WO2016068450A1 - Élément optoélectronique organique et dispositif d'affichage - Google Patents

Élément optoélectronique organique et dispositif d'affichage Download PDF

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WO2016068450A1
WO2016068450A1 PCT/KR2015/007506 KR2015007506W WO2016068450A1 WO 2016068450 A1 WO2016068450 A1 WO 2016068450A1 KR 2015007506 W KR2015007506 W KR 2015007506W WO 2016068450 A1 WO2016068450 A1 WO 2016068450A1
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Korean (ko)
Inventor
오재진
김훈
조영경
강기욱
강의수
김동영
김영권
김윤환
박재한
양용탁
유은선
이한일
정성현
정우석
정호국
조평석
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Samsung SDI Co Ltd
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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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—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
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • An organic optoelectronic device and a display device An organic optoelectronic device and a display device.
  • An organic optoelectric diode is a device capable of converting electrical energy and light energy.
  • Organic optoelectronic devices can be divided into two types according to the principle of operation.
  • One is an optoelectronic device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electrical energy. It is a light emitting device that generates light energy from electrical energy.
  • organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.
  • organic light emitting diodes have attracted much attention recently as demand for flat panel displays increases.
  • the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material.
  • the organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode.
  • the present invention is to provide a long life blue organic light emitting device to solve this problem.
  • One embodiment provides an organic optoelectronic device capable of realizing high efficiency characteristics.
  • Another embodiment provides a display device including the organic optoelectronic device.
  • the electron transport auxiliary layer located between the light emitting layer, the electron transport auxiliary layer comprises at least one crab 1 compound represented by the following formula (1) and at least one crab 2 compound represented by the formula (2)
  • the hole transport auxiliary layer is an organic optoelectronic device comprising a third compound represented by a combination of a moiety represented by the formula (3), a moiety represented by the formula (4) and a moiety represented by the formula (5) To provide.
  • Z 1 to Z 9 are each independently N or CR a ,
  • At least one of Z 1 to Z 9 is N,
  • R 1 to R 15 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and L 1 is substituted or unsubstituted C6 to C30 arylene group,
  • nl to n3 are each independently an integer of 0 or 1
  • L 2 and L 3 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
  • R 16 to R 29 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof ego,
  • X 1 and X 2 are each independently 0, S or CR b R c ,
  • R 30 to R 35 , R b and! are each independently hydrogen, deuterium, substituted or unsubstituted
  • Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group
  • L 4 to L 6 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof
  • Adjacent two * of Formula 3 are combined with two * of Formula 4 to form a fused ring
  • a *, b * of Formula 3 or 4 and any one of R 30 to R 35 is
  • a *, b * and R 30 to R 35 which are not bonded to c * of Formula 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C3 to C30 heteroaryl group or a combination thereof.
  • substituted means that at least one hydrogen is deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group Substituted with a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group Means)
  • a display device including the organic optoelectronic device is provided.
  • 1 and 2 are cross-sectional views schematically illustrating an organic optoelectronic device according to an embodiment.
  • substituted means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted Ring C1 to C40 silyl group, C1 to C30 alkyl group, CI to CI O alkylsilyl group, C3 to C30 cycloalkyl group, C2 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group, trifluoro It means substituted by C1-C10 trifluoroalkyl group or cyano group, such as a methyl group.
  • C 1 to C 10 trifluoroalkyl group or cyano group such as heterocycloalkyl group, C 6 to C 30 aryl group, C 2 to C 30 heteroaryl group, C 1 to C 20 alkoxy group, fluoro group, trifluoromethyl group It may be fused to form a ring.
  • the substituted C6 to C30 aryl group can be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
  • hetero means one to three hetero atoms selected from the group consisting of ⁇ , ⁇ , S, P, and Si in one functional group, and the remainder is carbon unless otherwise defined. do.
