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WO2015099450A1 - Composé organique et élément électroluminescent organique le contenant - Google Patents

Composé organique et élément électroluminescent organique le contenant Download PDF

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Publication number
WO2015099450A1
WO2015099450A1 PCT/KR2014/012813 KR2014012813W WO2015099450A1 WO 2015099450 A1 WO2015099450 A1 WO 2015099450A1 KR 2014012813 W KR2014012813 W KR 2014012813W WO 2015099450 A1 WO2015099450 A1 WO 2015099450A1
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substituted
unsubstituted
formula
aryl
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Korean (ko)
Inventor
심재의
손효석
이재훈
박호철
이창준
신진용
백영미
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Doosan Corp
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Doosan Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • H10K50/00—Organic light-emitting devices
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and to an organic electroluminescent device in which the luminous efficiency, driving voltage, lifespan, etc. of the device are improved.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
  • a host / dopant system may be used as a light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp).
  • Metal complex compounds containing Ir, such as 2 are used.
  • 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
  • the existing materials have low glass transition temperature, which leads to poor thermal stability, and thus are not satisfactory in terms of lifespan in OLED devices, and need to be improved in terms of light emission characteristics. Therefore, the development of the material which is more excellent in performance is calculated
  • An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improving the binding force between holes and electrons, thereby improving luminescence properties.
  • an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
  • the present invention provides a compound represented by Formula 1:
  • X 1 to X 3 are the same as or different from each other, and each independently CR 3 or N, and at least one or more of X 1 to X 3 is N, wherein when there are a plurality of CR 3 , a plurality of R 3 are the same as each other; Or different;
  • R 1 to R 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2
  • An alkenyl group of ⁇ C 40 a substituted or unsubstituted alkynyl group of C 2 to C 40 , a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group of 3 to 40 nuclear atoms , Substituted or unsubstituted C 6 ⁇ C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 ⁇ C 40 alkyloxy group, substituted or unsubstituted C 6 ⁇ C 60 aryloxy group, substituted or unsubstit
  • R 1 to R 3 has a structure of Formula 2 or Formula 3;
  • Y 1 to Y 8 are the same as or different from each other, and each independently CR 4 or N, wherein when CR 4 is plural, a plurality of R 4 are the same or different from each other;
  • R 4 and R 5 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2
  • An alkenyl group of ⁇ C 40 a substituted or unsubstituted alkynyl group of C 2 to C 40 , a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group of 3 to 40 nuclear atoms , Substituted or unsubstituted C 6 ⁇ C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 ⁇ C 40 alkyloxy group, substituted or unsubstituted C 6 ⁇ C 60 aryloxy group, substituted or unsubstit
  • L 1 is a single bond or is selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms;
  • n is an integer from 0 to 4.
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, at least one of the one or more organic material layers is an organic electric field characterized in that it comprises a compound of the formula (1) Provided is a light emitting device.
  • At least one of the one or more organic material layers including the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, it is preferable that the light emitting layer.
  • the compound represented by Chemical Formula 1 may be a blue, green or red phosphorescent host material.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability and phosphorescence properties, it may be used as a material of the organic material layer of the organic EL device.
  • the compound represented by Chemical Formula 1 according to the present invention when used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.
  • the novel organic light emitting compound according to the present invention has a structure represented by Chemical Formula 1 in which various substituents, especially N-containing heterocycles, aromatic rings, etc. are connected to a triazolopyridine core.
  • the triazolopyridine core is a core having high triplet energy and stable structure and having electron withdrawing characteristics.
  • a blue phosphorescent host material having excellent efficiency by introducing substituents of carbazoles having high triplet energy and excellent luminescent properties.
  • the triazolopyridine derivatives developed in the present invention have bipolar characteristics throughout the molecule due to a core having electron withdrawing characteristics and carbazole substituents having large electron donating properties. Since the bipolar compound represented by Chemical Formula 1 of the present invention can increase the binding force between holes and electrons, the bipolar compound is not only advantageous as a host in the phosphorescent light emitting layer, but also may be applied as a hole transport layer, a hole injection layer, an electron transport layer, and the like. . Therefore, the compound of Formula 1 may improve the phosphorescence property of the organic EL device, and also improve the carrier transport ability or the luminous efficiency.
  • the compound represented by Chemical Formula 1 may improve the solubility of the core itself, and thus may be utilized as a soluble material as well as a deposition material. Therefore, not only the organic material layer of the organic EL device may be formed through vacuum deposition but also the device may be manufactured by a solution process.
  • the compound of Formula 1 according to the present invention when used as a hole injection / transport layer material or a blue, green and / or red phosphorescent host material, an electron injection / transport layer material of an organic electroluminescent device, For example, compared to CBP), the efficiency and lifespan of the organic EL device can be greatly improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • X 1 to X 3 are the same as or different from each other, and each independently CR 3 or N, at least one or more of X 1 to X 3 is N.
  • a plurality of CR 3 a plurality of R 3 are the same or different from each other.
  • the X 1 to X 3 are all N.
  • R 1 to R 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 ⁇ C 40 alkenyl group, a substituted or unsubstituted C 2 ⁇ C 40 of the alkynyl group, a substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 hetero Cycloalkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or Unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C
  • R 1 to R 3 has the structure of Formula 2 or Formula 3.
