WO2014104665A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2014104665A1
WO2014104665A1 PCT/KR2013/011962 KR2013011962W WO2014104665A1 WO 2014104665 A1 WO2014104665 A1 WO 2014104665A1 KR 2013011962 W KR2013011962 W KR 2013011962W WO 2014104665 A1 WO2014104665 A1 WO 2014104665A1
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group
compound
substituted
unsubstituted
synthesis
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PCT/KR2013/011962
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Korean (ko)
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김영배
김회문
백영미
김태형
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주식회사 두산
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Publication of WO2014104665A1 publication Critical patent/WO2014104665A1/fr

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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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
    • H10K85/60—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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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 and the like 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.
  • 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:
  • R 3 to R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 2 -C 40 alkenyl group , Substituted or unsubstituted C 2 -C 40 alkynyl group, substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkyloxy group, substituted or unsubstituted C 6 ⁇ C 40 arylamine group, substituted or unsubstituted C 3 ⁇ C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40
  • R 3 and R 4, R 4 and R 5, and R 5 and R 6 may be bonded to each other to form a condensed ring represented by Formula 2 below;
  • the dotted line is a site where condensation occurs with the compound of Formula 1;
  • R 1 , R 2 , and R 7 to R 10 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C Alkenyl group of 2 to C 40 , substituted or unsubstituted alkynyl group of C 2 to C 40 , substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C 6 -C 40 aryloxy group, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or unsubstituted C 6 -C 40 arylamine group, substituted or unsubstituted A substituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having
  • n is an integer from 0 to 4, and if n is an integer from 1 to 4, at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C 1 -C 40 alkyl group, substituted or unsubstituted C Alkenyl group of 2 to C 40 , substituted or unsubstituted alkynyl group of C 2 to C 40 , substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C 6 -C 40 aryloxy group, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or unsubstituted C 6 -C 40 arylamine group, substituted or unsubstituted A substituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group
  • X 1 and X 2 are each independently selected from O, S, Se, N (Ar 1 ) and C (Ar 2 ) (Ar 3 ), wherein at least one of X 1 and X 2 is N (Ar 1 ) and ;
  • Ar 1 to Ar 3 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 ⁇ C 40 alkyl group, a substituted or unsubstituted C 2 ⁇ C 40 alkenyl group, a substituted or unsubstituted C 2 ⁇ C 40 alkynyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 aryloxy group , Substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 1 to C
  • an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group 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, 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 Alkyl jade C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, C 3
  • the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, characterized in that at least one of the at least one organic layer comprises the compound.
  • An organic electroluminescent device is provided.
  • At least one of the one or more organic material layers containing the compound is preferably a light emitting layer.
  • 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.
  • novel compound according to the present invention forms a basic skeleton by fusion of an indole moiety at the end of an indenoindole moiety, and a structure in which various substituents are bonded to the basic skeleton, represented by Chemical Formula 1 It is characterized by.
  • the compound represented by Chemical Formula 1 is a structure in which an indole moiety having a large electron donor is bonded to an end of an indenoindole moiety.
  • Various aromatic ring substituents having electrophoretic (Electron Withdrawing) properties can enhance the binding force between holes and electrons while the entire molecule has bipolar properties. Therefore, when the compound is applied to the organic EL device, since it can exhibit excellent properties as a host material of the light emitting layer compared to the conventional CBP, the phosphorescence property of the device is improved, and at the same time, the hole injection capacity and / or transport capacity, luminous efficiency, Driving voltage, lifespan characteristics and the like can be improved.
  • the energy level may be adjusted according to the substituents to have a wide band gap (sky blue to red), and thus may be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, and the like.
  • the host material should have a triplet energy gap of the host higher than the dopant. That is, in order to effectively provide phosphorescence from the dopant, the lowest excited state of the host must be higher in energy than the lowest emitted state of the dopant.
  • the compound represented by Formula 1 of the present invention has an indole moiety as a central skeleton and has triplet energy suitable for phosphorescence emission.
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the bound indole moiety, thereby improving glass transition temperature, and thus, the conventional CBP (4,4). -dicarbazolybiphenyl) may have a higher thermal stability.
  • thermal stability of the compound may be improved and crystallization of the organic material layer including the compound of Formula 1 may be improved. Effective at suppressing Therefore, the organic EL device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
  • the compound represented by the formula (1) according to the present invention when adopted as a material of the hole injection / transport layer of the organic EL device, phosphorescent host material of blue, green and / or red, the efficiency and lifespan are superior to the conventional CBP. It can be effective. Therefore, the compound represented by Formula 1 of the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the life of the organic EL device has a great effect on maximizing the performance in the full color organic light emitting panel.
  • R 3 to R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted A C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted nuclear atom having 5 to 40 Heteroaryl group, substituted or unsubstituted C 6 -C 40 aryloxy group, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or unsubstituted C 6 -C 40 arylamine group, substituted Or an unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to
