WO2020116875A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2020116875A1
WO2020116875A1 PCT/KR2019/016837 KR2019016837W WO2020116875A1 WO 2020116875 A1 WO2020116875 A1 WO 2020116875A1 KR 2019016837 W KR2019016837 W KR 2019016837W WO 2020116875 A1 WO2020116875 A1 WO 2020116875A1
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group
aryl
compound
formula
nuclear atoms
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손호준
김회문
김영배
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
    • 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
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic 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
    • H10K50/16—Electron transporting layers

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more specifically, an organic compound having excellent electron transport ability and improved characteristics such as luminous efficiency, driving voltage, and lifetime by including it in one or more organic material layers. It relates to an electroluminescent device.
  • organic electroluminescent (EL) devices (hereinafter simply referred to as'organic EL devices'), which led to blue electroluminescence using anthracene single crystals in 1965 from the point of view of organic thin film emission by Bernanose in the 1950s, was conducted in 1987.
  • An organic EL device having a stacked structure divided by a functional layer of a hole layer and a light emitting layer by (Tang) has been proposed. 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 layer in the device, leading to the development of specialized materials used therein.
  • 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, etc. according to its function.
  • the light emitting layer forming material of the organic EL device can be divided 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 for realizing better natural colors.
  • a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
  • the dopant material may be divided 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. The development of such a phosphorescent material can theoretically improve the luminous efficiency up to 4 times that of fluorescence, and thus, attention is 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 are widely known, and anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials.
  • a metal complex compound containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which has a great advantage in terms of efficiency improvement, is a blue, green, red dopant material Is being used as To date, CBP has shown excellent properties as a phosphorescent host material.
  • the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device.
  • An object of the present invention is to provide a novel compound that can be used as an organic material layer material, specifically a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material of an organic electroluminescent device, which is excellent in electron injection and transport, luminescence, etc. Is done.
  • Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel compounds described above.
  • the present invention provides a compound represented by the following formula (1), specifically an electron transport layer or a compound for an electron transport auxiliary layer.
  • X 1 to X 3 are the same as or different from each other, and each independently CR 4 or N, provided that at least one of X 1 to X 3 is N,
  • L 1 is a single bond, or is selected from the group consisting of C 6 ⁇ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
  • a 1 and A 2 are the same as or different from each other, and each independently a substituent represented by the following Chemical Formula 2,
  • a plurality of L 2 are the same as or different from each other, and each independently selected from the group consisting of C 6 to C 18 arylene groups and 5 to 18 heteroarylene groups of nuclear atoms;
  • a is an integer from 0 to 3
  • R 1 to R 4 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 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkyl silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an aryl amine of
  • At least one of A 1 and A 2 is a nitrogen-containing heteroaryl group different from a ring containing X 1 to X 3 or an aryl group substituted with one or more electron withdrawing groups (EWG),
  • the arylene group and heteroarylene group of L 1 to L 2, the alkyl group of the R 1 to R 4 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, phosphine group, phosphine oxide group, and arylamine group are each independently hydrogen, deuterium (D), 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 present invention provides an electron transport layer or an electron transport auxiliary layer comprising the compound represented by Formula 1 described above.
  • the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the organic material layers of the one or more layers includes an organic electric field comprising a compound represented by Formula 1 described above A light emitting device is provided.
  • the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a light emitting layer, a light emitting 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 Chemical Formula 1 according to the present invention has excellent electron transport ability and luminescence ability, it can be used as an organic material layer material for an organic electroluminescent device.
  • the compound represented by Formula 1 of the present invention when used as a phosphorescent host, electron transport layer, or electron transport auxiliary layer material, it has higher thermal stability, lower driving voltage, faster mobility, and higher current efficiency than conventional host materials or electron transport materials. And it is possible to manufacture an organic electroluminescent device having a long life property, and furthermore, it can be effectively applied to a full color display panel with improved performance and life.
  • the compound represented by the formula (1) according to the present invention centered on the oxanthrene (oxanthrene)-based nucleus, at least two different electron attracting groups (EWG) different from each other on either side of the direct or linker (eg, L 1 , L 2 ) has a basic framework structure (eg, EWG1-oxatrene-EWG2/EWG3; dual EWG).
