WO2023167253A1 - トリアリールアミン高分子量化合物および有機エレクトロルミネッセンス素子 - Google Patents

トリアリールアミン高分子量化合物および有機エレクトロルミネッセンス素子 Download PDF

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WO2023167253A1
WO2023167253A1 PCT/JP2023/007667 JP2023007667W WO2023167253A1 WO 2023167253 A1 WO2023167253 A1 WO 2023167253A1 JP 2023007667 W JP2023007667 W JP 2023007667W WO 2023167253 A1 WO2023167253 A1 WO 2023167253A1
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molecular weight
high molecular
structural unit
layer
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French (fr)
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優太 三枝
和法 富樫
秀良 北原
美香 篠田
由香 吉澤
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保土谷化学工業株式会社
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Priority to JP2024504733A priority patent/JPWO2023167253A1/ja
Priority to KR1020247015836A priority patent/KR20240155182A/ko
Publication of WO2023167253A1 publication Critical patent/WO2023167253A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
    • C08G2261/3162—Arylamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/51—Charge transport
    • C08G2261/512—Hole transport
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/52—Luminescence

Definitions

  • the present invention relates to high-molecular-weight compounds suitable for organic electroluminescence elements (organic EL elements), which are self-luminous elements suitable for various display devices, and the elements.
  • organic EL elements are self-luminous elements, they are brighter than liquid crystal elements, have excellent visibility, and are capable of a clear display.
  • An organic EL element has a structure in which a thin film (organic layer) of an organic compound is sandwiched between an anode and a cathode.
  • Methods for forming a thin film are roughly classified into a vacuum deposition method and a coating method.
  • the vacuum deposition method is a method of forming a thin film on a substrate in a vacuum using mainly low-molecular-weight compounds, and is a technology that has already been put to practical use.
  • the coating method mainly uses polymer compounds and forms a thin film on the substrate using a solution such as inkjet or printing. It is an essential technology for future large-area organic EL displays.
  • the vacuum deposition method using low-molecular-weight materials has extremely low material usage efficiency, and if the size is increased, the deflection of the shadow mask increases, making it difficult to perform uniform deposition on large substrates. There is also the problem of high manufacturing costs.
  • polymer materials can form a uniform film even on a large substrate by applying a solution dissolved in an organic solvent. law can be used. As a result, it is possible to increase the efficiency of material use, and to significantly reduce the manufacturing cost required for manufacturing the device.
  • TFB fluorene polymer
  • Patent Documents 6 and 7 a fluorene polymer called TFB has been known as a typical hole-transporting material that has hitherto been used in polymer organic EL devices (see Patent Documents 6 and 7).
  • TFB has insufficient hole-transporting properties and insufficient electron-blocking properties, some of the electrons pass through the light-emitting layer, and an improvement in luminous efficiency cannot be expected.
  • the film adhesion to the adjacent layer is low, there is a problem that the device cannot be expected to have a long life.
  • the present inventors have focused on the fact that triarylamine high-molecular-weight compounds containing naphthalene structural units and triarylamine structural units in the molecular main chain have high hole injection/transport capabilities and are expected to widen the gap.
  • the present invention was completed by discovering a high molecular weight compound with a novel wide-gap structure in addition to the hole injection/transport ability.
  • a repeating structural unit represented by the following general formula (3) which consists of a triarylamine structural unit represented by the following general formula (1) and a connecting structural unit represented by the general formula (2)
  • a high molecular weight compound comprising:
  • an organic EL device comprising an organic layer formed using the high molecular weight compound.
  • the organic layer is preferably a hole-transporting layer, an electron-blocking layer, a hole-injecting layer, or a light-emitting layer.
  • a repeating structural unit represented by the following general formula (3) which consists of a triarylamine structural unit represented by the following general formula (1) and a connecting structural unit represented by the following general formula (2). and having a weight average molecular weight of 10,000 or more and less than 1,000,000 in terms of polystyrene.
  • each R 1 is independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 8 carbon atoms, or an alkyloxy group. , a cycloalkyl or cycloalkyloxy group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms.
  • Each R 2 independently represents an alkyl group, cycloalkyl group or alkyloxy group having 3 to 40 carbon atoms.
  • X represents a hydrogen atom, an amino group, a monovalent aryl group, or a monovalent heteroaryl group.
  • L represents a divalent phenylene group or naphthylene group, and n represents an integer of 0-3.
