WO2020027589A1 - Nouveau polymère et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau polymère et dispositif électroluminescent organique le comprenant Download PDF

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WO2020027589A1
WO2020027589A1 PCT/KR2019/009568 KR2019009568W WO2020027589A1 WO 2020027589 A1 WO2020027589 A1 WO 2020027589A1 KR 2019009568 W KR2019009568 W KR 2019009568W WO 2020027589 A1 WO2020027589 A1 WO 2020027589A1
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group
substituted
unsubstituted
polymer
compound
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Korean (ko)
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강에스더
배재순
이재철
신지연
강범구
서민섭
박형일
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주식회사 엘지화학
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Priority claimed from KR1020190092669A external-priority patent/KR102153086B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP19843951.5A priority Critical patent/EP3699231B1/fr
Priority to US16/652,899 priority patent/US20200291175A1/en
Priority to CN201980004730.XA priority patent/CN111148791B/zh
Priority to JP2020525875A priority patent/JP6983460B2/ja
Publication of WO2020027589A1 publication Critical patent/WO2020027589A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a novel polymer and an organic light emitting device comprising the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices using a solution process in particular, an inkjet process
  • organic light emitting devices were developed by coating all organic light emitting device layers by solution process, but there are limitations in current technology, so only HIL, HTL, and EML are used as solution process in regular structure, and further processes are conventional deposition processes.
  • a hybrid process that utilizes is under study.
  • the present invention provides a novel organic light emitting device material that can be used in an organic light emitting device and can be deposited in a solution process at the same time.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel polymer and an organic light emitting device comprising the same.
  • the present invention provides a polymer comprising a repeating unit represented by the following Formula 1, a repeating unit represented by the following Formula 2, and a repeating unit represented by the following Formula 3.
  • R 1 to R 3 are each independently hydrogen or C 1-10 alkyl
  • L 1 is substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • L 2 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 1 is substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from the group consisting of N, O and S,
  • Ar 2 and Ar 3 are each independently selected from the group consisting of substituted or unsubstituted C 1-60 alkoxy, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted N, O and S C 2-60 heteroaryl containing at least one,
  • R 4 to R 6 are each independently hydrogen or C 1-10 alkyl
  • L 3 is a single bond; Substituted or unsubstituted C 6-60 arylene; (Substituted or unsubstituted C 6-60 arylene) -O-; (Substituted or unsubstituted C 6-60 arylene) -O- (substituted or unsubstituted C 1-60 alkylene); Or C 2-60 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • R 7 to R 9 are each independently hydrogen or C 1-10 alkyl
  • L 4 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 4 comprises any one or more selected from the group consisting of substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted N, O and S C 2-60 heteroaryl,
  • Ar 5 is hydrogen or substituted or unsubstituted C 6-60 aryl
  • n is an integer of 0-5.
  • the present invention is an anode; A cathode provided to face the anode; A light emitting layer provided between the anode and the cathode; And a hole transport layer provided between the anode and the light emitting layer, wherein the hole transport layer includes the polymer.
  • the polymer according to the present invention may be used as a material for the hole transport layer of the organic light emitting device, and may be deposited by a solution process, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting device.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, and a cathode 5. As shown in FIG.
  • an organic light emitting element is shown.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O, and S atoms, or two or more substituents connected to the substituents
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a straight chain, branched chain or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, And so on.
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the present invention provides a polymer comprising a repeating unit represented by Formula 1, a repeating unit represented by Formula 2, and a repeating unit represented by Formula 3.
  • the solution deposition material used in the related art has a problem in that even if there is solubility in a solvent, the material is dissolved in a solvent used in the next layer deposition and the layers are mixed to degrade device performance.