  • EWG electron attracting groups
  • Such a compound has an electron donating group having large electron donating group (EDG) characteristics, and at least two substituents having electron withdrawing characteristics (EWG) on both sides thereof, preferably at least two substituents, preferably Three substituents (eg, X 1 to X 3 containing heterocyclic rings and A 1 to A 2 ) are formed by bonding, respectively.
  • EDG electron donating group
  • EWG electron withdrawing characteristics
  • X 1 to X 3 containing heterocyclic rings and A 1 to A 2
  • 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 light emitting layer material.
  • one heteroaryl group eg, X 1 to X 3 containing heterocyclic ring located on one side of the oxanthrene parent nucleus of the present invention is introduced with pyrimidine or triazine. Since each of these triazines and pyrimidines is a type of 6-membered heterocyclic ring having excellent electron withdrawing group (EWG) properties, it has strong electron receiving properties.
  • EWG electron withdrawing group
  • two substituents located on the other side of the oxanthrene parent nucleus are introduced with a monocyclic or polycyclic nitrogen-containing heterocycle (eg, pyridine) different from the heterocycle containing X 1 to X 3 or
  • a monocyclic or polycyclic nitrogen-containing heterocycle eg, pyridine
  • at least one aryl group in which at least one electron attracting agent (EWG) is introduced in the art is combined. While the nitrogen-containing heterocyclic or aryl group has lower electron absorption than the aforementioned pyrimidines and triazines, one or two EWGs are introduced into one side of the conventional oxanthrene nucleus because a plurality of (2) rather than one are introduced.
  • EWG on both sides exhibits stronger electronic properties than materials introduced one by one. Accordingly, when the compound of Formula 1 is applied as a material for the electron transport layer or the electron transport auxiliary layer, electrons can be well received from the cathode, and thus electrons can be smoothly transferred to the light emitting layer, thereby lowering the driving voltage of the device and achieving high efficiency and It can induce long life. As a result, the organic electroluminescent device can maximize the performance of the full color organic light emitting panel.
  • the compound represented by the formula (1) is asymmetrical based on the long axis of the oxanthrene parent nucleus due to the difference between the EWG groups (X 1 to X 3 containing hetero rings and A 1 to A 2 ) located at both ends of the molecular structure. (asymmetry) structure.
  • a 1 and A 2 introduced on the other side of the oxanthrene nucleus may also have different substituents, and thus may have a secondary asymmetric structure.
  • the compound of Formula 1 has a significant increase in the molecular weight of the compound through controlling various kinds of substituents introduced into the oxanthrene parent nucleus and the position of introduction, and thus has improved glass transition temperature and high thermal stability. Can be. And since it is also effective in suppressing the crystallization of the organic layer, the organic electroluminescent device including the compound according to the present invention can greatly improve durability and life characteristics.
  • the compound represented by Chemical Formula 1 is not only very advantageous for electron transport, but also exhibits low driving voltage, high efficiency, and long life characteristics.
  • the excellent electron transport ability of these compounds can have high efficiency and fast mobility in organic electroluminescent devices, and it is easy to control 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 red and green light-emitting layers of the organic electroluminescent device use phosphorescent materials, respectively, and their technology maturity is high.
  • the blue light emitting layer has a fluorescent material and a phosphorescent material, of which the fluorescent material needs to improve performance, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, since the blue light emitting layer has a great possibility of development, the technical difficulty is relatively high, and thus there is a limit to improve the performance (eg, driving voltage, efficiency, life, etc.) of the blue organic light emitting device having the same.
  • 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 material of the electron transport layer or the electron transport auxiliary layer used as a common layer in the organic electroluminescent device may be improved to improve the performance of the light emitting layer, specifically the blue light emitting layer and the organic electroluminescent device having the same. It has the advantage of being able to.
  • the compound represented by the formula (1) according to the present invention at least two electron attracting each other at both ends of the center of the oxanthrene (Oxanthrene) nucleus (eg, X 1 ⁇ X 3 containing heterocyclic ring and A 1 ⁇ A 2 ) It has a basic framework structure that is directly or linked through a linker group (L 1 ⁇ L 2 ).
