WO2022131768A1 - Composé électroluminescent organique et élément électroluminescent organique l'utilisant - Google Patents

Composé électroluminescent organique et élément électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2022131768A1
WO2022131768A1 PCT/KR2021/019005 KR2021019005W WO2022131768A1 WO 2022131768 A1 WO2022131768 A1 WO 2022131768A1 KR 2021019005 W KR2021019005 W KR 2021019005W WO 2022131768 A1 WO2022131768 A1 WO 2022131768A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
synthesis
substituted
unsubstituted
formula
Prior art date
Application number
PCT/KR2021/019005
Other languages
English (en)
Korean (ko)
Inventor
김충한
신환규
Original Assignee
솔루스첨단소재 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 솔루스첨단소재 주식회사 filed Critical 솔루스첨단소재 주식회사
Publication of WO2022131768A1 publication Critical patent/WO2022131768A1/fr

Links

Images

Classifications

    • 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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent electron transport ability and an organic compound having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers. It relates to an electroluminescent device.
  • An organic electroluminescent display device is different from a liquid crystal display device, and by recombination of holes and electrons injected from the first and second electrodes in the light emitting layer, the light emitting material containing the organic compound is emitted in the light emitting layer to realize display. It is a so-called self-emission type display device.
  • organic electroluminescent devices In the application of organic electroluminescent devices to display devices, low driving voltage, high luminous efficiency and long lifespan of the organic electroluminescent devices are required, and the development of materials for organic electroluminescent devices that can stably implement these is continuously required. have.
  • TTA triplet-triplet annihilation
  • An object of the present invention is to provide an excellent novel organic compound that can apply a novel organic compound to an organic electroluminescent device, and improves high efficiency and long life characteristics by using the novel organic compound in an organic layer of an organic electroluminescent device.
  • Another object of the present invention is to provide an organic electroluminescent device including a thermally activated delayed fluorescence emitting material and a thermally activated delayed fluorescence emitting material including the novel organic compound.
  • the present invention provides a compound represented by the following formula (1).
  • Ar 1 To Ar 4 are the same as or different from each other, and each independently a C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 30 aryl group, heteroaryl group having 2 to 30 nuclear atoms, 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 Aryl phosphine group , C 6 ⁇ C 60 Mono or diarylphosphinyl group and C 6 ⁇ C 60 Selected from the group consisting of an arylamine group,
  • the Ar 1 To Ar 4 Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , mono or diarylphosphinyl group and arylamine group are each independently a C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, C 6 to C 60 Arylox Period, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Aryls
  • X is hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, CF 3 group, B(OR 5 ) 2 group, Si(R 5 ) 3 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, heterocycloalkyl group having 3 to 40 nuclear atoms, C 5 ⁇ C 40 aryl group, 2 to 30 nuclear atoms Heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 15 ⁇ C 40 Aryloxy group, C 15 ⁇ C 40 Heteroaryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 of Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 1 ⁇ C 10 Alkanesulfide group, C 6 ⁇ C 60
  • R 5 is hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C 1 ⁇ C 30 alkyl group, substituted or unsubstituted C 2 ⁇ C 30 alkenyl group, substituted or unsubstituted C 2 ⁇ C 30 alkynyl group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 30 substituted or unsubstituted aryl group , a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms.
  • the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) 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 the first It provides an organic electroluminescent device comprising the compound represented by the formula (1) of claim 1.
  • the organic material layer may include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.
  • the light emitting layer may emit delayed fluorescence.
  • the emission layer may be a delayed fluorescence emission layer including a host and a dopant, and the dopant may include the compound represented by Formula 1 of claim 1 .
  • the light emitting layer may be a thermally activated delayed fluorescent light emitting layer that emits blue light.
  • substituted or unsubstituted means a deuterium atom, a halogen atom, a cyano group, a nitro group, an amine group, a silyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an aryl group, and It may mean unsubstituted or substituted with one or more substituents selected from the group consisting of heterocyclic groups.