  • the polymer according to the present invention as described in detail below, together with the excellent hole transport properties by the repeating unit represented by the formula (1), after evaporation to cure the repeating unit represented by the formula (2) solvent orthogonality (solvent orthogonality)
  • solvent orthogonality solvent orthogonality
  • the intermixing is suppressed, and the solubility improvement and the curing temperature can be lowered in the solution process by the repeating unit represented by the above formula (3).
  • each repeating unit will be described.
  • the 'first repeating unit' is a repeating unit represented by Chemical Formula 1 included in the polymer according to the present invention, and has excellent hole transport characteristics.
  • R 1 to R 3 are each independently hydrogen or methyl, and more preferably all are hydrogen.
  • L 1 is substituted or unsubstituted C 6-12 arylene, more preferably phenylene or biphenylylene, most preferably 1,4-phenylene, or 4,4'- Biphenylylene.
  • L 2 is a single bond, substituted or unsubstituted C 6-18 arylene, more preferably phenylene, biphenylylene, or terphenylylene, most preferably 1,4-phenylene , 1,1'-biphenylylene, or to be.
  • Ar 1 is phenyl, biphenylyl, dimethylfluorenyl, or diphenylfluorenyl, wherein Ar 1 is unsubstituted or substituted with C 1-4 alkyl or C 1-4 alkoxy. . More preferably, Ar 1 is phenyl, biphenylyl, dimethylfluorenyl, or diphenylfluorenyl, wherein Ar 1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, methoxy , Ethoxy, propoxy, butoxy, isobutoxy, or neobutoxy.
  • Ar 2 and Ar 3 are each independently C 6-25 aryl, and more preferably each independently is phenyl, biphenylyl, dimethylfluorenyl, or diphenylfluorenyl.
  • Formula 1 is any one selected from the group consisting of repeating units represented by:
  • R 1 to R 3 , L 1 , L 2, and Ar 1 to Ar 3 are the same as defined in Formula 1 above.
  • the compound represented by Chemical Formula 1-1 may be prepared by the same method as in Scheme 1 below.
  • Scheme 1 the remaining definitions except for X 1 are as defined above, and X 1 is halogen, preferably bromo, or chloro.
  • Scheme 1 is an amine substitution reaction, in which a palladium catalyst is reacted with a base to prepare a compound represented by Chemical Formula 1-1. The manufacturing method may be more specific in the production examples to be described later.
  • the 'second repeating unit' is a repeating unit represented by Chemical Formula 2 included in the polymer according to the present invention, and includes a benzocyclobutane which is a curable reactor.
  • the deposited polymer After depositing the polymer according to the present invention, through the cycloaddition reaction of the benzocyclobutane and the alkene of the third repeating unit to be described later in the thermal process, the deposited polymer has a solvent resistance, it is applied to the organic light emitting device in a solution process can do.
  • Chemical Formula 2 is represented by the following Chemical Formula 2 '.
  • R 4 to R 6 are each independently hydrogen or methyl, and more preferably all are hydrogen.
  • L 3 is a single bond, substituted or unsubstituted C 6-12 arylene, (substituted or unsubstituted C 6-12 arylene) -O-; (Substituted or unsubstituted C 6-12 arylene) -O- (substituted or unsubstituted C 1-10 alkylene), more preferably a single bond, phenylene,-(phenylene) -O-, -(Phenylene) -O- (butane-1,4-diyl), or biphenylylene, most preferably 1,4-phenylene or 4,4'-biphenylylene.
  • Formula 2 is any one selected from the group consisting of repeating units represented by:
  • the compound represented by Chemical Formula 2-1 may be prepared by the same method as in Scheme 2 below.
  • Scheme 2 is a Suzuki coupling reaction, in which a compound represented by Chemical Formula 2-1 is prepared by reacting a palladium catalyst in the presence of a base.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the 'third repeating unit' is a repeating unit represented by Chemical Formula 3 included in the polymer according to the present invention, and may improve the solubility of the polymer according to the present invention or lower the curing temperature because it includes a vinyl group. .
  • R 7 to R 9 are each independently hydrogen or methyl, and more preferably all are hydrogen.
