WO2014104663A1 - Composé organique et élément électroluminescent organique comprenant ce composé - Google Patents

Composé organique et élément électroluminescent organique comprenant ce composé Download PDF

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WO2014104663A1
WO2014104663A1 PCT/KR2013/011957 KR2013011957W WO2014104663A1 WO 2014104663 A1 WO2014104663 A1 WO 2014104663A1 KR 2013011957 W KR2013011957 W KR 2013011957W WO 2014104663 A1 WO2014104663 A1 WO 2014104663A1
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group
substituted
unsubstituted
aryl
compound
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Korean (ko)
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김성무
배형찬
백영미
손효석
김태형
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주식회사 두산
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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • 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
    • C07D487/12—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 three hetero rings
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • 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
    • C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C09K2211/1081—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with sulfur

Definitions

  • the present invention relates to a novel organic compound which can be used as a material for an organic electroluminescent device, and an organic electroluminescent device in which the luminous efficiency, driving voltage, lifetime, 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 hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer
  • anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is 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 the following formula (1).
  • At least one of R 3 and R 4, R 4 and R 5 , and R 5 and R 6 may be combined with Formula 2 to form a condensed ring;
  • the dotted line is a condensation site
  • At least one of R 7 and R 8, R 8 and R 9 , and R 9 and R 10 may be combined with Formula 3 to form a condensed ring;
  • X 1 is selected from O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 )
  • R 1 to R 14 which form a condensed ring are the same 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
  • Ar 1 to Ar 7 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a 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
  • C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, a nuclear atom in R 1 to R 14 and Ar 1 to Ar 7 the number of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C arylamine group of 6 ⁇ C 40, aryl group of C 6 ⁇ C 40, C 3 C 40 -cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkylboron group, C 6 -C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group, and a C 6 ⁇ C 40 aryl silyl groups are each independently selected from deuterium,
  • the present invention also provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes the compound of Formula 1
  • an organic electroluminescent device characterized by.
  • At least one of the one or more organic material layers 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 is a blue, green or red phosphorescent host material.
  • the compound represented by Formula 1 of the present invention is excellent in thermal stability and phosphorescence properties, it may be applied to the light emitting layer of the organic EL device.
  • the novel compound according to the present invention is a structure in which an indole moiety is fused to a terminal of a pyrrolocarbazole moiety to form a basic skeleton, and a variety of substituents are bonded to the basic skeleton. It is characterized by being displayed.
  • the compound represented by Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], and has a wide energy band gap, The bonding force of the electrons can be increased. Therefore, when the compound of Formula 1 is used in an organic EL device, the driving voltage, efficiency (light emitting efficiency, power efficiency), lifetime, and luminance of the device may be improved.
  • the conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the compound not only has a wide bandgap due to the indole moiety bound to the terminal of the pyrrolocarbazole moiety, but also the bipolar properties of the entire molecule due to various aromatic ring substituents. Since the bonding force between the holes and the electrons can be increased, superior characteristics as the host material of the light emitting layer can be exhibited compared to the conventional CBP. As a result, the phosphorescent property of the device may be improved, and the hole injection ability and / or the transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics may be improved. In addition, the energy level may be controlled by the substituents to have a wide bandgap (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 molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced to the bound indole moiety, the glass transition temperature (Tg) can be improved, which is why compared to the conventional CBP It can have high thermal stability.
  • Tg glass transition temperature
  • the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
  • the compound of Chemical Formula 1 according to the present invention when adopted as a hole injection / transport layer material of an organic EL device, a phosphorescent host material of blue, green and / or red color, the compound having the excellent efficiency and lifespan may be superior to the conventional CBP. Can be. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect on maximizing the performance in the full color organic light emitting panel.
  • At least one of R 3 and R 4, R 4 and R 5 , R 5 and R 6 may be combined with Formula 2 to form a pyrrolocarbazole skeleton condensed ring, At the same time, at least one of R 7 and R 8, R 8 and R 9 , R 9 and R 10 in Formula 2 is combined with Formula 3 of an indole-based structure to form a condensed ring.
  • the compound represented by Chemical Formula 1 of the present invention may be further embodied as a compound represented by any one of the following Chemical Formulas C-1 to C-36.
  • R 1 to R 14 In Formulas C-1 to C-36, R 1 to R 14 , X 1, and Ar 1 to Ar 2 are the same as defined in Formula 1, respectively.
  • X 1 may be selected from O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 ), preferably Is S or N (Ar 3 ), more preferably N (Ar 3 ).
  • a substituent which does not form a condensed ring with Formula 2 and / or Formula 3, for example, at least one of R 3 and R 4, R 4 and R 5 , R 5 and R 6 ; And R 1 to R 14 except for at least one of R 7 and R 8, R 8 and R 9 , R 9 and 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 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 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 unsubsti