  • X is a hydrogen atom, diphenylamino group, phenyl group, naphthyl group, dibenzofuranyl group, dibenzothienyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, indeno
  • the dashed line indicates a bond to the adjacent structural unit, and the solid line with a free tip extending from the ring indicates that the tip is a methyl group. showing.
  • An organic electroluminescence device comprising an organic layer formed using the high molecular weight compound according to any one of [1] to [7].
  • the high molecular weight compound of the present invention comprises a triarylamine structural unit (divalent group) represented by the above-described general formula (1) and a linking structural unit (divalent group) represented by general formula (2).
  • the high molecular weight compound of the present invention is (1) good hole injection characteristics; (2) high hole mobility; (3) having a wide gap and excellent electron blocking ability; (4) that the thin film state is stable; It has the characteristic of
  • An organic EL device in which an organic layer formed from the high molecular weight compound of the present invention, such as a hole transport layer, an electron blocking layer, a hole injection layer or a light emitting layer, is formed between a pair of electrodes, (1) high luminous efficiency and power efficiency; (2) low practical drive voltage; (3) long life; has the advantage of
  • Both the triarylamine structural unit and the linking structural unit possessed by the high molecular weight compound of the present invention are divalent groups represented by the following general formulas (1) and (2), respectively.
  • each R 1 is independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and having 1 to 1 carbon atoms.
  • alkyl group, alkyloxy group, cycloalkyl group, cycloalkyloxy group, alkenyl group and aryloxy group represented by R 1 include the following groups.
  • alkyl groups (having 1 to 8 carbon atoms) include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl group, n-hexyl group, isohexyl group, neohexyl group, n-heptyl group, isoheptyl group, neoheptyl group, n-octyl group, isooctyl group, neooctyl group and the like.
  • alkyloxy groups (having 1 to 8 carbon atoms) include methyloxy, ethyloxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, n-pentyloxy, n -hexyloxy group, n-heptyloxy group, n-octyloxy group and the like.
  • cycloalkyl groups (having 5 to 10 carbon atoms) include cyclopentyl, cyclohexyl, 1-adamantyl and 2-adamantyl groups.
  • Examples of cycloalkyloxy groups include cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, 1-adamantyloxy, and 2-adamantyloxy groups.
  • Examples of alkenyl groups include vinyl groups, allyl groups, isopropenyl groups and 2-butenyl groups.
  • Examples of aryloxy groups include phenyloxy groups and tolyloxy groups.
  • R 1 is preferably a deuterium atom. Synthetically, it is most preferred that a, b and c are zero.
  • each R 2 independently represents an alkyl group, a cycloalkyl group or an alkyloxy group having 3 to 40 carbon atoms.
  • Examples of the alkyl group, cycloalkyl group and alkyloxy group represented by R 2 include the same groups as those represented by R 1 .
  • R 2 is preferably an alkyl group having 3 to 40 carbon atoms, most preferably an n-hexyl group or an n-octyl group, in order to increase the solubility. is.
  • X represents a hydrogen atom, an amino group, a monovalent aryl group, or a monovalent heteroaryl group.
  • Examples of the monovalent aryl group and monovalent heteroaryl group include the following groups.
  • aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl, and fluoranthenyl groups.
  • heteroaryl groups include pyridyl, pyrimidinyl, triazinyl, furyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, indenocarbazolyl. benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl, and carbolinyl groups.
  • amino group, aryl group, and heteroaryl group described above may have a substituent.
  • Substituents include deuterium atoms, cyano groups, nitro groups, and the like, halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; Alkyl groups, particularly those having 1 to 8 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, neohexyl, n-heptyl, isoheptyl, neoheptyl, n-octyl, isooctyl, and neooctyl; alkyloxy groups, especially those having 1 to 8 carbon atoms
  • substituents may further have the substituents exemplified above.
  • substituents preferably exist independently, but these substituents are separated from each other via a single bond, an optionally substituted methylene group, an oxygen atom or a sulfur atom. may be bonded to each other to form a ring.
  • X is a hydrogen atom, a diphenylamino group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothienyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, an indenocarbazolyl group, or an acridinyl group. is preferred, and from the viewpoint of synthesis, a hydrogen atom is particularly preferred.
  • the above aryl group and heteroaryl group may have a phenyl group as a substituent, and this phenyl group may further have a phenyl group as a substituent.
  • the aryl group can be a biphenylyl group, a terphenylyl group, and a triphenylenyl group.
  • L represents a divalent phenylene group or naphthylene group
  • n represents an integer of 0-3.
  • n is preferably 0.
  • the above L may have a substituent.
