WO2014193153A1 - Nouveau composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2014193153A1
WO2014193153A1 PCT/KR2014/004737 KR2014004737W WO2014193153A1 WO 2014193153 A1 WO2014193153 A1 WO 2014193153A1 KR 2014004737 W KR2014004737 W KR 2014004737W WO 2014193153 A1 WO2014193153 A1 WO 2014193153A1
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formula
compound
light emitting
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함호완
안현철
한정우
김동준
김근태
이형진
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주식회사 동진쎄미켐
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Priority to CN201480038742.1A priority Critical patent/CN105473594B/zh
Priority claimed from KR1020140063461A external-priority patent/KR102245921B1/ko
Publication of WO2014193153A1 publication Critical patent/WO2014193153A1/fr

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Definitions

  • the present invention relates to a novel organic compound, and more particularly to a novel organic compound having easy charge transfer characteristics and at the same time having a high triplet energy and a high glass transition temperature, and an organic light emitting device comprising the same.
  • an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and an organic layer between the two electrodes.
  • the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML).
  • an electron injection layer and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the light emission characteristics of the light emitting layer.
  • the organic light emitting device When an electric field is applied to the organic light emitting device having such a structure, holes are injected from the anode, electrons are injected from the cathode, and holes and electrons are recombined in the light emitting layer through the hole transport layer and the electron transport layer, respectively, thereby excitons ).
  • the formed light exciton emits light as it transitions to ground states.
  • the light emitting material may be doped into the light emitting layer (host).
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors according to light emission wavelengths.
  • a host / dopant system may be used as a light emitting material.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.
  • the present invention has excellent charge transfer characteristics, and at the same time an organic compound having a high triplet energy and a high glass transition temperature (Tg) and low drive voltage, high efficiency, low power consumption and long life, including the same It is an object to provide an organic light emitting device having a.
  • X is O, S, Se, Te or NR, wherein R is hydrogen, deuterium, a halogen, an amino group, a nitrile group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ of C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 40 heteroaryl group, C 6 ⁇ C 20 An alkylamine group, a C 6 -C 20 arylamine group, a C 4 -C 30 heteroarylene group, or a C 6 -C 60 condensed polycyclic group;
  • L is directly linked; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 of the heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 alkyl amine group, C 6 ⁇ C 20 aryl amine group and C 3 ⁇ C 40 heteroaryl group selected from the group consisting of C 6 -C 60 aryl group, C 4 -C 60 heteroaryl group, C 6 -C 30 arylene group, C 4 -C 30 heteroarylene group, or C 6 -C 60 condensation substituted or unsubstituted with one or more groups Ventilation,
  • R 1 to R 9 are each independently connected to L, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 40 heteroaryl group, C 6 ⁇ C 20
  • n is an integer from 2 to 10, preferably n is 2 or 3.
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the compound of Formula 1 of the present invention includes two or more ring-closed structures of indole and furan to facilitate charge transfer characteristics, and at the same time have high triplet energy and high glass transition temperature. It can be usefully used as a hole injection material, a hole transport material or a host material having excellent hole injection characteristics and hole transfer characteristics suitable for fluorescent and phosphorescent devices of all colors such as white and white.
  • the compound of Formula 1 when used in the hole injection layer, the hole transport layer or the light emitting layer, an organic light emitting device having low driving voltage, high efficiency, low power consumption, and long life can be manufactured.
  • FIG. 1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.
  • the compound of the present invention represented by the following Chemical Formula 1 is characterized in that it has two or more structures in which indole and furan are ring-closed structures:
  • X is O, S, Se, Te or NR, wherein R is hydrogen, deuterium, a halogen, an amino group, a nitrile group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ of C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 40 heteroaryl group, C 6 ⁇ C 20 An alkylamine group, a C 6 -C 20 arylamine group, a C 4 -C 30 heteroarylene group, or a C 6 -C 60 condensed polycyclic group;
  • L is directly linked; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 of the heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 alkyl amine group, C 6 ⁇ C 20 aryl amine group and C 3 ⁇ C 40 heteroaryl group selected from the group consisting of C 6 -C 60 aryl group, C 4 -C 60 heteroaryl group, C 6 -C 30 arylene group, C 4 -C 30 heteroarylene group, or C 6 -C 60 condensation substituted or unsubstituted with one or more groups Ventilation,
  • R 1 to R 9 are each independently connected to L, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 40 heteroaryl group, C 6 ⁇ C 20
  • n is an integer from 2 to 10, preferably n is 2 or 3.
