WO2020209599A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2020209599A1
WO2020209599A1 PCT/KR2020/004748 KR2020004748W WO2020209599A1 WO 2020209599 A1 WO2020209599 A1 WO 2020209599A1 KR 2020004748 W KR2020004748 W KR 2020004748W WO 2020209599 A1 WO2020209599 A1 WO 2020209599A1
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group
formula
compound
aryl
synthesis
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손호준
김회문
정화순
배형찬
김진웅
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두산솔루스 주식회사
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    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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 organic compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent electron transport ability and an organic electric field having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the compound in one or more organic material layers. It relates to a light emitting device.
  • organic electroluminescent (EL) devices hereinafter simply referred to as'organic EL devices'
  • blue electroluminescence using an anthracene single crystal in 1965 starting from Bernanose's observation of organic thin-film emission in the 1950s, was conducted in 1987.
  • An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer by (Tang) was presented. Since then, in order to make a high-efficiency, high-life organic EL device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used for this.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.
  • the material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the light emission color.
  • yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors.
  • a host/dopant system may be used as a light emitting material.
  • the dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Development of such a phosphorescent material can theoretically improve the luminous efficiency of up to 4 times compared to fluorescence, and thus attention is being focused on phosphorescent host materials as well as phosphorescent dopants.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like represented by the following formula
  • anthracene derivatives as a light emitting material are reported as fluorescent dopant/host materials.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2 are blue, green, and red dopant materials. Is being used.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the existing materials have an advantage in terms of light emission characteristics, but the glass transition temperature is low and the thermal stability is very poor, so that the lifespan of the organic EL device is not satisfactory.
  • the present invention provides a novel compound that can be used as an organic material layer material of an organic electroluminescent device, specifically, a light emitting layer material (green), an electron transport layer material, or an electron transport auxiliary layer material, etc., due to its excellent electron injection and transport ability and luminous ability. It aims to do.
  • Another object of the present invention is to provide an organic electroluminescent device including the above-described novel compound, capable of low voltage driving, high luminous efficiency, and implementing long life characteristics.
  • the present invention provides a compound represented by the following formula (1), specifically an electron transport layer, an electron transport auxiliary layer, or a compound for a light emitting layer material.
  • X 1 to X 3 are the same as or different from each other, and each independently C(R 1 ) or N, provided that at least one of X 1 to X 3 is N,
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Of an alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, C 1 to C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, a C 6 ⁇ C 60 monoaryl Phosphinicosuccinic group, diaryl pho
  • a is an integer of 0 to 3
  • b is an integer of 0 to 4
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Of an alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, C 1 to C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, a C 6 ⁇ C 60 monoaryl Phosphinicosuccinic group, diaryl pho
  • L is a single bond, or is selected from the group consisting of an arylene group of C 6 to C 18 and a heteroarylene group of 5 to 18 nuclear atoms,
  • the arylene group and heteroarylene group of L the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group in the R 1 to R 2 , and Ar 1 to Ar 2 , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylsilyl group, each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom number 5 ⁇ 40 heteroaryl group, C 6 ⁇ C 40 Aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 ary
  • the present invention provides an electron transport layer or an electron transport auxiliary layer including the compound represented by Formula 1 above.
  • the present invention includes an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer is an organic electric field including the compound represented by the above-described formula (1). It provides a light emitting device.
  • the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of an emission layer, a light emission auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer.
  • the compound represented by Formula 1 according to the present invention has excellent electron transport and luminescence properties, it can be used as an organic material layer material of an organic electroluminescent device.
  • the compound represented by Formula 1 of the present invention when used as a material for a green light-emitting layer (phosphorescent host), an electron transport layer, or an auxiliary electron transport layer, it has higher thermal stability, lower driving voltage, and faster than the conventional host material or electron transport material.
  • An organic electroluminescent device having mobility, high current efficiency, and long life can be manufactured, and further, it can be effectively applied to a full color display panel with improved performance and lifetime.
  • the compound represented by Formula 1 includes a carbazole moiety in which a phenyl group is bonded to carbon positions 2 and 4; And a nitrogen-containing heteroaryl group (X 1 to X 3 containing ring), and the carbazole group and the heteroaryl group are directly bonded or linked through a linker (L) as a basic skeleton structure.
  • the compound represented by Formula 1 having such a structure is a nitrogen-containing aromatic ring (e.g., pyridine), a carbazole group having electron donor (EDG) characteristics and a kind of azine group, which is an electron attracting group (EWG) having high electron absorption. , pyrazine, triazine) in the molecule at the same time.