  • the substituents are the same as the substituents that X may have, and these substituents may further have a substituent.
  • FIGS. 1 and 2 specific examples of the linking structural unit represented by the general formula (2) are shown in FIGS. 1 and 2 as structural units 1 to 26.
  • the dashed line indicates a bond to the adjacent structural unit, and the solid line extending from the ring indicates that the free tip is a methyl group. showing.
  • Preferred specific examples of the linking structural unit are shown, but the linking structural unit used in the present invention is not limited to these structural units.
  • the high molecular weight of the present invention comprising a repeating unit represented by general formula (3), which consists of the triarylamine structural unit represented by general formula (1) and the linking structural unit represented by general formula (2).
  • the compound has excellent properties such as hole injection properties, hole mobility, electron blocking ability, thin film stability, and heat resistance.
  • the weight average molecular weight in terms of polystyrene measured by GPC is preferably 10,000 or more and less than 1,000,000, more preferably 10,000 or more and less than 500,000, and further It is preferably in the range of 10,000 or more and less than 200,000.
  • the high-molecular-weight compound of the present invention when applied to the formation of an organic layer in an organic EL device by coating, in order to ensure coatability, adhesion to other layers, and durability, other structural units It is preferred to include Such other structural units include, for example, a structural unit for enhancing thermal crosslinkability (thermal crosslinkable structural unit), and a triarylamine structural unit different from the triarylamine structural unit represented by general formula (1). There are structural units.
  • thermally crosslinkable structural unit examples include the structural units represented by the general formulas (4-1) to (4-143).
  • the dashed line indicates a bond to an adjacent structural unit
  • R is a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or having 3 to 40, an alkyl group, an alkyloxy group, a cycloalkyl group, a cycloalkyloxy group, an alkenyl group, or an aryloxy group.
  • Examples of the alkyl group, alkyloxy group, cycloalkyl group, cycloalkyloxy group, alkenyl group, and aryloxy group represented by R include the same groups as those shown for R 1 .
  • Preferred specific examples of the thermally crosslinkable structural unit have been shown, but the thermally crosslinkable structural unit used in the present invention is not limited to these structural units.
  • the triarylamine structural unit represented by general formula (1) is "structural unit A”
  • the linking structural unit represented by general formula (2) is “structural unit B”
  • thermal crosslinking 1 mol of structural unit A is represented by “structural unit C”
  • “structural unit D” is a triarylamine structural unit different from the triarylamine structural unit represented by general formula (1).
  • % or more particularly 20 mol % or more
  • the structural unit B is 1 mol % or more, particularly 30 to 70 mol %.
  • it preferably contains structural unit C in an amount of 1 mol% or more, particularly 5 to 20 mol%.
  • a copolymer is most suitable for forming an organic layer of an organic EL device.
  • the high-molecular-weight compounds of the present invention are synthesized by forming carbon-carbon bonds or carbon-nitrogen bonds, respectively, and linking structural units by Suzuki polymerization reaction or HARTWIG-BUCHWALD polymerization reaction. Specifically, a unit compound having each structural unit is prepared, the unit compound is appropriately boric acid esterified or halogenated, and polycondensation reaction is performed using an appropriate catalyst to obtain the high molecular weight compound of the present invention. Can be synthesized.
  • a triarylamine derivative represented by the following general formula (1a) can be used as a compound for introducing the triarylamine structural unit represented by the general formula (1).
  • Q is a hydrogen atom or a halogen atom (particularly preferably Br), and R 1 , R 2 and L are all the same as defined in general formula (1) above. be.
  • the compound in which Q is a hydrogen atom is a unit compound for introducing the triarylamine structural unit represented by the general formula (1), and the compound in which Q is a halogen atom. is the halide used to synthesize the polymer.
  • thermally crosslinkable structural unit C (general thermally crosslinkable structural unit A copolymer containing 5 mol % of formula (4-5)) is represented by the following general formula (5).
  • the intermediate for introducing the structural unit A and the structural unit C is a borate ester
  • the intermediate for introducing the structural unit B is a halide
  • the structural The intermediate for introducing the unit A and the structural unit C must be a halide
  • the intermediate for introducing the structural unit B must be a boric acid ester. That is, the molar ratios of halide and borate esters must be equal.
  • the above-described high molecular weight compound of the present invention is dissolved in an aromatic organic solvent such as benzene, toluene, xylene and anisole to prepare a coating liquid, which is coated on a predetermined substrate and dried by heating.
  • an aromatic organic solvent such as benzene, toluene, xylene and anisole.