  • an "alkyl group” is aliphatic
  • the alkyl group may be a "saturated alkyl group" "that does not contain any double or triple bonds.
  • the alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group.
  • a C1 to C4 alkyl group means one to four carbon atoms in the alkyl chain, methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and t-butyl It is selected from the group consisting of.
  • alkyl group is a specific example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t- butyl, pentyl, nuclear group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cycloalkyl It means a nuclear skill.
  • an "aryl group” refers to a substituent in which all elements of a cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic, polycyclic or Fused ring polycyclic (ie, rings having adjacent pairs of carbon atoms) functional groups.
  • heteroaryl group means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S, P and Si in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
  • a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl, substituted or unsubstituted
  • Phenanthryl group substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted Or an unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perrylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group , Substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or
  • Acridinyl group substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenthiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group , It may be a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group or a combination thereof, but is not limited thereto.
  • the hole characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and injecting holes formed at the anode into the light emitting layer having conductive properties along the HOMO level, and emitting layer. It refers to a property that facilitates the movement of the hole formed in the anode and movement in the light emitting layer.
  • the electron characteristic refers to a characteristic that can receive electrons when an electric field is applied, and has a conductivity characteristic along the LUMO level, and injects electrons formed in the cathode into the light emitting layer, moves electrons formed in the light emitting layer to the cathode, and Faint characteristics that facilitate movement.
  • the organic optoelectronic device is not particularly limited as long as the device can switch electrical energy and light energy. Examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.
  • an organic light emitting device as an example of an organic optoelectronic device will be described as an example, but the present invention is not limited thereto and may be similarly applied to other organic optoelectronic devices.
  • 1 and 2 are cross-sectional views schematically illustrating an organic optoelectronic device according to an embodiment.
  • an organic optoelectronic device is disposed between an anode 10 and a cathode 20 facing each other, and between the anode 10 and the cathode 20.
  • the anode 10 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the anode 10 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold Or alloys thereof; Zinc oxide, indium oxide, indium tin oxide ( ⁇ ),
  • Metal oxides such as indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-.dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrene and polyaniline, It is not limited to this.
  • the cathode 20 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the cathode 20 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or an alloy thereof; Multi-layered materials such as LiF / Al, Li (3 ⁇ 4 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
  • the organic layer 30 includes a hole transport layer 31, a light emitting layer 32, and a hole transport auxiliary layer 33 positioned between the hole transport layer 31 and the light emitting layer 32.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron injection layer 36 between the electron transport layer 34 and the cathode 20. It may further include a. .
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and between the electron transport layer 34 and the cathode 20.
  • the electron injection layer 36 may be further included.
  • the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 not only improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31, but also the surface thereof. It is applied on top of the uneven ⁇ ⁇ to soften the surface of ITO.
  • the hole injection layer 37 is formed of the work function level of ITO and the HOMO level of the hole transport layer 31 in order to control the difference between the work function level of ⁇ and the HOMO level of the hole transport layer 31 which can be used as an anode.
  • the material having a median value a material having a particularly suitable conductivity is selected.
  • '-Diamine (4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3- ⁇ Can be used, but is not limited thereto.
  • it can be used together with the conventional materials constituting the hole injection layer 37, for example, copper
  • phenylamino] biphenyl DNTPD
  • HAT-CN hexaazatriphenylene-hexacarbonitirile
  • PEDOT poly (3,4-ethylenedioxythiophene) -poly (stymesulfonate)
  • the hole injection layer 37 may be coated on top of ⁇ used as an anode, for example, at a thickness of 10 to 300 A.
  • the electron injection layer 36 is a layer that is stacked on top of the electron transport layer to facilitate electron injection from the cathode and ultimately improves power efficiency, and may be used without particular limitation as long as it is commonly used in the art.
  • materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO, and the like may be used.
  • the hole transport layer 31 is a layer for facilitating hole transfer from the anode 10 to the light emitting layer 32, and may be, for example, an amine compound, but is not limited thereto.