  • EWG electron attracting group
  • pyrazine, triazine in the molecule at the same time.
  • the organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.
  • the EWG group and the EDG group contained in the molecule it is advantageous as a host in the phosphorescent light emitting layer due to the bipolar property, and the charge balance can be adjusted through linkage conversion and sub moiety conversion.
  • a bipolar compound can improve hole injection/transport capability, luminous efficiency, driving voltage, life characteristics, durability, etc. due to high recombination power between holes and electrons.
  • by combining the positions 2 and 4 of the carbazole with a specific substituent and blocking conventional unsubstituted carbazole or carbazole containing an aryl group substituted at other positions (eg, 1 and 3) Compared to the compound, it is possible to improve the driving voltage and efficiency characteristics of the device.
  • the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a green light emitting layer material (eg, a phosphorescent host material).
  • an organic material layer material of an organic electroluminescent device preferably an electron transport layer, an electron transport auxiliary layer material, and a green light emitting layer material (eg, a phosphorescent host material).
  • the compound represented by Formula 1 is not only very advantageous for electron transport, but also exhibits low driving voltage, high efficiency, and long life.
  • the excellent electron transport ability of such a compound can have high efficiency and fast mobility in an organic electroluminescent device, and it is easy to adjust the HOMO and LUMO energy levels according to the direction or position of the substituent. Therefore, it is possible to exhibit high electron transport properties in an organic electroluminescent device using such a compound.
  • the host material in the phosphorescent emission layer, the host material must have a triplet energy gap of the host higher than that of the dopant, because in order to provide effective phosphorescence emission from the dopant, the lowest excited state of the host must have a higher energy than the lowest emission state of the dopant.
  • Conventional carbazole moieties have a large triplet energy of 3.0 eV and a low HOMO energy level of 6.0 eV, and are mainly used for blue phosphorescent hosts.
  • the compound according to the present invention is lower than the triplet energy of a compound having a simple carbazole moiety as a basic skeleton by bonding a phenyl group at positions 2 and 4 of the carbazole group, respectively, and is suitable for green phosphorescence emission. You can have energy.
  • the compound represented by Formula 1 of the present invention is used as an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (a phosphorescent host material in blue, green and/or red), an electron transport layer/injection layer material, When applied as a light emitting auxiliary layer material, the performance and lifetime characteristics of the organic electroluminescent device can be greatly improved. As a result, the organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.
  • a light emitting layer material a phosphorescent host material in blue, green and/or red
  • an electron transport layer/injection layer material When applied as a light emitting auxiliary layer material, the performance and lifetime characteristics of the organic electroluminescent device can be greatly improved. As a result, the organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.
  • the red and green emission layers of organic electroluminescent devices each use phosphorescent materials, and their technology maturity is high.
  • the blue light-emitting layer includes a fluorescent material and a phosphorescent material, of which the fluorescent material is in a state in which performance improvement is required, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, while the blue light emitting layer has a high possibility of development, the technical difficulty is relatively high, so there is a limit to improving the performance (eg, driving voltage, efficiency, life, etc.) of the blue organic light emitting device having the blue light emitting layer.
  • the compound of Formula 1 may be applied as an electron transport layer (ETL) or an electron transport auxiliary layer material in addition to the light emitting layer (EML).
  • ETL electron transport layer
  • EML electron transport auxiliary layer material
  • the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic EL device having the same can be improved. There is an advantage that you can.
  • the compound represented by Formula 1 according to the present invention includes a carbazole moiety in which a plurality of phenyl groups are bonded at a specific position on both sides of the molecule, and a nitrogen-containing heteroaryl group (X 1 to X 3 containing ring), and they are directly bonded or have a basic skeleton structure linked through a linker (L).
  • the nitrogen-containing heteroaryl group may be a monocyclic or polycyclic heteroaryl group containing at least one nitrogen atom.
  • a nitrogen-containing azine derivative eg, X 1 to X 3 containing heterocycle
  • X 1 to X 3 are the same as or different from each other, and each independently N or CR 1 , but X 1 to At least one of X 3 is N.
  • a plurality of X 1 to X 3 includes 1 to 3 N, preferably 2 to 3, more preferably 3 N.
  • R 1 may be plural, and a plurality of R 1 may be the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atom number 5 to 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 groups of an alkyl boron, C 6 ⁇ aryl boronic of C 60, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ selected from the
  • R 1 is preferably selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C 1 to C 40 alkyl group, C 6 to C 60 aryl group, and heteroaryl group having 5 to 60 nuclear atoms. Do.