  • R 1 to R 3 which do not have a structure of Formula 2 or 3 are each independently a substituted or unsubstituted C 6 ⁇ C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms is preferred, and in particular R 2 is more preferably a substituted or unsubstituted C 6 ⁇ C 60 aryl group, a substituted or unsubstituted heteroaryl group number of from 5 to 60 nucleus atoms.
  • R 1 is carbazole or pyridoindole
  • R 2 or R 3 is preferably a substituted or unsubstituted aryl group or heteroaryl group.
  • Y 1 to Y 8 are the same as or different from each other, and are each independently CR 4 or N, wherein when a plurality of CR 4 are provided, a plurality of R 4 are the same or different from each other.
  • R 4 and / or R 5 which is non-bonded with Formula 1 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, substituted or unsubstituted C 1 ⁇ C 40 alkyl group, substituted or unsubstituted C 2 ⁇ C 40 alkenyl group, substituted or unsubstituted C 2 ⁇ C 40 alkynyl group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, Substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted A substituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group,
  • L is a divalent group linker known in the art, which is a single bond or a substituted or unsubstituted C 6 -C 60 arylene group, and a substituted or unsubstituted nuclear atom 5 To 60 heteroarylene groups.
  • examples of the C 6 to C 60 arylene group and the heteroarylene group having 5 to 60 nuclear atoms include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, and a pyrantrenylene group , Carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group, pyrimididi Nylene groups and the like.
  • L is preferably selected from a single bond, a phenylene group, or a biphenylene group.
  • C 6 ⁇ C 60 arylene group nuclear arylene group having 5 to 60 nuclear atoms are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group , C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 Alkylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 with an aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group
  • n is an integer of 0-4.
  • C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ C 60 aryl amine groups are each independently Deuterium, halogen, cyano, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6 -C 60 amine groups are each independently Deuterium, hal
  • each of these substituents may be the same or different from each other.
  • Compound represented by the formula (1) of the present invention can be more specific to any one of the compounds represented by the following formula (4) to formula (6).
  • X 1 to X 3 , Y 1 to Y 8 , R 1 to R 5 and L 1 are the same as defined in Chemical Formulas 1 to 3.
  • X 1 to X 3 are all N, when L 1 is a phenylene (phenyl linker) group R 1 is a carbazole or pyridoindole group, R 2 is The aromatic compounds may be formed of CC bonds, for example, a substituted or unsubstituted aryl group or heteroaryl group.
  • the compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds, and examples thereof include ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, singly or in combination of two or more rings.
  • a form in which two or more rings are pendant or condensed with each other may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 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 simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 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 1 to 40 alkyl, and is linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention 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, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or 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 5 to 40 carbon atoms
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the compound of Chemical Formula 1 of the present invention may be synthesized in various ways with reference to the synthesis example, and for example, the compound of Formula 1 may be prepared by the following Schemes I and II.
  • step a is a reaction for forming a substituent through a Suzuki coupling reaction
  • step b is an amine (NH 2 ) group.
  • step c is Suzuki coupling when the linker is introduced, Buchwald when reacting with carbazole or pyridoindole It illustrates the progress of the coupling reaction.
  • Scheme II also differs in order only, and the type of reaction used is the same.
  • another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone, or two or more may be used in combination.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1).
  • the organic material layer including the compound of Formula 1 may be a light emitting layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, wherein the host material may include the compound of formula (1).
  • the compound of Formula 1 when included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.
  • the compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green, blue and / or red phosphorescent host, a fluorescent host, or a dopant material.
  • the structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be.
  • the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer.
  • An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • non-limiting furnaces of the positive electrode material usable include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methyl
  • non-limiting examples of the negative electrode material that can be used include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.
  • EtOH / MeOH (1: 1, 1.5 L) mixed solvent was added to 180.5 g (2.60 mol) of hydroxylamine hydrochloride.
  • 271 mL (1.56 mol) of N, N-Diisopropylethylamine was added to the reaction solution, and the mixture was stirred for 1 hour.
  • 158 g (0.52 mol) of 1- (3-Bromo-pyridine-2-yl) -3-carboethoxy-thiourea was added, and the temperature was gradually raised to reflux for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered off. The filtrate was distilled under reduced pressure and the resulting solid was filtered.
  • the obtained solid product was combined, washed with purified water, EtOH / MeOH mixed solvent, n-hexane, and warmed to obtain 91 g (yield 82%) of the title compound.
  • Preparation Example 3 was added 7.0 g (15.9 mmol) and Preparation Example 6 6.5 g toluene 200 mL, EtOH 50 mL, H 2 O 50 mL in (17.5 mmol). 0.92 g (0.8 mmol) of Pd (PPh 3 ) 4 and 5.1 g (47.8 mmol) of Na 2 CO 3 were added thereto, followed by heating to reflux at 120 ° C. for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 13.0 g (yield 74%) of the title compound.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.
  • a solvent such as isopropyl alcohol, acetone, methanol
  • Example 1 Except for using the compound 1, 10, 23, 28, 40, 54, 65, 82, 88, 100 instead of compound 1 used as a host material in forming the light emitting layer in Example 1, the same procedure as in Example 1 This produced a blue organic EL device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1, which was used as a host material, to form an emission layer in Example 1.
  • Example 1 Compound 1 7.38 456 6.20
  • Example 2 Compound 10 7.50 470 6.30
  • Example 3 Compound 23 7.45 475 6.44
  • Example 4 Compound 28 7.40 465 6.36
  • Example 5 Compound 40 7.55 480 6.33
  • Example 6 Compound 54 7.60 477 6.60
  • Example 7 Compound 65 7.45 485 6.20
  • Example 8 Compound 82 7.50 470 6.47
  • Example 9 Compound 88 7.44 466 6.36
  • Example 10 Compound 100 7.55 450 6.29 Comparative Example 1 CBP 7.80 474 5.80