  • L 4 is a single bond, substituted or unsubstituted C 6-12 arylene, more preferably a single bond, phenylene, or biphenylylene, most preferably a single bond, 1,4- Phenylene or 4,4'-biphenylylene.
  • Ar 4 is C 3-10 cycloalkyl, or C 6-12 aryl, more preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, one or two C 1- Phenyl substituted with 4 alkyl, or biphenylyl.
  • Ar 5 is hydrogen, phenyl, biphenylyl, terphenylyl, or quarterphenylyl.
  • Formula 3 is any one selected from the group consisting of repeating units represented by:
  • TMS means trimethylsilyl and t-Bu means tert-butyl.
  • R 7 to R 9 , L 4 , Ar 4 , Ar 5 , and n are the same as defined in Formula 3 above.
  • the compound represented by Chemical Formula 3-1 may be prepared by the same method as in Scheme 3 below.
  • Scheme 3 is a Suzuki coupling reaction, in which a palladium catalyst is reacted with a base to prepare a compound represented by Chemical Formula 3-1.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the polymer according to the present invention may be prepared by polymerizing the monomer represented by Formula 1-1, the monomer represented by Formula 2-1, and the monomer represented by Formula 3-1.
  • the polymer according to the present invention is a random copolymer including the repeating unit.
  • x, y and z are molar ratios of the repeating unit of Formula 1, the repeating unit of Formula 2 and the repeating unit of Formula 3 in the polymer, x: y: z is 0.5 to 0.9: 0.05 to 0.45: 0.05-0.45.
  • the molar ratio of the polymer may be controlled by controlling the reaction molar ratio of the monomer represented by Formula 1-1, the monomer represented by Formula 2-1, and the monomer represented by Formula 3-1.
  • the weight average molecular weight of the polymer is 15,000 to 1,000,000, more preferably 40,000 to 100,000.
  • the polymer may be used with the doping material.
  • the doping material may be a compound of Formula (K), an ionic compound of Formula (L) or Formula (M), but is not limited thereto.
  • the polymer according to the present invention may form an organic material layer, particularly a hole transport layer, of the organic light emitting device by a solution process.
  • the present invention provides a coating composition comprising a polymer and a solvent according to the present invention described above.
  • the solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the polymer according to the present invention.
  • chloroform methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o Chlorine solvents such as dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone; Ester solvents such as ethyl ket
  • the viscosity of the coating composition is preferably 1 cP to 10 cP, the coating is easy in the above range.
  • the concentration of the polymer according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.
  • the coating composition may further include one or two or more additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.
  • methyl ethyl ketone peroxide methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide Oxides, peroxides such as bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, or azobis isobutyl nitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile There is an azo system, but is not limited thereto.
  • photoinitiator diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4- (2-hydroxyethoxy ) Phenyl- (2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2-hydroxy-2-methyl-1- Phenyl propane-1-one, 2-methyl-2-morpholino (4-methyl thiophenyl) propane-1-one, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) Acetophenone type or ketal type photoinitiators, such as an oxime; Benzoin ether type photoinitiators, such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Benzophenone photopolymerization initiators such as benzophenone, 4-hydroxy
  • photopolymerization promoting effect can also be used individually or in combination with the said photoinitiator.
  • examples include triethanolamine, methyldiethanolamine, 4-dimethylaminobenzoic acid ethyl, 4-dimethylamino benzoic acid isoamyl, benzoic acid (2-dimethylamino) ethyl, 4,4'-dimethylaminobenzophenone, and the like. It is not limited.
  • the present invention also provides a method of forming a hole transport layer using the above-described coating composition. Specifically, coating the coating composition according to the invention described above on a positive electrode, or on a hole injection layer formed on the positive electrode by a solution process; And heat treating or phototreating the coated coating composition.
  • the solution process is to use the coating composition according to the present invention described above, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited to these.