  • the nitrogen-containing heterocycle (X 1 to X 3 containing ring) may be any one selected from the group of substituents represented by the following formulas A-1 to A-5.
  • R 1 , Ar 1 and Ar 2 are each as defined in Formula 1.
  • Ar 1 and Ar 2 in the nitrogen heterocycle or different each independently represent hydrogen, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ alkynyl group of C 40 , C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 aryl phosphine oxide group and C 6 ⁇ C 60 It may be selected from the arylamine group. Specifically, Ar 1 ⁇ C 40 alkyl group
  • the nitrogen-containing heteroaryl group (X 1 to X 3 containing ring) is directly or through a linker (L) connected to a carbazole moiety to which a plurality of phenyl groups are bonded.
  • the carbazole moiety according to the present invention is blocked by bonding a phenyl group at positions 2 and 4, respectively, it is lower than the triplet energy of a compound having a simple carbazole moiety as a basic skeleton, and green It may have triplet energy suitable for phosphorescence emission.
  • R 2 may be introduced into the carbazole moiety as various substituents.
  • R 2 is not particularly limited, and hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 monoarylphosfinyl group, C 6 ⁇ C 60 diarylphosphinyl group
  • R 2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and in the heteroaryl group having 5 to 60 nuclear atoms It is preferably selected.
  • the number of R 2 introduced into the carbazole group may be an integer of 0 to 4.
  • R 2 may be hydrogen.
  • a plurality of R 2 may be the same or different from each other, and each independently may be the remaining substituents excluding hydrogen in the definition of R 2 .
  • L which is a linker
  • X 1 to X 3 containing ring nitrogen-containing indene derivative
  • carbazole group such a linker may use a divalent linker known in the art without limitation.
  • L may be a single bond or may be selected from a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms.
  • L may be a substituent represented by any one of the following formulas 2 and 3.
  • Y is selected from the group consisting of O, S and Se,
  • n is an integer of 0 to 3.
  • the number of L may be an integer of 0 to 3.
  • L may be a single bond (direct bond).
  • a plurality of L may be the same or different from each other, and each independently may be the remaining substituents excluding a single bond in the definition of L described above, such as an aryl group or a heteroaryl group.
  • L may be each independently a single bond, or may be any one selected from the group of substituents represented by the following structural formula.
  • Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group , Heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group,
  • the compound represented by Formula 1 may be further specified in any one of the following Formulas 4 to 9 depending on the type and position of the linker (L).
  • X 1 to X 3 , Y, Ar 1 , Ar 2 , R 2 , b and n are each as defined in Formula 1.
  • Chemical Formulas 4 to 9 When the above-described Chemical Formulas 4 to 9 are more specific, it may be represented by a compound represented by any one of the following Chemical Formulas 4a to 9a.
  • Y, Ar 1 , Ar 2 , R 2 and n are each as defined in Formula 1.
  • X 1 to X 3 are the same as or different from each other, and each independently N or C (R 1 ), but X 1 to X 3 is all N,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
  • R 1 and R 2 are different from each other, and each independently hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, or a heteroaryl group having 5 to 60 nuclear atoms,
  • a plurality of Y is the same as or different from each other, each independently O or S, n is an integer of 0 to 3, b is an integer of 0 to 4,
  • the compound represented by Formula 1 of the present invention described above may be further embodied as a compound illustrated below, for example, a compound represented by 1 to 71.
  • the compound represented by Formula 1 of the present invention is not limited by those illustrated below.
  • alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
  • alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined.
  • a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se.
  • heteroatoms such as N, O, S or Se.
  • a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, and R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include.
  • R' refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • arylamine refers to an amine substituted with an aryl having 6 to 40 carbon atoms.
  • cycloalkyl refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine and piperazine.
  • alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl refers to silyl substituted with aryl having 5 to 40 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention provides an electron transport layer comprising the compound represented by Chemical Formula 1.
  • the electron transport layer serves to move electrons injected from the cathode to an adjacent layer, specifically a light emitting layer.
  • the compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
  • ETL electron transport layer
  • the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
  • electron transport materials that can be used include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylenes ( perylene) compounds, aluminum complexes (e.g. Alq 3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq) There are '2OAc, 2(Gaq'2)), etc. These can be used alone or two or more types can be used in combination.
  • the mixing ratio thereof is not particularly limited, and may be appropriately adjusted within a range known in the art.
  • the present invention provides an auxiliary electron transport layer comprising the compound represented by the formula (1).
  • the electron transport auxiliary layer is disposed between the light emitting layer and the electron transport layer, and serves to prevent diffusion of excitons or holes generated in the light emitting layer into the electron transport layer.