  • each of the exemplified substituents may be substituted or unsubstituted, but is not limited thereto.
  • the biphenyl group may mean an aryl group or a phenyl group.
  • halogen atom in the present invention may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, but is not limited thereto.
  • the alkyl group may be linear, branched or cyclic.
  • Carbon number of an alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methyl
  • the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the number of ring carbon atoms of the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less.
  • aryl group examples include a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a quinkphenyl group, a sexyphenyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group , may be a chrysenyl group, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure, but is not limited thereto.
  • the fluorenyl group when substituted, it may have the following structure, but is not limited thereto.
  • the heteroaryl group may be a heteroaryl group including at least one of O, N, P, Si, and S as a heterogeneous element.
  • the number of ring carbon atoms in the heteroaryl group is 2 or more and 30 or less, or 2 or more and 20 or less.
  • the heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the polycyclic heteroaryl group may have, for example, a bicyclic or tricyclic structure.
  • heteroaryl group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phenoxazyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group,
  • the number of carbon atoms in the amine group is not particularly limited, but may be 1 or more and 30 or less.
  • the amine group may include an alkyl amine group and an aryl amine group. Examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, and a triphenylamine group.
  • the organic compound of the present invention can be used as a material for an organic material layer of an organic electroluminescent device because it improves high efficiency and long life characteristics.
  • an organic electroluminescent device having excellent light emitting performance, driving voltage, efficiency and lifespan characteristics can be manufactured, and furthermore, a full color display panel with improved performance and lifespan can be manufactured.
  • FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • the organic compound of the present invention is a compound in which N-B-N is condensed to an aromatic ring to form a parent nucleus, and various substituents are bonded to the parent nucleus, and is represented by Formula 1 above.
  • a portion of the ring structure formed by N-B-N is an electron donor, and a portion bonded to nitrogen and/or a portion of the electron donor serves as an electron acceptor.
  • the organic compound includes an electron acceptor bonded to nitrogen of the electron donor site, thereby localizing the electron density in the molecule, and the absolute value ( ⁇ Est) of the difference between the singlet energy level (S1) and the triplet energy level (T1) is small.
  • the rate constant of reverse intersystem crossing (RISC) in which the triplet energy level (T1) is converted to the singlet energy level (S1) increases, thereby contributing to the long lifespan of the organic electroluminescent device.
  • the organic compound of the present invention when applied to the organic material layer of the organic electroluminescent device, the light emitting characteristics of the organic electroluminescent device are improved, and at the same time, the hole injection/transport ability and electron injection/transport ability are improved, so that the driving voltage is low and the lifespan is reduced. It is possible to provide an organic electroluminescent device.
  • the organic compound of the present invention may be applied to an organic material layer of an organic electroluminescent device, and the compound represented by Formula 1 may be a delayed fluorescence emitting material.
  • the organic compound may be a thermally activated delayed fluorescence material.
  • the organic compound of the present invention has a small difference between the singlet energy level (S1) and the triplet energy level (T1), so that it can be used as a thermally activated delayed fluorescent light emitting material.
  • the organic compound may be a thermally activated delayed fluorescent material emitting blue light, green light or red light. More preferably, the compound represented by Formula 1 may be used as a blue light emitting material emitting thermally activated delayed fluorescence, but is not limited thereto.
  • the compound represented by Chemical Formula 1 of the present invention may be embodied in the group consisting of compounds represented by the following Chemical Formulas 2 to 8.
  • Ar 1 to Ar 4 are as defined in Formula 1 above.
  • Ar 1 to Ar 2 are the same as or different from each other, and it is preferable that each independently be represented by any one of Formulas A-1 to A-5.