  • the furan since the furan has a high triplet energy, when applied to the organic light emitting device, serves to provide a low driving voltage, high efficiency and low power consumption, indole facilitates charge transfer, When the furan and the indole are ring-closed and two or more are included, a high glass transition temperature can be obtained, and thus, when applied to an organic light emitting device, thermal stability and long life can be obtained.
  • the compound of Formula 1 is preferably selected from the group consisting of the compounds represented by the following formula 1-1 to 1-10, but is not limited thereto:
  • X, L and R 1 to R 9 are as defined above,
  • R 10 to R 27 are each independently connected to L or a hydrogen atom, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 1 ⁇ C 40 alkoxy groups, C 3 to C 40 cycloalkyl groups, C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups, C 6 to C 40 heteroaryl groups, C 6 to C 20 alkyl An amine group, a C 6 -C 20 arylamine group, a C 4 -C 30 heteroarylene group, or a C 6 -C 60 condensed polycyclic group.
  • the compound of the present invention includes two or more groups in which the indole which is easy to transfer charges and a furan high triplet energy ring-closing group facilitates charge transfer characteristics, and at the same time may have a high triplet energy and a high glass transition temperature. .
  • the compound of formula 1 according to the present invention may be prepared through one of the following reaction schemes, but is not limited thereto:
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1) or a mixture thereof.
  • the compound is used as a hole injection material, a hole transport material or a host material.
  • the organic light emitting device of the present invention includes one or more organic thin film layers including the compound represented by Chemical Formula 1, and the method of manufacturing the organic light emitting device is as follows.
  • at least one organic thin film layer including the compound represented by Chemical Formula 1 is a hole injection layer, a hole transport layer, or a light emitting layer.
  • the organic light emitting device is an organic thin film layer, such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between the anode (anode) and the cathode (cathode) It may include one or more.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron transport layer
  • EIL electron injection layer
  • an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
  • the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
  • the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
  • the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
  • the compound represented by the formula (1) or a known hole injection layer material on the anode electrode can be formed by a method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, It is preferable to form by the vacuum evaporation method from the point of obtaining a uniform film
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the desired hole injection layer, and generally, a deposition temperature of 50 to 500 ° C., It is preferable to select appropriately from a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 kPa to 5 mu m.
  • the well-known hole injection layer material is not particularly limited, and TCTA (4,4 ′, 4 ′′ -tri (N-carbazolyl), which is a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Pat. No. 4,356,429.
  • Triphenylamine Triphenylamine
  • m-MTDATA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine
  • m-MTDAPB (4,4', 4" -tris (3-methylphenylamino) phenoxy Cybenzene)
  • HI-406 N 1 , N 1 '-(biphenyl-4,4'-diyl) bis (N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenylbenzene-1 , 4-diamine) and the like can be used as the hole injection layer material.
  • the compound represented by Chemical Formula 1 or a known hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but it is easy to obtain a uniform film quality. It is preferable to form by the vacuum evaporation method in that pinholes are unlikely to generate
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.
  • the well-known hole transport layer material is not particularly limited, and may be arbitrarily selected and used from the conventional well-known materials used in the hole transport layer.
  • the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Derivatives and the like can be used.
  • carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phen
  • the light emitting layer material may be coated on the hole transport layer by a deposition method or a solution process.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same conditions as the formation of the hole injection layer.
  • the light emitting layer material a compound represented by Chemical Formula 1 or a known light emitting layer material may be used, and a light emitting layer may be formed by using a phosphorescent or fluorescent dopant together.
  • the fluorescent dopant may be IDE102 or IDE105, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethycrylicene- which can be purchased from Idemitsu Co., Ltd.).
  • 6,12-diamine can be used as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6] -Difluorophenyl) -pyridinato-N, C2 '] picolinate), red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
  • Ir (ppy) 3 tris (2-phenylpyridine) iridium
  • blue phosphorescent dopant F2Irpic iridium (III) bis [4,6] -Difluorophenyl) -pyridinato-N, C2 '] picolinate
  • red phosphorescent dopant RD61 from UDC and the like can be co-vacuum deposited (doped).
