a hole blocking material and the like for improvement (low voltage drive) of the drive voltage of the organic electroluminescent device
  • a light emitting material such as an electron transport material, a hole transport material, an electron blocking material, a hole blocking material and the like for improvement (low voltage drive) of the drive voltage of the organic electroluminescent device
  • the functions of materials become important, and in parallel with the development of light emitting materials, development and improvement of their charge transport materials are also in progress.
  • the electron blocking material is provided between the light emitting layer and the hole transport layer, and prevents electrons present in the light emitting layer from being released from the light emitting layer to the hole transport layer, and from the hole transport layer
  • mCP and mCBP represented by the following formula have been widely used conventionally.
  • the electron blocking layer composed of mCP and mCBP has low thermal stability, which causes the thermal stability of the entire light emitting device to be deteriorated. Since organic light emitting devices are expected to be used in high temperature environments such as application to car navigation systems, securing thermal stability becomes extremely important. On the other hand, in order to improve the energy efficiency of the organic light emitting device, it is effective to reduce the driving voltage by providing the electron blocking layer, and the electron blocking layer is an essential element for the organic light emitting device. Under such circumstances, development of a charge transport material having a function as an electron blocking material and higher thermal stability than mCP and mCBP is strongly desired.
  • the present inventors found that a compound having a structure in which a linked ring structure consisting of an aromatic ring or two aromatic rings linked to each other is substituted with four or more 9-carbazolyl groups is electron blocking. It has been found that they have high performance as well as high thermal stability and are useful as charge transport materials for use in electron blocking layers.
  • the present invention is provided based on such findings, and specifically, has the following configurations.
  • a charge transport material comprising a compound represented by the following general formula (1).
  • Cz represents a substituted or unsubstituted 9-carbazolyl group (however, another ring may be fused to each benzene ring constituting the 9-carbazolyl group).
  • R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R is a substituted or unsubstituted 9-carbazolyl group, and a group having a structure in which another ring is fused to each benzene ring constituting the substituted or unsubstituted 9-carbazolyl group.
  • Ar represents an aromatic ring or a linked ring structure consisting of two aromatic rings linked to each other.
  • m represents an integer of 4 or more, and n represents an integer of 0 or more. However, m + n does not exceed the maximum value of the number of substitutable substituents for Ar.
  • Cz may mutually be same or different.
  • n is an integer of 2 or more, plural R's may be the same as or different from each other.
  • the charge transport material according to [1], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3).
  • R 11 to R 16 each independently represent a substituted or unsubstituted 9-carbazolyl group (with the proviso that each benzene ring constituting the 9-carbazolyl group is
  • R 11 to R 16 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted hetero. Represents an aryl group.
  • R 11 to R 16 each represent a substituted or unsubstituted 9-carbazolyl group, and a group having a structure in which another ring is fused to each benzene ring constituting the substituted or unsubstituted 9-carbazolyl group There is no such thing.
  • An organic light emitting device comprising the charge transport material according to any one of [1] to [12].
  • a compound represented by the above general formula (1) [20] The compound according to [19], wherein Ar in General Formula (1) is a benzene ring. [21] The compound according to [20], wherein 1, 2, 4 and 5 positions of the benzene ring are substituted by Cz, and each Cz may be the same or different.
  • the compounds of the present invention are useful as charge transport materials.
  • the thermal stability is higher than when the electron transport layer is formed with mCP, and an organic light emitting device having a low driving voltage can be realized. .
  • FIG. 7 is a graph showing current density-external quantum efficiency characteristics of the organic electroluminescent device of Production Example 1.
  • 15 is a graph showing current density-external quantum efficiency characteristics of the organic electroluminescent device of Production Example 2.
  • 15 is a graph showing current density-external quantum efficiency characteristics of the organic electroluminescent device of Production Example 3.
  • 15 is a graph showing current density-external quantum efficiency characteristics of the organic electroluminescent device of Production Example 4.
  • 7 is a graph showing voltage-current density characteristics of Production Examples 1, 3 and 5.
  • a numerical range represented using “to” means a range including numerical values described before and after “to” as the lower limit value and the upper limit value.
  • aromatic hydrocarbon ring means an aromatic ring consisting of hydrocarbons
  • aromatic heterocycle means an aromatic ring containing a hetero atom.
  • the isotope species of hydrogen atoms present in the molecule of the compound used in the present invention is not particularly limited. For example, all hydrogen atoms in the molecule may be 1 H, or some or all may be 2 H It may be Lilium D).
  • the charge transport material of the present invention is characterized by comprising a compound represented by the following general formula (1).
  • Cz represents a substituted or unsubstituted 9-carbazolyl group (however, another ring may be fused to each benzene ring constituting the 9-carbazolyl group).
  • the cyclic structures formed by condensation of another ring to each benzene ring constituting the 9-carbazolyl group the cyclic structures formed by combining the following R 1 and R 2 etc. Descriptions and examples can be referred to.
  • Cz preferably has a structure represented by the following general formula (2).
  • R 1 to R 8 in the general formula (2) each independently represent a hydrogen atom or a substituent.
  • the number of substituents among R 1 to R 8 is not particularly limited, and all of R 1 to R 8 may be unsubstituted (that is, hydrogen atoms).
  • the substituent is preferably at least one of R 2 to R 4 and R 5 to R 7 and is at least one of R 3 and R 6 Is more preferred.
  • R 1 to R 8 may have include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, carbon Alkyl substituted amino group having 1 to 20 carbon atoms, acyl group having 2 to 20 carbon atoms, aryl group having 6 to 40 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, 6 to 20 aryloxy group, 6 to 20 carbon atoms 20 arylthio group, aryl substituted amino group having 6 to 20 carbon atoms, arylsulfonyl group having 6 to 20 carbon atoms, alkenyl group having 2 to 10 carbon atoms, alkynyl group having 2 to 10 carbon atoms, 2 to 10 carbon atoms An alkoxycarbonyl group, an alkylsulfonyl group having 1 to 10 carbon
  • substituents are a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, carbon They are a substituted or unsubstituted heteroaryl group having a number of 40 to 40, and a dialkyl substituted amino group having a carbon number of 1 to 20.
  • substituents are a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substitution of 6 to 15 carbon atoms Or an unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 may be combined with each other to form a cyclic structure.
  • the cyclic structure may be an aromatic ring or an aliphatic ring, and may contain hetero atoms, and the cyclic structure may be a condensed ring of two or more rings.
  • the hetero atom as referred to herein is preferably selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom.
  • Examples of the cyclic structure formed include benzene ring, naphthalene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, imidazoline ring, oxazole ring, isoxazole ring, thiazole And rings such as isothiazole ring, cyclohexadiene ring, cyclohexene ring, cyclopentene ring, cycloheptatriene ring, cycloheptadiene ring and cycloheptene ring.
  • R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R is a substituted or unsubstituted 9-carbazolyl group, and a group having a structure in which another ring is fused to each benzene ring constituting the substituted or unsubstituted 9-carbazolyl group.
  • the alkyl group in R may be linear, branched or cyclic.
  • the preferred carbon number is 1 to 20, more preferably 1 to 10, and still more preferably 1 to 6.
  • methyl, ethyl, n-propyl, isopropyl and the like can be exemplified.