  • the high molecular weight compound can be used as a constituent material of the hole injection layer and/or the hole transport layer of the organic EL device.
  • a hole injection layer and a hole transport layer formed of such a high molecular weight compound have higher hole injection properties, higher hole mobility, and electron blocking properties than those formed of conventional materials. is high, excitons generated in the light-emitting layer can be confined, the probability of recombination of holes and electrons can be improved, high luminous efficiency can be obtained, and the driving voltage can be lowered, and the organic EL The advantage of improved device durability can be realized.
  • the high molecular weight compound of the present invention having the above-described electrical properties has a wider gap than conventional materials and is effective in confining excitons, so it is naturally suitable for use in electron blocking layers and light-emitting layers. can do.
  • An organic EL device having an organic layer formed using the high-molecular-weight compound of the present invention has a structure shown in FIG. 3, for example. That is, a transparent anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are formed on a glass substrate 1 (a transparent substrate such as a transparent resin substrate may be used). is provided.
  • the organic EL device to which the high molecular weight compound of the present invention is applied is not limited to the layer structure described above, and a hole blocking layer can be provided between the light emitting layer 5 and the electron transport layer 6, and , as in the structure shown in FIG. Furthermore, an electron injection layer can be provided between the cathode and the electron transport layer. Additionally, some layers may be omitted. For example, a simple layer structure in which an anode, a hole-transporting layer, a light-emitting layer, an electron-transporting layer and a cathode are provided on a substrate may be employed. It is also possible to have a two-layer structure in which layers having the same function are superimposed.
  • the high-molecular-weight compound of the present invention utilizes its properties such as hole-injecting properties and hole-transporting properties to provide an organic layer (for example, a hole-injecting layer, a hole-transporting layer) provided between the anode and the cathode. , light emitting layer and electron blocking layer).
  • organic layer for example, a hole-injecting layer, a hole-transporting layer
  • light emitting layer and electron blocking layer for example, a light emitting layer and electron blocking layer.
  • the transparent anode may be formed of an electrode material known per se, and an electrode material having a large work function such as ITO and gold is vapor-deposited on a substrate (a transparent substrate such as a glass substrate). It is formed by
  • the hole injection layer provided on the transparent anode can be formed using a coating solution prepared by dissolving the high molecular weight compound of the present invention in an aromatic organic solvent such as toluene, xylene and anisole. can.
  • the hole injection layer can be formed by coating this coating liquid on the transparent anode by spin coating, inkjet, or the like.
  • the hole injection layer is formed of a conventionally known material such as the following, without using the high molecular weight compound of the present invention. It can also be formed using a material.
  • PEDOT poly(3,4-ethylenedioxythiophene)
  • PSS poly(styrene sulfonate)
  • a layer (thin film) using such a material can be formed by a coating method such as vapor deposition, spin coating, and inkjet. The same applies to other layers, and the film is formed by vapor deposition or coating depending on the type of film-forming material.
  • the hole transport layer provided on the hole injection layer can also be formed using the high molecular weight compound of the present invention by a coating method such as spin coating or inkjet. can.
  • a hole transport layer can be formed using a conventionally known hole transport material.
  • Typical examples of such hole transport materials are as follows.
  • benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (hereinafter abbreviated as TPD); N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)benzidine (hereinafter abbreviated as NPD); N,N,N',N'-tetrabiphenylylbenzidine;
  • Amine derivatives such as 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC); various triphenylamine trimers and tetramers;
  • a coating-type polymer material that is also used as a hole injection layer.
  • the compounds for the hole transport layer described above including the high-molecular-weight compound of the present invention, may be formed individually, or two or more of them may be mixed to form a film. Also, a multilayer film in which a plurality of layers are formed using one or more of the above compounds and such layers are laminated can be used as the hole transport layer.
  • a layer that serves both as a hole-injecting layer and a hole-transporting layer can be used.
  • the transport layer can be formed by a coating method using a polymeric material such as PEDOT.
  • the hole-transporting layer (the same applies to the hole-injecting layer), tris(4-bromophenyl)ammoniumylhexachloroantimonate or a radialene derivative (see, for example, WO2014/009310) is used as a material normally used for the layer. etc. can be used by P-doping.
  • the hole transport layer (and the hole injection layer) can be formed using a polymer compound having a TPD basic skeleton.