  • the compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
  • the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
  • the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a heterocyclic derivative containing nitrogen, and the like.
  • the mixing ratio thereof is not particularly limited, and may be appropriately adjusted within a range known in the art.
  • organic electroluminescent device including the compound represented by Formula 1 according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers It includes a compound represented by Formula 1.
  • the compounds may be used alone or in combination of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, an emission layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer is represented by Formula 1 above.
  • a hole injection layer a hole transport layer, an emission layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer is represented by Formula 1 above.
  • the organic material layer containing the compound of Formula 1 is preferably a green light-emitting layer material (specifically, a phosphorescent host material), an electron transport layer, or an electron transport material for an electron transport auxiliary layer.
  • the emission layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and in this case, the compound of Formula 1 may be included as a host material.
  • the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.
  • the compound represented by Formula 1 is included as a material for an emission layer of an organic electroluminescent device, preferably a phosphorescent host material of blue, green, and red, the binding force between holes and electrons in the emission layer increases, so the efficiency of the organic electroluminescent device (Light emission efficiency and power efficiency), life, brightness, and driving voltage can be improved.
  • the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material.
  • the compound represented by Formula 1 of the present invention is a green phosphorescent exciplex N-type host material of a light emitting layer having high efficiency.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, but may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Formula 1, preferably a light-emitting layer, more preferably a phosphorescent host May include the compound represented by Formula 1 above.
  • an electron injection layer may be additionally stacked on the electron transport layer.
  • the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at an interface between an electrode and an organic material layer.
  • the organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one of the aforementioned organic material layers contains the compound represented by Chemical Formula 1. have.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
  • the substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, and the like may be used.
  • a cathode material a cathode material known in the art may be used without limitation.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);
  • Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb;
  • Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline;
  • carbon black but is not limited thereto.
  • a negative electrode material a negative electrode material known in the art may be used without limitation.
  • metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof;
  • a multi-layered material such as LiF/Al or LiO2/Al, but is not limited thereto.
  • hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.
  • Target compound of step 1 (89.1 g, 336.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (102.5 g, 403.8 mmol) and Pd(dppf)Cl 2 (8.2 g, 10.1 mmol), Xphos (16.0 g, 33.6 mmol), KOAc (66.0 g, 673.1 mmol) were added to 500 ml of 1,4-Dioxane for 12 hours. During heating to reflux. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto and filtered.
  • the target compound 2-([1,1':3',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl was used by column chromatography. -1,3,2-dioxaborolane (85.1 g, yield 71%) was obtained.
  • Target compound of step 2 (64.1 g, 179.9 mmol1-bromo-2-nitrobenzene (36.3 g, 179.9 mmol) and Pd(PPh 3 ) 4 (10.4 g, 9.0 mmol), K 2 CO 3 (74.6 g, 539.7 mmol) was added to 500ml of Toluene, 100ml of EtOH, 100ml of H 2 O, and heated to reflux for 12 hours After completion of the reaction, the mixture was extracted with methylene chloride, added with MgSO 4 , and filtered, and the solvent of the filtered organic layer was removed, followed by column chromatography. Compound 2-nitro-4'-phenyl-1,1':2',1''-terphenyl (50.6 g, 80% yield) was obtained.
  • the target compound of step 3 (50.6 g, 143.9 mmol), triphenylphosphine (113.3 g, 431.9 mmol), and 500 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, followed by extraction with dichloromethane. Water was removed from the extracted organic layer with MgSO 4 , and the target compound, 2,4-diphenyl-9H-carbazole (36.8 g, yield 80%) was obtained by column chromatography.
  • the target compound of Preparation Example 1 (2.1 g, 6.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (1.8 g, 6.6 mmol) Pd 2 (dba) 3 (0.3 g, 0.3 mmol) ), P(t-bu) 3 (0.1 g, 0.6 mmol), NaO(t-bu) (1.3 g, 13.5 mmol) was added to 500 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO 4 was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound (3.0 g, yield 81%) was obtained by column chromatography.
  • ITO Indium tin oxide
  • a thin film coated glass substrate with a thickness of 1500 ⁇ with distilled water and ultrasonic waves.
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power Sonic 405, Hwashin Tech
  • a blue organic electroluminescent device of Comparative Example 1 was manufactured in the same manner as in Example 1, except that Alq3 was used instead of Compound 1 as the electron transport layer material.
  • a blue organic electroluminescent device of Comparative Example 2 was manufactured in the same manner as in Example 1, except that Compound 1 was not used as the electron transport layer material.