  • substituents that may be substituted on the alkyl group include an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, and an alkynyl group having 2 to 10 carbon atoms. Can. These substituents may be further substituted by a substituent.
  • the aromatic hydrocarbon ring constituting the aryl group in R may be a single ring or a condensed ring in which two or more aromatic hydrocarbon rings are condensed.
  • the aryl group also has a linked ring structure in which each aromatic hydrocarbon ring is linked to at least one of the other aromatic hydrocarbon rings by a single bond or a spiro bond, having two or more aromatic hydrocarbon rings. It may be When two or more aromatic hydrocarbon rings are linked, they may be linked in a linear manner or may be linked in a branched manner.
  • the carbon number of the aromatic hydrocarbon ring constituting the aryl group is preferably 6 to 40, more preferably 6 to 22, still more preferably 6 to 18, and 6 to 14.
  • the aromatic heterocyclic ring constituting the heteroaryl group in R may be a single ring or a condensed ring in which one or more heterocyclic rings and one or more aromatic hydrocarbon rings or aromatic heterocyclic rings are condensed.
  • the heteroaryl group has a linked ring structure in which each hetero ring is linked to at least one other hetero ring by a single bond or a spiro bond, and each has two or more hetero rings. It is also good.
  • two or more aromatic heterocycles When two or more aromatic heterocycles are linked, they may be linked in a linear form or may be linked in a branched form.
  • the carbon number of the aromatic heterocyclic ring constituting the heteroaryl group is preferably 3 to 40, more preferably 5 to 22, still more preferably 5 to 18, still more preferably 5 to 14. It is further more preferable, and particularly preferably 5 to 10.
  • a hetero atom which comprises an aromatic heterocyclic ring a nitrogen atom, an oxygen atom, a sulfur atom etc. can be mentioned, It is preferable that it is a nitrogen atom.
  • Specific examples of the heterocyclic ring include pyridine ring, pyridazine ring, pyrimidine ring, triazine ring, triazole ring and benzotriazole ring.
  • the description and the preferred range of the substituent which can be substituted for the heteroaryl group the description and the preferred range of the substituent which can be taken by R 1 to R 8 can be referred to.
  • Ar represents an aromatic ring or a linked ring structure consisting of two aromatic rings linked to each other.
  • the aromatic ring in Ar and each aromatic ring constituting the linking ring structure may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • the two aromatic rings constituting the linking ring structure may be identical to or different from each other, and the combination of the two aromatic rings is a combination of an aromatic hydrocarbon ring and an aromatic hydrocarbon ring, an aromatic ring It may be any of a combination of a heterocyclic ring and an aromatic heterocyclic ring, and a combination of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • the two aromatic rings constituting the linking ring structure are preferably a combination of an aromatic hydrocarbon ring and an aromatic hydrocarbon ring, and more preferably a combination of identical aromatic hydrocarbon rings.
  • a single bond, a spiro bond, etc. can be mentioned as a bond which connects two aromatic rings which comprise a connection ring structure, It is preferable that it is a single bond.
  • the aromatic hydrocarbon ring may be a single ring or two or more aromatic hydrocarbon rings. It may be a fused ring fused.
  • the carbon number of the aromatic hydrocarbon ring is preferably 6 to 40, more preferably 6 to 22, still more preferably 6 to 18, and still more preferably 6 to 14. It is preferably 6 to 10, particularly preferably.
  • a benzene ring and a naphthalene ring can be mentioned as a specific example of the aromatic hydrocarbon ring which comprises the aromatic ring and connecting ring structure in Ar.
  • the aromatic heterocyclic ring may be a single ring, one or more heterocyclic rings and one or more heterocyclic rings. It may be a fused ring in which an aromatic hydrocarbon ring or a heteroaromatic ring is fused.
  • the carbon number of the aromatic heterocyclic ring is preferably 5 to 22, more preferably 5 to 18, still more preferably 5 to 14, and still more preferably 5 to 10. .
  • a hetero atom which comprises an aromatic heterocyclic ring a nitrogen atom, an oxygen atom, a sulfur atom etc. can be mentioned, It is preferable that it is a nitrogen atom.
  • a pyridine ring, a pyridazine ring, a pyrimidine ring, a triazole ring, and a benzotriazole ring can be mentioned as a specific example of the aromatic heterocyclic ring which comprises the aromatic ring and connecting ring structure in Ar.
  • Ar is preferably a benzene ring, a biphenyl ring or a pyridine ring, and more preferably a benzene ring.
  • n represents an integer of 4 or more and n represents an integer of 0 or more. However, m + n does not exceed the maximum value of the number of substitutable substituents for Ar.
  • m represents the number of Cz substituted by Ar.
  • Plural Cz's substituted with Ar may be identical to or different from each other.
  • n represents the number of R substituted by Ar. When n is an integer of 2 or more, plural Rs substituted with Ar may be identical to or different from each other.
  • n is preferably smaller than m, and more preferably 0.
  • the maximum value of the number of substitutable substituents in Ar is, in other words, when it is assumed that the aromatic ring or linked ring structure represented by Ar is a non-substituted aromatic ring or linked ring structure having a common ring structure, the aromatic ring or linked ring It corresponds to the number of hydrogen atoms that can be substituted by a substituent in the structure.
  • the maximum number of substitutable substituents is, for example, 6 in the benzene ring, 12 in the biphenyl ring, and 5 in the pyridine ring. It is preferable that m + n be smaller than the maximum number of substitutable substituents. That is, it is preferable that at least one of the substitutable positions of Ar is unsubstituted.
  • the compound represented by General formula (1) is a compound represented by following General formula (3).
  • R 11 to R 16 each independently represent a substituted or unsubstituted 9-carbazolyl group (with the proviso that each benzene ring constituting the 9-carbazolyl group has another ring
  • R 11 to R 16 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl. Represents a group.
  • R 11 to R 16 each represent a substituted or unsubstituted 9-carbazolyl group, and a group having a structure in which another ring is fused to each benzene ring constituting the substituted or unsubstituted 9-carbazolyl group There is no such thing.
  • substituted or unsubstituted 9-carbazolyl group in R 11 to R 16 (however, another ring may be condensed to each benzene ring constituting the 9-carbazolyl group). May be referred to as “substituted or unsubstituted 9-carbazolyl group etc.”
  • the plurality of substituted or unsubstituted 9-carbazolyl groups among R 11 to R 16 may be the same as or different from each other.
  • R 11 to R 16 when two of R 11 to R 16 are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, the groups represented by the two are identical to each other Or may be different.
  • the substituted or unsubstituted 9-carbazolyl group and the like may be four or five or six of R 11 to R 16 , but four or five. Is preferable, and four are more preferable.
  • R 11 to R 16 When four of R 11 to R 16 are a substituted or unsubstituted 9-carbazolyl group or the like, it is preferred that R 11 , R 12 , R 14 and R 15 are a substituted or unsubstituted 9-carbazolyl group or the like preferable.
  • R 11 , R 12 , R 14 and R 15 When four or five of R 11 to R 16 are a substituted or unsubstituted 9-carbazolyl group or the like, the other R 11 to R 16 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Or a substituted or unsubstituted heteroaryl group, preferably a hydrogen atom. That is, a hydrogen atom (unsubstituted) other than a substituted or unsubstituted 9-carbazolyl group among R 11 to R 16 is preferable.