  • the dotted line means the part where the condensation takes place
  • Z 1 are the same as or different from each other, each independently C or N,
  • R 1 To R 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C 1 ⁇ C 30 alkyl group, substituted or unsubstituted C 2 ⁇ C 30 alkenyl group, substituted or unsubstituted C 2 ⁇ C 30 alkynyl group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 30 A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms.
  • Ar 3 to Ar 4 are the same as or different from each other, and it is preferable that each independently be represented by any one of Formulas B-1 to B-3.
  • Z 2 are the same as or different from each other, each independently C or N,
  • R 3 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C 1 ⁇ C 30 alkyl group, substituted or unsubstituted C 2 ⁇ C 30 alkenyl group, substituted or unsubstituted C 2 ⁇ C 30 alkynyl group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 30 A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms.
  • R 1 to R 4 when Z 1 to Z 2 of Ar 1 to Ar 4 are all C, at least one of R 1 to R 4 is substituted or unsubstituted having 2 to 30 nuclear atoms It is preferred that the compound is a heteroaryl group.
  • the compound represented by Formula 1 of the present invention may be further specified as a compound represented by any one selected from the group consisting of the compounds exemplified below.
  • the compound represented by Formula 1 of the present invention is not limited by those exemplified below.
  • the present invention provides an organic electroluminescent device comprising the compound represented by Formula 1 above.
  • the organic compound of the present invention can be used in an organic electroluminescent device to improve the efficiency and lifespan of the organic electroluminescent device.
  • the organic compound of the present invention can be used in the light emitting layer (EML) of the organic electroluminescent device to improve the luminous efficiency and lifespan of the organic electroluminescent device.
  • EML light emitting layer
  • the organic electroluminescent device may include a first electrode EL1 , a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 that are sequentially stacked.
  • the first electrode EL1 and the second electrode EL2 may face each other, and a plurality of organic layers may be disposed between the first electrode EL1 and the second electrode EL2 .
  • the plurality of organic layers may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR.
  • the organic electroluminescent device may include the compound represented by Formula 1 in the light emitting layer (EML).
  • the first electrode EL1 has conductivity.
  • the first electrode EL1 may be formed of a metal alloy or a conductive compound.
  • the first electrode EL1 may be an anode.
  • the first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
  • the first electrode EL1 is preferably a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc (ITZO). oxide) and the like.
  • the first electrode EL1 When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg).
  • a plurality of transparent conductive layers including a reflective or semi-transmissive layer formed of the above-described material and a transparent conductive layer formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. It may have a layer structure.
  • the first electrode EL1 may include a plurality of layers of ITO/Ag/ITO.
  • the hole transport region HTR is provided on the first electrode EL1 .
  • the hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer, and an electron blocking layer (EBL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • the hole transport region HTR may include a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.
  • the hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure including a hole injection material and a hole transport material.
  • the hole transport region HTR has a single layer structure made of a plurality of different materials, or a hole injection layer HIL/hole transport layer HTL, which are sequentially stacked from the first electrode EL1 , hole injection layer (HIL) / hole transport layer (HTL) / hole buffer layer, hole injection layer (HIL) / hole buffer layer, hole transport layer (HTL) / hole buffer layer, or hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL), but is not limited thereto.
  • the hole transport region may be formed by various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.
  • LB Langmuir-Blodgett
  • LITI laser induced thermal imaging
  • the hole injection layer (HIL) of the organic electroluminescent device may include a known hole injection material.
  • the hole injection layer (HIL) is triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodoniumtetrakis(pentafluorophenyl)borate (PPBI), N, N Phthalocyanine compounds, such as '-diphenyl-N, N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-phenyl-4, 4'-diamine (DNTPD), copper phthalocyanine, 4, 4 ',4''-tris(3-methylphenyl phenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), N ,N'-bis(1-naph