  • an electron-blocking layer (which can be provided between the hole-transporting layer 11 and the light-emitting layer 13, as shown in FIG. 4) is also coated using the high-molecular-weight compound of the present invention by a coating method such as spin coating and inkjet. can be formed by
  • an electron-blocking compound having an electron-blocking action such as a carbazole derivative or a triphenylsilyl group
  • An electron blocking layer can also be formed using a compound having a triarylamine structure.
  • carbazole derivatives and compounds having a triarylamine structure are as follows.
  • carbazole derivatives such as 4,4′,4′′-tri(N-carbazolyl)triphenylamine (hereinafter abbreviated as TCTA); 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene; 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP); 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter abbreviated as Ad-Cz); Compounds having a triarylamine structure, such as 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene.
  • TCTA 4,4′,4′′-tri(N-carbazolyl)triphenylamine
  • mCP 1,3-bis(carbazol-9-yl)benzene
  • Ad-Cz 2,2-bis(4-carbazol-9
  • the electron blocking layer including the high molecular weight compound of the present invention, may be formed independently, but it is also possible to form a film by mixing two or more kinds. Also, a multilayer film in which a plurality of layers are formed using one or more of the above compounds and such layers are laminated can be used as the electron blocking layer.
  • the light-emitting layer comprises metal complexes of quinolinol derivatives such as Alq3 ; various metal complexes such as zinc, beryllium and aluminum; It can be formed using a light-emitting material such as an anthracene derivative; a bisstyrylbenzene derivative; a pyrene derivative; an oxazole derivative;
  • the light-emitting layer can be composed of a host material and a dopant material.
  • a host material in addition to the light-emitting materials described above, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, and the like can be used, and furthermore, the high molecular weight compounds of the present invention described above can also be used.
  • Quinacridone, coumarin, rubrene, perylene, and derivatives thereof; benzopyran derivatives; rhodamine derivatives; aminostyryl derivatives and the like can be used as dopant materials.
  • Such a light-emitting layer can also have a single-layer structure using one or more of each light-emitting material, or can have a multi-layer structure in which a plurality of layers are laminated.
  • the light-emitting layer can also be formed using a phosphorescent light-emitting material as the light-emitting material.
  • a phosphorescent light-emitting material phosphorescent emitters of metal complexes such as iridium and platinum can be used.
  • green phosphorescent emitters such as Ir(ppy) 3
  • blue phosphorescent emitters such as FIrpic and FIr6
  • red phosphorescent emitters such as Btp2Ir (acac) can be used.
  • These phosphorescent materials are used by doping a hole-injecting/transporting host material or an electron-transporting host material.
  • doping of the host material with the phosphorescent light-emitting material is preferably carried out by co-evaporation in the range of 1 to 30% by weight with respect to the entire light-emitting layer.
  • the high molecular weight compound of the present invention carry a fluorescent emitter, a phosphorescent emitter, or a material that emits delayed fluorescence, which is called a dopant, to form a light-emitting layer, the driving voltage is lowered and the luminous efficiency is improved. It is possible to realize an organic EL element with
  • the high molecular weight compound of the present invention can be used as a hole-injecting/transporting host material.
  • CBP 4,4'-di(N-carbazolyl)biphenyl
  • carbazole derivatives such as TCTA and mCP, and the like can also be used.
  • p-bis(triphenylsilyl)benzene (hereinafter abbreviated as UGH2) is used as the electron-transporting host material.
  • UGH2 p-bis(triphenylsilyl)benzene
  • TPBI 2,2′,2′′-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole)
  • a hole-blocking layer (not shown in the figure) provided between the light-emitting layer and the electron-transporting layer includes It can be formed using a compound having a known hole-blocking action. Examples of known compounds having such a hole-blocking action include the following.
  • phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP); metal complexes of quinolinol derivatives such as aluminum (III) bis(2-methyl-8-quinolinate)-4-phenylphenolate (hereinafter abbreviated as BAlq); various rare earth complexes; triazole derivatives; triazine derivatives; Oxadiazole derivatives.
  • BCP bathocuproine
  • BAlq metal complexes of quinolinol derivatives
  • BAlq aluminum (III) bis(2-methyl-8-quinolinate)-4-phenylphenolate
  • various rare earth complexes such as triazole derivatives; triazine derivatives; Oxadiazole derivatives.
  • These materials can also be used to form the electron-transporting layer described below, and can also be used as both a hole-blocking layer and an electron-transporting layer.
  • Such a hole-blocking layer can also have a single-layer or multi-layer laminated structure, and each layer is formed using one or more of the compounds having the hole-blocking action described above.