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

Abstract

L'invention concerne un nouveau composé et un élément électroluminescent organique le contenant. Le composé selon la présente invention permet d'améliorer ledit élément électroluminescent organique en termes d'efficacité lumineuse, de tension de commande, de durée de vie et analogues, du fait que ledit composé est utilisé dans une couche organique, de préférence une couche d'émission de lumière de l'élément électroluminescent organique.
PCT/KR2014/012813 2013-12-27 2014-12-24 Composé organique et élément électroluminescent organique le contenant Ceased WO2015099450A1 (fr)

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KR10-2013-0166182 2013-12-27

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CN107266438A (zh) * 2017-08-09 2017-10-20 上海道亦化工科技有限公司 一种杂环类有机电致发光化合物及其有机电致发光器件
CN112300152A (zh) * 2019-07-25 2021-02-02 南京高光半导体材料有限公司 新型双极性绿色磷光主体材料及含有该材料的oled发光器件

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CN111848604B (zh) * 2019-04-25 2022-02-11 上海钥熠电子科技有限公司 有机电致发光材料及其应用
CN110590770B (zh) * 2019-08-22 2020-12-25 武汉尚赛光电科技有限公司 一种基于三唑并吡啶的有机电致发光材料及有机电致发光器件
CN110452689B (zh) * 2019-08-22 2023-02-28 武汉尚赛光电科技有限公司 一种基于三唑并吡啶的有机电致发光材料及有机电致发光器件

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WO2011122381A1 (fr) * 2010-03-31 2011-10-06 Canon Kabushiki Kaisha Nouveau composé de benzoxazolylcarbazole et dispositif électroluminescent organique comprenant celui-ci
WO2013009095A1 (fr) * 2011-07-11 2013-01-17 주식회사 두산 Composé à base de triphénylène et diode électroluminescente organique l'utilisant
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WO2011055934A2 (fr) * 2009-11-03 2011-05-12 제일모직 주식회사 Composé pour dispositif photoélectrique organique et dispositif photoélectrique organique en contenant
WO2011122381A1 (fr) * 2010-03-31 2011-10-06 Canon Kabushiki Kaisha Nouveau composé de benzoxazolylcarbazole et dispositif électroluminescent organique comprenant celui-ci
WO2013009095A1 (fr) * 2011-07-11 2013-01-17 주식회사 두산 Composé à base de triphénylène et diode électroluminescente organique l'utilisant
DE102012022880A1 (de) * 2011-12-22 2013-06-27 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend organische Schichten

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Publication number Priority date Publication date Assignee Title
CN106632325A (zh) * 2017-01-25 2017-05-10 上海道亦化工科技有限公司 一种含有氮杂环的化合物及其有机电致发光器件
CN107266438A (zh) * 2017-08-09 2017-10-20 上海道亦化工科技有限公司 一种杂环类有机电致发光化合物及其有机电致发光器件
CN112300152A (zh) * 2019-07-25 2021-02-02 南京高光半导体材料有限公司 新型双极性绿色磷光主体材料及含有该材料的oled发光器件
CN112300152B (zh) * 2019-07-25 2021-11-19 南京高光半导体材料有限公司 新型双极性绿色磷光主体材料及含有该材料的oled发光器件

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