  • the hole transport layer (HTL) of the organic electroluminescent device may include a known hole transport material.
  • the hole transport layer (HTL) is 1,1-bis[(di-4-trilamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole (N-Phenylcarbazole), polyvinyl carbazole (Polyvinyl carbazole) carbazole derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4', 4''-tris(N-carbazolyl)triphenylamine (TCTA) N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB) and N,N'-bis( 1-naphthyl)-N,N'-diphenyl-4,4'-di
  • the hole transport region HTR may further include an electron blocking layer EBL, and the electron blocking layer EBL may be disposed between the hole transport layer HTL and the emission layer EML.
  • the electron blocking layer EBL serves to prevent electron injection from the electron transport region ETR to the hole transport region HTR.
  • the electron blocking layer (EBL) may include a general material known in the art to which the present invention pertains.
  • the electron blocking layer (EBL) is, for example, a carbazole-based derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine-based derivative, or TPD (N,N'-bis(3-methylphenyl)-N).
  • Triphenylamine derivatives such as ,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(Ncarbazolyl)triphenylamine), NPD(N, N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4, 4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl) and mCP
  • the electron blocking layer (EBL) is an organic compound of the present invention may include
  • the hole transport region HTR may have a thickness of about 100 ⁇ to about 10000 ⁇ . Preferably, it may be from about 100 Angstroms to about 5000 Angstroms.
  • the thickness of the hole injection layer (HIL) may be about 30 ⁇ to about 1000 ⁇
  • the thickness of the hole transport layer (HTL) may be about 30 ⁇ to about 1000 ⁇
  • the thickness of the electron blocking layer (EBL) may be about 10 ⁇ to about 1000 ⁇ .
  • the hole transport region HTR may further include a charge generating material to improve conductivity.
  • the charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR.
  • the charge generating material may be a p-dopant.
  • the p-dopant may be any one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.
  • non-limiting examples of the p-dopant include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), and metal oxides such as tungsten oxide and molybdenum oxide. may be mentioned, but is not limited thereto.
  • quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane)
  • metal oxides such as tungsten oxide and molybdenum oxide.
  • the hole transport region may further include any one or more of a hole buffer layer and an electron blocking layer (EBL) in addition to the hole injection layer (HIL) and the hole transport layer (HTL).
  • the hole buffer layer may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer EML.
  • a material included in the hole buffer layer a material capable of being included in the hole transport region (HTR) may be used.
  • the emission layer EML is provided on the hole transport region HTR.
  • the thickness of the emission layer EML may be greater than or equal to about 100 ⁇ and less than or equal to 600 ⁇ .
  • the emission layer EML may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.
  • the emission layer EML may emit one of red light, green light, blue light, white light, yellow light, and cyan light.
  • the emission layer EML may include a fluorescent light emitting material or a phosphorescent light emitting material.
  • the emission layer EML may be a fluorescent emission layer. Some of the light emitted from the emission layer EML may be due to thermally activated delayed fluorescence (TADF).
  • the light emitting layer (EML) may include a light emitting component that emits thermally activated delayed fluorescence, and more preferably, the light emitting layer (EML) may be a light emitting layer that emits thermally activated delayed fluorescence that emits green light or red light.
  • the emission layer EML may include a host and a dopant, the host may be a host for delayed fluorescence emission, and the dopant may be a dopant for delayed fluorescence emission.
  • the organic compound of the present invention may be included as a dopant material of the emission layer (EML).
  • the organic compound of the present invention may be one used as a TADF dopant.
  • the emission layer EML may include a known host material.
  • the light emitting layer (EML) is a host material, Alq3 (tris (8-hydroxyquinolino) aluminum), CBP (4,4'-bis (N-carbazolyl) -1,1'-biphenyl), PVK (poly (n) -vinylcabazole), ADN(9,10-di(naphthalene-2-yl)anthracene), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3, 5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4'- bis(9-carbazolyl)-2,2'-dimethyl-biphenyl
  • the emission layer EML may further include a known dopant material.