  • N-Bu represents a normal butyl group
  • t-Bu represents a tertiary butyl group
  • s-Bu represents a secondary butyl group
  • iso-Bu represents an isobutyl group
  • Ph represents a phenyl group
  • MeO represents a methoxy group.
  • the molecular weight of the compound represented by the general formula (1) is, for example, 1,500 or less, when it is intended that the organic layer containing the compound represented by the general formula (1) is formed into a film by vapor deposition and used. Some are preferable, 1200 or less is more preferable, 1000 or less is further preferable, and 800 or less is even more preferable.
  • the lower limit value of the molecular weight is preferably 738 or more, which is the molecular weight of the minimum compound represented by the general formula (1).
  • the compound represented by the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using a coating method, even a compound having a relatively large molecular weight can be formed into a film.
  • the compound containing a plurality of structures represented by the general formula (1) in the molecule as the charge transport material by applying the present invention.
  • a polymer obtained by polymerizing a polymerizable group in the structure represented by the general formula (1) in advance as the charge transport material.
  • a monomer having a polymerizable functional group is prepared in any of Cz, Ar, and R in the general formula (1), and the monomer is polymerized alone or copolymerized with another monomer, It is conceivable to obtain a polymer having a repeating unit and use the polymer as a charge transport material. Alternatively, it is also conceivable to obtain a dimer or trimer by coupling compounds having a structure represented by the general formula (1) to use them as a charge transport material.
  • Q represents a group containing the structure represented by the general formula (1)
  • L 1 and L 2 represent a linking group.
  • the carbon number of the linking group is preferably 0 to 20, more preferably 1 to 15, and still more preferably 2 to 10.
  • X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • L 11 represents a linking group and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted group It is more preferable that it is a phenylene group.
  • each of R 101 , R 102 , R 103 and R 104 independently represents a substituent.
  • it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, and more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms And an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom and a chlorine atom, and more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms and an unsubstituted alkoxy group having 1 to 3 carbon atoms.
  • the linking group represented by L 1 and L 2 is any of Cz, Ar, and R in the structure of General Formula (1) constituting Q, any of R 1 to R 8 in General Formula (2), and General It may be bonded to any one of R 11 to R 16 in the structure of formula (3).
  • Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • a hydroxy group is introduced into any of Cz, Ar and R in the structure of general formula (1),
  • the compound is reacted to introduce a polymerizable group, and the compound can be synthesized by polymerizing the polymerizable group.
  • the polymer containing the structure represented by the general formula (1) in the molecule may be a polymer consisting of only repeating units having the structure represented by the general formula (1), It may be a polymer containing repeating units.
  • the repeating unit having a structure represented by General Formula (1) contained in the polymer may be a single type or two or more types.
  • a repeating unit which does not have a structure represented by General formula (1) what is derived from the monomer used for normal copolymerization can be mentioned.
  • the repeating unit derived from the monomer which has an ethylenically unsaturated bond, such as ethylene and styrene, can be mentioned.
  • the compound represented by the general formula (1) can be synthesized, for example, by reacting the compound represented by the following general formula (2 ′) with the compound represented by the following general formula (1 ′) It is.
  • X represents a halogen atom, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • X 1 is provided at a position where Cz 1 is desired to be introduced.
  • the compound represented by the general formula (1) of the present invention is useful as a charge transport material of an organic light emitting device. Therefore, the compound represented by the general formula (1) of the present invention can be effectively used as a material of an electron blocking layer or a hole transporting layer of an organic light emitting device or as a host material of a light emitting layer.
  • the compound represented by the general formula (1) of the present invention for the electron blocking layer it is possible to achieve low voltage driving of the device, and heat compared to the case where mCP is used for the electron blocking layer. The stability is improved and high practicability can be realized.
  • an excellent organic light emitting device such as an organic photoluminescent device (organic PL device) or an organic electroluminescent device (organic EL device) is provided.
  • the organic photoluminescent device has a structure in which at least a light emitting layer is formed on a substrate.
  • the organic electroluminescent device has a structure in which an organic layer is formed at least an anode, a cathode, and between the anode and the cathode.
  • the organic layer includes at least a light emitting layer, and may be formed only of the light emitting layer, or may have one or more organic layers in addition to the light emitting layer.
  • a hole transport layer As such another organic layer, a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, an exciton blocking layer and the like can be mentioned.
  • the hole transport layer may be a hole injection transport layer having a hole injection function
  • the electron transport layer may be an electron injection transport layer having an electron injection function.
  • FIG. 1 A specific structural example of the organic electroluminescent device is shown in FIG. In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport layer, and 8 is a cathode.
  • Each member and each layer of an organic electroluminescent element are demonstrated below. The description of the substrate and the light emitting layer also applies to the substrate and the light emitting layer of the organic photoluminescence device.
  • the organic electroluminescent device of the present invention is preferably supported on a substrate.
  • the substrate is not particularly limited as long as it is conventionally used conventionally in organic electroluminescent devices, and for example, those made of glass, transparent plastic, quartz, silicon or the like can be used.
  • anode As an anode in an organic electroluminescent element, what makes an electrode material the large (4 eV or more) metal of a work function, an alloy, an electrically conductive compound, and these mixtures is used preferably.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • ITO indium tin oxide
  • ZnO ZnO
  • an amorphous material such as IDIXO (In 2 O 3 -ZnO) which can be used to form a transparent conductive film may be used.
  • the anode may form a thin film by depositing or sputtering these electrode materials, and may form a pattern of a desired shape by photolithography, or if it does not require much pattern accuracy (about 100 ⁇ m or more). ), A pattern may be formed through a mask of a desired shape during deposition or sputtering of the electrode material. Or when using the material which can be apply
  • cathode one having a metal having a small work function (4 eV or less) (referred to as electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O) 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals etc. may be mentioned.
  • a mixture of an electron-injectable metal and a second metal which is a stable metal having a larger work function value such as a magnesium / silver mixture, Magnesium / aluminium mixtures, magnesium / indium mixtures, aluminum / aluminium oxide (Al 2 O 3 ) mixtures, lithium / aluminium mixtures, aluminum etc. are preferred.
  • the cathode can be produced by forming a thin film of such an electrode material by a method such as vapor deposition or sputtering. Further, the sheet resistance as a cathode is preferably several hundreds ⁇ / sq.
  • the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • a light emission luminance will improve and it is convenient.
  • a transparent or translucent cathode can be produced, and by applying this, an element in which both the anode and the cathode are transparent can be produced. It can be made.
  • the light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons respectively injected from the anode and the cathode, and a light emitting material may be used alone in the light emitting layer.
  • a light emitting material may be used alone in the light emitting layer.
  • the light emitting material and the host material are included.
  • the light emitting material may be any of a fluorescent material, a delayed fluorescent material, and a phosphorescent material, but it is preferable to use the delayed fluorescent material because it is easy to obtain high luminous efficiency.