  • an electron withdrawing group (EWG) coupled to one phenyl group of the oxanthrene parent nucleus may be a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom (eg, a heterocycle containing X 1 to X 3 ).
  • EWG electron withdrawing group
  • X 1 to X 3 are the same as or different from each other, and each independently is CR 4 or N, provided that at least one of X 1 to X 3 is N.
  • X 1 to X 3 contain 2 or 3 Ns.
  • R 4 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyl silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 phosphine group may be selected from a phosphine oxide group, and the group consisting of C 6 ⁇ C 60 aryl amine of the C 1
  • R 4 is preferably selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and heteroaryl group having 5 to 60 nuclear atoms. Do.
  • R 1 and R 2 may be substituted as various substituents.
  • R 1 to R 2 are the same or different from each other, and each independently a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, and a C 3 to C 40 cyclo.
  • Alkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryl of C 6 to C 60 Oxy 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 aryl phosphine group may be selected from the aryl phosphine oxide group, and a group consisting of arylamine C 6 ⁇ C 60 of the C 6 ⁇ C 60.
  • R 1 to R 2 are each independently a C 1 ⁇ C 40 alkyl group, a C 6 ⁇ C 60 aryl group, a nuclear number of 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 6 ⁇ C 60 It is preferably selected from aryl phosphine oxide groups and C 6 ⁇ C 60 arylamine groups, more preferably C 6 ⁇ C 60 aryl group and a heteroaryl of 5 to 60 nuclear atoms Group.
  • a linker (L 1 ) may be a conventional divalent group linker known in the art.
  • L 1 is a single bond or may be selected from the group consisting of C 6 ⁇ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms.
  • arylene group and heteroarylene group include phenylene group, biphenylene group, naphthylene group, anthracenyl group, indylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, fury And an alkylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylylene group, and a pyrimidinylene group.
  • L 1 is preferably a single bond or a phenylene group.
  • a 1 and A 2 substituents that are bonded to the other phenyl group of the oxanthrene parent nucleus are the same as or different from each other, and electron attracters (EWG) known in the art may be introduced, respectively.
  • EWG electron attracters
  • at least one of A 1 and A 2 may be a nitrogen-containing heteroaryl group different from a ring containing X 1 to X 3 or an aryl group substituted with one or more electron withdrawing groups (EWG).
  • both A 1 and A 2 may be nitrogen-containing heteroaryl groups or aryl groups described above.
  • a 1 and A 2 may each be a substituent represented by the following Chemical Formula 2. At this time, although A 1 and A 2 are the same, they may be the same or different from each other.
  • the plurality of L 2 may be the same or different from each other, and may be linkers of a common divalent group known in the art.
  • L 2 may be a single bond or may be 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.
  • a specific example of L 2 may be the same as the definition of L 1 described above.
  • a is an integer from 0 to 3.
  • a plurality of R 3 are the same or different from each other, and each independently hydrogen, 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, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkyl silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an
  • a plurality of R 3 are the same as or different from each other, and each independently an aryl group of C 6 to C 60 substituted with one or more electron withdrawing groups (EWG groups), or a nitrogen atom having 5 to 60 nuclear atoms. It is preferably a heteroaryl group. However, in the nitrogen-containing heteroaryl group, pyrimidine and triazine are respectively excluded.
  • the arylene group and heteroarylene group of L 1 ⁇ L 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of the R 1 to R 4 , Cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, phosphine group, phosphine oxide group, and arylamine group are each independently hydrogen, deuterium (D), 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, a nuclear number of 5 to 60 heteroaryl group, C 1
  • the compound represented by Chemical Formula 1 may be more specifically embodied in any of the following Chemical Formula 3 or Chemical Formula 4. However, it is not limited thereto.
  • X 1 to X 3 , A 1 to A 2 , L 1 and R 1 to R 2 are each as defined in Formula 1.
  • X 1 to X 3 include 2 or 3 N
  • L 1 may be a phenylene group
  • R 1 and R 2 are each independently As C 6 ⁇ C 60 It may be an aryl group or a heteroaryl group having 5 to 60 nuclear atoms.
  • a 1 and A 2 are the same as or different from each other, and each independently may be a monocyclic or polycyclic heteroaryl group containing one nitrogen atom or a monocyclic or polycyclic aryl group substituted with one or more electron withdrawing groups (EWG). have.