  • the hole suppression material HBL
  • HBL hole suppression material
  • the hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
  • an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited.
  • Oxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound e.g., BCP (vasocuproin) from UDC
  • BCP vasocuproin
  • An electron transport layer is formed on the light emitting layer formed as above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.
  • the electron transport material as a function to transport a steady stream of electrons injected from the electron injecting electrode that kind is not particularly limited, for example, quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3 ), Or ET4 (6,6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine).
  • an electron injection layer (EIL) which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
  • the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.
  • an electron injection layer material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by.
  • a cathode forming metal is formed on the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode.
  • the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
  • a transmissive cathode using ITO and IZO may be used to obtain a top emitting element.
  • the organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.
  • each organic thin film layer formed according to the present invention as described above can be adjusted according to the required degree, preferably 10 to 1,000 nm, more preferably 20 to 150 nm.
  • the organic thin film layer including the compound represented by Chemical Formula 1 has an advantage that the surface is uniform and excellent in shape stability because the thickness of the organic thin film layer can be adjusted in molecular units.
  • the starting material was 86.7 g of (1-phenyl-1H-indol-3-yl) boronic acid instead of benzofuran-3-ylboronic acid. 83.9 g of intermediate 5 ⁇ -1 (yield 70%), 47.3 g of 5'-2 (yield 62%) and 17.9 g of 5'-3 (yield 37%) were synthesized.
  • the starting material was 86.7 g of (1-phenyl-1H-indol-3-yl) boronic acid instead of benzofuran-3-ylboronic acid. 87.5 g of intermediate 6 ⁇ -1 (yield 73%), 47.4 g of 6′-2 (yield 59%) and 18.7 g of 6′-3 (yield 33%) were synthesized.
  • Compound 2 was synthesized in the same manner as Compound 1, using Intermediate 2 ⁇ -3 instead of Intermediate 1 ⁇ -3.
  • Compound 5 was synthesized in the same manner as Compound 4, except that Interaction 5′-3 was used instead of Intermediate 1′-3.
  • Compound 8 was synthesized in the same manner as Compound 4, using Starting 3 as Intermediate 3 ⁇ -3 instead of Intermediate 1 ⁇ -3.
  • Compound 9 was synthesized in the same manner as Compound 3, using 5'-iodo-1,1 ': 3', 1 ''-terphenyl as a starting material instead of 9- (3-iodophenyl) -9H-carbazole.
  • Compound 12 was synthesized by the same method as Compound 9, using Intermediate 7 ⁇ -2 as 9 ⁇ -2.
  • Compound 13 was synthesized in the same manner as in compound 11, using intermediates 1 ⁇ -2 and 1 ⁇ -3 as 3 ⁇ -2 and 3 ⁇ -3.
  • Compound 16 was synthesized by the same method as Compound 15 using Intermediate 15-1 to Intermediate 1 ⁇ -2-1.
  • Compound 17 was synthesized in the same manner as Compound 16 after synthesis of 1′-2-2 using pyridin-4-ylboronic acid instead of pyridin-3-ylboronic acid in the same manner as Intermediate 1′-2-1 of Compound 16.
  • Compound 18 was synthesized in the same manner as Compound 16 after synthesis of Intermediate 1 ⁇ -2-3 using pyrimidin-4-ylboronic acid instead of pyridin-3-ylboronic acid in the same manner as Compound 1 ⁇ -2-1. .
  • An organic light emitting device was manufactured according to the structure of FIG. 1.
  • the organic light emitting element is stacked in the order of the hole injection electrode 11 / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transfer layer 15 / electron injection electrode 16 from below.
  • the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of Examples and Comparative Examples used the following materials.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then a thermal vacuum evaporator An evaporator was used to form HATCN 50 kV as the hole injection layer and HT01 400 kV as the hole transport layer. Subsequently, Compound 1 synthesized as a buffer layer was doped with 200 ⁇ of the light emitting layer at BH01: BD01 5% to form 300 ⁇ .