  • delayed fluorescence is emitted from the excited singlet state back to the ground state after a reverse intersystem crossing from the excited triplet state to the excited singlet state occurs in the compound in the excited state It is fluorescence, and is usually observed later than the fluorescence from the excited singlet state directly transitioned from the ground state (normal fluorescence).
  • the delayed fluorescent material is a light emitting material that emits such delayed fluorescence.
  • an organic compound in which at least one of excited singlet energy and excited triplet energy has a value higher than that of the light-emitting material of the present invention can be used.
  • singlet excitons and triplet excitons generated in the light emitting material of the present invention can be confined in the molecules of the light emitting material of the present invention, and the light emission efficiency can be sufficiently extracted.
  • high luminous efficiency may be obtained in some cases, so a host material that can realize high luminous efficiency is particularly restricted. Can be used in the present invention.
  • light emission is generated from the light emitting material of the present invention contained in the light emitting layer.
  • This light emission may be any of fluorescence, delayed fluorescence and phosphorescence, and may include two or more of these light emissions.
  • part or part of light emission may be emitted from the host material.
  • the content of the compound of the present invention as a light emitting material in the light emitting layer is preferably 0.1% by weight or more, more preferably 1% by weight or more, and 50 The content is preferably at most weight percent, more preferably at most 20 weight percent, and still more preferably at most 10 weight percent.
  • the host material in the light emitting layer is preferably an organic compound having a hole transporting ability and an electron transporting ability, preventing long wavelength of light emission, and having a high glass transition temperature.
  • an assist dopant for assisting light emission of the light emitting material may be used together with the light emitting material and the host material.
  • the assist dopant has an excited singlet energy level between the excited singlet energy of the host material and the excited singlet energy of the light emitting material, and the reverse intersystem crossing from the excited triplet state to the excited singlet state
  • the compound which produces can be used.
  • the compound that causes reverse intersystem crossing can be determined by confirming the emission of delayed fluorescence.
  • the light-emitting material of the light-emitting layer is preferably a delayed fluorescence material because high light emission efficiency can be obtained. It is based on the following principle that high luminous efficiency can be obtained by the delayed fluorescent material.
  • the organic electroluminescent element carriers are injected into the light emitting material from both positive and negative electrodes to generate a light emitting material in an excited state and cause the light emitting material to emit light.
  • carriers are injected into the light emitting material from both positive and negative electrodes to generate a light emitting material in an excited state and cause the light emitting material to emit light.
  • a carrier injection type organic electroluminescent device of the generated excitons, 25% are excited to an excitation singlet state, and the remaining 75% are excited to an excitation triplet state. Therefore, using phosphorescence, which is light emission from the excited triplet state, has higher energy utilization efficiency.
  • the excited triplet state has a long lifetime, saturation of the excited state and deactivation of energy by interaction with excitons of the excited triplet state occur, and generally the quantum yield of phosphorescence is often not high.
  • the reverse intersystem crosses to the excited singlet state due to triplet-triplet annihilation or absorption of thermal energy to emit fluorescence.
  • a thermally activated delayed fluorescent material by absorption of thermal energy is particularly useful.
  • excitons in the excited triplet state absorb heat generated by the device, undergo intersystem crossing to excited singlets, and emit fluorescence.
  • the lifetime (emission lifetime) of the light generated by the reverse intersystem crossing from the excitation triplet state to the excitation singlet state is usually Because it is longer than the fluorescence of, it is observed as a delayed fluorescence than these. This can be defined as delayed fluorescence.
  • the ratio of the compound in the singlet state of excitation which is usually only 25% is 25% or more by absorption of thermal energy after carrier injection.
  • the injection layer is a layer provided between the electrode and the organic layer to lower the driving voltage and improve the luminance, and includes the hole injection layer and the electron injection layer, and between the anode and the light emitting layer or the hole transport layer, And between the cathode and the light emitting layer or the electron transport layer.
  • An injection layer can be provided as needed.
  • the blocking layer is a layer capable of blocking the diffusion of charges (electrons or holes) present in the light emitting layer and / or excitons out of the light emitting layer.
  • An electron blocking layer can be disposed between the light emitting layer and the hole transport layer to block electrons from passing through the light emitting layer towards the hole transport layer.
  • a hole blocking layer can be disposed between the light emitting layer and the electron transport layer to block holes from passing through the light emitting layer towards the electron transport layer.
  • the blocking layer can also be used to block the diffusion of excitons out of the light emitting layer. That is, each of the electron blocking layer and the hole blocking layer can also have the function as an exciton blocking layer.
  • the electron blocking layer or the exciton blocking layer as used herein is used in a sense including one layer having a function of the electron blocking layer and the exciton blocking layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense.
  • the hole blocking layer plays the role of transporting electrons and blocking the arrival of holes to the electron transporting layer, which can improve the recombination probability of electrons and holes in the light emitting layer.
  • the material of the hole blocking layer the material of the electron transport layer described later can be used as needed.
  • the electron blocking layer has a function of transporting holes in a broad sense.
  • the electron blocking layer plays the role of transporting holes and blocking the arrival of electrons to the hole transport layer, which can improve the probability of recombination of electrons and holes in the light emitting layer.
  • As a material of the electron blocking layer one or more selected from the compound group of the present invention represented by the general formula (1) can be used. As a result, the thermal stability of the element can be effectively enhanced, and low voltage driving can be achieved.
  • the exciton blocking layer is a layer for blocking the diffusion of excitons generated by the recombination of holes and electrons in the light emitting layer into the charge transport layer, and the insertion of this layer results in the formation of excitons.
  • the light can be efficiently confined in the light emitting layer, and the light emission efficiency of the device can be improved.
  • the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both of them can be simultaneously inserted.
  • the layer when an exciton blocking layer is provided on the anode side, the layer can be inserted between the hole transport layer and the light emitting layer adjacent to the light emitting layer, and when inserted on the cathode side, the light emitting layer and the cathode And the light emitting layer may be inserted adjacent to the light emitting layer.
  • a hole injection layer or an electron blocking layer can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer, and the cathode and the excitation adjacent to the cathode side of the light emitting layer.
  • an electron injecting layer, an electron transporting layer, a hole blocking layer, and the like can be provided.
  • the blocking layer is disposed, at least one of the excitation singlet energy and the excitation triplet energy of the material used as the blocking layer is preferably higher than the excitation singlet energy and the excitation triplet energy of the light emitting material.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material is one having either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • Examples of known hole transport materials that can be used include triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, Amino substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers, etc., but porphyrin compounds, aroma Group tertiary amine compounds and styrylamine compounds are preferred, and aromatic tertiary amine compounds are more preferred.
  • the electron transporting layer is made of a material having a function of transporting electrons, and the electron transporting layer can be provided in a single layer or a plurality of layers.
  • the electron transporting material (which may also be a hole blocking material) may have a function of transferring electrons injected from the cathode to the light emitting layer.
  • Examples of the electron transport layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, flareylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like.
  • a thiadiazole derivative h wherein the oxygen atom of the oxadiazole ring is substituted by a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material. It can. Furthermore, it is also possible to use a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain.
  • the compound represented by the general formula (1) may be used in a layer other than the electron blocking layer.
  • the compound represented by General Formula (1) can be used for the host material of the light emitting layer, the hole transporting layer, and the like.