  • EWG electron withdrawing groups
  • a 1 and A 2 may be the same as or different from each other, and each independently selected from the following substituent groups.
  • Z can be applied without limitation to the electron attraction (EWG) known in the art.
  • EWG electron attraction
  • it may be at least one selected from the group consisting of halogen groups, -CF 3 and cyano groups.
  • the Z when the Z is plural, they may be the same or different from each other.
  • at least one or more substituents eg, the same as the definition part of R 1 ) known in the art may be substituted.
  • X 1 to X 3 , L 1 to L 2 , and R 1 to R 3 are each as defined in Formula 1.
  • a plurality of L 2 are the same or different from each other, and are each independently an arylene group of C 6 to C 18 or a heteroarylene group having 5 to 18 nuclear atoms.
  • a is an integer from 0 to 3
  • a plurality of R 3 are the same as or different from each other, and each independently is an aryl group of C 6 to C 60 substituted with one or more electron withdrawing groups (EWG groups), or a nuclear atom. It may be 5 to 60 nitrogen-containing heteroaryl groups, except pyrimidine and triazine.
  • the compound represented by the formula (1) of the present invention described above may be more specifically exemplified by the following compounds, for example, compounds represented by A-1 to E-24.
  • the compound represented by Formula 1 of the present invention is not limited by those exemplified below.
  • alkyl means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of this include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl (alkynyl) means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.
  • 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. Also, two or more rings may be simply attached to each other or condensed. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.
  • heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, 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 condensed form with an aryl group may also be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, and indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, and indolyl
  • polycyclic rings such as indolyl, purinyl, quinolyl, benzo
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
  • R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
  • alkyloxy refers to 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. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • arylamine means an amine substituted with aryl having 6 to 40 carbon atoms.
  • Cycloalkyl in the present invention means 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 means 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 morpholine and piperazine, but are not limited thereto.
  • alkylsilyl refers to 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 a compound represented by Formula 1 above.
  • 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.
  • usable electron transport materials include oxazole-based compounds, isooxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, and perylene ( perylene) compounds, aluminum complexes (e.g. Alq 3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.
  • 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 electron transport auxiliary layer comprising the compound represented by Chemical Formula 1.
  • the electron transport 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 compound of Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited, and can be appropriately adjusted within a range known in the art.
  • organic electroluminescent device comprising the compound represented by Chemical 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 is It includes a compound represented by the formula (1). At this time, the compound 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, a light emitting layer, a light emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 Compounds.
  • the organic material layer containing the compound of Formula 1 is preferably a phosphorescent host material of the light emitting layer, an electron transport layer, or an electron transport material of an electron transport auxiliary layer.
  • the light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, wherein the compound of Formula 1 may be included as a host material.
  • the light emitting layer of the present invention may contain a compound known in the art as a host other than the compound of the formula (1).
  • the compound represented by Chemical Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a phosphorescent host material of blue, green, or red, the bonding force between holes and electrons in the light emitting layer increases, so that 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 Chemical Formula 1 is preferably included in an organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material.
  • the compound represented by Chemical Formula 1 of the present invention is preferably a green phosphorescent 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 be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
  • 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 It may include a compound represented by the formula (1).
  • 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 the interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention can be produced 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 a compound represented by Chemical Formula 1 above. have.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
  • the substrate used in manufacturing 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 may be used.
  • a positive electrode material known in the art can be used as the positive electrode material 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);
  • a combination of metal and oxide 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.
  • the negative electrode material a negative electrode material known in the art can be used without limitation.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof;
  • multilayer structure materials such as LiF/Al or LiO2/Al, but are not limited thereto.
  • the 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 can be used without limitation.
  • A-14_D-1 (3.2 g, 5.6 mmol) and pyridin-2-ylboronic acid (1.4 g, 5.6 mmol) and Pd(PPh 3 ) 4 (0.2 g, 0.3 mmol), K 2 CO 3 (2.3 g, 16.8 mmol) was put in 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, A-14 (1.96 g, yield 57%) was obtained using column chromatography.