  • the amine compound may include, for example, at least one aryl group and / or heteroaryl group.
  • the amine compound may be represented by, for example, the following Chemical Formula a or Chemical Formula b, but is not limited thereto.
  • Ar a to ⁇ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to
  • At least one of Ar a internal Ar c and at least one of Ar d to Ar g is substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
  • Ar h is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.
  • the electron transport layer 34 is a layer for facilitating electron transfer from the cathode 20 to the light emitting layer 32, for example, aluminum as the electron transport layer material.
  • Trihydroxyquinoline (aluminum trihydroxyquinoline, Alq 3 ), 1,3,4-oxadiazole derivative 2- (4-biphenylyl-5-phenyl-1,3,4-oxadiazole (2- (4 -biphenylyl) -5-phenyl-l, 3,4-oxadiazole, PBD), a quinoxaline derivative 1,3,4-tris [(3-phenyl-6-trifluoromethyl) quinoxalin-2-yl] Benzene (1,3,4-tris [(3-penyl-6-trifluoromethyl) quino-xaline-2-yl] benzene, TPQ), triazole derivatives and triazine derivatives may be used, but is not limited thereto. .
  • the light emitting insect 32 is an organic layer having a light emitting function, and includes a host and a dopant when a doping system is employed.
  • the host mainly has a function of promoting recombination of electrons and holes and confining excitons in a light emitting layer, and the dopant has a function of efficiently emitting excitons obtained by recombination.
  • the light emitting layer may include a known host and a dopant.
  • Known hosts include, for example, Alq3, CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole)), 9,10-di (naphthalene-2- yl) anthracene (ADN), TCTA, TPBI ( 1,3, 5 - tris (N- phenyl-benzimidazol-2-yl) benzene (l, 3,5-tris (N -phenylbenzimidazole-2-yl) benzene) ), TBADN (3-tert-butyl- 9 , 10-di (naphth- 2 -yl) anthracene), mCP, OXD- 7 and the like can be used, but
  • the dopant may be at least one of a fluorescent dopant and a phosphorescent dopant.
  • the phosphorescent dopant may be, but is not limited to, an organometallic complex including 11 ′′, 03, 1,, 3 ⁇ 4, 1 1, or a combination of two or more thereof.
  • blue dopants examples include F 2 Irpic, (F 2 ppy) 2 Ir (tmd), Ir (dfppz) 3 , ter-fluorene, 4,4′-bis (4-diphenylamino Styryl) biphenyl (DP A VBi), 2,5,8,11-tetra-butyl perylene (TBPe), DPVBi, pyrene derivatives (KR0525408, LG Electronics Co., Ltd.) and the like, but are not limited thereto. .
  • the content of the dopant is typically from about 0.01 to about 15 weight 0 per 100 weight 0 /. It may be selected from the range of / 0 , but is not limited thereto.
  • the light emitting layer has a thickness of about 200 A to about 700 A.
  • the electron transport auxiliary layer 35 includes one compound having a relatively strong electronic property and two compounds having a relatively strong hole property.
  • the first compound is a compound having a relatively strong electronic property, it may be represented by the following formula (1).
  • Z 1 to Z 9 are each independently N or CR a ,
  • At least one of Z 1 to Z 9 is N,
  • R 1 to R 15 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
  • L 1 is a substituted or unsubstituted C6 to C30 arylene group
  • nl to n3 are each independently an integer of 0 or 1, and nl + n2 + n3 ⁇ l.
  • the first compound may be represented by, for example, the following Chemical Formula 1-I or Chemical Formula 1- ⁇ depending on the bonding position of the triphenylene group. -1] [Formula 1- ⁇ ]
  • X 1 to X 9 , ⁇ to 1 15 , and nl to n 3 are as described above.