  • the compound represented by the general formula (1) may be used only in the layers other than the electron blocking layer, or may be used in both the electron blocking layer and the layers other than the electron blocking layer.
  • the compound represented by the general formula (1) used for the electron blocking layer and a layer other than the electron blocking layer may be the same or different.
  • each organic layer which comprises an organic electroluminescent element is formed into a film in order on a board
  • the film forming method of these layers is not particularly limited, and may be produced by either a dry process or a wet process.
  • the preferable material which can be used for an organic electroluminescent element is illustrated concretely.
  • the materials that can be used in the present invention are not limitedly interpreted by the following exemplified compounds. Moreover, even if it is the compound illustrated as a material which has a specific function, it is also possible to divert it as a material which has another function.
  • a light emitting material that can be used for the light emitting layer.
  • the light emitting material may be a delayed fluorescent material that emits delayed fluorescence or a fluorescent material that does not emit delayed fluorescence. Preferred is when using compounds that emit delayed fluorescence.
  • the type of delayed fluorescent material that can be used for the light emitting layer is not particularly limited. As preferred delayed fluorescence materials, paragraphs 0008 to 0048 and 0095 to 0133 of WO 2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO 2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO 2013/011955.
  • exemplary compounds may include those that emit delayed fluorescence.
  • Unexamined-Japanese-Patent 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121 are included.
  • WO 2014/136860 WO 2014/196585, WO 2014/189122, WO 2014/168101, WO 2015/008580, WO 2014/203840, WO 2015/002213, WO 2015/016200, WO 2015/019725, WO 2015/072470, WO 2015/108049, WO 2015 / 80182, WO2015 / 072537, WO2015 / 080183, JP2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / No.
  • one 0-4 of R 1 ⁇ R 5 represents a cyano group, at least one of R 1 ⁇ R 5 represents a substituted amino group, the remaining R 1 ⁇ R 5 are a hydrogen atom, Or a substituent other than cyano and a substituted amino group.
  • the substituted amino group as referred to herein is preferably a substituted or unsubstituted diarylamino group, and two aryl groups constituting the substituted or unsubstituted diarylamino group may be linked to each other.
  • the linkage may be a single bond (in which case a carbazole ring is formed), -O-, -S-, -N (R 6 )-, -C (R 7 ) (R 8 )
  • a linking group such as —, —Si (R 9 ) (R 10 ) — may be used.
  • R 6 to R 10 each represent a hydrogen atom or a substituent
  • R 7 and R 8 , and R 9 and R 10 may be linked to each other to form a cyclic structure.
  • the substituted amino group may be any of R 1 to R 5 , such as R 1 and R 2 , R 1 and R 3 , R 1 and R 4 , R 1 and R 5 , R 2 and R 3 , R 2 And R 4 , R 1 and R 2 and R 3 , R 1 and R 2 and R 4 , R 1 and R 2 and R 5 , R 1 and R 3 and R 4 , R 1 and R 3 and R 5 , R 2 and R 3 and R 4 , R 1 and R 2 and R 3 and R 4 , R 1 and R 2 and R 3 and R 4 , R 1 and R 2 and R 3 and R 4 , R 1 and R 2 and R 3 and R 5 , R 1 and R 2 and R 4 and R 5 , R 1 and R 2 and R 3 , R 4 and R 5 can be substituted amino groups, and the like.
  • the cyano group may also be any of R 1 to R 5 , for example R 1 , R 2 , R 3 , R 1 and R 2 , R 1 and R 3 , R 1 and R 4 , R 1 and R 5 , R 2 and R 3 , R 2 and R 4 , R 1 and R 2 and R 3 , R 1 and R 2 and R 4 , R 1 and R 2 and R 5 , R 1 and R 3 and R 4 , R 1 And R 3 and R 5 , R 2 , R 3 and R 4 can be cyano groups, etc.
  • R 1 to R 5 which are neither a cyano group nor a substituted amino group represent a hydrogen atom or a substituent.
  • Examples of the substituent referred to herein include a hydroxyl group, a halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), an alkyl group (eg, 1 to 40 carbon atoms), an alkoxy group (eg, 1 to 40 carbon atoms) , Alkylthio group (eg, 1 to 40 carbon atoms), aryl group (eg, 6 to 30 carbon atoms), aryloxy group (eg, 6 to 30 carbon atoms), arylthio group (eg, 6 to 30 carbon atoms), heteroaryl group (eg, 6 to 30 carbon atoms)
  • the ring skeleton has 5 to 30 atoms, a heteroaryloxy group (eg, having 5 to 30 ring atoms), a heteroarylthio group (eg, having 5 to 30 ring atoms), an acyl group (eg, 1 carbon atom) To 40), an alkenyl
  • Substituent Group A consisting of groups further substituted by one or more of the groups listed herein.
  • substituents of the above-mentioned Substituent Group A can be mentioned, and furthermore, a cyano group and a substituted amino group can also be mentioned.
  • Paragraphs 0008 to 0048 of WO 2013/154064, and paragraphs 0009 to WO 2015/080183, which are incorporated herein as a part of this specification, are examples of the compounds included in the general formula (1) and the compounds.
  • Formulas (B) to (D) are generalized ones of preferred compounds among those included in Formula (A) above as examples.
  • R 1 ⁇ R 5 represents a cyano group
  • at least one of R 1 ⁇ R 5 represents a group represented by the following general formula (11)
  • the remaining R 1 To R 5 each represent a hydrogen atom or a substituent.
  • R 21 to R 28 each independently represent a hydrogen atom or a substituent.
  • ⁇ A> R 25 and R 26 together form a single bond
  • ⁇ B> R 27 and R 28 together represent a group necessary to form a substituted or unsubstituted benzene ring.
  • R 31 to R 38 , R 41 to R 46 , R 51 to R 62 and R 71 to R 80 each independently represent a hydrogen atom or a substituent.
  • the substitution position and the number of substitutions are not particularly limited. When they have a plurality of substituents, they may be identical to or different from one another.
  • general formula (B) For details of the compounds represented by general formula (B), reference can be made to paragraphs 0013 to 0048 of WO 2013/060582, which is incorporated herein by reference.
  • R 1 , R 2 , R 3 , R 4 and R 5 are each independently a 9-carbazolyl group having a substituent at at least one of 1-position or 8-position And a 10-phenoxazyl group having a substituent at at least one of the 1- and 9-positions, or a 10-phenothiazyl group having a substituent at at least one of the 1- and 9-positions.
  • the remainder represents a hydrogen atom or a substituent
  • the substituent is a 9-carbazolyl group having a substituent at at least one of the 1- or 8-positions, and a 10-phenoxazyl having a substituent at at least one of the 1-position It is not a group or a 10-phenothiazyl group having a substituent at at least one of 1- and 9-positions.
  • One or more carbon atoms constituting each ring skeleton of the 9-carbazolyl group, the 10-phenoxazyl group and the 10-phenothiazyl group may be substituted by a nitrogen atom.
  • R 1 , R 2 , R 4 and R 5 each independently represent a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted Or an unsubstituted 10-phenothiazyl group or a cyano group.
  • the rest represent a hydrogen atom or a substituent, but the substituent is not a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group.