  • E-15_D-1 (3.9 g, 6.0 mmol) and (4-cyanophenyl)boronic acid (0.9 g, 6.0 mmol) and Pd(PPh 3 ) 4 (0.3 g, 0.3 mmol), K 2 CO 3 (2.5 g, 18.1 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, E-15 (2.42 g, yield 60%) was obtained using column chromatography.
  • a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 ⁇ was washed with distilled water.
  • ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, and then dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed for 5 minutes using UV.
  • the substrate was transferred to a vacuum evaporator.
  • Electron transport layer Compounds A-1 to A-12, A-14, B-1 to B-12, C-1 to C-12, D-1 to D-12, E-1 to E-12, E-15 30 Electron injection layer LiF One cathode Al 200
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 was used instead of Compound A-1 as the electron transport layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 was not used as the electron transport layer material.
  • Blue organic electroluminescent devices of Comparative Examples 3 and 4 were manufactured in the same manner as in Example 1, except that the following materials OA-1 and OA-2 were used instead of Compound A-1 as the electron transport layer material. .
  • NPB, AND, Alq3, OA-1 and OA-2 structures used in Examples 1 to 62 and Comparative Examples 1 to 2 are as follows.
  • Example 1 A-1 3.4 458 6.8 Example 2 A-2 3.6 456 7.1 Example 3 A-3 3.2 457 6.7 Example 4 A-4 3.2 456 6.9 Example 5 A-5 3.8 457 7.1 Example 6 A-6 3.6 456 6.7 Example 7 A-7 3.9 456 6.9 Example 8 A-8 3.6 457 6.7 Example 9 A-9 3.6 456 7.0 Example 10 A-10 3.2 457 7.1 Example 11 A-11 3.2 456 6.8 Example 12 A-12 3.1 456 7.3 Example 13 B-1 3.9 457 6.9 Example 14 B-2 3.9 452 6.8 Example 15 B-3 3.3 448 6.7 Example 16 B-4 3.6 460 6.8 Example 17 B-5 3.8 456 6.9 Example 18 B-6 3.2 456 6.8 Example 19 B-7 3.2 457 7.1 Example 20 B-8 3.9 465 6.9 Example 21 B-9 3.7 455 6.8 Example 22 B-10 3.9 459 7.1 Example 23 B-11 3.8 457 7.1 Example 24 B
  • the blue organic electroluminescent elements of Examples 1 to 62 using the compound of the present invention in the electron transport layer had no blue organic electroluminescent elements and electron transport layers of Comparative Example 1 using Alq3 as the electron transport layer. It was found that the blue organic electroluminescent device of Comparative Example 2 exhibited excellent performance in terms of driving voltage, emission peak, and current efficiency.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne : un nouveau composé présentant une excellente capacité de transport d'électrons et une excellente luminescence ; ainsi qu'un élément électroluminescent organique qui comprend ce nouveau composé dans une ou plusieurs couches de matière organique et qui présente ainsi une amélioration des caractéristiques telles que l'efficacité lumineuse, la tension de commande et la durée de vie.
PCT/KR2019/016837 2018-12-03 2019-12-02 Composé organique et élément électroluminescent organique le comprenant WO2020116875A1 (fr)

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CN112390778A (zh) * 2020-10-14 2021-02-23 武汉尚赛光电科技有限公司 一种杂蒽衍生物及其应用和有机电致发光器件

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KR20150077263A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR20180055206A (ko) * 2016-11-16 2018-05-25 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180066339A (ko) * 2016-12-07 2018-06-19 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20180125775A (ko) * 2017-05-16 2018-11-26 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

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WO2009069442A1 (fr) * 2007-11-26 2009-06-04 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'affichage et dispositif d'éclairage
KR20150077263A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR20180055206A (ko) * 2016-11-16 2018-05-25 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180066339A (ko) * 2016-12-07 2018-06-19 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20180125775A (ko) * 2017-05-16 2018-11-26 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112390778A (zh) * 2020-10-14 2021-02-23 武汉尚赛光电科技有限公司 一种杂蒽衍生物及其应用和有机电致发光器件
CN112390778B (zh) * 2020-10-14 2022-03-22 武汉尚赛光电科技有限公司 一种杂蒽衍生物及其应用和有机电致发光器件

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