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WO2018128470A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2018128470A1
WO2018128470A1 PCT/KR2018/000274 KR2018000274W WO2018128470A1 WO 2018128470 A1 WO2018128470 A1 WO 2018128470A1 KR 2018000274 W KR2018000274 W KR 2018000274W WO 2018128470 A1 WO2018128470 A1 WO 2018128470A1
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carbon atoms
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Korean (ko)
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이순창
정재호
강현빈
유지웅
홍상훈
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Material Science Co Ltd
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Material Science Co Ltd
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Priority claimed from KR1020180001610A external-priority patent/KR102095449B1/ko
Publication of WO2018128470A1 publication Critical patent/WO2018128470A1/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electroluminescent device, and more particularly to an organic electroluminescent device comprising a novel pyrene-based organic compound and an anthracene-based organic compound in at least one organic layer included in the organic electroluminescent device.
  • OLEDs were manufactured in 1987 by Kodak's C.W. Since Tang developed the first organic EL devices (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987) using aluminum compounds in aromatic diamines as light emitting layers, multi-layer thin film organic electroluminescence Research on devices and organic materials is being actively conducted.
  • the organic light emitting display device is simpler in structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP), and a field emission display (FED), has various advantages in the manufacturing process, and has high luminance and viewing angle. Due to its excellent characteristics, fast response speed and low driving voltage, it has been commercialized as a light source such as a back light of a flat panel display such as a wall-mounted TV or a display, an illumination, a billboard.
  • a light source such as a back light of a flat panel display such as a wall-mounted TV or a display, an illumination, a billboard.
  • an organic light emitting display device is a device in which holes and electrons meet and emit light when a voltage is applied to a cathode (electron injection electrode) and an anode (hole injection electrode). It has a structure including an organic layer.
  • the organic light emitting device may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection, in addition to the light emitting layer (EML).
  • Electron Injection Layer (EIL) may be included, and may further include an Electron Blocking Layer (EBL) or a Hole Blocking Layer (HBL) as necessary to increase the efficiency of the light emitting layer. have.
  • the organic light emitting device including all of these organic layers has a structure stacked in the order of anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode.
  • a host / dopant system may be used as the light emitting material to increase the color purity and the light emission efficiency through energy transfer.
  • the principle is that when a small amount of a dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • the light emitting layer is composed of a red host / dopant, a green host / dopant and a blue host / dopant, respectively.
  • the blue light emitting layer is a host and a dopant capable of achieving excellent blue color in terms of lifetime, efficiency and color purity compared to other colors. Development is required.
  • An object of the present invention is to provide a host / dopant system that minimizes the phenomenon that the maximum emission wavelength is shifted to long wavelength (red) when using a compound contained in Dibenzofuran as a host, resulting in excellent color purity, low driving voltage, high It is an object to provide an organic electroluminescent device having characteristics such as luminous efficiency and long life.
  • alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, dimethylfluorenyl, and the like.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • arylamine refers to an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the first electrode Second electrode; And at least one organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the light emitting layer provides an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (2):
  • L 1 includes C 1 , C 2 and C 3 to form a saturated or unsaturated condensed ring of C 4 to C 7 , the ring may be substituted with C 1 to C 10 alkyl,
  • R 1 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitro group , cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alken having 2 to 30 carbon atoms Nyl group, substituted or unsubstituted 2 to 30 carbon atoms Alkynyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C2-C30 heteroalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 of Aryl groups, substituted or unsubstituted 6 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted 6 to 30 carbon atoms A heteroarylalkyl group, a substituted or unsubstituted C1-C30 alkyl
  • R 11 to R 20 are the same as or different from each other, and at least one is -L 2 -Ar 1 And / or -L 3 -Ar 2 ,
  • L 2 and L 3 are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 heteroarylene groups, a substituted or unsubstituted carbon number 2-10 alkylene group, substituted or unsubstituted C2-C10 cycloalkylene group, substituted or unsubstituted C2-C10 alkenylene group, substituted or unsubstituted C2-C10 cycloalkenylene group substituted or unsubstituted C2-C10 heteroalkylene group, substituted or unsubstituted C2-C10 heterocycloalkylene group, substituted or unsubstituted C2-C10 heteroalkenylene group, and substituted or unsubstituted C2-C10 heterocycloalkenylene Is selected from the group consisting of groups,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , Substituted or unsubstituted C1-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C1-C20 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkenyl group, A substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
  • R 11 to R 20 other than -L 3 -Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms , Substituted or unsubstituted C2-C24 alkynyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C2-C30 heteroalkyl group, substituted or unsubstituted C7-C30 aralkyl group, substituted Or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms,
  • R 1 to R 8, L 2 to L 3 , Ar 1 to Ar 2, and R 11 to R 20 are each independently hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted A C2-C24 alkynyl group of a ring, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heteroalkyl group, a substituted or unsubstituted C7-C30 aralkyl group, a substituted or unsubstituted carbon number 6 to 30 aryl groups, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl groups having 3 to 30 carbon
  • the compound represented by Chemical Formula 1 represents a compound represented by the following Chemical Formula 3.
