WO2014051244A1 - Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le comprenant et dispositif d'affichage comprenant ledit dispositif électroluminescent organique - Google Patents

Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le comprenant et dispositif d'affichage comprenant ledit dispositif électroluminescent organique Download PDF

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WO2014051244A1
WO2014051244A1 PCT/KR2013/005237 KR2013005237W WO2014051244A1 WO 2014051244 A1 WO2014051244 A1 WO 2014051244A1 KR 2013005237 W KR2013005237 W KR 2013005237W WO 2014051244 A1 WO2014051244 A1 WO 2014051244A1
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substituted
unsubstituted
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formula
organic
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유동규
류동완
정성현
채미영
허달호
홍진석
김준석
이한일
장유나
조영경
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제일모직 주식회사
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/17—Carrier injection layers
    • 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
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Definitions

  • the present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having excellent lifetime, efficiency, electrochemical stability, and thermal stability, an organic light emitting device including the same, and a display device including the organic light emitting device.
  • the organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.
  • the organic optoelectronic device can be divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.
  • the second type is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with electrodes by applying voltage or current to at least two electrodes, and operated by the injected electrons and holes.
  • organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, organic photo conductor drums, and organic transistors, all of which are used to inject or transport holes to drive the device. It requires an electron injection or transport material, or a luminescent material.
  • organic light emitting diodes are attracting attention as the demand for flat panel displays increases.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device converts electrical energy into light by applying an electric current to the 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 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 light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc., depending on their function. have.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
  • a host / dopant system may be used as a light emitting material.
  • a material forming an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting material deposition host, and / or
  • the dopant should be supported by a stable and efficient material, and the development of stable and efficient organic light emitting material for organic light emitting device has not been completed yet. Therefore, the development of new materials is required. It is becoming. The necessity of such a material development is the same in other organic optoelectronic devices described above.
  • low molecular weight organic light emitting diodes are manufactured in the form of thin films by vacuum evaporation, so that the yield and lifespan are good.
  • High molecular weight organic light emitting diodes use inkjet or spin coating methods. Therefore, the initial investment cost is small and large area is advantageous.
  • the low molecular weight organic light emitting diodes and the 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 range.
  • conventional liquid crystal display (LCD) Compared with the self-luminous type, it has good cyanity even in the dark or outside light, and it can reduce thickness and weight by 1/3 of LCD because it does not need backlight.
  • the luminous efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting.
  • the electron mobility of the organic material is generally slower than the hole mobility, in order to effectively combine the holes and the electrons in the light emitting layer, the electron transport and the mobility from the cathode can be controlled using an efficient electron transport layer. At the same time, it must be able to block the movement of holes.
  • a compound for an organic optoelectronic device which can play a role of hole injection and transport, or electron ' injection and transport, and can act as a light emitting host with an appropriate dopant.
  • An organic light emitting diode having excellent lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability and a display device including the same are provided.
  • a compound for an organic optoelectronic device represented by a combination of the following Chemical Formulas 1 and 2 is provided.
  • Formula 1 may be represented by the following formula (3). ⁇ 26>
  • R ', R ", R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferrocenyl , 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 Acyl oxy group, substituted or unsubsti
  • Formula 2 may be represented by the following formula (4). ⁇ 30> [Formula 4]
  • L is a single bond, a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, substituted or Unsubstituted C2 to C30 heteroarylene group or a combination thereof, n is an integer of 0 to 3, and Ar 1 and Ar 2 are each independently substituted or unsubstituted C6 to C30 aryl group or substituted or It is an unsubstituted C2 to C30 heteroaryl group, any one of a * increase of Formula 1 is connected to b * of Formula 4 by a sigma bond.
  • Formula 1 may be represented by the following formula (5).
  • R ', R ", R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferrocenyl , 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 Acyl oxy, substituted or unsubstit
  • Formula 1 may be represented by the following formula (6).
  • R ', R ", R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferrocenyl , 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 Acyl oxy, substituted or unsubstit
  • Formula 1 may be represented by the following formula (7).
  • R ', R 11 , R 1 and R 2 are each independently 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 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 Acyl
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphtha Senyl group, substituted or unsubstituted pyrenyl group, substituted or Unsubstituted biphenylyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted Substituted perylyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted
  • L is 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, a substituted or unsubstituted Substituted phenanthryl groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted fluorenylene groups, substituted or unsubstituted naphthacenyl groups, substituted or unsubstituted chrysenyl groups, substituted or unsubstituted triphenyles Nyl group, substituted or unsubstituted peryleneyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted
  • At least one of Ar 1 and Ar 2 may be a substituted or unsubstituted biphenyl group.
