WO2020122460A1 - Composition pour diode optoélectronique organique, diode optoélectronique organique et dispositif d'affichage - Google Patents

Composition pour diode optoélectronique organique, diode optoélectronique organique et dispositif d'affichage Download PDF

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WO2020122460A1
WO2020122460A1 PCT/KR2019/016165 KR2019016165W WO2020122460A1 WO 2020122460 A1 WO2020122460 A1 WO 2020122460A1 KR 2019016165 W KR2019016165 W KR 2019016165W WO 2020122460 A1 WO2020122460 A1 WO 2020122460A1
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substituted
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organic optoelectronic
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Korean (ko)
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강동민
이병관
김준석
이남헌
이상신
김동영
류진현
유은선
이윤만
정호국
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Samsung SDI Co Ltd
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Samsung SDI Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—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
    • 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
    • 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

Definitions

  • It relates to a compound for an organic optoelectronic device, an organic optoelectronic device and a display device.
  • Organic optoelectronic devices is a device that can switch between electrical energy and light energy.
  • Organic optoelectronic devices can be roughly divided into two types according to the operating principle.
  • One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes and electrons and holes are transferred to different electrodes, and the other is an electrical energy by supplying voltage or current to the electrodes.
  • It is a light emitting element that generates light energy from.
  • Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photoconductor drum.
  • organic light emitting diodes have attracted much attention in recent years due to an increase in demand for flat panel display devices.
  • the organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by organic materials positioned between electrodes.
  • One embodiment provides a compound for an organic optoelectronic device capable of realizing a high efficiency and long life organic optoelectronic devices.
  • Another embodiment provides an organic optoelectronic device comprising the compound.
  • Another embodiment provides a display device including the organic optoelectronic device.
  • a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.
  • X is O or S
  • Ar is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
  • Z 1 to Z 3 are each independently N or CR a ,
  • At least two of Z 1 to Z 3 are N,
  • R a and R 1 to R 6 are each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 To C30 heterocyclic group.
  • an organic optoelectronic device including an anode and a cathode facing each other, at least one organic layer positioned between the anode and the cathode, and the organic layer comprising the compound for an organic optoelectronic device described above .
  • a display device including the organic optoelectronic device is provided.
  • FIG 1 and 2 are cross-sectional views each showing an organic light emitting device according to an embodiment.
  • At least one hydrogen in a substituent or compound is deuterium, halogen group, hydroxyl group, amino group, substituted or unsubstituted C1 to C30 amine group, nitro group, substituted or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted with a heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.
  • substitution means that at least one hydrogen in the substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, and a C2 to C30 heteroaryl group.
  • substitution means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.
  • substitution means that at least one hydrogen in the substituent or compound is deuterium, C1 to C5 alkyl group, C6 to C18 aryl group, dibenzofuranyl group, dibenzothiophenyl group or carbazole group Means substituted with.
  • substitution means that at least one hydrogen in a substituent or compound is substituted with a C6 to C18 aryl group.
  • substitution means that at least one hydrogen in the substituent or compound is substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, or triphenylene group. do.
  • hetero means one to three heteroatoms selected from the group consisting of N, O, S, P, and Si in one functional group, and the rest being carbon. .
  • aryl (aryl) group is a concept that collectively refers to a group having one or more hydrocarbon aromatic moieties, while all elements of the hydrocarbon aromatic moiety have p-orbitals, these p-orbitals are conjugated. It forms a form, such as a phenyl group, a naphthyl group, etc., and two or more hydrocarbon aromatic moieties are connected via a sigma bond, such as biphenyl group, terphenyl group, quarterphenyl group, etc., and two or more hydrocarbon aromatic moieties These may include non-aromatic fused rings fused directly or indirectly, such as a fluorenyl group and the like.
  • Aryl groups include monocyclic, polycyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
  • heterocyclic group is a higher concept including a heteroaryl group, N, O, instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring or a combination thereof, It means to contain at least one hetero atom selected from the group consisting of S, P and Si.
  • the heterocyclic group is a fused ring, the heterocyclic group may include one or more hetero atoms for all or each ring.
  • heteroaryl (heteroaryl) group means that the aryl group contains at least one hetero atom selected from the group consisting of N, O, S, P and Si. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other. 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 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a 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 unsubstituted o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perenyl group, substituted or unsubstit