  • the electron-transporting layer is composed of an electron-transporting compound known per se, such as a quinolinol derivative such as Alq 3 and BAlq. It can be formed using metal complexes, various metal complexes, pyridine derivatives, pyrimidine derivatives, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silole derivatives, benzimidazole derivatives, and the like. can.
  • an electron-transporting compound known per se such as a quinolinol derivative such as Alq 3 and BAlq. It can be formed using metal complexes, various metal complexes, pyridine derivatives, pyrimidine derivatives, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivative
  • This electron-transporting layer can also have a single-layer or multi-layer laminated structure, and each layer is formed using one or more of the electron-transporting compounds described above.
  • the electron injection layer (not shown in the figure) provided as necessary is also known per se, such as , alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal oxides such as aluminum oxide, and organometallic complexes such as lithium quinoline. .
  • an electrode material having a low work function such as aluminum, and a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy can be used.
  • An alloy with a lower work function, such as, is used as an electrode material.
  • the high molecular weight compound of the present invention is used to form at least one layer of a hole injection layer, a hole transport layer, a light emitting layer, and an electron blocking layer, thereby improving luminous efficiency and power consumption.
  • An organic EL device having high efficiency, low practical driving voltage, low light emission start voltage, and extremely excellent durability can be obtained.
  • this organic EL element while having high luminous efficiency, the driving voltage is lowered, the current resistance is improved, and the maximum luminous luminance is improved.
  • the structural unit represented by the general formula (1) of the high molecular weight compound of the present invention is "structural unit A”
  • the connecting structural unit represented by general formula (2) is “structural unit B ”
  • Example 1 Synthesis of High Molecular Weight Compound A; The following ingredients were added to a reaction vessel purged with nitrogen, and nitrogen gas was bubbled through for 30 minutes.
  • Intermediate 1 5.6 g
  • Intermediate 2 0.4g
  • Intermediate 3 2.2 g
  • Tripotassium phosphate 6.9 g
  • Toluene 9ml
  • Water 5ml 1,4-dioxane: 27 ml
  • 1.4 mg of palladium(II) acetate and 11.5 mg of tri-o-tolylphosphine were added, heated, and stirred at 87° C. for 14 hours.
  • the average molecular weight and dispersity of high molecular weight compound A measured by GPC were as follows. Number average molecular weight Mn (converted to polystyrene): 60,000 Weight average molecular weight Mw (converted to polystyrene): 108,000 Dispersity (Mw/Mn): 1.8
  • this high molecular weight compound A contained 45 mol% of structural unit A, 50 mol% of structural unit B, and 5 mol% of structural unit C.
  • Example 2 Synthesis of high molecular weight compound B; The following ingredients were added to a reaction vessel purged with nitrogen, and nitrogen gas was bubbled through for 30 minutes.
  • Intermediate 1 5.4 g
  • Intermediate 3 2.2 g
  • Intermediate 4 0.5g Tripotassium phosphate: 7.4 g
  • 1.5 mg of palladium(II) acetate and 14.4 mg of tri-o-methoxyphenylphosphine were added, heated, and stirred at 87° C. for 10 hours.
  • the crude polymer was dissolved in toluene, silica gel was added for adsorption purification, and the silica gel was removed by filtration.
  • the obtained filtrate was concentrated under reduced pressure, 100 ml of toluene was added to the dried solid to dissolve it, and the solution was added dropwise to 300 ml of n-hexane, and the resulting precipitate was collected by filtration. 100 ml of toluene was added to the obtained precipitate to dissolve it, and the solution was added dropwise to 200 ml of n-hexane, and the obtained precipitate was collected by filtration. This operation was repeated one more time and dried to obtain 3.2 g of high molecular weight compound B (yield: 67%).
  • the average molecular weight and dispersity of high molecular weight compound B measured by GPC were as follows. Number average molecular weight Mn (converted to polystyrene): 73,000 Weight average molecular weight Mw (converted to polystyrene): 139,000 Dispersity (Mw/Mn): 1.9
  • this high molecular weight compound B contained 44 mol% of structural unit A, 50 mol% of structural unit B, and 6 mol% of structural unit C.
  • Example 3 Using the high molecular weight compounds A and B synthesized in Examples 1 and 2, a coating film having a thickness of 80 nm was prepared on an ITO substrate, and an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS- 202 type) to measure the work function. The results were as follows. High molecular weight compound A: 5.63 eV High molecular weight compound B: 5.61 eV
  • the high molecular weight compound A of the present invention exhibits a favorable energy level compared to the work function of 5.4 eV of general hole-transporting materials such as NPD and TPD, and exhibits good hole-transporting ability. I know you have.