  • an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron Group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group 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, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C
  • R 3 to R 6 are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.
  • R 3 and R 4, R 4 and R 5, and R 5 and R 6 may be bonded to each other to form a condensed ring represented by Formula 2 above.
  • R 3 and R 4 combine with each other to form a condensed ring represented by Formula 2, a compound represented by Formula 3 or 4 below is formed.
  • a dotted line means a site where condensation occurs with at least one of R 3 and R 4, R 4 and R 5, and R 5 and R 6 of Chemical Formula 1.
  • R 1 , R 2 , and R 7 to R 10 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, 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 6 ⁇ C 40 aryl group, a substituted or unsubstituted number of 5 to 40 heteroaryl unsubstituted nucleus atoms
  • Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes 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 the , C 6 -C 40
  • R 1 , R 2 , and R 7 to R 10 are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.
  • N is an integer of 0 to 4.
  • n 0, it means that hydrogen is not substituted by the substituent Ra.
  • n is an integer of 1 to 4
  • Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or Unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted nuclear atom 5 to 5 40 heteroaryl groups, substituted or unsubstituted C 6 -C 40 aryloxy groups, substituted or unsubstituted C 1 -C 40 alkyloxy groups, substituted or unsubstituted C 6 -C 40 arylamine groups , Substituted or unsubstituted C 3 to C 40 cycl
  • Arylphosphine group, arylphosphine oxide group and arylsilyl group 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, nuclear atom 5 ⁇ 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycl
  • n is an integer of 0 to 4, when n is an integer of 1 to 4, one or more Ra may be selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.
  • X 1 and X 2 are each independently selected from O, S, Se, N (Ar 1 ) and C (Ar 2 ) (Ar 3 ), wherein X 1 and X 2 At least one is N (Ar 1 ), preferably X 1 and X 2 may both be N (Ar 1 ).
  • Ar 1 to Ar 3 are the same as or different from each other, and each independently substituted or unsubstituted C 1 ⁇ C 40 Alkyl group, substituted or unsubstituted C 2 ⁇ C 40 Alkenyl group, substituted or unsubstituted C 2 Alkynyl group of -C 40 , substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group of 5 to 40 nuclear atoms, substituted or unsubstituted C 6 -C 40 aryl jade Periodic, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyl
  • Ar 1 to Ar 3 may be the same as or different from each other, and each independently selected from the group consisting of structures represented by the following substituents S1 to S206, but is not limited thereto.
  • Examples of the compound represented by Formula 1 according to the present invention include, but are not limited to, compounds represented by the following Formulas 3 to 8.
  • R 1 to R 10 , Ra, X 1 and X 2 , Ar 1 to Ar 3 and n are the same as defined in Chemical Formula 1, respectively.
  • alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, and iso-amyl. And hexyl.
  • alkenyl is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl, and the like.
  • 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 at least one carbon-carbon triple bond, and examples thereof include ethynyl, 2-propynyl etc. are mentioned.
  • Aryl in the present invention 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 aryls include 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 attached to each other (pendant) or fused (fused) may also be included, and further construed to include a form 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, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furany
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • R'O- monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • alkyloxy include 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 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 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 present invention provides an organic electroluminescent device comprising a compound represented by Formula 1, preferably a compound represented by Formula 3 to Formula 8.
  • the present invention is an organic electroluminescent device comprising an anode (anode), a cathode (cathode) and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic material layer is It includes a compound represented by the formula (1), preferably a compound represented by the formula (3) to (8). In this case, the compounds may be used alone or in combination of two or more.
  • 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 containing the compound of Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention 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 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 represented by Formula 1 of the present invention 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 may be formed using other materials and methods known in the art, except that one or more layers (eg, a light emitting layer) of the organic material layer are formed to include the compound represented by Chemical Formula 1. It can be prepared by forming an 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.
  • examples of the anode material 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-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • Step 1 9-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole, and 7-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b ] indole synthesis
  • a compound 22 (3.14 g) was obtained by the same procedure as in Synthesis Example 2, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 2. , Yield: 59%).
  • a compound 23 (3.47 g) was prepared in the same manner as in Synthesis Example 3, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 3. , Yield: 59%).
  • a compound 27 (2.81 g) was prepared by the same procedure as in Synthesis Example 15, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 15. , Yield: 62%).
  • Compound 29 (3.83g) was prepared in the same manner as in Synthesis Example 17, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 17. , Yield: 75%).
  • Compound 35 (3.47 g) was prepared by the same procedure as in Synthesis Example 4, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 4. , Yield: 59%).
  • Compound 40 (3.21g) was prepared in the same manner as in Synthesis Example 17, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 17. , Yield: 63%).
  • Compound 50 (3.17g) was prepared in the same manner as in Synthesis Example 16, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 16. , Yield: 62%).
  • a compound 51 (3.52g) was prepared in the same manner as in Synthesis Example 17, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 17. , Yield: 69%).
  • a compound 57 (3.27 g) was prepared by the same procedure as in Synthesis Example 1, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 1. , Yield: 69%).
  • a compound 61 (3.45 g) was prepared by the same procedure as in Synthesis Example 20, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 20. , Yield: 55%).