  • a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted Or an unsubstituted imidazolyl group, a substituted or unsubstituted triazole group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted Thiadiazole group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group,
  • the hole characteristic refers to a property that can form a hole by donating electrons when an electric field is applied, and has conductivity characteristics along the HOMO level, and injection of the hole formed at the anode into the light emitting layer, the light emitting layer It means a property that facilitates the movement of the holes formed in the anode to the anode and the light emitting layer.
  • the electronic property refers to a property that can receive electrons when an electric field is applied, and has conductivity characteristics along the LUMO level, injecting electrons formed from the cathode into the light emitting layer, moving electrons formed from the light emitting layer to the cathode, and in the light emitting layer. It means a property that facilitates movement.
  • X is O or S
  • Ar is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
  • Z 1 to Z 3 are each independently N or CR a ,
  • At least two of Z 1 to Z 3 are N,
  • R a and R 1 to R 6 are each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 To C30 heterocyclic group.
  • the compound represented by Chemical Formula 1 is connected to a para-phenylene unsubstituted naphthyl group centered on a pyrimidine or triazine core, and dibenzofuran (or dibenzothiophene) is directly substituted on the core without a linking group. It is a structure.
  • an appropriate LUMO energy and a T1 energy level suitable for a red host can be developed to develop a red host exhibiting long life/low voltage driving characteristics.
  • the dibenzofuran (or dibenzothiophene) is directly substituted in the core without a linking group, it has a fast electron transfer property, and the low drive property can be further improved.
  • the Chemical Formula 1 may be represented by one of the following Chemical Formulas 1-1 to 1-4.
  • Formula 1 may be represented by Formula 1-1 or Formula 1-3.
  • Ar may be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, for example, Ar may be a substituted or unsubstituted C6 to C18 aryl group or a C2 to C12 heterocycle.
  • Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
  • Ar may be an unsubstituted phenyl group, an unsubstituted biphenyl group, a dibenzofuranyl group unsubstituted or substituted with a phenyl group, or a dibenzothiophenyl group unsubstituted or substituted with a phenyl group.
  • Ar may be one selected from the substituents listed in Group I below.
  • Z 1 to Z 3 may each be N.
  • R 1 to R 6 may each independently be hydrogen or a C6 to C18 aryl group, for example, R 1 to R 6 may each independently be hydrogen or a C6 to C12 aryl group.
  • each of R 1 to R 3 may be independently hydrogen or a phenyl group, for example, R 1 and R 2 may be hydrogen and R 3 may be a phenyl group, for example, any one of R 1 and R 2 is a phenyl group and R 3 may be hydrogen.
  • R 4 to R 6 may be each independently hydrogen.
  • R 1 to R 3 are each independently hydrogen, or any one of R 1 to R 3 is a phenyl group and the rest is hydrogen, and R 4 to R 6 may be each independently hydrogen.
  • Z 1 to Z 3 may each be N.
  • the compound for an organic optoelectronic device may be any one of the compounds listed in Group 1 below.
  • the organic optoelectronic device is not particularly limited as long as it is a device capable of mutually converting electrical energy and light energy, and examples thereof include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photoconductor drums.
  • FIG 1 and 2 are cross-sectional views showing an organic light emitting diode according to an embodiment.
  • the organic light emitting diode 100 includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110. Includes.
  • the anode 120 may be made of a conductor having a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide, and/or a conductive polymer.
  • the anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Metal and oxide combinations such as ZnO and Al or SnO 2 and Sb; Conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, but are not limited thereto. It is not.
  • the cathode 110 may be made of, for example, a conductor having a low work function to facilitate electron injection, for example, a metal, a metal oxide, and/or a conductive polymer.
  • the negative electrode 110 may include, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Multilayer structure materials such as LiF/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca may be mentioned, but are not limited thereto.
  • the organic layer 105 includes the compound for an organic optoelectronic device described above.
  • the organic layer 105 may include a light emitting layer 130, and the light emitting layer 130 may include, for example, a compound for an organic optoelectronic device.
  • the light-emitting layer 130 may include, for example, a compound for an organic optoelectronic device described above as a phosphorescent host.
  • the light emitting layer 130 may include a composition further comprising one or more compounds.
  • the dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red phosphorescent dopant.
  • the maximum emission wavelength of the red phosphorescent dopant may be 550 nm to 750 nm.
  • phosphorescent dopants include organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof.
  • the phosphorescent dopant may be, for example, a compound represented by the following Chemical Formula Z, but is not limited thereto.
  • M is a metal
  • L and X a are the same or different from each other and are ligands forming a complex with M.
  • the M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, and L and X a are, for example, Weiden It may be a tate ligand.
