WO2014104500A1 - Composé pour dispositif optoélectronique organique, diode électroluminescente organique le comprenant, et appareil d'affichage comprenant une diode électroluminescente organique - Google Patents

Composé pour dispositif optoélectronique organique, diode électroluminescente organique le comprenant, et appareil d'affichage comprenant une diode électroluminescente organique Download PDF

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WO2014104500A1
WO2014104500A1 PCT/KR2013/005239 KR2013005239W WO2014104500A1 WO 2014104500 A1 WO2014104500 A1 WO 2014104500A1 KR 2013005239 W KR2013005239 W KR 2013005239W WO 2014104500 A1 WO2014104500 A1 WO 2014104500A1
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substituted
unsubstituted
group
formula
organic
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이한일
정성현
채미영
강의수
김윤환
김준석
류동완
유동규
이승재
장유나
조영경
허달호
홍진석
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제일모직 주식회사
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Priority to JP2015551050A priority Critical patent/JP2016505611A/ja
Publication of WO2014104500A1 publication Critical patent/WO2014104500A1/fr

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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/12—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 linked by a chain containing hetero atoms as chain links
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • a compound for an organic optoelectronic device, an organic light emitting device including the same, and a display device including the organic light emitting device is provided.
  • An organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.
  • Organic optoelectronic devices can be divided into two types according to the operation principle.
  • It is an electronic device of the form.
  • the second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which inject holes or transport materials and electrons to drive the devices. Or a transport material or a luminescent material.
  • organic light emitting diodes are attracting attention as demand for flat panel displays increases recently.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode.
  • the organic material layer is often composed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, can be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. have.
  • the material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve better natural colors according to the light emitting color.
  • the maximum emission wavelength is shifted to a long wavelength due to intermolecular interaction, and color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect, thereby increasing color purity and energy.
  • a host / dopant system may be used as a light emitting material.
  • the organic layer of the material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or dopant in the light emitting material
  • the back should be supported by a stable and efficient material, and the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials is still required. .
  • the necessity of such a material development is the same in other organic optoelectronic devices described above.
  • the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum evaporation method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode using the inkjet or spin coating method has an initial investment cost. Small and large area is advantageous.
  • Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high-definition, durability, and wide driving temperature range.
  • it is a self-luminous type, compared to conventional LCD (liquid crystal display), and has good cyanity even in the dark or outside light. It can reduce thickness and weight by 1/3 of LCD because no backlight is required.
  • the response speed is KXX) times faster than LCD, making it possible to realize a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era. Based on these advantages, it has undergone rapid technological advancement of 80 times efficiency and 100 times life span since the first development in the late 1980s. Increasingly, large-scaled developments are being made with the introduction of organic light emitting diode panels.
  • An organic light emitting device including the compound for an organic optoelectronic device and a display device including the organic light emitting device are provided.
  • a compound for an organic optoelectronic device represented by the following formula (1) is provided.
  • Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L 1 to L 3 are independently from each other, substituted or unsubstituted A substituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof
  • nl To n3 are each independently an integer of any one of 0 to 3
  • A is the following formula A-2
  • B is K-2, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group:
  • X is -0- or ⁇ S-, R and R are independently of each other, hydrogen, hydrogen, halogen, cyano group, hydroxyl group amino group, substituted or unsubstituted C1 to C20 Amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxy Carbonyl group, substituted or unsubstituted C2 to C20 acyl
  • C2 to C20 acylamino group substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocyclothiol group, substituted or unsubstituted C1 To C20 uride group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.
  • B may be A-2.
  • Ar 1 may be represented by Formula B-1.
  • R to R are independently of each other, hydrogen hydrogen, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferrocenyl Group, substituted or unsubstituted C1 to C20 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubsti
  • Ar 1 may be the following Formula B-2.
  • R to R are independently of each other, hydrogen, hydrogen, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group , Ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted Or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstit
  • R to R are independently of each other, hydrogen, hydrogen, halogen, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferro Senyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted A substituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy
  • Ar 1 may be the following Formula B-4.