  • R 9 and R 10 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted carbon group having 1 to 10 carbon atoms
  • R 9 and R 10 are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , May be further substituted with one or more substituents selected from the group consisting of an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and a heteroalkyl group having 2 to 30 carbon atoms, and when the substituents are plural, Same or different,
  • n is an integer of 1 to 3
  • R 1 to R 8 are as defined in claim 1.
  • any one of R 1 to R 8 of Formula 1 represents a functional group represented by the following formula (4).
  • L is a single bond, a substituted or unsubstituted C 6 -C 18 arylene group or a substituted or unsubstituted C 6 -C 18 heteroarylene group,
  • M is hydrogen, deuterium or a functional group represented by the formula (5),
  • Ar 3 and Ar 4 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Alkenyl groups having 2 to 30 carbon atoms, substituted or unsubstituted 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and
  • L, Ar 3 and Ar 4 are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group of 1 to 30 carbon atoms, of 2 to 30 carbon atoms Alkenyl groups, alkynyl groups of 2 to 24 carbon atoms, cycloalkyl groups of 3 to 30 carbon atoms, heteroalkyl groups of 2 to 30 carbon atoms, aralkyl groups of 7 to 30 carbon atoms, aryl groups of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms Group, C3-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 hetero At least one substituent selected from the group consisting of an arylamino group, an alkylsily
  • Ar 3 and Ar 4 of Chemical Formula 5 represent a substituent selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 11.
  • p is an integer from 0 to 4,
  • q is an integer of 0 to 3
  • X 1 is selected from the group consisting of C (R 23 ), N, S and O,
  • X 2 , X 3 , X 4 and X 6 are the same as or different from each other, and are each independently selected from the group consisting of C (R 23 ) (R 24 ), N (R 23 ), S and O,
  • X 5 and X 7 are the same as or different from each other, and each independently C (R 23 ) or N,
  • R 21 to R 24 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted C 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkyl
  • R 19 to R 21 are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms Alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, Heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, heteroarylaryl group having 2 to 24 carbon atoms At least one substitu
  • M is a functional group represented by Formula 5
  • Ar 3 and Ar 4 Is connected to N of M to form a ring, and represents a compound represented by any one of the following formula (12) or (13).
  • X 8 and X 9 are the same as or different from each other, and are each independently selected from the group consisting of C (R 25 ) (R 26 ), N (R 25 ), C, N, O and S,
  • R 25 and R 26 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted C 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkyl
  • R 25 to R 26 are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms Alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, Heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, heteroarylaryl group having 2 to 24 carbon atoms At least one substitu
  • the compound represented by Chemical Formula 2 represents a compound represented by the following Chemical Formula 14.
  • R 1 to R 8 , Ar 1 to Ar 2 and L 2 to L 3 are as defined in claim 1.
  • L 2 and L 3 of Formula 14 are the same as or different from each other, each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted nuclear atom 6 Organic electroluminescent device which is from 30 to 30 heteroarylene groups.
  • At least one or more of Ar 1 and Ar 2 of Formula 14 represent a compound represented by the following Formula 15.
  • R 27 to R 34 are the same as or different from each other, and at least one is -L 2 -Ar 1 And / or -L 3 -Ar 2 ,
  • X is O or S
  • R 27 to R 34 other than -L 3 -Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or
  • R 27 to R 34 and the saturated or unsaturated condensed ring formed by them are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, carbon number 1
  • Chemical Formula 15 represents a compound represented by the following Chemical Formulas 16 to 24.
  • X is O or S
  • e is an integer from 0 to 6
  • f is an integer of 0 to 6
  • g is an integer of 0 to 4,
  • h is an integer from 0 to 4,
  • R 35 to R 37 are the same as or different from each other, and each independently a single bond, hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroaryl
  • R 35 to R 37 is combined with L 2 or L 3 .
  • R 11 to R 18 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclo having 3 to 30 carbon atoms Alkyl group and substituted or unsubstituted C6-C30 It is selected from the group consisting of an aryl group.