  • the M may be Ir or Pt.
  • the dopant is a material that causes a small amount of light mixed with a compound for an organic optoelectronic device in the light-emitting layer 130, and a metal complex that emits light by multiple excitations, which excite more than a triplet state.
  • the same material can be used.
  • the dopant may be, for example, an inorganic, organic or organic compound, and may be included in one or two or more.
  • a compound having hole characteristics may be further included as a second host.
  • the above-described organic optoelectronic device compound and the second host having hole characteristics may be included in a weight ratio of 1:99 to 99:1, respectively.
  • Examples of the second host having hole characteristics include a compound containing a carbazole moiety, a compound containing a benzocarbazole moiety, and the like.
  • a compound containing a carbazole moiety for example, an indolocarbazole or a compound in which an amine is substituted for carbazole may be used, but is not limited thereto.
  • a compound containing the benzocarbazole moiety for example, a compound in which amine is substituted for benzoindolocarbazole or benzocarbazole may be used, but is not limited thereto.
  • the organic light emitting device 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130.
  • the hole auxiliary layer 140 may further increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
  • the hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and/or an electron blocking layer, and may include at least one layer.
  • the hole auxiliary layer 140 may include, for example, at least one of compounds listed in Group E below.
  • the hole auxiliary layer 140 may include a hole transport layer between the anode 120 and the light emitting layer 130, and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and in Group E below At least one of the listed compounds may be included in the hole transport auxiliary layer.
  • the organic light emitting device may further include an electron transport layer, an electron injection layer, a hole injection layer, etc. as the organic layer 105 in FIG. 1 or 2.
  • the organic light emitting devices 100 and 200 After forming an anode or a cathode on the substrate, the organic light emitting devices 100 and 200 form an organic layer by a vacuum deposition method such as evaporation, sputtering, plasma plating, and ion-plating to form an organic layer. It can be produced by forming a cathode or an anode.
  • a vacuum deposition method such as evaporation, sputtering, plasma plating, and ion-plating to form an organic layer. It can be produced by forming a cathode or an anode.
  • the above-described organic light emitting device can be applied to an organic light emitting display device.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone or methanol, dried and then transferred to a plasma scrubber, and then the substrate was cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum evaporator.
  • an organic light emitting device is formed by vacuum-depositing Compound D and Liq on the light emitting layer at a 1:1 ratio simultaneously to form an electron transport layer having a thickness of 300 ⁇ , and sequentially vacuum depositing Liq 15 ⁇ and Al 1200 ⁇ on the electron transport layer to form a cathode.
  • a cathode was produced.
  • the organic light emitting device has a structure having five layers of organic thin films, and is specifically as follows.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except for using any one of Compound 3, Compound 9, Compound 11, Compound 25, and Compound 37 of Synthesis Examples 2 to 6 instead of Compound 1 of Synthesis Example 1 Did.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that any one of Compounds Y-1 to Y-8 of Comparative Synthesis Examples 1 to 8 was used instead of Compound 1 of Synthesis Example 1.
  • the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400), and the measured current value was divided by area to obtain a result.
  • the luminance at that time was measured using a luminance meter (Minolta Cs-1000A) to obtain a result.
  • the result was obtained by maintaining the luminance (cd/m2) at 6000 cd/m2 and measuring the time at which the current efficiency (cd/A) decreased to 90%.
  • the driving voltage of each device was measured at 15 mA/cm 2 using a current-voltmeter (Keithley 2400) to obtain results.
  • the organic light emitting device according to Examples 1 to 6 has significantly improved driving voltage, efficiency, and lifetime compared to the organic light emitting device according to Comparative Examples 1 to 8.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
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  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un composé pour une diode optoélectronique organique représenté par la formule chimique 1; une diode optoélectronique organique et un dispositif d'affichage comprenant le composé. Les détails de la formule chimique 1 sont tels que définis dans la spécification.
PCT/KR2019/016165 2018-12-12 2019-11-22 Composition pour diode optoélectronique organique, diode optoélectronique organique et dispositif d'affichage Ceased WO2020122460A1 (fr)

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KR1020180160135A KR20200072211A (ko) 2018-12-12 2018-12-12 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
KR10-2018-0160135 2018-12-12

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JP7679586B2 (ja) * 2021-02-24 2025-05-20 エルジー・ケム・リミテッド 有機発光素子
KR102830323B1 (ko) * 2021-05-12 2025-07-07 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
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CN116162083A (zh) * 2021-11-20 2023-05-26 北京夏禾科技有限公司 一种具有氰基取代的杂环化合物
CN116162083B (zh) * 2021-11-20 2026-04-21 北京夏禾科技股份有限公司 一种具有氰基取代的杂环化合物
CN117143030A (zh) * 2022-05-20 2023-12-01 烟台显华科技集团股份有限公司 萘基取代吸电片段化合物、电子传输材料及应用

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