  • At least one of Ar 1 and Ar 2 may be a substituted or unsubstituted fluorenyl group.
  • L may be a substituted or unsubstituted phenylene group.
  • At least one of the R ', R ", R 1 and R 2 increase is substituted or unsubstituted C3 to
  • At least one of R ′, R ′′, R 1, and R 2 is a substituted C3 to C40 silyl group, and at least one of hydrogen of the substituted silver silyl group is C1 to C10 alkyl group or C6 To C15 aryl group.
  • the compound for an organic optoelectronic device may have a triplet excitation energy ( ⁇ ) of 2.0 eV or more.
  • the organic optoelectronic device may be 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 including 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 It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to an embodiment of the present invention described above.
  • the organic thin film layer may be 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 hole transport layer or a hole injection layer.
  • the compound for an organic optoelectronic device may be included in a light emitting layer.
  • a display device including the organic light emitting device according to the embodiment of the present invention described above may be provided.
  • Such a compound may be used as a hole injection / transport material, a host material, or an electron injection / transport material for the light emitting layer.
  • the organic optoelectronic device using the same has excellent electrochemical and thermal stability, and thus has excellent life characteristics and high luminous efficiency even at a low driving voltage.
  • FIG. 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 'C1 to C30 amine group, nitro group wherein at least one hydrogen of a substituent or compound compound is deuterium, halogen, hydroxy group, amino group, substituted or unsubstituted , Substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, trifluoro Mean substituted by a C1 to C10 trifluoroalkyl group or a cyano group such as a methyl group.
  • Two adjacent substituents of C1 to C10 triple fluoroalkyl group or cyano group, such as C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluturo group and trifluoromethyl group, are fused to form a ring You may. -
  • hetero 1 means N, within one functional group, unless otherwise defined.
  • alkyl group refers to an aliphatic hydrocarbon group, which refers to “saturated alkyl” which does not contain any divalent or trivalent bonds. Group ".
  • the alkyl group may be branched, straight chain or cyclic.
  • Alkenyl group means a functional group consisting of at least two carbon atoms with at least one carbon-carbon double bond
  • an "alkynyl group” means at least one carbon atom with at least one It means a functional group consisting of a carbon-carbon triple bond.
  • the alkyl group may be an alkyl group having from 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 has 1 to 4 carbon atoms in the alkyl chain, that is, the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec ⁇ butyl and t It is selected from the group consisting of butyl.
  • the alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a nuclear group, an ethenyl group, a propenyl group, a butenyl group, or a cyclopropyl group.
  • a group, a cyclobutyl group, a cyclopentyl group, a cyclonuclear group, etc. mean.
  • Aryl groups include monocyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
  • Heteroaryl group ' 1 means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, 0, S, and P, and the rest are carbons. When the heteroaryl group is a fused ring, each ring may contain 1 to 1 hetero atom.
  • the carbazole derivative refers to a structure in which a nitrogen atom of a substituted or unsubstituted carbazolyl group is substituted with a hetero atom or carbon instead of nitrogen.
  • Specific examples thereof include dibenzofuran (dibenzofuranyl group), dibenzothiophene (dibenzothiophenyl group), fluorene (fluorenyl group) and the like.
  • the hetero atom may include -0-, -S-, -S (0)-, -S (0) 2-, or -NR'-.
  • the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate the injection and movement of the holes formed at the anode into the light emitting layer.
  • the electronic characteristic means a characteristic that has conductivity characteristics along the LUM0 level, thereby facilitating injection of electrons formed at the cathode into the light emitting insect and movement in the light emitting layer. All.
  • the compound for an organic optoelectronic device may have a structure selectively including various substituents on a fused ring core.
  • the core structure may be used as a light emitting material, a hole injection material or a hole transport material of an organic optoelectronic device. It may be particularly suitable for hole injection materials or hole transport materials.
  • the compound for an organic optoelectronic device is a core portion and the value substituted in the core portion
  • the hole-transfer capacity or the electron-transfer capacity is enhanced to have an excellent effect in terms of efficiency and driving voltage.
  • Excellent stability can improve life characteristics when driving organic optoelectronic devices.
  • the compound for an organic optoelectronic device may be represented by a combination of the following Chemical Formulas (1) and (2).