  • the heat treatment temperature is preferably 150 to 230 °C.
  • the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour.
  • the heat treatment is preferably carried out in an inert gas atmosphere such as argon, nitrogen.
  • the method may further include evaporating the solvent between the coating step and the heat treatment or light treatment step.
  • the present invention provides an organic light emitting device comprising the polymer according to the present invention described above.
  • the present invention is an anode; A cathode provided to face the anode; A light emitting layer provided between the anode and the cathode; And a hole transport layer provided between the anode and the light emitting layer, wherein the hole transport layer comprises a polymer according to the present invention.
  • FIGS. 1 and 2 The structure of the organic light emitting device according to the embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, and a cathode 5.
  • FIG. 2 is composed of a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 3, a light emitting layer 4, an electron transport layer 7, an electron injection layer 8 and a cathode 5
  • An example of an organic light emitting element is shown.
  • the organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that the hole transport layer includes the polymer according to the present invention and is manufactured as described above.
  • the organic light emitting device may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material may be a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and styrylamine compounds may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the arylamine, and a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted.
  • a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • an electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and a hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the polymer according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Methyltriphenylphosphonium bromide (13.41 g, 37.532 mmol) and potassium t-butoxide (4.21 g, 37.532 mmol) were added to anhydrous THF (300 mL) and stirred first. Then compound 4 (8 g, 18.766 mmol) dissolved in anhydrous THF (60 mL) was slowly added dropwise and reacted for 5 hours. After the reaction was terminated with an aqueous solution of sodium carbonate, the mixture was extracted with an organic layer using methylene chloride and water, and residual moisture was removed using MgSO 4 . The reaction solution was concentrated and then column chromatography with methylene chloride and hexane to give compound 5 (7.8g, 98%).
  • a compound A2 was prepared by the same method as the method for preparing compound A1, except that (4- (dibiphenyl-4-ylamino) phenyl) boronic acid was used instead of (4- (diphenylamino) phenyl) boronic acid. .
  • a compound A5 was prepared by the same method as the method for preparing compound A4, except that dibiphenyl-4-ylamine was used instead of diphenylamine.
  • Compound A6 was prepared by the same method as the method for preparing compound A4, except that N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine was used instead of diphenylamine. .
  • a compound A7 was prepared by the same method as the method for preparing compound A1, except that compound 6 was used instead of compound 5.
  • Compound 6 is used instead of compound 5, and 4- (biphenyl-4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl instead of (4- (diphenylamino) phenyl) boronic acid
  • a compound A9 was prepared by the same method as the method for preparing compound A1, except that boronic acid was used.
  • Methyltriphenylphosphonium bromide (13.41 g, 37.532 mmol) and potassium t-butoxide (4.21 g, 37.532 mmol) were added to anhydrous THF (30 mL) and stirred. Then compound 7 (3.90 g, 18.766 mmol) dissolved in anhydrous THF (10 mL) was slowly added dropwise and reacted for 4 hours. After the reaction was terminated with an aqueous solution of sodium carbonate, the organic layer was extracted using methylene chloride and water, and residual moisture was removed using MgSO 4 . The reaction solution was concentrated and then column chromatography with methylene chloride and hexane to give compound B2 (3.2 g, yield 84%).
  • Compound D2 was prepared by the same method as the method for preparing compound D1, except that 8-bromooctene was used instead of 6-bromohexene.
  • Compound A1 500 mg
  • Compound B2 22 mg
  • Compound D1 45 mg
  • AIBN 1.2 mg
  • Precipitated polymer C1 was prepared by precipitation in ethyl acetate.
  • the number average molecular weight and the weight average molecular weight of the prepared polymer were measured by GPC using PC standard (Standard) using Agilent 1200 series.
  • Copolymer C2 was prepared in the same manner as preparing Copolymer C1, except that Compound A3 was used instead of Compound A1 and 4-bromobenzocyclobutane was used instead of Compound B2.