  • R 3 each independently represents a hydrogen atom or a substituent, and the substituent is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a cyano group, a substituted or unsubstituted 10 Not a phenothiazyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkynyl group.
  • Cz is a 9-carbazolyl group having a substituent at at least one of 1- and 8-positions (in this case, at least one of carbon atoms 1 to 8 constituting the ring skeleton of carbazole ring of 9-carbazolyl group is a nitrogen atom
  • other rings are fused to each benzene ring constituting the 9-carbazolyl group, and the 1- and 8-positions are not both substituted with a nitrogen atom.
  • Ar is a benzene ring having a substituent containing a moiety having a positive Hammett's ⁇ p value (with the exception of a cyano group), or a substituent containing a moiety having a positive Hammett 's ⁇ p value (a cyano group)
  • a cyano group Represents a biphenyl ring having a represents an integer of 1 or more, but does not exceed the maximum number of substituents that can be substituted on the benzene ring or biphenyl ring represented by Ar.
  • a plurality of Cz may be the same as or different from each other.
  • R 1 and R 2 each independently represent a fluorinated alkyl group
  • D represents a substituent having a negative Hammett ⁇ p value
  • A has a positive Hammett ⁇ p value Represents a substituent.
  • R 1 to R 8 , R 12 and R 14 to R 25 each independently represent a hydrogen atom or a substituent, and R 11 represents a substituted or unsubstituted alkyl group.
  • R 2 to R 4 is a substituted or unsubstituted alkyl group
  • at least one of R 5 to R 7 is a substituted or unsubstituted alkyl group.
  • any two of Y 1 , Y 2 and Y 3 represent a nitrogen atom and the remaining one represents a methine group, or all of Y 1 , Y 2 and Y 3 represent a nitrogen atom.
  • Z 1 and Z 2 each independently represent a hydrogen atom or a substituent.
  • R 11 to R 18 each independently represent a hydrogen atom or a substituent, and at least one of R 11 to R 18 is a substituted or unsubstituted arylamino group, or a substituted or unsubstituted carbazolyl group preferable.
  • the benzene ring constituting the arylamino group and the benzene ring constituting the carbazolyl group may be combined with R 11 to R 18 to form a single bond or a linking group.
  • the compound represented by the general formula (2) contains at least two carbazole structures in the molecule. Examples of the substituents Z 1, Z 2 may take, may be exemplified by the substituents of the above substituent group A.
  • R 11 to R 18 the above-mentioned arylamino group and carbazolyl group can adopt are the substituents of the above-mentioned Substituent Group A, cyano group, substituted arylamino group and substituted alkylamino group be able to.
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 are combined with each other to form a cyclic structure. It is also good.
  • the compound represented by the general formula (H ′) is particularly useful.
  • any two of Y 1 , Y 2 and Y 3 represent a nitrogen atom and the remaining one represents a methine group, or all of Y 1 , Y 2 and Y 3 represent a nitrogen atom
  • Z 2 represents a hydrogen atom or a substituent.
  • R 11 to R 18 and R 21 to R 28 each independently represent a hydrogen atom or a substituent.
  • at least one of R 11 to R 18 and / or at least one of R 21 to R 28 represents a substituted or unsubstituted arylamino group or a substituted or unsubstituted carbazolyl group.
  • the benzene ring constituting the arylamino group and the benzene ring constituting the carbazolyl group may form a single bond or a linking group together with R 11 to R 18 or R 21 to R 28 respectively.
  • substituents Z 2 may take, may be exemplified by the substituents of the above substituent group A.
  • specific examples of the substituent that R 11 to R 18 , R 21 to R 28 , the above-mentioned arylamino group and carbazolyl group can adopt are the substituents of the above-mentioned Substituent Group A, a cyano group, a substituted arylamino group, Mention may be made of substituted alkylamino groups.
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 may be bonded to each other to form a cyclic structure.
  • Specific examples of the compounds and compounds included in the general formula (H) are described in paragraphs 0020 to 0062 of WO 2013/081088, which is herein incorporated as a part of the present specification, Appl. Phys. Reference can be made to the compounds described in Let, 98, 083302 (2011).
  • Specific examples of the compound represented by formula (H) include compounds 1 to 89 described in paragraphs 0041 to 0056 of WO2018 / 081088.
  • Compounds 1 to 89 referred to herein are referred to as compounds 1h to 89h in the present application.
  • the following compound 90h (PIC-TRZ) can be mentioned as a specific example of a preferable compound.
  • delayed fluorescent material represented by the above general formula
  • the following delayed fluorescent material can also be employed.
  • the electron blocking material it is most preferable to use a compound represented by the general formula (1), but when the compound represented by the general formula (1) is used for a layer other than the electron blocking layer, Materials other than the compounds represented by 1) can also be used as the electron blocking material. In the following, examples of compounds that can be used as an electron blocking material in that case are listed.
  • the organic electroluminescent device produced by the above-mentioned method emits light by applying an electric field between the anode and the cathode of the obtained device.
  • light emission by excited singlet energy light of a wavelength corresponding to the energy level is confirmed as fluorescence emission and delayed fluorescence emission.
  • the wavelength according to the energy level will be confirmed as phosphorescence. Since the ordinary fluorescence has a shorter fluorescence lifetime than the delayed fluorescence, the emission lifetime can be distinguished by the fluorescence and the delayed fluorescence.
  • excited triplet energy is unstable and converted to heat and the like, and its lifetime is short and it is immediately inactivated, so it can hardly be observed at room temperature.
  • the excited triplet energy of a normal organic compound it can be measured by observing the light emission under conditions of extremely low temperature.
  • the organic electroluminescent device of the present invention can be applied to any of a single device, a device having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix.
  • the thermal stability is high and the driving is performed.
  • An organic light emitting element with low voltage can be realized.
  • the organic light emitting device such as the organic electroluminescent device of the present invention can be applied to various applications.
  • organic electroluminescent display device using the organic electroluminescent device of the present invention, and for details, Shimizu Tokishi, Senya Adachi, Hideyuki Murata “Organic EL Display” (Ohm Corporation) ) Can be referenced.
  • the organic electroluminescent element of this invention can also be especially applied to the organic electroluminescent illumination and back light with large demand.
  • a light emitting device comprising a layer containing a delayed fluorescent material and a layer containing a hole transporting material, wherein the delayed fluorescent material and the hole transporting material satisfy the relationship of the following formula (1).
  • HOMO H represents the energy level of HOMO (Highest Occupied Molecular Orbital) of the hole transport material
  • HOMO T represents the energy level of HOMO (Highest Occupied Molecular Orbital) of the delayed fluorescent material .
  • Each unit is eV.
  • [4a] The light emitting device according to any one of [1a] to [3a], wherein the layer containing the delayed fluorescent material contains a host material in addition to the delayed fluorescent material.
  • [5a] The light emitting device according to [4a], wherein a difference between absolute values of energy levels of the host material and HOMO (Highest Occupied Molecular Orbital) of the hole transport material is 0.4 eV or less.
  • [6a] The light emitting device according to [4a] or [5a], wherein the host material and the hole transport material are made of the same compound.
  • [7a] The light emitting device according to any one of [1a] to [6a], wherein the absolute value of the energy level of the HOMO (Highest Occupied Molecular Orbital) of the delayed fluorescent material is larger than 5.6 eV.