  • At least two of Z 1 to Z 3 in Formula 1, Formula 1-1 3 ⁇ 4 1-II may be N, and in one embodiment of the present invention, all of Z 1 to Z 3 may be N .
  • the C1 compound comprises a heteroaryl group containing a triphenylene group and at least one nitrogen atom.
  • the C1 compound may include a ring containing at least one nitrogen, and thus may have a structure in which electrons are easily received when an electric field is applied, thereby increasing an electron injection amount, thereby lowering a driving voltage of the organic optoelectronic device to which the first compound is applied. Can also improve the efficiency.
  • the C 1 compound may be represented by any one of the following Formulas 1-1 to 1-4.
  • Y 1 to Y 6 are each independently N or CH;
  • At least one of Y 1 to Y 6 is N
  • R 36 to R 41 are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
  • n4 to n9 are each independently an integer of 0 or 1
  • nl O is an integer of 1 or 2.
  • substituted at least one hydrogen is deuterium, halogen, hydroxy group, amino group, substituted or unsubstituted C1 to C30 amine group, nitro group, substituted or unsubstituted C1 to C40 silyl group, C 1 to C30 alkyl group, C3 to C30 cycloalkyl group, C2 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group, C1 to C10 trifluoroalkyl group or cyano group
  • the first compound may be represented by Chemical Formula 1-3.
  • the first compound represented by Chemical Formula 1 has an arylene group and / or a heteroarylene group with at least one kink structure.
  • the fold structure refers to a structure in which two connecting portions of an arylene group and / or a heteroarylene group do not form a straight structure.
  • a structure in which two connecting portions of an arylene group and / or a heteroarylene group do not form a straight structure For example, in the case of phenylene, p-phenylene (o-phenylene) and meta-phenylene (m-phenylene), in which the linking portions do not form a linear structure, have the bending structure, and para-phenylene (p- phenylene) does not have this bending structure.
  • the bending structure is a linking group (L 1 ) and / or
  • It may be formed around the arylene group / hetero arylene group.
  • nl of Formula 1 is an integer of 0, that is, in a structure without a linking group (L ′), a fold structure can be formed around an arylene group / heteroarylene group, for example, a compound represented by the following formula la or lb Can be.
  • a folding structure may be formed around the linking group (L 1 ), and for example, L ′ may be a substituted or unsubstituted biphenyl of a substituted or unsubstituted phenylene group folding structure. It may be a phenylene group or a substituted or unsubstituted terphenylene group of a folding structure.
  • L 1 may be at least one selected from, for example, linkage groups listed in Group 1 below.
  • the C 1 compound may preferably have at least two folding structures, for example, may have two to four folding structures.
  • the first compound may improve the efficiency of the organic optoelectronic device to which the composition is applied by appropriately localizing the charge and effectively controlling the flow of the conjugated system by having the above-described bending structure.
  • the first compound may be represented by, for example, any one of Formulas lc to It. [Formula lc] [Formula
  • the compound 1 may be, for example, a compound listed in Group 2, but is not limited thereto.
  • R 16 to R 29 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C30 heteroaryl group in C2, or a combination thereof ⁇
  • Compound represented by the formula (2) is a compound having a relatively strong hole characteristics, it is included in the electron transport auxiliary layer with the Crab compound, Crab 1
  • the electron injection amount of the compound can be adjusted, and the stability of the device can be improved by preventing the accumulation of holes at the interface between the light emitting layer and the electron transport auxiliary layer. Therefore, the luminous efficiency and lifespan characteristics of the organic optoelectronic device can be significantly improved.
  • the second compound may be represented by at least one of, for example, the following Chemical Formula 2- 1 to Chemical Formula 2-below depending on the binding position of bicarbazole.
  • the second compound has a structure in which two carbazolyl groups having a substituent are connected.
  • Ar 1 and Ar 2 of the second compound are substituents having hole or electronic properties, each independently a substituted or unsubstituted phenyl group, substituted or unsubstituted, for example.