  • the number average molecular weight and the weight average molecular weight of the prepared polymer were measured by GPC using PC standard (Standard) using Agilent 1200 series.
  • Copolymer C3 was prepared in the same manner as in the preparation of Copolymer C1, except that Compound A6 was used instead of Compound A1, 4-bromobenzocyclobutane was used instead of Compound B2, and Compound D2 was used instead of Compound D1. It was.
  • the number average molecular weight and the weight average molecular weight of the prepared polymer were measured by GPC using PC standard (Standard) using Agilent 1200 series.
  • a copolymer C4 was prepared in the same manner as the preparation of the copolymer C1, except that the compound A9 was used instead of the compound A1.
  • the number average molecular weight and the weight average molecular weight of the prepared polymer were measured by GPC using PC standard (Standard) using Agilent 1200 series.
  • Copolymer C6 was prepared in the same manner as preparing Copolymer C1, except that Compound A3 was used instead of Compound A1 and 4-bromobenzocyclobutane was used instead of Compound B2.
  • the number average molecular weight and the weight average molecular weight of the prepared polymer were measured by GPC using PC standard (Standard) using Agilent 1200 series.
  • Methyltriphenylphosphonium bromide (15.3 g, 42.830 mmol) and t-butoxide (6.4 g, 57.106 mmol) were added to THF (70 mL) and stirred, followed by the preparation of Compound 10 (10 g, 28.553 mmol). Further put and stirred for 4 hours. After removing the remaining base using a saturated aqueous sodium bicarbonate solution, the organic layer was extracted using ethyl acetate and water. After dehydration using MgSO 4 , the solvent was removed under reduced pressure. The obtained material was column chromatographed with ethyl acetate and hexane to obtain compound 11 (9.5 g, yield: 96%).
  • the glass substrate coated with ITO (indium tin oxide) to a thickness of 1,500 kPa was put in distilled water in which detergent was dissolved and ultrasonically washed.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • the ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl, acetone and drying washed the substrate for 5 minutes and then transported the substrate to the glove box.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec, LiF was 0.3 ⁇ / sec, aluminum was maintained at the deposition rate of 2 ⁇ / sec, the vacuum degree during deposition is 2 ⁇ 10 -7 ⁇ 5 X10 -8 torr was maintained.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that the copolymer shown in Table 1 was used instead of the copolymer C1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that Copolymer F was used instead of Copolymer C1.
  • Table 1 shows the results of measuring the driving voltage, external quantum efficiency (EQE), luminance and lifetime of the organic light emitting diodes manufactured in the Experimental and Comparative Experimental Examples at a current density of 10 mA / cm 2 . It was.
  • the external quantum efficiency was calculated as (number of photons emitted) / (number of charged carriers).
  • T80 refers to the time it takes for the luminance to decrease to 80% from the initial luminance (500 nit).
  • the copolymer according to the present invention was confirmed to include the formula (2) and formula (3), the efficiency and life is improved compared to the copolymer that is not.
  • the copolymer according to the present invention is excellent in solubility in organic solvents, it is easy to prepare a coating composition.
  • Table 1 it was confirmed that a uniform coating layer can be formed by using the coating composition, the stability of the film is excellent, showing better performance in the organic light emitting device.
  • a glass substrate on which ITO (indium tin oxide) was deposited at a thickness of 1500 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically washed. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing with a solvent of isopropyl alcohol and acetone for 30 minutes each and dried, and then transported the substrate to the glove box.
  • ITO indium tin oxide
  • the following compound A 'and the following compound M were mixed at a weight ratio of 8: 2 on the prepared ITO transparent electrode by spin coating a solution dissolved in cyclohexanone to form a film having a thickness of 400 ⁇ . This was heated at 220 ° C. for 30 minutes in a nitrogen atmosphere to form a hole injection layer.