  • Ar may be the following Formula B-5. [Formula B-5]
  • X is -0-, -S- or NR ', R', R and R are independently of each other, hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substitution or Unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, Substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyl oxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted Substituted C2 to C20 alkoxycarbony
  • C20 sulfamoylamino group substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiyl group, substituted or unsubstituted C1 to C20 solution
  • a tercyclocyclo group a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.
  • Ar 1 may be the following Formula B-6.
  • R and R are independently of each other, hydrogen, hydrogen, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferro Cenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted Substituted C6 to C20 Aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstit
  • Ar 1 may be a substituted or unsubstituted biphenyl group.
  • a and B may be a substituent represented by Formula A-2.
  • R 3 and R 4 may be hydrogen.
  • the compound for an organic optoelectronic device may have a molecular weight of 700 or less.
  • the compound for an organic optoelectronic device may have a molecular weight of 600 or less.
  • the organic optoelectronic device may be any one selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode
  • at least one of the organic thin film layer is the organic optoelectronic device It provides an organic light emitting device comprising a compound for.
  • the organic thin film layer may be any one selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a combination thereof.
  • the compound for an organic optoelectronic device may be included in a light emitting layer.
  • the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material in the light emitting layer.
  • a display device including the organic light emitting diode is provided.
  • the organic optoelectronic device including the compound for an organic optoelectronic device has excellent electrochemical and thermal stability, has excellent life characteristics, and may have high luminous efficiency even at a low driving voltage.
  • 1 to 5 are cross-sectional views illustrating various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • substituted means that at least one hydrogen in a substituent or compound is a deuterium, halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C30 amine group, nitro group, substituted or unsubstituted C1 to C40 silyl groups, C1 to C30 alkyl groups, C1 to C10 alkylsilyl groups, C3 to C30 cycloalkyl groups, C6 to C30 aryl groups, C1 to C20 alkoxy groups, fluoro groups, trifluoromethyl groups and the like Substituted by a C10 trifluoroalkyl group or a cyano group.
  • hetero means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S, and P in one functional group, and remaining carbon.
  • alkyl (alkyl) group 1 means, unless otherwise defined, it refers to a desired aliphatic hydrocarbon. Alkyl groups that do not contain any double bonds or triple bonds come “saturated alkyl (saturated alkyl) group” 1 Can be.
  • the alkyl group may be an alkyl group that is C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group means one to four carbon atoms in the alkyl chain, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl In a group consisting of Selected.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t'butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
  • Aryl group means a substituent in which all elements of the cyclic substituent have p-orbitals, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic ( That is, ring groups that share adjacent pairs of carbon atoms.
  • Heteroaryl group means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.
  • the hole property means a property that has conductivity in accordance with the HOMO level, thereby facilitating injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer. More specifically, it may be similar to the property of repelling electrons.
  • the electronic characteristic means a characteristic that has conductivity characteristics along the LUM0 level, thereby facilitating injection and movement of the electrons formed in the cathode into the light emitting layer. More specifically, it may be similar to the property of attracting electrons.
  • a compound for an organic optoelectronic device represented by Formula 1 may be provided.
  • Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L 1 to L 3 are independently from each other, substituted or unsubstituted A substituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, nl To n3 .
  • A is the following formula A-2
  • B is the following formula A-2, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 Heteroaryl group.
  • X is -0- or -S-, R to R are independently of each other, hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 Alkoxy carbonyl group, substituted or unsubstituted C2 to C
  • the compound represented by Chemical Formula 1 may have an amine group including a substituent including an indeno structure as a core structure.
  • the substituent having the hole property in the structure of Ar 1 may be combined with the amine group core to have a structure that can easily flow electrons or holes.
  • the substituent of the indeno structure is a structure having a non-covalent pair of electrons to improve the flow of electrons or holes, small molecular weight is suitable as a deposition material. In general, in the case of the deposition material, if the molecular weight exceeds 1000 may cause thermal stability problems.