  • the mobility is a distance that charged particles move in a unit time in an electric field of unit intensity and may indicate a degree of ease of movement by the electric field.
  • the device using such a material can be improved in efficiency.
  • the brightness of the panel can be increased at the same driving (voltage), and the heat received by the device and the panel is reduced, thereby improving the life characteristics of the device itself.
  • Chemical Formula 1 may be represented by Chemical Formula 3 below.
  • the compound for an organic optoelectronic device may be improved.
  • the compound may have a significantly low HOMO value, thereby increasing the band value of the entire compound. From this, the compound for an organic optoelectronic device can be applied to various devices.
  • Chemical Formula 1 may be represented by the following Chemical Formula 5.
  • R ', R ", R 1 and R 2 are each independently hydrogen, deuterium, halogen cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, pe
  • R 6 and R 7 may be fused to each other to form a fused ring, and Ar 3 may be substituted or unsubstituted C6 to C30 aryl group or substituted
  • the mobility of electrons in the compound may be improved. More specifically, when X 1 is S, 0, the electron density of the compound is high, the hole characteristics can be improved because the non-covalent electron pair does not play a role. This may further improve the mobility of the compound to improve the efficiency characteristics of the device, it may be lower the drive voltage.
  • Formula 1 may be represented by the following Formula 6.
  • R 1 , R “, R 1 and R 2 are each independently 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 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 Acyl oxy
  • X 1 is a substituent for pulling an electron
  • the electron density of the compound causes deformation. This makes it possible to appropriately control the mobility of the compound.
  • Chemical Formula 1 may be represented by the following Chemical Formula 7. ⁇ 108>
  • R 1 , R “, R 1 and R 2 independently of one another are hydrogen, hydrogen, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferrocene Nyl 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 acyl
  • R ', R ", R 1 and R 2 are hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted Dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted Fluorenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, or substituted or unsubstituted phenanthrenyl group.
  • Chemical Formula 2 may be represented by the following Chemical Formula 4.
  • L is a single bond, substituted or unsubstituted C2 to C6 alkenylene group, substituted or unsubstituted C2 to C6 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 heteroarylene group or a combination thereof, n is an integer of 0 to 3, and Ar 1 and are independently substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to It is a C30 heteroaryl group, and any one of a * of Formula 1 is connected to b * of Formula 4 by a sigma bond. That is, in Formula 2, X 3 may be N. In this case, the compound may be used as a hole injection material or a hole transport material by increasing the hole transport ability of the compound. Since the compound has a relatively high molecular weight, it is possible to suppress decomposition during compounding.
  • the L can be selectively adjusted to determine the conjugation length of the entire compound, 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 photoelectric device.
  • the triple energy band gap can be adjusted by changing the combined value of the small, para, and meta.
  • L is 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 polorenylene group, substituted or unsubstituted naphthalenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted Substituted triphenylenyl group, substituted or unsubstituted perylenyl group substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted
  • Substituted or unsubstituted indolyl group substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted Substituted naphthyridinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted phenazinyl groups, substituted or unsubstituted phenyls Nothiazineyl group and substituted or unsubstituted phenoxazineyl group.
  • L may be a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group. However, it is not limited thereto.
  • the compound since the compound has steric hindrance, the interaction between molecules is small, so that crystallization can be suppressed. This can improve the yield of manufacturing the device. In addition, the life characteristics of the manufactured device can be improved.
  • the compound since the compound has a relatively high molecular weight, decomposition of the compound upon deposition can be suppressed.
  • Ar 1 to Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, and a substitution.
  • an unsubstituted naphthacenyl group a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted ⁇ -terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group Chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted peryleneyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted A substituted pyridyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or un
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted Phenanthryl groups, substituted or unsubstituted naphthacenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted biphenylyl groups, substituted or unsubstituted P-terphenyl groups, substituted or unsubstituted m-terphenyl groups Substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perenyl group, substituted or unsubstituted indenyl group / substituted or unsubstituted furanyl group, substituted
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted di Benzothiophenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, or substituted or unsubstituted Phenanthrenyl groups, substituted or unsubstituted benzofluorenenofuran.
  • this is not limitative.
  • At least one of Ar 1 and Ar 2 may be a substituted or unsubstituted biphenyl group.
  • the whole conjugation length (pi -conjugation length) is adjusted, thereby adjusting the triplet energy bend gap, thereby improving the luminous efficiency of the device.