  • Biphenyl group substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted Benzothiophenyl group, substituted or unsubstituted
  • Fluorenyl group substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted triphenylene group, substituted or Unsubstituted dibenzofuranyl group, substituted or unsubstituted Dibenzothiophenyl group, or a combination thereof.
  • the second compound may be represented by any one of the following Formulas 2-1 to 2-3 according to the properties of Ar 1 and Ar 2 .
  • ET1 to ET3 are each independently a substituent having electronic properties, and HT1 to HT3 are each independently substituents having hole characteristics.
  • Substituents ⁇ , 2 ⁇ 2 ", and" ET3 "having electronic properties among Ar 1 and Ar 2 of the second compound may be, for example, substituents represented by the following Chemical Formula A.
  • Z are each independently N or CR k ,
  • A1, A2 and R k are each independently a substituted or unsubstituted C6 to C30 aryl group a substituted or unsubstituted C2 to C30 heteroaryl group or a combination thereof,
  • At least one of ⁇ , ⁇ and A2 comprises ⁇ ,
  • a and b are each independently an integer of 0 or 1.
  • Substituents represented by Formula A for example, ET1 to ET3 may be independently represented by any one of the functional groups listed in Group 3 below. Group 3]
  • ' ⁇ “ ⁇ 2” and ⁇ 3, which are substituents having hole characteristics among Ar 1 and Ar 2 of the Crab 2 compound, may be independently represented by any one of the functional groups listed in Group 4 below.
  • the Crab 2 compound may be represented by Chemical Formula 2-3.
  • the second compound may be selected from, for example, the compounds listed in Group 5 below, but is not limited thereto.
  • One kind or two or more kinds of the second compound may be used.
  • Secondary electron transport layer is strong first compound and a hole-characteristic electronic properties in accordance with one embodiment of the invention is to a river, may comprise a second compound at the same time.
  • At least one of the first compounds represented by the general formula (1-3) and at least one of the two compounds represented by the general formula (2-3) may be used together.
  • the first compound and the crab 2 compound may be included, for example, in a weight ratio of about 1:99 to 99: 1. Specifically, 10:90 to 90: 10, 20:80 to 80:20, 30:70 to 70:30, and 40:60 to 60:40, most specifically, 50:50.
  • a mixture of two materials may be deposited in advance, or each compound may be simultaneously deposited at a weight ratio. .
  • the hole transport auxiliary layer 33 includes a third compound having good hole transport properties, and adjusts the hole injection property by reducing the difference in the HOMO energy level between the hole transport layer 31 and the light emitting layer 32 to provide the hole transport auxiliary layer. Extinction of the axtone due to polaron at the interface is reduced by reducing the accumulation of holes at the interface between the 33 and the light emitting layer 32
  • the quenching can be reduced. Accordingly, deterioration of the device may be reduced and the device may be stabilized to improve efficiency and lifespan.
  • the crab compound 3 may be a compound represented by a combination of a moiety represented by Formula 3, a moiety represented by Formula 4, and a moiety represented by Formula 5.
  • X 1 and X 2 are each independently 0, S or CR b R c ,
  • R 30 to R 35 , R b and! are each independently hydrogen, deuterium, substituted or unsubstituted
  • Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
  • L 4 to L 6 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof,
  • Adjacent two * of Formula 3 are combined with two * of Formula 4 to form a fused ring
  • a *, b *, R 30 to R 35 of 3 or 4 is connected to c * of Formula 5 by a sigma bond
  • the remaining a *, b * and R 30 to R 35 which are not bonded to c * of Formula 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C3 to C30 heteroaryl group or a combination thereof.
  • the third compound may be represented by any one of the following Formulas 3-1 to 3-3.
  • R 42 and R 43 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof .
  • the third compound may be represented by any one of the following Formulas 3-4 to 3-6. [Formula 3-4] [Formula 3-5]
  • Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted
  • Quarterphenyl groups substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted triphenylene groups, substituted Or unsubstituted fluorenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted di It may be a benzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, the following formula w, the formula X, the formula y, the formula z or a combination thereof.
  • Biphenyl group substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted pyrenyl group, substituted or Unsubstituted triphenylene group, substituted or unsubstituted
  • Fluorenyl group substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted
  • Dibenzothiophenyl group or a combination thereof.
  • the third compound may be represented by Chemical Formula 3-1 or 3-2.
  • the third compound may be selected from, for example, the compounds listed in Group 6 below, but is not limited thereto.
  • the organic optoelectronic device includes the electron transport auxiliary layer including the first compound having strong electronic properties and the crab 2 compound having strong hole properties, and the HOMO energy between the hole transport layer 31 and the light emitting layer 32.
  • the electron transport auxiliary layer including the first compound having strong electronic properties and the crab 2 compound having strong hole properties
  • the HOMO energy between the hole transport layer 31 and the light emitting layer 32.
  • the hole injection control ability of the hole transport auxiliary layer can be adjusted to improve efficiency by adjusting the charge balance, and deterioration of the device by applying a hole transport auxiliary layer and an electron transport auxiliary layer to prevent charge accumulation at each interface of the organic layer. The phenomenon is reduced, and the device can be stabilized to improve the lifetime.
  • the electron transport auxiliary layer comprises at least one of the first compound represented by the formula 1-3 and at least one of the second compound represented by the formula 2-3, the hole transport auxiliary layer is At least one of the third compounds represented by the formula (3-1) or (3-2) may be included.
  • the hole transport auxiliary layer 33 and the electron transport auxiliary layer 35 can be applied on the hole transport layer in a thickness of 0.1 nm to 20.0 nm by a deposition or ink set process, for example, 0.2 nm to l ON., 0.3 nm to 5 nm. , 0.3 nm to 2 nm, 0.4 nm to l .Onm thickness, and the like can also be applied.
  • the organic layer 30 is optionally positioned between the hole injection layer 37 and / or the cathode 20 and the electron transport layer 34 located between the anode 10 and the hole transport layer 31.
  • the electron injection layer 36 may be further included.
  • the hole transport auxiliary layer may be in contact with the hole transport layer and the light emitting layer, respectively, and the electron transport auxiliary layer may be an organic optoelectronic device in contact with the electron transport layer and the light emitting layer, respectively.
  • the light emitting layer may further include a dopant, for example, may further include a phosphorescent dopant, a fluorescent dopant and the like.
  • the organic optoelectronic device may be any one selected from the group consisting of an organic light emitting device, an organic photoelectric device, an organic solar cell organic transistor, an organic photosensitive drum and an organic memory device.
  • the organic light emitting diode described above may be applied to an organic light emitting diode display.
  • 9-phenyl-9H-carbazol-3-yl boronic acid (9-phenyl-9H-carbazol-3-yl boronic acid, TCI) 10 g (34.83 mmol), 3-bromo-9-phenylcarbazole ( 3-bromo-9-phenylcarbazole, Aldrich), 1 1.77 g (38.31 mmol) and potassium carbonate 14.44 g (104.49 mmol), tetrakis- (triphenylphosphine) palladium (0) 0.80 g (0.7 mmmol) It was suspended in 140 ml, 50 ml of distilled water and stirred under reflux for 12 hours.
  • Tetrakistriphenylphosphinepalladium 1.09 g (94 mmol) was added thereto, and the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate, the extract was dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-nucleic acid / dichloromethane (9: 1 volume ratio) to give 37 g (90% yield) of the intermediate compound M-13.
  • Compound E-58 obtained in Synthesis Example 45 was vacuum deposited to form a hole transport auxiliary layer having a thickness of 50 A on the hole transport layer.