  • the compound represented by Formula 1 is selected from the group consisting of:
  • the compound represented by Formula 2 is selected from the group consisting of:
  • the light emitting layer of the organic light emitting device of the present invention comprises a dopant and a host
  • the dopant comprises a compound represented by the formula (1)
  • the host is a compound represented by the formula (2) It may include.
  • the organic compound represented by Formula 1 of the present invention may be used as a dopant material, and is preferably a blue dopant material.
  • the organic compound is a blue dopant material and provides a dark blue blue host / dopant system suitable for AM-OLED by shifting an emission wavelength toward shorter wavelengths of 7 nm or more compared to a conventional blue dopant.
  • the organic compound represented by the general formula (1) of the present invention prevents excited dimer formation of the dopant by introducing an alkyl group of a cyclic compound inside the pyrene molecular core and increases the electron density of the core and the stability of the dopant. Increases its efficiency and lifespan.
  • the organic compound represented by Chemical Formula 1 of the present invention has excellent solubility in solution, and thus has an easy characteristic in manufacturing a solution process OLED device and reduces the production process cost.
  • One embodiment of the present invention provides a material for forming an emission layer comprising an organic compound represented by Formula 1 and an organic compound represented by Formula 2.
  • the light emitting layer forming material may include a conventionally added material, for example, a known dopant and a host material.
  • the host material may be an organic compound represented by Formula 2, but is not limited thereto.
  • the organic compound represented by Chemical Formula 1 in which an organic thin film layer including one or more layers including at least one light emitting layer is stacked between a cathode and an anode, the organic compound represented by Chemical Formula 1 and There is provided an organic light emitting device comprising the compound represented by the formula (2).
  • the organic light emitting device of the present invention is a cathode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML) and a cathode (electron injection electrode) in sequence It may have a stacked structure, and preferably, may further include an electron blocking layer (EBL) between the anode and the light emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the light emitting layer. .
  • a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer.
  • the organic electroluminescent device of the present invention will be described by way of example. However, the contents exemplified below do not limit the organic light emitting device of the present invention.
  • Another embodiment of the present invention provides a method of manufacturing an organic light emitting display device according to the present invention, but the contents exemplified below do not limit the method of manufacturing the organic light emitting display device of the present invention.
  • a positive electrode is coated on a surface of a substrate by a conventional method to form a positive electrode.
  • the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproof.
  • the positive electrode material indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.
  • a hole injection layer is formed on the surface of the anode by vacuum thermal evaporation or spin coating of a hole injection layer (HIL) material in a conventional manner.
  • hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4', 4" -tris (3-methylphenyl Amino) phenoxybenzene (m-MTDAPB), starburst amines 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4', 4" -tris Examples include (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA) or IDE406 available from Idemitsu.
  • a hole transport layer is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating of a hole transport layer (HTL) material in a conventional manner.
  • HTL hole transport layer
  • the hole transport layer material bis (N- (1-naphthyl-n-phenyl)) benzidine ( ⁇ -NPD), N, N'-di (naphthalen-1-yl) -N, N'-biphenyl -Benzidine (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD).
  • the compound represented by Chemical Formula 2 may be preferably used as a single light emitting material or a light emitting host material among the light emitting layer materials used, but in the case of green, tris (8-hydroxyquinolinolato) aluminum (Alq 3 ), Blue, Balq (8-hydroxyquinolineberyllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, Spiro ) Material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzooxazolyl) -phenol lithium salt ), Bis (biphenylvinyl) benzene, aluminum-quinoline metal complex, metal
  • an organic compound represented by Chemical Formula 1 of the present invention may be preferably used as a blue fluorescent dopant, IDE102, which is available from Idemitsu as another fluorescent dopant, IDE105
  • phosphorescent dopants include tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinato-N, C-2 ') Picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084), Platinum (II) octaethylporphyrin (PtOEP), TBE002 ) May be used.
  • an electron blocking layer EBL may be further formed between the hole transport layer and the light emitting layer.
  • An electron transport layer is formed on the surface of the light emitting layer by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material in a conventional manner.
  • ETL electron transport layer
  • the electron transport layer material used is not particularly limited, and preferably tris (8-hydroxyquinolinolato) aluminum (Alq 3 ) may be used.
  • HBL hole blocking layer
  • the hole blocking layer may be formed by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but is preferably (8-hydroxyquinolinola).
  • Earth) lithium (Liq) bis (8-hydroxy-2-methylquinolinolato) -aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF and the like can be used.
  • An electron injection layer is formed on the surface of the electron transport layer by vacuum thermal evaporation or spin coating of an electron injection layer (EIL) material in a conventional manner.