  • the previously prepared copolymer C1 was dissolved in toluene, spin coated on the hole injection layer to form a film at 200 Pa, and heated to 190 ° C. under nitrogen atmosphere for 1 hour to form a hole transport layer.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec, LiF was 0.3 ⁇ / sec, aluminum was maintained at the deposition rate of 2 ⁇ / sec, the vacuum degree during deposition is 2 ⁇ 10 -7 ⁇ 5 X10 -8 torr was maintained.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that the copolymer shown in Table 2 was used instead of the copolymer C1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that copolymer F was used instead of copolymer C1.
  • Table 2 shows the results of measuring the driving voltage, external quantum efficiency (EQE), brightness, and lifetime of the organic light emitting diodes manufactured in the Experimental and Comparative Experimental Examples at a current density of 10 mA / cm 2 . It was.
  • the external quantum efficiency was calculated as (number of photons emitted) / (number of charged carriers).
  • T80 refers to the time it takes for the luminance to decrease to 80% from the initial luminance (500 nit).
  • the copolymer according to the present invention was confirmed by including the formula (2) and formula (3), the efficiency and life is improved compared to the copolymer that is not.
  • the copolymer according to the present invention is excellent in solubility in organic solvents, it is easy to prepare a coating composition.
  • Table 2 it was confirmed that a uniform coating layer can be formed using the coating composition, and the film has excellent stability, and thus shows better performance in an organic light emitting device.
  • substrate 2 anode
  • hole transport layer 4 light emitting layer

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  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

La présente invention concerne un nouveau polymère et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/009568 2018-07-31 2019-07-31 Nouveau polymère et dispositif électroluminescent organique le comprenant WO2020027589A1 (fr)

Priority Applications (4)

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EP19843951.5A EP3699231B1 (fr) 2018-07-31 2019-07-31 Nouveau polymère et dispositif électroluminescent organique le comprenant
US16/652,899 US20200291175A1 (en) 2018-07-31 2019-07-31 Novel Polymer and Organic Light Emitting Device Comprising the Same
CN201980004730.XA CN111148791B (zh) 2018-07-31 2019-07-31 新的聚合物和包含其的有机发光器件
JP2020525875A JP6983460B2 (ja) 2018-07-31 2019-07-31 新規な高分子およびこれを含む有機発光素子

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000051826A (ko) 1999-01-27 2000-08-16 성재갑 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
WO2017031622A1 (fr) * 2015-08-21 2017-03-02 Dow Global Technologies Llc Couche de transfert de charge polymère et dispositif électronique organique la contenant
WO2017107117A1 (fr) * 2015-12-24 2017-06-29 Dow Global Technologies Llc Couche polymère et dispositif électronique organique la comprenant
KR20170077774A (ko) * 2015-12-28 2017-07-06 삼성전자주식회사 중합체, 이를 포함하는 유기 발광 소자 재료 및 이를 포함하는 유기 발광 소자
WO2018005318A1 (fr) * 2016-06-28 2018-01-04 Dow Global Technologies Llc Dispositifs électroluminescents à points quantiques

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* Cited by examiner, † Cited by third party
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KR20000051826A (ko) 1999-01-27 2000-08-16 성재갑 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
WO2017031622A1 (fr) * 2015-08-21 2017-03-02 Dow Global Technologies Llc Couche de transfert de charge polymère et dispositif électronique organique la contenant
WO2017107117A1 (fr) * 2015-12-24 2017-06-29 Dow Global Technologies Llc Couche polymère et dispositif électronique organique la comprenant
KR20170077774A (ko) * 2015-12-28 2017-07-06 삼성전자주식회사 중합체, 이를 포함하는 유기 발광 소자 재료 및 이를 포함하는 유기 발광 소자
WO2018005318A1 (fr) * 2016-06-28 2018-01-04 Dow Global Technologies Llc Dispositifs électroluminescents à points quantiques

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