  • the emission layer (EML) is a dopant, and a styryl derivative (eg, 1,4-bis[2-(3-Nethylcarbazoryl)vinyl]benzene(BCzVB), 4-(di-p-tolylamino)-4 '-[(di-p-tolylamino)styryl]stilbene(DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl) vinyl)phenyl)phenylbenzenamine (NBDAVBi), perylene and its derivatives (eg 2, 5, 8, 11-Tetra-t-butylperylene (TBP)) and pyrene and its derivatives (eg 1, 1 2,5,8,11-Tetra-tbutylperylene (TBP)) such as -dipyrene,
  • the electron transport region ETR is provided on the emission layer EML.
  • the electron transport region ETR may include at least one of an electron blocking layer, an electron transport layer ETL, and an electron injection layer EIL, but is not limited thereto.
  • the electron transport region ETR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.
  • the electron transport region ETR may have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single layer structure including an electron injection material and an electron transport material.
  • the electron transport region ETR has a single layer structure made of a plurality of different materials, or an electron transport layer ETL/electron injection layer EIL and hole blocking layer sequentially stacked from the first electrode EL1 . It may have a layer/electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto.
  • the thickness of the electron transport region ETR may be about 100 ⁇ to about 1500 ⁇ .
  • the electron transport region is formed by various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI).
  • LB Langmuir-Blodgett
  • LITI laser induced thermal imaging
  • the electron transport region ETR includes Alq3 (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)- phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazolyl) -1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4 ,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-
  • the thickness of the electron transport layers ETL may be about 100 ⁇ to about 1000 ⁇ .
  • the thickness of the electron transport layers (ETL) may be about 150 ⁇ to about 500 ⁇ .
  • the electron transport region ETR includes the electron injection layer EIL
  • the electron transport region ETR includes a lanthanide metal such as LiF, lithium quinolate (LiQ), Li O, BaO, NaCl, CsF, Yb, or A metal halide such as RbCl, RbI, or KI may be used, but is not limited thereto.
  • a lanthanide metal such as LiF, lithium quinolate (LiQ), Li O, BaO, NaCl, CsF, Yb, or A metal halide such as RbCl, RbI, or KI may be used, but is not limited thereto.
  • the electron injection layer EIL may also be made of a material in which an electron transport material and an insulating organo metal salt are mixed.
  • the organometallic salt may be a material having an energy band gap of about 4 eV or more.
  • the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate or metal stearate.
  • the electron injection layers EIL may have a thickness of about 1 ⁇ to about 100 ⁇ .
  • the thickness of the electron injection layers EIL may be about 3 ⁇ to about 90 ⁇ .
  • the electron transport region ETR may include a hole blocking layer, which includes 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl- (Bphen). 1,10-phenanthroline), but is not limited thereto.
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • Bphen 4,7-diphenyl-
  • the second electrode EL2 is provided on the electron transport region ETR.
  • the second electrode EL2 has conductivity.
  • the second electrode EL2 may be formed of a metal alloy or a conductive compound.
  • the second electrode EL2 may be a cathode.
  • the second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
  • the second electrode EL2 DL is a transmissive electrode
  • the second electrode EL2 is preferably a transparent metal oxide, preferably indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc (ITZO). oxide) and the like.
  • the second electrode EL2 When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg).
  • a plurality of transparent conductive layers including a reflective or semi-transmissive layer formed of the above-described material and a transparent conductive layer formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. It may have a layer structure.
  • the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
  • the organic electroluminescent device As a voltage is applied to each of the first electrode EL1 and the second electrode EL2 , holes injected from the first electrode EL1 pass through the hole transport region HTR Electrons moved to the emission layer EML and injected from the second electrode EL2 move to the emission layer EML through the electron transport region ETR. Electrons and holes recombine in the emission layer EML to generate excitons, and the excitons fall from the excited state to the ground state and emit light.
  • the organic electroluminescent device is a top emission type
  • the first electrode EL1 may be a reflective electrode
  • the second electrode EL2 may be a transmissive electrode or a transflective electrode.
  • the organic EL device 10 When the organic EL device 10 is a bottom emission type, the first electrode EL1 may be a transmissive electrode or a transflective electrode, and the second electrode EL2 may be a reflective electrode.