  • At least one of Ar 1 and Ar 2 may be a substituted or unsubstituted fluorenyl group.
  • the planarity of the molecules may be increased to increase the mobility of holes. Therefore, when a different compound is applied to the hole injection and hole transport layer of the organic light emitting device, the long life and / or high efficiency characteristics of the device can be achieved.
  • At least one of the R 1 , R, R 1 and R 2 may be a substituted or unsubstituted C3 to C40 silyl group.
  • the silyl group may lower the deposition temperature when manufacturing the organic optoelectronic device, and may increase the solubility in a solvent to convert the device manufacturing process into a solution process.
  • At least one of the R ', R ", 1 and R 2 is a substituted C3 to C40 silyl group, wherein at least any one of hydrogen substituted of the substituted silver silyl group is C1 to C10 alkyl group or C6 To C15 may be substituted with an aryl group.
  • substituted silyl group examples include a trimethylsilyl group, triphenylsilyl group, methylsilyl, dimethylsilyl, phenylsilyl, diphenylsilyl, trichlorosilyl, and aloxysilyl l trialkoxysilyl group.
  • Compound for an organic optoelectronic device exhibits a maximum emission wavelength of about 320 to 500 nm, triplet excitation energy (T1) is more than 2.0 eV 'more specifically 2.0 to 4.Q as the eV range, high triplet excitation energy Since the charge of the host is well transferred to the dopant, the light emission effect of the dopant can be increased, and the homogeneous (HOMO) and lumo (LUM0) energy levels of the material can be freely adjusted to lower the driving voltage. It can be very useful as a host material or a charge transport material.
  • the compound for an organic optoelectronic device has photoactive and electrical activity, a nonlinear optical material, an electrode material, a color change material, an optical switch, a sensor, a mod waveguide, an organic transistor, a laser, an optical absorber, and a dielectric And it can be very usefully applied as a material of the membrane round (membrane).
  • the compound for an organic optoelectronic device including the compound as described above has a glass transition temperature.
  • the compound for an organic optoelectronic device including the compound as described above may emit light or electrons.
  • the compound for an organic optoelectronic device may be used as a host material of phosphorescence or fluorescence, a light emitting dopant material of blue color, or an electron transporting material.
  • Compound for an organic optoelectronic device according to an embodiment of the present invention is used in the 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.
  • one embodiment of the present invention provides an organic optoelectronic device comprising the compound for an organic optoelectronic device.
  • the organic optoelectronic device refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, and the like.
  • a compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, an electrode material in a gate, a source-drain electrode, or the like Can be used as
  • Another embodiment of the present invention is an 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 any one of the organic thin film layer is It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to the embodiment.
  • the organic thin film layer which may include the compound for an organic optoelectronic device may include a layer selected from the group consisting of a light emitting layer hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a combination thereof. Bar, at least one of these The layer comprises a compound for an organic optoelectronic device according to the present invention.
  • the hole transport layer or the hole injection layer may include a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the compound for an organic optoelectronic device when included in a light emitting layer, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material. '
  • FIG. 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.
  • an organic light emitting device 100 according to an embodiment of the present invention.
  • 200, 300, 400, and 500 have a structure including an anode 120, a cathode 110, and at least one organic thin film layer 105 interposed between the anode and the cathode.
  • the positive electrode 120 includes a positive electrode material, and a material having a large work function is preferable as the positive electrode material so that hole injection can be smoothly performed into an organic thin film insect.
  • the anode material include metals such as nickel, platinum, barnacle, crumb, copper, zinc, and gold or alloys thereof, zinc oxide, phosphate oxide, indium tin oxide ⁇ , phosphorus zinc oxide ( IZ0) and metal oxides such as ⁇ ⁇ and A1 or Sn0 2 and Sb, and poly (3-methylthiophene), poly [3, 4— (erylene-).
  • 1,2-dioxy) thiophene] polyehtylenedioxythiophene: PEDT
  • conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • 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 the organic thin film layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, barium, or alloys thereof, and LiF / Al.
  • Multilayer structure materials such as Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
  • 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, and the organic thin film layer 105 exists only as a light emitting layer 130. Can be.
  • 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 an organic thin film layer 105.
  • the organic thin film layer 105 may be a two-layer type including a light emitting layer 230 and a 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 IT0.
  • FIG. 3 is an organic transport layer 150, an electron transport layer 150, and an emission layer.
  • the electron transport layer 150 and the hole transport layer 140 are shown stacked in separate layers.