  • the structure to be substituted in Ar 1 is characterized by having abundant electrons (rich in the bond, electron donor group)
  • the substituent of the indeno structure between the amines is a good structure for drawing electrons of Ar 1 (withdraw group) to prevent electron polarization in the compound, resulting in high efficiency and long life of the device.
  • the compound for an organic optoelectronic device represented by Formula 1 may be a compound having a variety of energy band gap by introducing a variety of further substituents to the substituents substituted in the core portion and the core portion.
  • the hole transfer ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in electrochemical and thermal stability It can improve the life characteristics when driving the optoelectronic device.
  • 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, substituted or unsubstituted naph Tyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted P-terpenyl group, substituted or unsubstituted m—terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted peryleny
  • the L 1 to L 3 by selectively adjusting the conjugate of the entire compound
  • the conjugation length can be determined, from which the triplet energy bandgap can be adjusted. Through this, it is possible to realize the characteristics of the material required in the organic optoelectronic device.
  • the tridental energy band gap can be controlled by changing the binding positions of olso, para, and meta.
  • L 1 to L 3 are a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted Anthracenylene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted p—terphenyl group, substituted or unsubstituted m-ter Phenyl group, substituted or unsubstituted perenyl group, and the like.
  • L 1 to L 3 may be, independently of each other, a phenylene group.
  • L 1 to L 3 is a phenylene group
  • both core parts may be bonded to ortho, meta or para based on the phenylene group.
  • Formula B may be represented by Formula A-2.
  • Formula (A-2) has a non-shared electron pair can improve the flow of electrons or holes is advantageous to make a high efficiency device.
  • the molecular weight is smaller than that of dibenzofuran or dibenzothiophene generally used, and may be advantageous as a deposition material.
  • the substituents (withdraw group) of Formula A-2 may be evenly distributed throughout the compound, thereby making a device having high efficiency / long lifespan. More specifically, when the compound for an organic optoelectronic device includes two indeno structures, the electrons may be evenly distributed.
  • Ar 1 may be the following Formula B-1.
  • R to R are independently of each other, hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, ni. Tro, carboxyl, ferrocenyl, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C1 to C20 Alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted Or unsubstituted C2 to C20 acyloxy group, substituted or unsub
  • the carbon bond (C) is formed without a double bond, and thus the pi bond is broken. For this reason, it becomes easy to form a hole, and can harmonize with the substituent of the indeno structure centered on amine (N).
  • the substituents that can form holes well and the substituents that form electrons must go well together, and the fluorene group is a substituent that can form holes well.
  • the fluorene group is a substituent that can form holes well.
  • Ar 1 may be the following Formula B-2.
  • R to R are independently of each other, hydrogen, hydrogen, halogen, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferro Senyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted A substituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 To C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted
  • the substituent represented by Formula B-2 may be combined with the amine nitrogen, which is a core, to a position that can be easily synthesized.
  • Ar 1 may be the following Formula B-3.
  • R to R are independently of each other, hydrogen, deuterium, halogen, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl Groups, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C1 to C20 alkoxy groups, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 Acyloxy group, substituted or unsub
  • a phenanthrene group such as Chemical Formula B-3
  • a lower HOMO level may be achieved.
  • the phenanthrene (B-2) group is known to have a structure in which three phenyl groups are broken to easily form holes.
  • the thermal stability (the phenyl group all have a resonance structure) is superior to the fluorene (B-1) group.
  • Ar 1 may be the following Formula B-4.
  • a lower HOMO level when a lower HOMO level is required than the phenanthrene (Formula B-2) group, it may be controlled by introducing a triphenylene (Formula B-3) group.
  • the triphenylene group may be enriched with three phenyl groups to provide a rich electron group, and when combined with a structure capable of attracting electrons (withdraw group, for example, an indeno substituent), it is easy to form a hole allol. It may be one structure. In addition, it has excellent thermal stability (all phenyl groups have resonance structures) compared to fluorene groups.