  • ITO indium tin oxide
  • Alq 3 Liq (1: 1) 300 ⁇ was deposited using an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ .
  • the organic light emitting device was manufactured by encapsulating the device in a glove box. .
  • a buffer layer was prepared in the same manner as in Example 1, but instead of Compound 1, an organic light emitting diode was formed by using Compounds 2 to 13.
  • the hole transport layer HT01 of Example 1 was set to 600 Hz, and the device was manufactured in the same manner without using the buffer layer.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then a thermal vacuum evaporator An evaporator was used to form HATCN 50 kV as the hole injection layer and HT01 400 kV as the hole transport layer.
  • Compound 1 synthesized as a buffer layer was doped with 200 ⁇ of the light emitting layer to compound 14: Ir (ppy) 3 9% to form 300 ⁇ .
  • Alq 3 Liq (1: 1) 300 ⁇ was deposited using an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ .
  • the organic light emitting device was manufactured by encapsulating the device in a glove box. .
  • An organic light emitting diode was manufactured as a light emitting layer in the same manner as in Example 14. However, instead of compound 14, an organic light emitting diode was manufactured by using the compounds 15 to 19, respectively.
  • a device was manufactured in the same manner as in Example 14, except that CBP was used as the emission layer host.
  • Example 1 @ 10mA / cm2 OP. V Cd / A CIE xy Half-life Example 1 3.95 6.12 0.142, 0.137 350 Example 2 3.91 6.31 0.144, 0.136 380 Example 3 3.82 6.62 0.142, 0.139 390 Example 4 3.81 6.71 0.142, 0.137 420 Example 5 3.97 6.85 0.143, 0.137 450 Example 6 3.93 6.22 0.141, 0.136 430 Example 7 3.88 6.15 0.142, 0.138 380 Example 8 3.78 6.65 0.143, 0.139 400 Example 9 4.01 6.19 0.142, 0.137 360 Example 10 3.92 6.16 0.143, 0.138 370 Example 11 3.87 6.29 0.141, 0.138 380 Example 12 3.89 6.33 0.142, 0.139 380 Example 13 3.99 6.07 0.142, 0.140 400 Comparative Example 1 4.51 4.75 0.146, 0.142 120
  • the embodiments of the present invention can be confirmed that the physical properties are excellent in all aspects compared to the comparative examples.
  • the compound of Formula 1 of the present invention includes two or more ring-closed structures of indole and furan to facilitate charge transfer characteristics, and at the same time have high triplet energy and high glass transition temperature. It can be usefully used as a hole injection material, a hole transport material or a host material having excellent hole injection characteristics and hole transfer characteristics suitable for fluorescent and phosphorescent devices of all colors such as white and white.
  • the compound of Formula 1 when used in the hole injection layer, the hole transport layer or the light emitting layer, an organic light emitting device having low driving voltage, high efficiency, low power consumption, and long life can be manufactured.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Cette invention concerne un nouveau composé organique et, plus spécifiquement, un nouveau composé organique comprenant deux structures ou plus dans lesquelles l'indole et le furanne sont cyclisés, et un dispositif électroluminescent organique le comprenant. Le composé organique selon la présente invention a des caractéristiques de transfert de charge simples et simultanément une énergie triplet élevée et une température de transition vitreuse élevée, et peut par conséquent être utilisé en particulier en tant de matériau d'injection de trous, matériau de transport de trous ou matériau de couche électroluminescent, pour conférer ainsi des caractéristiques de basse tension de commande, haute efficacité, faible consommation d'énergie et longue durée de vie à un dispositif électroluminescent organique.
PCT/KR2014/004737 2013-05-28 2014-05-27 Nouveau composé organique et dispositif électroluminescent organique le comprenant WO2014193153A1 (fr)

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JP2017197482A (ja) * 2016-04-28 2017-11-02 コニカミノルタ株式会社 π共役系化合物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜、有機エレクトロルミネッセンス素子、表示装置及び照明装置

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US20170098783A1 (en) * 2015-10-01 2017-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US10593892B2 (en) * 2015-10-01 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
JP2017197482A (ja) * 2016-04-28 2017-11-02 コニカミノルタ株式会社 π共役系化合物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜、有機エレクトロルミネッセンス素子、表示装置及び照明装置
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