  • EIL electron injection layer
  • a material such as LiF, Liq, Li 2 O, BaO, NaCl, CsF may be used as the electron injection layer material.
  • the negative electrode material is formed on the surface of the electron injection layer by vacuum thermal deposition in a conventional manner.
  • the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like can be used.
  • indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.
  • the capping layer CPL may be formed on the surface of the cathode by the composition for capping layer formation of the present invention.
  • an organic electroluminescent device including an organic compound capable of sublimation and deposition even at a low temperature, realizing a darker blue color, and increasing the efficiency and life of the device.
  • An electroluminescent element is provided.
  • a deep blue series blue host / dopant system suitable for AM-OLED, and as a result, an organic EL device having low driving voltage, high luminous efficiency, and long life is provided. do.
  • An organic electroluminescent device comprising at least one organic film between the first electrode and the second electrode,
  • the organic layer includes at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer,
  • the light emitting layer is an organic electroluminescent device comprising a compound represented by the following formula (1) and a compound represented by the following formula (2):
  • L 1 includes C 1 , C 2 and C 3 to form a saturated or unsaturated condensed ring of C 4 to C 7 , the ring may be substituted with C 1 to C 10 alkyl,
  • R 1 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitro group , cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alken having 2 to 30 carbon atoms Nyl group, substituted or unsubstituted 2 to 30 carbon atoms Alkynyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C2-C30 heteroalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 of Aryl groups, substituted or unsubstituted 6 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted 6 to 30 carbon atoms A heteroarylalkyl group, a substituted or unsubstituted C1-C30 alkyl
  • R 11 to R 20 are the same as or different from each other, and at least one is -L 2 -Ar 1 and / or -L 3 -Ar 2 ,
  • L 2 and L 3 are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 heteroarylene groups, a substituted or unsubstituted carbon number 2-10 alkylene group, substituted or unsubstituted C2-C10 cycloalkylene group, substituted or unsubstituted C2-C10 alkenylene group, substituted or unsubstituted C2-C10 cycloalkenylene group substituted or unsubstituted C2-C10 heteroalkylene group, substituted or unsubstituted C2-C10 heterocycloalkylene group, substituted or unsubstituted C2-C10 heteroalkenylene group, and substituted or unsubstituted C2-C10 heterocycloalkenylene Is selected from the group consisting of groups,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , Substituted or unsubstituted C1-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C1-C20 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkenyl group, A substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
  • R 11 to R 20 other than -L 3 -Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms , Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted Or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroary
  • R 1 to R 8, L 2 to L 3 , Ar 1 to Ar 2, and R 11 to R 20 are each independently hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 to 30 aryl groups, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylal
  • reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol and water, and then recrystallized with toluene and n-heptane to obtain 2.58 g (52%) of compound 2-5.
  • reaction mixture was then cooled to room temperature, and the resulting solid was washed with toluene, methanol and water and recrystallized with toluene and n-heptane to give 2.33 g (47%) of compound 2-6.
  • a blue host a compound having no polar group and a compound having a polar substituent were used, and the wavelength when the dopant of the present invention was used as a blue dopant was measured. It can be confirmed that there is no change in wavelength even if used.
  • the substrate in which the Ag alloy, which is a light-reflective layer, and ITO (10 nm), which is an anode of the organic light emitting device, were sequentially stacked was patterned by dividing the substrate into a cathode, an anode region, and an insulating layer through a photo-lithograph process. Afterwards, UV Ozone treatment and O2: N2 plasma were used for the purpose of increasing the work-function and descum of the anode (ITO). 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed on the hole injection layer (HIL) to a thickness of 100 mm 3.
  • HIL hole injection layer
  • N4, N4, N4 ', N4'-tetra ([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -4,4'- Diamine was vacuum deposited to form a hole transport layer having a thickness of 1000 mm 3.
  • EBL electron blocking layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • HTL hole transport layer
  • Electron transport layer was deposited to a thickness of 360 ⁇ by mixing, and magnesium (Mg) and silver (Ag) were deposited to a thickness of 160 ⁇ at a ratio of 9: 1 as the cathode.
  • -Biphenyl] -4,4'-diamine was deposited to a thickness of 63-65 nm.
  • the organic electroluminescent device was manufactured by bonding a seal cap with a UV curable adhesive on a capping layer (CPL) to protect the organic light emitting device from O 2 or moisture in the air.
  • An organic light emitting diode device was manufactured according to the same method as Example 1 except for using the compound as described in Table 4 below instead of the compound 1-1 as a dopant, and adjusting the doping amount of the dopant. .