  • [8a] The light-emitting device according to any one of [1a] to [7a], wherein the layer containing the hole transport material comprises only the hole transport material.
  • the delayed fluorescence material is a compound in which a donor group and an acceptor group are bonded to a conjugated linking group, and the hole transport material is a diarylamino group (wherein the two aryl groups are heteroaryl groups)
  • a combination of a delayed fluorescent material capable of expressing high luminous efficiency and a hole transporting material can be selected with certainty, and by using these materials, a light emitting element with extremely high luminous efficiency can be realized.
  • the light emitting device of the present invention includes the layer containing the delayed fluorescence material and the layer containing the hole transporting material, and is characterized by satisfying the relationship of the following formula (1).
  • HOMO H represents the energy level of HOMO (Highest Occupied Molecular Orbital) of the hole transport material
  • HOMO T represents the energy levels of HOMO (Highest Occupied Molecular Orbital) of the delayed fluorescent material.
  • the energy level of HOMO (Highest Occupied Molecular Orbital) in the present invention refers to a value obtained by atmospheric photoelectron spectroscopy (such as AC-3 manufactured by Riken Keiki Co., Ltd.).
  • the “delayed fluorescent material” in the present invention means an inverted intersystem crossing from an excited triplet state to an excited singlet state in the excited state, and fluorescence (delayed fluorescence) when returning from the excited singlet state to the ground state Means an organic compound that emits
  • a fluorescence life measurement system such as a streak camera system manufactured by Hamamatsu Photonics Co., Ltd.
  • the delayed fluorescent material preferably has a difference ⁇ E ST of 0.4 eV or less, preferably 0.3 eV or less, between the lowest excitation singlet energy level (E S1 ) and the lowest excitation triplet energy level (E T1 ). Is more preferably 0.2 eV or less, still more preferably 0.1 eV or less.
  • the smaller the ⁇ E ST of the delayed fluorescent material the easier the reverse intersystem crossing from its excited triplet state to the excited singlet state to occur, and excitation triplet energy can be efficiently converted to excited singlet energy.
  • the method of measuring the lowest excitation singlet energy level ( ES1 ) and the lowest excitation triplet energy level ( ET1 ) will be described later.
  • the "hole transport material" in the present invention means an organic compound having a function of receiving and transporting holes.
  • the light emitting device of the present invention has a layer containing a delayed fluorescent material, and when the delayed fluorescent material and the hole transporting material satisfy the relationship of Formula (1), extremely high luminous efficiency can be obtained. We speculate that this is due to the following reasons. That is, the light emitting element including the delayed fluorescent material emits light by being deactivated by radiation after the delayed fluorescent material is in the excited state.
  • the light-emitting material is excited to the excited singlet state and the excited triplet state by carrier recombination, but in the delayed fluorescent material, the excitation triplet state is excited from the excited triplet state Since the reverse intersystem crossing to the state occurs, not only the energy of the excited singlet state directly generated by the carrier recombination but also the energy of the excited triplet state can be effectively used as excitation singlet energy for fluorescence emission. . Therefore, if a delayed fluorescent material is used, much higher luminous efficiency should be obtained as compared to the case where a normal fluorescent material is used as a light emitting material.
  • the present inventors fabricated a current excitation type light emitting element (organic electroluminescent element) by laminating a hole transport layer made of TrisPCz which is a hole transport material on the light emitting layer containing 4CzIPN which is a delayed fluorescence material.
  • a hole transport layer made of TrisPCz which is a hole transport material on the light emitting layer containing 4CzIPN which is a delayed fluorescence material.
  • TrisPCz were found to be derived from the exciplex (excitation state formed in an aggregate of 4CzIPN and TrisPCz).
  • the exciplex since the exciplex has an energy level lower than that of an excited state formed by a single 4CzIPN, the energy of the 4CzIPN in the singly excited state is easily transferred to the exciplex, and a part of the energy is lost It is considered to be In the light emitting element using the conventional delayed fluorescent material, an exciplex with a low energy level is thus formed at the interface between the light emitting layer and the hole transport layer to sufficiently express the light emission efficiency to be provided potentially. It is thought that it did not get.
  • the delayed fluorescent material and the hole transporting material satisfy the relationship of formula (1), that is,
  • it is larger than 0.2 eV it is inferred that charge transfer interaction does not occur between the hole transport material and the delayed fluorescence material in the excitation process, and formation of an exciplex is suppressed. Therefore, it is considered that the energy of the delayed fluorescent material which has been in the excited state alone is effectively confined in the delayed fluorescent material molecule and utilized for light emission, and high luminous efficiency is expressed.
  • preferably at least equivalent, that it is preferable to satisfy the relation of the following formula (2).
  • is not particularly limited, but is preferably 6.2 eV or less, more preferably 6.1 eV or less, from the viewpoint of the hole injection efficiency into the layer containing the hole transport material, for example, 6. It can also be set to 0 eV or less, or 5.8 eV or less.
  • the delayed fluorescent material may have a function of assisting light emission of another light emitting material contained in the layer containing the delayed fluorescent material as a so-called assist dopant. That is, the delayed fluorescent material is the lowest between the lowest excited singlet energy level of the host material contained in the layer containing the delayed fluorescent material and the lowest excited singlet energy levels of other light emitting materials contained in this layer. It may have an excited singlet energy level.
  • the formation of the exciplex between the hole transport material and the delayed fluorescent material is suppressed, whereby the energy of the delayed fluorescent material as the assist dopant is prevented from being transferred to the exciplex and being lost.
  • the light emission of other light emitting materials can be effectively assisted by the delayed fluorescent material, and high light emission efficiency can be obtained.
  • E S1 Lowest excited singlet energy level
  • a sample with a thickness of 100 nm is produced on a Si substrate by co-evaporation of the compound to be measured and mCP so that the concentration of the compound to be measured is 6% by weight.
  • the fluorescence spectrum of this sample is measured at normal temperature (300 K), and the emission intensity from the vertical axis is obtained and the fluorescence spectrum for the wavelength is obtained by integrating the emission from immediately after the excitation light incidence to 100 nanoseconds after the incidence.
  • the vertical axis represents light emission
  • the horizontal axis represents wavelength.
  • a tangent is drawn to the rise on the short wavelength side of the emission spectrum, and a wavelength value ⁇ edge [nm] at the intersection of the tangent and the horizontal axis is determined.
  • Conversion formula: E S1 [eV] 1239.85 / ⁇ edge
  • a nitrogen laser MNL 200, manufactured by Lasertechnik Berlin
  • a streak camera C 4334, manufactured by Hamamatsu Photonics K.K.
  • the maximum point with a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the above-described local maximum on the shortest wavelength side, and the slope value closest to the local maximum on the short wavelength side is the maximum
  • the tangent drawn at the value taking point is taken as the tangent to the rise on the short wavelength side of the phosphorescence spectrum.
  • the delayed fluorescent material and the hole transporting material, the host material, the layer configuration of the light emitting device, and the materials of the other organic layers which can be used for the light emitting device according to [1a] to [11a]
  • the light emitting devices described in [1a] to [11a] may or may not include the charge transport material composed of the compound represented by the above general formula (1), Is preferred.