  • Ar 1 may be represented by the following Formula B-5.
  • X is 0-, -S- or NR ', R', R and R are independently of each other, hydrogen, hydrogen, halogen, cyano group, hydroxyl group, amino group, substitution Or an unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group , Substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyl oxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or Unsubstituted C2 to C20
  • Ar 1 may be the following Formula B-6.
  • R and R are independently of each other, hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl Groups, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C1 to C20 alkoxy groups, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 Acyloxy group, substituted or un
  • carbazole groups such as Chemical Formula B-6
  • the pi bond is broken around the amine (N) to form holes.
  • the carbazole group such as Formula B-6 has a very high hole transport ability compared to the electron transport ability, so when applied to the device, a high-efficiency low voltage device is used when used as a host having a hole transport layer, an auxiliary layer of the hole transport layer, or a hole characteristic.
  • Ar 1 may be a substituted or unsubstituted biphenyl group. More specifically, for example, Arl may be represented by Chemical Formula B-7 or B-8.
  • B-7 and / or B-8 substituents provide excellent thermal and electrical stability, making them suitable for high lifetime devices.
  • a and B may be represented by Chemical Formula A-2. That is, when the substituent represented by the formula (A-2) is present at the same time the core amine group, the driving voltage of the device can be lowered and the efficiency can be increased due to the presence of the formula (A-2) excellent in hole or electron transport.
  • the chemical formula A-2 has excellent thermal and electrical stability due to its simple molecular structure.
  • R 3 and R 4 may be hydrogen, but are not limited thereto.
  • the compound for an organic optoelectronic device may have a molecular weight of 700 or less. More specifically, it may have a molecular weight of 600 or less. In this case, since the deposition is possible at low temperatures during device manufacturing, the deposition is easy, and the thermal stability may increase. From this, the stability of the device can be improved.
  • the compound for an organic optoelectronic device is used in an organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
  • the organic thin film layer may be a light emitting layer.
  • the organic optoelectronic device may be an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photosensitive drum, or an organic memory device.
  • the organic optoelectronic device may be an organic light emitting device.
  • 1 to 5 are cross-sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the organic light emitting diodes 100, 200, 300, 400, and 500 according to the embodiment of the present invention are interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.
  • the anode 120 includes an anode material, which is typically an organic thin film layer.
  • anode material may include metals such as nickel, platinum, vanadium, chromium, copper zinc, and gold or alloys thereof, and include zinc oxide, phosphate oxide, tin oxide (ITO), and indium zinc oxide (IZ0).
  • Metal oxides such as ⁇ and A1 or combinations of metals and oxides such as Sn0 2 and Sb; poly (3-methylthiophene), poly (3,4- (ethylene-1, 1,2 Conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole, and polyaniline, and the like, but are not limited thereto. More specifically, a transparent electrode including indium tin oxide (IT0) may be used as the anode.
  • I0 indium tin oxide
  • the negative electrode 110 includes a negative electrode material, and the negative electrode material is generally a material having a small work function to facilitate electron injection into an organic thin film insect.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Multi-layered materials such as Al, Li0 2 / AI, LiF / Ca, LiF / Al, and BafVCa, and the like, but are not limited thereto. More specifically, a metal electrode such as aluminum may be used as the cathode.
  • FIG. 1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105.
  • the organic thin film layer 105 may exist only as a light emitting layer 130.
  • FIG. 2 illustrates a two-layered organic light emitting diode 200 including a light emitting layer 230 including an electron transport layer and a hole transport layer 140 as the organic thin film layer 105.
  • the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140.
  • the light emitting layer 130 functions as an electron transporting layer
  • the hole transporting layer 140 functions to improve adhesion and hole transportability with a transparent electrode such as ITO.
  • FIG. 3 is a three-layer organic light emitting device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, which is the organic thin film layer 105. ),
  • the light emitting layer 130 is in an independent form, and the film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties and hole transport properties is stacked in separate layers.