  • An organic light emitting diode device was manufactured according to the same method as Example 1 except for using the compound 1-A to 1-C instead of the compound 1 as a dopant.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Compound 2-A to Compound 2-B as a host.
  • the driving voltage Volt is equal to or less than the comparative example (low driving voltage), and the light emission efficiency (Cd / A) is improved. have.
  • the present invention relates to an organic electroluminescent device, and more particularly to an organic electroluminescent device comprising a novel pyrene-based organic compound and an anthracene-based organic compound in at least one organic layer included in the organic electroluminescent device.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un élément électroluminescent organique et, plus spécifiquement, un élément électroluminescent organique, dans lequel de nouveaux composés organiques à base de pyrène et d'anthracène sont contenus dans au moins une couche organique incluse dans l'élément électroluminescent organique.
PCT/KR2018/000274 2017-01-05 2018-01-05 Élément électroluminescent organique Ceased WO2018128470A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109867646A (zh) * 2018-12-31 2019-06-11 瑞声科技（南京）有限公司 一种杂环化合物及其应用
CN110571340A (zh) * 2019-08-23 2019-12-13 陕西莱特光电材料股份有限公司 有机电致发光器件、电子装置
CN111434658A (zh) * 2019-01-15 2020-07-21 机光科技股份有限公司 有机电致发光材料和器件
KR20200090122A (ko) * 2019-01-18 2020-07-28 주식회사 엘지화학 유기 발광 소자
CN112334474A (zh) * 2018-11-13 2021-02-05 株式会社Lg化学 化合物及包含其的有机发光器件
CN113149943A (zh) * 2021-05-10 2021-07-23 吉林奥来德光电材料股份有限公司 荧光化合物及其制备方法和包含其的有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040076853A1 (en) * 2002-04-24 2004-04-22 Eastman Kodak Company Organic light-emitting diode devices with improved operational stability
KR20150054654A (ko) * 2013-11-08 2015-05-20 주식회사 엠비케이 신규한 유기화합물, 이를 포함하는 유기전계발광소자 및 전자 기기
KR20150064687A (ko) * 2013-12-03 2015-06-11 주식회사 동진쎄미켐 신규한 청색 형광 호스트 화합물 및 이를 포함하는 유기발광소자
KR20150115227A (ko) * 2014-04-03 2015-10-14 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150139124A (ko) * 2014-06-02 2015-12-11 삼성디스플레이 주식회사 아민계 화합물 및 이를 포함한 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040076853A1 (en) * 2002-04-24 2004-04-22 Eastman Kodak Company Organic light-emitting diode devices with improved operational stability
KR20150054654A (ko) * 2013-11-08 2015-05-20 주식회사 엠비케이 신규한 유기화합물, 이를 포함하는 유기전계발광소자 및 전자 기기
KR20150064687A (ko) * 2013-12-03 2015-06-11 주식회사 동진쎄미켐 신규한 청색 형광 호스트 화합물 및 이를 포함하는 유기발광소자
KR20150115227A (ko) * 2014-04-03 2015-10-14 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150139124A (ko) * 2014-06-02 2015-12-11 삼성디스플레이 주식회사 아민계 화합물 및 이를 포함한 유기 발광 소자

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112334474A (zh) * 2018-11-13 2021-02-05 株式会社Lg化学 化合物及包含其的有机发光器件
CN112334474B (zh) * 2018-11-13 2023-07-21 株式会社Lg化学 化合物及包含其的有机发光器件
CN109867646A (zh) * 2018-12-31 2019-06-11 瑞声科技（南京）有限公司 一种杂环化合物及其应用
CN111434658A (zh) * 2019-01-15 2020-07-21 机光科技股份有限公司 有机电致发光材料和器件
TWI809238B (zh) * 2019-01-15 2023-07-21 機光科技股份有限公司 有機電致發光材料和裝置
KR20200090122A (ko) * 2019-01-18 2020-07-28 주식회사 엘지화학 유기 발광 소자
KR102405389B1 (ko) * 2019-01-18 2022-06-07 주식회사 엘지화학 유기 발광 소자
CN110571340A (zh) * 2019-08-23 2019-12-13 陕西莱特光电材料股份有限公司 有机电致发光器件、电子装置
CN113149943A (zh) * 2021-05-10 2021-07-23 吉林奥来德光电材料股份有限公司 荧光化合物及其制备方法和包含其的有机电致发光器件
CN113149943B (zh) * 2021-05-10 2023-08-22 吉林奥来德光电材料股份有限公司 荧光化合物及其制备方法和包含其的有机电致发光器件

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