  • a blue fluorescent light emitting host and a dopant on the hole transport auxiliary layer were Using BH113 and BD370 sold, doped BD370 to 5wt% and deposited to a thickness of 200A to form a light emitting layer.
  • an electron transport auxiliary layer having a thickness of 50 A was formed on the light emitting layer by vacuum deposition of Compound A-33 obtained in Synthesis Example 8 and Compound B-43 obtained in Synthesis Example 11.
  • Compound A-33 and Compound B-43 were used in a 1: 1 weight ratio.
  • an electron transport material product name NET164 (Compound E) sold by Noval Red and Liq were vacuum deposited on the electron transport auxiliary layer at a 1: 1 ratio simultaneously to form an electron transport layer having a thickness of 310 A, and Liq on the electron transport layer.
  • the organic light emitting device was manufactured by sequentially vacuuming l5A and A1 1200A to form a cathode.
  • the organic light emitting device has a structure having six organic thin film layers, specifically
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound F-5 obtained in Synthesis Example 38 instead of the compound E-58 for the hole transport auxiliary layer.
  • Reference Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound F-5 obtained in Synthesis Example 38 instead of the compound E-58 for the hole transport auxiliary layer.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound C was deposited to a thickness of 750 A without forming a hole transport auxiliary layer, thereby forming a hole transport layer. Comparative Example 1
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for depositing l: l (360A). evaluation
  • the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting diode was measured using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
  • a luminance meter Minolta Cs-IOOOA
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
  • the organic light emitting device according to Examples 1 and 2 compared with the organic light emitting device according to Reference Example 1 and Comparative Example 1, respectively, it can be seen that the luminous efficiency and life characteristics are significantly improved at the same time.
  • the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

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

Abstract

Cette invention concerne un élément optoélectronique organique et un dispositif d'affichage le comprenant, l'élément optoélectronique organique comprenant : une anode et une cathode, en regard l'une de l'autre ; une couche électroluminescente située entre l'anode et la cathode ; une couche de transport de trous située entre l'anode et la couche électroluminescente ; une couche de transport de trous auxiliaire située entre la couche de transport de trous et la couche électroluminescente ; une couche de transport d'électrons située entre la cathode et la couche électroluminescente ; et une couche de transport d'électrons auxiliaire située entre la couche de transport d'électrons et la couche électroluminescente, la couche de transport d'électrons auxiliaire comprenant au moins un premier composé représenté par une formule chimique particulière et au moins un deuxième composé représenté par une formule chimique particulière, et la couche de transport de trous auxiliaire comprenant au moins un troisième composé représenté par une combinaison de fragments représentés par des formules chimiques particulières.
PCT/KR2015/007506 2014-10-30 2015-07-20 Élément optoélectronique organique et dispositif d'affichage Ceased WO2016068450A1 (fr)

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JP2018534238A (ja) * 2016-02-23 2018-11-22 エルジー・ケム・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
USRE47654E1 (en) 2010-01-15 2019-10-22 Idemitsu Koasn Co., Ltd. Organic electroluminescence device
US11578063B2 (en) 2017-10-17 2023-02-14 Merck Patent Gmbh Materials for organic electroluminescent devices
US11814395B2 (en) 2018-06-22 2023-11-14 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN118724797A (zh) * 2023-03-31 2024-10-01 中南大学 一种三联吡啶锌配合物及其制备方法和应用

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KR102078301B1 (ko) * 2017-07-12 2020-02-17 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102649289B1 (ko) * 2019-05-27 2024-03-19 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102771628B1 (ko) 2020-03-10 2025-02-26 삼성디스플레이 주식회사 발광 소자 및 이를 포함하는 전자 장치
KR20250085474A (ko) * 2023-12-05 2025-06-12 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR20250086230A (ko) * 2023-12-06 2025-06-13 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치

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CN118724797A (zh) * 2023-03-31 2024-10-01 中南大学 一种三联吡啶锌配合物及其制备方法和应用

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