  • An organic EL device having a layered structure shown in FIG. 3 was produced by the following method. Specifically, after washing the glass substrate 1 with an ITO film having a film thickness of 50 nm with an organic solvent, the ITO surface was washed with UV/ozone treatment. PEDOT/PSS (manufactured by Ossila) was spin-coated to a thickness of 50 nm so as to cover the transparent anode 2 (ITO) provided on the glass substrate 1, and dried on a hot plate at 200° C. for 10 minutes. Then, a hole injection layer 3 was formed.
  • PEDOT/PSS manufactured by Ossila
  • a coating liquid was prepared by dissolving 0.6 wt % of the high molecular weight compound A obtained in Example 1 in toluene.
  • the substrate on which the hole injection layer 3 is formed as described above is transferred into a glove box replaced with dry nitrogen, dried on a hot plate at 230° C. for 10 minutes, and then placed on the hole injection layer 3.
  • a coating layer having a thickness of 25 nm was formed by spin coating using the above coating liquid, and dried on a hot plate at 220° C. for 30 minutes to form a hole transport layer 4 .
  • the substrate on which the hole transport layer 4 was formed as described above was mounted in a vacuum deposition machine, and the pressure was reduced to 0.001 Pa or less.
  • ETM-1 and ETM-2 compounds of the following structural formulas, were prepared as electron transport materials.
  • an electron-transporting layer 6 having a thickness of 20 nm was formed by binary vapor deposition using the electron-transporting materials ETM-1 and ETM-2.
  • a cathode 7 was formed by vapor-depositing aluminum to a film thickness of 100 nm.
  • the glass substrate on which the transparent anode 2, the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, the electron transport layer 6 and the cathode 7 are formed is placed in a glove box filled with dry nitrogen. It was moved, and another glass substrate for sealing was bonded together using a UV curable resin to form an organic EL element.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Further, the luminescence characteristics were measured when a DC voltage was applied to the produced organic EL device. The measurement results are shown in Table 1.
  • Example 4 except that a coating solution prepared by dissolving 0.6 wt % of the following TFB (hole-transporting polymer) in toluene instead of the high-molecular-weight compound A was used to form the hole-transporting layer 4.
  • An organic EL device was produced in the same manner as above.
  • TFB hole-transporting polymer
  • PFA hole-transporting polymer
  • Various characteristics of the organic EL device of Comparative Example 1 were evaluated in the same manner as in Example 4, and the results are shown in Table 1.
  • the voltage, luminance, luminous efficiency and power efficiency are obtained when a current with a current density of 10 mA/cm 2 is applied.
  • life of the element was measured by constant current driving with a light emission luminance of 700 cd/m 2 at the start of light emission (initial luminance) of 560 cd/m 2 (80% of the initial luminance of 100%). Equivalent: measured as the time to decay to 80% decay).
  • the luminous efficiency of the organic EL device of Comparative Example 1 was 5.52 cd/A when a current with a current density of 10 mA/cm 2 was applied, while the organic EL device of Example 4 was 7.52 cd/A. It was highly efficient at .83 cd/A.
  • the device life (80% attenuation) was 248 hours for the organic EL device of Example 4, which is longer than the 6 hours for the organic EL device of Comparative Example 1.
  • An organic EL device having a layer structure shown in FIG. 4 was produced by the following method. Specifically, after washing the glass substrate 8 with an ITO film having a thickness of 50 nm with an organic solvent, the ITO surface was washed with UV/ozone treatment. PEDOT/PSS (manufactured by Ossila) was spin-coated to a thickness of 50 nm so as to cover the transparent anode 9 (ITO) provided on the glass substrate 8, and dried on a hot plate at 200° C. for 10 minutes. Then, a hole injection layer 10 was formed.
  • PEDOT/PSS manufactured by Ossila
  • a coating liquid was prepared by dissolving 0.4 wt% of a high molecular weight compound HTM-1 having the following structural formula in toluene.
  • the substrate on which the hole injection layer 10 is formed as described above is transferred into a glove box replaced with dry nitrogen, and dried on a hot plate at 230° C. for 10 minutes.
  • a coating layer having a thickness of 15 nm was formed by spin coating using the above coating solution, and dried on a hot plate at 220° C. for 30 minutes to form a hole transport layer 11 .
  • a coating liquid was prepared by dissolving 0.4 wt % of the high molecular weight compound A obtained in Example 1 in toluene.