  • Figure 4 is an organic thin film layer 105 as an "electron injection layer 160, emitting layer 130, hole transport layer 140 and the hole injection layer of organic light emitting devices (400, 4-layer type to 170 is present )
  • the hole injection layer 170 may improve the adhesion to ⁇ 0 used as the anode.
  • FIG. 5 shows different organic thin film layers 105, such as an electron injection layer 160, an electron transport layer 150, an emission layer 130, a hole transport layer 140, and a hole injection layer 170.
  • a five-layered organic light emitting device 500 having five layers serving as a function is shown, and the organic light emitting device 500 is effective in lowering voltage by separately forming an electron injection layer 160. 1 to 5, the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, the hole injection layer 170, and the like forming the organic thin film layer 105 are described. Any one selected from the group consisting of a combination includes the organic optoelectronic device material.
  • the compound for an organic optoelectronic device may be used in the light emitting layers 130 and 230, and may be used as a green phosphorescent material in the light emitting layer.
  • the compound for an organic optoelectronic device may be used in the hole transport layer.
  • a plurality of hole transport layers may be present, and when the hole transport layer adjacent to the light emitting layer is viewed as an auxiliary layer, the compound for an organic optoelectronic device may be present in the auxiliary layer.
  • the organic light emitting device described above may include a dry film method such as an evaporation, sputtering, full-laser plating and ion plating after forming an anode on a substrate;
  • the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
  • a display device including the organic optoelectronic device is provided.
  • 1-3 In a nitrogen environment, 1-3 (30 g, 95.1 mmol) was dissolved in 0.3 L of dmtetrahydrofuran (THF), and 0.3 L of methanol was added and cooled to 0 ° C. After adding sodium brohydr ide (36.0 g, 951 ⁇ ol), tin (II) chloride (90.2 g, 475.5 ⁇ ol) was added thereto and reacted at room temperature for 2 hours. After completion of reaction, water was added to the reaction solution, extracted with ethylacetate (EA), water was removed with anhydrous MgS0 4 , filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining 1-4 (14.9 g, 55%).
  • EA ethylacetate
  • cabazole 50 g, 299.0 ⁇ ol
  • l_bromo_4—nitrobenzene 60.4 g, 299.0 ⁇ ol
  • tris di henyl ideneacet one
  • di al ladium (o) 8.24 g , 8.97 mmol
  • tris ⁇ tert Butylphosphine 7.26 g, 35.9 ⁇ ol
  • sodium tert-butoxide 34.5 g, 358.8 ⁇ ol
  • N- (biphenyl— 4 ⁇ yl) -9,9 ⁇ dimethyl-9H-fluoren-2-atnine (l () g, 27.7 ⁇ ol) was dissolved in 0.1 L of toluene, followed by intermediate 1-1.
  • biphenyl-4—amine (10 g, 59.1 ⁇ l ol) was dissolved in 0.16 L of toluene, followed by Intermediate I ⁇ 2 (31.8 g, 130.0 ⁇ l ol), tr is (diphenyl ideneacetone) dipal ladium (o) (1.62 g, 1.77 ramol), tris-tert butylphosphine (1.43 g, 7.09 mmol) and sodium tert-butoxide (12.5 g, 130.0 ⁇ ol) were dissolved sequentially 100 ° C Heated to reflux for 14 h.
  • a glass substrate coated with a thin film having an indium tinoxide (IT0) of 1500 A was washed with distilled water ultrasonically. After the distilled water was washed, isopropyl alcohol, acetone, and methane were ultrasonically cleaned with a round solvent, dried, transferred to a plasma cleaner, and then cleaned with 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator. .
  • IT0 indium tinoxide
  • 9,10-di- (2-naphthyl) anthracene is used as a host on the hole transport layer and 2,5,8, ll-tetra (tert-butyl) perylene (TBPe) is 3% by weight.