  • the organic electroluminescent device may exhibit improved luminous efficiency and lifetime characteristics by using the organic compound of the present invention as a light emitting layer material.
  • 26 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that N-phenylnaphthalen-2-amine and diphenylamine were used as reactants;
  • 21 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that N-phenylnaphthalen-1-amine and N-phenylnaphthalen-2-amine were used;
  • 29 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(naphthalen-2-yl)amine and N-(naphthalen-2-yl)naphthalen-1-amine were used as reactants;
  • 31 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(naphthalen-2-yl)amine and bis(4-(tert-butyl)phenyl)amine were used;
  • 35 g of the target compound was obtained in the same manner as in [Preparation Example 1] except that N-(4-(tert-butyl)phenyl)naphthalen-1-amine was used;
  • 29 g of the target compound was obtained by performing the same procedure as in [Preparation Example 3] except that N-(naphthalen-2-yl)naphthalen-1-amine and bis(4-(tert-butyl)phenyl)amine were used. got;
  • N-(4-(tert-butyl)phenyl)naphthalen-1-amine and N-(4-(tert-butyl)phenyl)naphthalen-2-amine are the same as in [Preparation Example 3] except that The procedure was carried out to obtain 28 g of the desired compound;
  • N-phenylphenanthren-9-amine and bis(4-(tert-butyl)phenyl)amine were used, and the same procedure as in [Preparation Example 3] was followed to obtain 32 g of the target compound;
  • 29 g of the desired compound was obtained in the same manner as in [Preparation Example 1] except that N-(4-(tert-butyl)phenyl)phenanthren-9-amine was used;
  • 29 g of the target compound was obtained in the same manner as in [Preparation Example 1] except that di(isoquinolin-6-yl)amine was used;
  • di(isoquinolin-6-yl)amine and diphenylamine were used, and the same procedure as in [Preparation Example 3] was performed to obtain 17 g of the desired compound;
  • di(isoquinolin-6-yl)amine and di(quinolin-5-yl)amine were used, and the same procedure as in [Preparation Example 3] was performed to obtain 15 g of the desired compound;
  • 31 g of the target compound was obtained in the same manner as in [Preparation Example 1] except that 4-bromo-3,5-difluoro-3'-(trifluoromethyl)-1,1'-biphenyl was used;
  • 16 g of the target compound was obtained by performing the same procedure as in [Preparation Example 56] except that (4-bromo-3,5-difluorophenyl)trimethylsilane was used;
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, ethanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and vacuum evaporator The substrate was transferred to
  • a hole injection layer was formed with a thickness of 80 nm DS-205 (Doosan Corporation) on the prepared ITO transparent electrode, and a-NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl -(1,1'-biphenyl)-4.4'-diamine) was vacuum deposited to a thickness of 30 nm to form a hole transport layer.
  • DS-205 Doosan Corporation
  • the compounds prepared in Synthesis Examples 1 to 97 as a green dopant material and DS-H522 and DS-TD-002 as green light-emitting host materials were applied as common hosts to form a light-emitting layer with a thickness of 30 nm.
  • An electron transport layer was formed on the light emitting layer by using an electron transport material, TPBi(2,2',2"-(Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)) to a thickness of 30 nm. Then, LiF was applied to a thickness of 1 nm.
  • a device was manufactured by forming an electron injection layer with a cathode and forming 200 nm of Al as a cathode.
  • a red organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, ethanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). The substrate was transferred to
  • a hole injection layer was formed with a thickness of 80 nm DS-205 (Doosan Corporation) on the prepared ITO transparent electrode, and a-NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl -(1,1'-biphenyl)-4.4'-diamine) was vacuum deposited to a thickness of 30 nm to form a hole transport layer.
  • DS-205 Doosan Corporation
  • the compounds prepared in Synthesis Examples 1 to 97 as a red dopant material and DS-H522 and DS-TD-018 as a red light-emitting host material were applied as a common host to form a light-emitting layer with a thickness of 30 nm.
  • an electron transporting material TPBi(2,2',2"-(Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)
  • TPBi(2,2',2"-(Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) was applied to a thickness of 30 nm to form an electron transport layer.
  • LiF was applied to a thickness of 1 nm.
  • a device was fabricated by forming an electron injection layer with a cathode and forming 200 nm of Al as a cathode.
  • An organic electroluminescent device was fabricated in the same manner as in the device fabrication example except for using DCM2, DCJTB, and DCDDC, which are representative of red light emitting materials, and the evaluation results of the fabricated device are shown in Table 2.
  • organic layer 31 hole transport layer