  • source meter made by Keithley: 2400 series
  • semiconductor parameter analyzer manufactured by Agilent Technologies: E5273A
  • optical power meter measuring device manufactured by Newport: 1930C
  • optical spectroscope Ocean Optics, Inc .: USB 2000
  • a spectroradiometer Topcon, SR: 3
  • a streak camera Hamamatsu Photonics Co., Ltd., C4334 type
  • Synthesis Example 1 Synthesis of Compound 1 Into a 200 mL three-necked flask, 4.07 g (24.4 mmol) of 9H-carbazole and 1.17 g (29.2 mmol) of sodium hydride (60% mineral oil dispersion) are added. Were replaced with nitrogen. After adding 100 mL of dehydrated tetrahydrofuran to this mixture, the mixture was stirred for 1 hour, and 1.50 g (4.87 mmol) of 1,4-dibromo-tetrafluorobenzene was added in an ice bath. The reaction vessel was heated and stirred at 160 ° C. for 12 hours under a nitrogen atmosphere.
  • ETM was formed as a 10 nm thick hole blocking layer.
  • ETM and Liq were co-deposited from different deposition sources and formed to a thickness of 40 nm.
  • ETM: Liq (weight ratio) was 7: 3.
  • Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode, thereby forming an organic electroluminescent device.
  • Production Example 2 Preparation of Organic Electroluminescent Device Using Compound 2 for Electron Blocking Layer and Light Emitting Layer Except that Compound 2 was used instead of Compound 1 used for the electron blocking layer and the light emitting layer of Production Example 1 An organic electroluminescent device was produced in the same manner as in Production Example 1.
  • Production Example 3 Preparation of an organic electroluminescent device using mCP as an electron blocking layer and Compound 1 as a light emitting layer Production Example except for using mCP instead of Compound 1 used for the electron blocking layer of Production Example 1
  • An organic electroluminescent device was produced in the same manner as in 1.
  • Production Example 4 Preparation of an organic electroluminescent device using mCP as an electron blocking layer and Compound 2 as a light emitting layer Production Example except for using mCP instead of Compound 2 used for the electron blocking layer of Production Example 2 In the same manner as in No. 2, an organic electroluminescent device was produced.
  • Production Example 5 Preparation of an organic electroluminescent device using mCP as an electron blocking layer and mCBP as a light emitting layer Compound using mCP instead of Compound 1 used for the electron blocking layer of Production Example 1 in a light emitting layer
  • An organic electroluminescent device was produced in the same manner as in Production Example 1 except that mCBP was used instead of 1.
  • An organic electroluminescent device produced by the same method as Production Example 1 using the compounds 1a2a and 4a to 6a represented by the above general formula (A) instead of 4CzIPN used in the above Production Example 1 is a device 1a , 2a, 4a-6a are disclosed herein.
  • Organic electroluminescent devices produced by the same method as in Production Example 1 using the compounds 1b to 1112b represented by the above general formula (B) instead of 4CzIPN used in the above Production Example 1 are elements 1b to 1112b.
  • Organic electroluminescent devices manufactured by the same method as in Production Example 1 using the compounds 1c to 2785c represented by the above general formula (C) instead of 4CzIPN used in Production Example 1 above are elements 1c to 2785c.
  • An organic electroluminescent device produced by the same method as in Production Example 1 using the compounds 1d to 901d represented by the above general formula (D) instead of 4CzIPN used in the above Production Example 1 is a device 1d to 901d As disclosed herein.
  • An organic electroluminescent device produced by the same method as in Production Example 1 using the compounds 1f to 60f represented by the above general formula (F) instead of 4CzIPN used in the above Production Example 1 is a device 1f to 60f As disclosed herein.
  • An organic electroluminescent device produced by the same method as in Production Example 1 using the compounds 1g to 4g represented by the above general formula (G) instead of 4CzIPN used in the above Production Example 1 is a device 1g to 4g As disclosed herein.
  • An organic electroluminescent device produced by the same method as in Production Example 1 using Compound 1h to 90h represented by General Formula (H) instead of 4CzIPN used in Production Example 1 is a device 1h to 90h. As disclosed herein.
  • Organic electroluminescent devices manufactured by the same method as in Production Example 1 using 10 compounds of the delayed fluorescence material group I instead of 4CzIPN used in the above Production Example 1 are referred to here as Devices 1i to 10i. Disclose. It manufactured by the same method as the manufacture example 1 using 8 compounds except HAT-CN mentioned above as what can be used as a hole injection material instead of HAT-CN used in the said manufacture example 1, respectively. Organic electroluminescent devices are disclosed herein as devices 1j-8j.
  • 4CzIPN and mCBP were co-deposited from different deposition sources to form a 30 nm thick layer as a light emitting layer. At this time, the concentration of 4CzIPN was 20% by weight.
  • T2T was vapor-deposited to a thickness of 10 nm to form a hole blocking layer
  • BPy-TP2 was vapor-deposited to a thickness of 40 nm thereon to form an electron transport layer.
  • Liq is vapor-deposited to a thickness of 1.0 nm to form an electron injection layer
  • aluminum (Al) is vapor-deposited to a thickness of 100 nm to form a cathode. 4 was produced.
  • the comparative element 1 is modified except that only one 30 nm thick TrisPCz layer is formed without forming two layers of the second hole transport layer and the first hole transport layer.
  • the layer configurations of the elements 1 to 4 and the comparison element 1 are shown in Table 1.
  • the elements 1 to 4 satisfying the condition of the equation (1) are compared with the comparison element 1 not satisfying the condition of the equation (1) Even the maximum external quantum efficiency and current efficiency were high. Further, as apparent from the comparison between the elements 5 to 7 using PICTRZ 2 as the delayed fluorescence material and the comparison element 2, the elements 5 to 7 satisfying the condition of the formula (1) do not satisfy the condition of the formula (1) Maximum external quantum efficiency and current efficiency were higher than 2.
  • the compounds of the present invention have high thermal stability and are useful as charge transport materials. Therefore, the compound of the present invention can be effectively used as a material of an electron blocking layer of an organic electroluminescent device or a host material of a light emitting layer. In particular, by using the compound of the present invention for the electron blocking layer, it is possible to realize an organic electroluminescent device having high thermal stability, capable of achieving low voltage drive, and having high practicability. Therefore, the present invention has high industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

L'invention concerne une utilisation d'un matériau de transport de charge qui comprend un composé représenté par la formule générale (1) permet de mettre en œuvre un élément électroluminescent organique ayant une stabilité thermique élevée et une faible tension d'attaque. Dans la formule générale (1), Cz représente un groupe 9-carbazolyle ; R représente un groupe alkyle, un groupe aryle ou un groupe hétéroaryle ; Ar représente un cycle aromatique, ou une structure cyclique de liaison comprenant deux cycles aromatiques reliés l'un à l'autre ; m représente un nombre entier supérieur ou égal à 4 ; et n représente un nombre entier supérieur ou égal à 0. Formule générale (1) : (Cz)m–Ar–(R)n
PCT/JP2018/036533 2017-09-29 2018-09-28 Matériau de transport de charge, élément électroluminescent organique et composé WO2019066054A1 (fr)

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