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique le comprenant, l'élément électroluminescent organique a une efficacité d'électroluminescence améliorée, une tension d'excitation améliorée et une durée de vie de service améliorée ou similaire par l'introduction, dans l'élément électroluminescent organique, d'une couche électroluminescent qui utilise le composé organique comme matière hôte.
PCT/KR2013/011962 2012-12-24 2013-12-20 Composé organique et élément électroluminescent organique le comprenant WO2014104665A1 (fr)

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KR20120152632 2012-12-24
KR10-2012-0152632 2012-12-24
KR1020130099015A KR101571598B1 (ko) 2012-12-24 2013-08-21 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2013-0099015 2013-08-21

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150380663A1 (en) * 2014-06-26 2015-12-31 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
CN105679950A (zh) * 2014-12-08 2016-06-15 乐金显示有限公司 有机发光显示装置
CN106935712A (zh) * 2015-12-29 2017-07-07 三星显示有限公司 有机发光器件
US9893298B2 (en) 2014-12-08 2018-02-13 Lg Display Co., Ltd. Organic light emitting display device

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WO1995002323A1 (fr) * 1993-07-16 1995-01-26 Astra Aktiebolag Utilisation de composes d'indenoindole
JP2010229353A (ja) * 2009-03-27 2010-10-14 Mitsubishi Paper Mills Ltd 光電変換材料、半導体電極並びにそれを用いた光電変換素子
JP2010270084A (ja) * 2009-05-25 2010-12-02 Idemitsu Kosan Co Ltd インドール誘導体及びそれを用いた有機薄膜太陽電池
WO2011120908A1 (fr) * 2010-03-29 2011-10-06 Basf Se Cellule solaire à colorant

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
WO1995002323A1 (fr) * 1993-07-16 1995-01-26 Astra Aktiebolag Utilisation de composes d'indenoindole
JP2010229353A (ja) * 2009-03-27 2010-10-14 Mitsubishi Paper Mills Ltd 光電変換材料、半導体電極並びにそれを用いた光電変換素子
JP2010270084A (ja) * 2009-05-25 2010-12-02 Idemitsu Kosan Co Ltd インドール誘導体及びそれを用いた有機薄膜太陽電池
WO2011120908A1 (fr) * 2010-03-29 2011-10-06 Basf Se Cellule solaire à colorant

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150380663A1 (en) * 2014-06-26 2015-12-31 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US10749118B2 (en) * 2014-06-26 2020-08-18 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
CN105679950A (zh) * 2014-12-08 2016-06-15 乐金显示有限公司 有机发光显示装置
CN105679950B (zh) * 2014-12-08 2017-11-28 乐金显示有限公司 有机发光显示装置
US9893298B2 (en) 2014-12-08 2018-02-13 Lg Display Co., Ltd. Organic light emitting display device
CN106935712A (zh) * 2015-12-29 2017-07-07 三星显示有限公司 有机发光器件
US11329231B2 (en) 2015-12-29 2022-05-10 Samsung Display Co., Ltd. Organic light-emitting device

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