  • a blue organic electroluminescent device of Comparative Example 3 was manufactured in the same manner as in Example 1, except that Ref-1 having the following structure was used instead of Compound 1 as the electron transport layer material.
  • a blue organic electroluminescent device of Comparative Example 4 was manufactured in the same manner as in Example 1, except that Ref-2 having the following structure was used instead of Compound 1 as the electron transport layer material.
  • Example 1 One 3.6 456 6.8 Example 2 2 3.2 456 6.7 Example 3 3 3.2 457 6.9 Example 4 4 3.6 456 7.1 Example 5 5 3.2 457 7.1 Example 6 6 3.2 456 7.1 Example 7 7 3.9 456 6.9 Example 8 8 3.6 457 6.7 Example 9 9 3.6 456 7.0 Example 10 10 3.2 457 7.1 Example 11 11 3.2 456 6.8 Example 12 12 3.1 456 7.3 Example 13 13 3.9 457 6.9 Example 14 14 3.9 452 6.8 Example 15 15 3.3 448 6.7 Example 16 16 3.6 460 6.8 Example 17 17 3.6 456 6.9 Example 18 18 3.2 456 7.1 Example 19 19 3.2 457 7.1 Example 20 20 3.2 456 6.8 Example 21 21 3.9 456 6.9 Example 22 22 3.6 457 6.7 Example 23 23 3.8 457 7.1 Example 24 24 3.2 452 6.9 Example 25 25 3.1 456 7.3 Example 26 26 26 26 .
  • the blue organic electroluminescent devices of Examples 1 to 71 using the compound of the present invention as an electron transport layer material include the blue organic electroluminescent devices of Comparative Example 1 using Alq3 for the electron transport layer; The blue organic electroluminescent device of Comparative Example 2 without an electron transport layer; The blue organic electroluminescent device of Comparative Example 3 using unsubstituted carbazole; And it was found that the blue organic light emitting device of Comparative Example 4 using a carbazole substituted with a phenyl group at carbon positions 1 and 3 showed superior performance in terms of driving voltage, emission peak, and current efficiency.
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwashin Tech
  • m-MTDATA 60 nm
  • TCTA 80 nm
  • the green organic electroluminescent device of Comparative Example 5 was manufactured in the same manner as in Example 72, except that CBP was used instead of Compound 1 as a light emitting host material when forming the emission layer.
  • the structure of the CBP used at this time is as follows.
  • the green organic electroluminescent device of Comparative Example 6 was manufactured in the same manner as in Example 72, except that Ref-1 was used instead of Compound 1 as a light emitting host material when forming the emission layer.
  • the green organic electroluminescent device of Comparative Example 7 was manufactured in the same manner as in Example 72, except that Ref-2 was used instead of Compound 1 as a light emitting host material when forming the emission layer.
  • Example 72 One 4.0 458 57.0
  • Example 73 2 3.6 458 59.5
  • Example 74 3 4.1 458 56.5
  • Example 75 4 3.8 458 58.3
  • Example 76 5 3.7 459 59.3
  • Example 77 6 4.1 458 57.0
  • Example 78 7 3.8 458 59.1
  • Example 79 8 4.1 458 57.0
  • Example 80 9 3.8 459 59.1
  • Example 81 10 3.9 458 58.0
  • Example 82 11 3.6 458 60.5
  • Example 83 12 3.8 459 57.7
  • Example 84 13 3.8 458 58.6
  • Example 85 14 3.7 458 55.9
  • Example 86 15 3.8 458 58.5
  • Example 88 17 3.7 458 59.1
  • Example 89 18 3.7 458 58.0
  • Example 90 19 3.8 458 60.0
  • Example 91 20 3.8 459 58.8
  • the green organic electroluminescent device of Examples 72 to 142 using the compound according to the present invention as a host material of the emission layer includes the green organic electroluminescent device of Comparative Example 5 in which CBP was applied as a host material; The green organic light-emitting device of Comparative Example 6 using unsubstituted carbazole; And it was found that the current efficiency and driving voltage were excellent compared to the green organic light emitting device of Comparative Example 7 using carbazole substituted with a phenyl group at carbon positions 1 and 3.

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  • Physics & Mathematics (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé ayant une excellente capacité de transport d'électrons et une excellente capacité d'émission de lumière, et un dispositif électroluminescent organique le comprenant dans une ou plusieurs couches de matériau organique, ayant ainsi des caractéristiques améliorées telles que l'efficacité lumineuse, la tension de commande et la durée de vie.
PCT/KR2020/004748 2019-04-10 2020-04-08 Composé organique et dispositif électroluminescent organique le comprenant WO2020209599A1 (fr)

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