  • TBPe 2,5,8, ll-tetra (tert-butyl) perylene
  • Alq 3 was vacuum deposited on the emission layer to form an electron transport layer having a thickness of 250 A.
  • the electron The organic light emitting device was manufactured by sequentially depositing LiF 10 A and Al 1000 A on the transport layer to form a cathode.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 2 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 3 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 4 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 5 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 6 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 7 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 8 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 9 instead of Example 1
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using Example 10 instead of Example 1.
  • Comparative Example 1 An organic light emitting diode was manufactured according to the same method as Example 11 except for using NPB instead of Example 1. The structure of the NPB is described below.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using HT1 instead of Example 1.
  • the structure of ⁇ is described below.
  • An organic light emitting diode was manufactured according to the same method as Example 11 except for using HT2 instead of Example 1.
  • the structure of the HT2 is described below.
  • the structure of DNTPD, AND, TBPe, NPB, HT1, and HT2 used in the organic light emitting device is as follows.
  • 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 luminance at that time was measured using (Minolta Cs-1000A) to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm2) was calculated using the brightness, current density, and voltage measured from (1) and (2).
  • organic light emitting element 110 cathode
  • hole injection layer 230 light emitting layer + electron transport layer

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Abstract

L'invention concerne un composé pour un dispositif optoélectronique organique, une diode électroluminescente organique le comprenant, et un appareil d'affichage comprenant la diode électroluminescente organique, lequel composé pour le dispositif optoélectronique organique est représenté par la formule chimique 1.
PCT/KR2013/005239 2012-12-31 2013-06-13 Composé pour dispositif optoélectronique organique, diode électroluminescente organique le comprenant, et appareil d'affichage comprenant une diode électroluminescente organique WO2014104500A1 (fr)

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CN112409326A (zh) * 2020-11-24 2021-02-26 吉林奥来德光电材料股份有限公司 一种芳胺类化合物及其制备方法和应用
CN112745264A (zh) * 2019-10-31 2021-05-04 东进世美肯株式会社 新型覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
WO2021093377A1 (fr) * 2019-11-12 2021-05-20 广州华睿光电材料有限公司 Dispositif électroluminescent organique contenant un matériau de couche d'extraction de lumière
WO2022100634A1 (fr) * 2020-11-12 2022-05-19 烟台海森大数据有限公司 Dispositif électroluminescent organique et appareil d'affichage le comprenant
CN116143735A (zh) * 2021-11-22 2023-05-23 奥来德(上海)光电材料科技有限公司 一种有机电致发光化合物及其制备方法和发光显示面板
KR20230156057A (ko) 2021-03-12 2023-11-13 호도가야 가가쿠 고교 가부시키가이샤 유기 일렉트로루미네센스 소자, 및 그 전자 기기

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KR101493482B1 (ko) * 2014-08-29 2015-02-16 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102475855B1 (ko) * 2019-02-15 2022-12-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102579367B1 (ko) * 2019-02-15 2023-09-14 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

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CN112745264A (zh) * 2019-10-31 2021-05-04 东进世美肯株式会社 新型覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
WO2021093377A1 (fr) * 2019-11-12 2021-05-20 广州华睿光电材料有限公司 Dispositif électroluminescent organique contenant un matériau de couche d'extraction de lumière
WO2022100634A1 (fr) * 2020-11-12 2022-05-19 烟台海森大数据有限公司 Dispositif électroluminescent organique et appareil d'affichage le comprenant
CN112409326A (zh) * 2020-11-24 2021-02-26 吉林奥来德光电材料股份有限公司 一种芳胺类化合物及其制备方法和应用
KR20230156057A (ko) 2021-03-12 2023-11-13 호도가야 가가쿠 고교 가부시키가이샤 유기 일렉트로루미네센스 소자, 및 그 전자 기기
CN116143735A (zh) * 2021-11-22 2023-05-23 奥来德(上海)光电材料科技有限公司 一种有机电致发光化合物及其制备方法和发光显示面板

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