Landscapes

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

Abstract

La présente invention concerne un nouveau composé ayant une excellente capacité d'émission de lumière, et un élément électroluminescent organique le comprenant, le composé selon la présente invention, lorsqu'il est utilisé dans un matériau de couche de matériau organique d'un élément électroluminescent organique, de préférence en tant qu'hôte à phosphorescence dans une couche électroluminescente, peut en améliorer les caractéristiques de capacité de photo-émission, de tension de commande, de rendement et de durée de vie.
PCT/KR2021/019005 2020-12-14 2021-12-14 Composé électroluminescent organique et élément électroluminescent organique l'utilisant WO2022131768A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2020-0174795 2020-12-14
KR1020200174795A KR20220084871A (ko) 2020-12-14 2020-12-14 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2022131768A1 true WO2022131768A1 (fr) 2022-06-23

Family

ID=82057921

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/019005 WO2022131768A1 (fr) 2020-12-14 2021-12-14 Composé électroluminescent organique et élément électroluminescent organique l'utilisant

Country Status (2)

Country Link
KR (1) KR20220084871A (fr)
WO (1) WO2022131768A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116332978A (zh) * 2023-05-30 2023-06-27 吉林奥来德光电材料股份有限公司 一种有机化合物及其制备方法、包含其的有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160119683A (ko) * 2014-02-18 2016-10-14 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
KR20180122298A (ko) * 2017-05-02 2018-11-12 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20190140421A (ko) * 2018-06-11 2019-12-19 주식회사 엘지화학 유기 발광 소자
KR20200070141A (ko) * 2018-12-07 2020-06-17 주식회사 엘지화학 유기 발광 소자
KR20210125621A (ko) * 2020-04-07 2021-10-19 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함한 장치

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150033082A (ko) 2013-09-23 2015-04-01 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160119683A (ko) * 2014-02-18 2016-10-14 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
KR20180122298A (ko) * 2017-05-02 2018-11-12 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20190140421A (ko) * 2018-06-11 2019-12-19 주식회사 엘지화학 유기 발광 소자
KR20200070141A (ko) * 2018-12-07 2020-06-17 주식회사 엘지화학 유기 발광 소자
KR20210125621A (ko) * 2020-04-07 2021-10-19 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함한 장치

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116332978A (zh) * 2023-05-30 2023-06-27 吉林奥来德光电材料股份有限公司 一种有机化合物及其制备方法、包含其的有机电致发光器件
CN116332978B (zh) * 2023-05-30 2023-08-29 吉林奥来德光电材料股份有限公司 一种有机化合物及其制备方法、包含其的有机电致发光器件

Also Published As

Publication number Publication date
KR20220084871A (ko) 2022-06-21

Similar Documents

Publication Publication Date Title
WO2020017931A1 (fr) Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2018186670A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2016167491A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et appareil électronique
WO2015156580A2 (fr) Composé organique et élément électroluminescent organique le contenant
WO2020050619A1 (fr) Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2012111927A2 (fr) Composé et élément électrique organique l'utilisant, et dispositif électronique et procédé de mesure de résistance associé
WO2019135633A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2018160003A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2021172664A1 (fr) Dispositif électroluminescent organique
WO2022131780A1 (fr) Composé électroluminescent organique et élément électroluminescent organique l'utilisant
WO2016137068A1 (fr) Composé hétérocyclique et élément luminescent organique comprenant celui-ci
WO2019078701A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021187923A1 (fr) Dispositif organique électroluminescent utilisant des composés dérivés aromatiques polycycliques
WO2017146483A1 (fr) Composé hétérocyclique et diode électroluminescente organique contenant ce composé
WO2022131547A1 (fr) Composé hétérocyclique, dispositif électroluminescent organique le comprenant, procédé de fabrication associé et composition pour couche organique
WO2021172905A1 (fr) Dispositif électroluminescent organique
WO2022045817A1 (fr) Dérivés de phénanthrène et diodes électroluminescentes organiques comprenant les dérivés
WO2022131768A1 (fr) Composé électroluminescent organique et élément électroluminescent organique l'utilisant
WO2021010631A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2023008865A1 (fr) Molécules organiques pour dispositifs optoélectroniques
WO2021182888A1 (fr) Composé amine ayant un cycle fusionné et dispositif électroluminescent organique le comprenant
WO2019117571A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2023229396A1 (fr) Composition pour élément électroluminescent organique et élément électroluminescent organique la comprenant
WO2018004318A2 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2023214820A1 (fr) Composition pour élément électroluminescent organique, et élément électroluminescent organique la comprenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21907072

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21907072

Country of ref document: EP

Kind code of ref document: A1