  • a coating layer having a thickness of 15 nm is formed on the hole transport layer 11 by spin coating using the above coating liquid, and dried on a hot plate at 220° C. for 30 minutes to form an electron blocking layer 12 . did.
  • the substrate on which the electron blocking layer 12 was formed as described above was mounted in a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less.
  • an electron transporting layer 14 having a thickness of 20 nm was formed by binary vapor deposition using the electron transporting materials ETM-1 and ETM-2.
  • a cathode 15 was formed by vapor-depositing aluminum to a film thickness of 100 nm.
  • the glass substrate on which the transparent anode 9, the hole injection layer 10, the hole transport layer 11, the electron blocking layer 12, the light emitting layer 13, the electron transport layer 14 and the cathode 15 are formed is replaced with dry nitrogen.
  • another glass substrate for sealing was attached using a UV curable resin to form an organic EL element.
  • the characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Further, the luminescence characteristics were measured when a DC voltage was applied to the produced organic EL device. The measurement results are shown in Table 2.
  • Example 5 except that the electron blocking layer 12 was formed using a coating liquid prepared by dissolving 0.4 wt % of the high molecular weight compound B obtained in Example 2 in toluene instead of the high molecular weight compound A.
  • An organic EL device was produced in exactly the same manner. Various characteristics of the produced organic EL device were evaluated in the same manner as in Example 5, and the results are shown in Table 2.
  • An organic EL device having a layer structure shown in FIG. 4 was produced by the following method. Specifically, after washing the glass substrate 8 with an ITO film having a thickness of 50 nm with an organic solvent, the ITO surface was washed with UV/ozone treatment. PEDOT/PSS (manufactured by Ossila) was spin-coated to a thickness of 50 nm so as to cover the transparent anode 9 (ITO) provided on the glass substrate 8, and dried on a hot plate at 200° C. for 10 minutes. Then, a hole injection layer 10 was formed.
  • PEDOT/PSS manufactured by Ossila
  • a coating liquid was prepared by dissolving 0.6 wt% of the high molecular weight compound HTM-1 in toluene.
  • the substrate on which the hole injection layer 10 is formed as described above is transferred into a glove box filled with dry nitrogen, and the above coating solution is applied onto the hole injection layer 3 by a spin coating method.
  • a coating layer having a thickness of 25 nm was formed and dried on a hot plate at 220° C. for 30 minutes to form hole transport layer 11 .
  • the substrate on which the hole transport layer 11 was formed as described above was mounted in a vacuum deposition machine, and the pressure was reduced to 0.001 Pa or less.
  • a cathode 15 was formed by vapor-depositing aluminum to a film thickness of 100 nm.
  • the glass substrate on which the transparent anode 9, the hole injection layer 10, the hole transport layer 11, the light emitting layer 13, the electron transport layer 14 and the cathode 15 are formed is placed in a glove box substituted with dry nitrogen. It was moved, and another glass substrate for sealing was bonded together using a UV curable resin to form an organic EL element.
  • the characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Further, the luminescence characteristics were measured when a DC voltage was applied to the produced organic EL device. The measurement results are shown in Table 2.
  • the voltage, luminance, luminous efficiency and power efficiency are obtained when a current with a current density of 10 mA/cm 2 is applied.
  • life of the element was measured by constant current driving with a light emission luminance of 700 cd/m 2 at the start of light emission (initial luminance) of 560 cd/m 2 (80% of the initial luminance of 100%). Equivalent: measured as the time to decay to 80% decay).
  • the luminous efficiency of the organic EL device of Comparative Example 2 was 7.56 cd/A when a current with a current density of 10 mA/cm 2 was applied, while the organic EL device of Example 5 was 8.56 cd/A. It was highly efficient at .68 cd/A.
  • the device life (80% decay) was 20 hours for the organic EL device of Comparative Example 2, 408 hours for the organic EL device of Example 5, and 558 hours for the organic EL device of Example 6. It had a long life.
  • the organic EL element having the organic layer formed using the high molecular weight compound of the present invention can realize an organic EL element with high luminous efficiency and long life as compared with conventional organic EL elements. I found out.
  • the high-molecular-weight compound of the present invention has high hole-transporting ability, excellent electron-blocking ability, and good thermal crosslinkability, so it is excellent as a compound for coating-type organic EL devices.
  • a coating-type organic EL device using the high molecular weight compound of the present invention high luminous efficiency and power efficiency can be obtained, and durability can be improved. As a result, it has become possible to develop it into a wide range of applications such as home appliances and lighting, for example.

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