  • FIG. 4 shows the electron injection layer 160 and the light emitting layer as the organic thin film layer 105.
  • the hole injection layer 170 may improve adhesion to ITO used as an anode.
  • FIG. 5 illustrates an organic injection layer 160 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.
  • the five-layered organic light emitting device 500 is shown in which five layers having different functions are present.
  • the organic light emitting device 500 is effective in lowering the voltage by separately forming the electron injection layer 160.
  • the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection insect 170 forming the organic thin film layer 105 any one selected from the group consisting of a combination thereof includes the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, even if included in the electron transport layer hole blocking layer (not shown) It is desirable to provide an organic light emitting device having a simpler structure since it is not necessary to form a separate).
  • the compound for an organic optoelectronic device when included in the light emitting layers 130 and 230, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.
  • the anode is formed on a substrate and then vacuum evaporated.
  • the organic thin film layer may be formed by a wet film method such as spin coating, dipping or flow coating, and then a cathode may be formed thereon.
  • a display including the organic light emitting device Provide the device.
  • the compound of A1 25 presented as a more specific example of the compound for an organic photoelectric device of the present invention was synthesized through a four-step route as shown in Banung Formula 1.
  • Example 1 Intermediate product (B) synthesized in Step 2 (B) 15.0 g (59.49 face 0 1), iodobenzene 14.6 g (71.39 ⁇ 01) sodium tert—subside 8.60 g (89.24 ⁇ 0 1), Tris 0.50 g (0.59 mmmol) of (dibenzylideneacetone) dipalladium (0) was suspended in 300 ml of toluene, and 0.80 mL (3.57 mmol) of tri-tert-butylphosphine was added thereto, followed by stirring under reflux for 12 hours. Extract with dichloromethane and distilled water and filter the organic layer with silica gel.
  • Example 1 Intermediate (B) Synthesized in Step 2 12.
  • the glass substrate coated with a thin film of Indium tinoxide (IT0) 1500 A was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing with isopropyl alcohol, acetone, and methane was carried out, and dried. . 4,4'-bis [N- [4- ⁇ N, N-bis (3-met hy 1 heny 1) am i no ⁇ -pheny 1] on the ⁇ substrate using the prepared ⁇ transparent electrode as the anode -N-pheny laminojbi heny 1 (DNTPD) was vacuum deposited to form a 600 A thick hole injection layer. A 300 A thick hole transport layer was then formed by vacuum deposition using Compound A-25 prepared in Example 1.
  • 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 as a dopant.
  • TBPe 2,5,8, ll-tetra (tert-butyl) perylene
  • Alq3 was vacuum-deposited on the light emitting layer to form an electron transport layer having a thickness of 250 A.
  • An organic light emitting diode was manufactured by sequentially depositing LiF 10 A and Al 1000 A on the electron transport layer to form a cathode.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using Example 2 instead of Example 1.
  • Example 4 an organic light emitting diode was manufactured according to the same method as Example 3 except for using Example 3 instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using NPB instead of Example 1.
  • the structure of the NPB is described below.
  • Example 4 Comparative Example 2
  • an organic light emitting diode was manufactured according to the same method except for using HT1 instead of Example 1.
  • the structure of ⁇ is described below.
  • the structures of DNTPD, AND, TBPe, NPB and ⁇ used in the organic light emitting device fabrication are as follows.
  • the current value flowing through the unit device was measured by using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V and dividing the measured current value by the area. Got it.
  • the luminance meter while increasing the voltage from 0V to 10V
  • 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 / cm 2 ) was calculated using the luminance, current density, and voltage measured from (1) and (2).
  • organic light emitting element 110 cathode

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Abstract

La présente invention porte sur un composé pour un dispositif optoélectronique organique, sur un dispositif électroluminescent organique le comprenant et sur un dispositif d'affichage comprenant ledit dispositif électroluminescent organique. Le composé pour un dispositif optoélectronique organique selon la présente invention est représenté par la combinaison des formules 1 et 2, ce qui permet ainsi la fabrication d'un dispositif électroluminescent organique ayant de bonnes caractéristiques de durée de vie utile en raison de son excellente stabilité électrochimique et thermique et ayant également un rendement d'électroluminescence supérieur même à une faible tension de fonctionnement.
PCT/KR2013/005237 2012-09-25 2013-06-13 Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le comprenant et dispositif d'affichage comprenant ledit dispositif électroluminescent organique WO2014051244A1 (fr)

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