  • R 1 to R 14 except for the substituents forming the condensed ring are the same or different from each other, each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 It is preferably selected from the group consisting of an aryl group of -C 40 , and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms.
  • Ar 1 to Ar 7 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 , 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 nuclear atoms,
  • substituents each introduced into an alkyl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group, and an arylsilyl group are each independently deuterium, halogen, cyano group, C 1 to C 40
  • Ar 1 to Ar 7 are each independently selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 aryl group and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms. Do.
  • one or more substituents respectively introduced into the aryl group and heteroaryl group of Ar 1 to Ar 7 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 A group consisting of -C 40 arylamine group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, and C 6 -C 40 arylsilyl group It may be substituted with one or more substituents selected from. In this case, when a plurality of substituents are introduced, these substituents may be the same or different from each other.
  • R 1 to R 14 and Ar 1 to Ar 7 are each more preferably selected from hydrogen or a substituent group consisting of the following substituents S1 to S204. However, it is not limited thereto.
  • R 1 to R 14 , Ar 1 to Ar 7 may be each independently selected from hydrogen or the following substituent group.
  • unsubstituted alkyl is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl and the like.
  • Unsubstituted alkenyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, examples of which include vinyl, allyl (allyl), isopropenyl, 2-butenyl, and the like, but are not limited thereto.
  • Unsubstituted alkynyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, examples being ethynyl , 2-propynyl, and the like, but is not limited thereto.
  • Unsubstituted aryl means a monovalent substituent derived from an aromatic hydrocarbon of 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or condensed form with one another. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Unsubstituted heteroaryl 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. It is understood that two or more rings may be attached in a simple or condensed form with each other and further include a condensed form 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 It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Unsubstituted aryloxy is a monovalent substituent represented by RO-, wherein R is an aryl having 5 to 60 carbon atoms.
  • R is an aryl having 5 to 60 carbon atoms.
  • aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Unsubstituted alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and has a linear, branched or cyclic structure It is to be interpreted as including. Examples of such alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Unsubstituted arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Unsubstituted cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Unsubstituted heterocycloalkyl 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 or S Is substituted with a hetero atom such as Non-limiting examples thereof 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 means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • 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 of the present invention includes an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, and at least one of the at least one organic layer Compound represented by the formula (1), preferably a compound represented by the formula (C-1) to a compound represented by the formula (C-36).
  • the compounds represented by any one of the formulas C-1 to C-36 may be used alone or two or more may be mixed.
  • 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, at least one of the organic material layer may include a compound represented by the formula (1).
  • the organic material layer including the compound of Compound 1 may be a light emitting layer.
  • the light emitting layer of the organic EL device may include a host material, wherein the host material may include the compound of Formula 1 as a host material.
  • the compound of Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage 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 of the present invention can be used as a phosphorescent host of the light emitting layer.
  • the 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, a 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.
  • at least one layer eg, a 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.
  • 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.
  • 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.
  • PCI-1 (3.0 g, 6.7 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.12 g, 8.04 mmol), which are the compounds prepared in Preparation Example 6, under a nitrogen stream.
  • Cu powder (0.21 g, 3.35 mmol)
  • K 2 CO 3 (0.92 g, 6.7 mmol
  • Na 2 SO 4 1.9 g, 13.4 mmol
  • nitrobenzene 80 ml
  • PCI-1 (3.0 g, 6.7 mmol), 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, which are the compounds prepared in Preparation Example 6 under a nitrogen stream, 1.93 g, 8.04 mmol), Pd (OAc) 2 (0.07 g, 0.33 mmol), NaO (t-bu) (1.28 g, 13.4 mmol), P (t-bu) 3 (0.13 g, 0.67 mmol) and Toluene (100 ml) was mixed and then stirred at 110 ° C. for 12 h.
  • PCI-13 (3.0 g, 6.7 mmol) is used instead of PCI-1, and 2- (3-bromophenyl) -4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-diphenylpyridine (3.1g 8.04 mmol), the same procedure as in Synthesis Example 2 was carried out to obtain 17 (3.2 g, yield 63%) as a target 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 transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • An organic EL device was manufactured in the same manner as in Example 1, except that Compounds 2 to 45, which were synthesized in Synthesis Examples 2 to 45, were used instead of Compound 1 used as the host material in forming the emission layer in Example 1. Prepared.
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1 used as a host material in forming the emission layer in Example 1.
  • the structure of CBP used is as follows.

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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne : un composé présentant une nouvelle structure dans laquelle une fraction indole est condensée avec l'extrémité terminale d'une fraction pyrrolocarbazole de sorte à constituer un squelette de base, et divers substituants sont liés au squelette de base ; et un élément électroluminescent organique comprenant ledit composé. Dans la présente invention, le composé peut être incorporé dans une ou plusieurs couches organiques et de préférence dans une couche luminescente de sorte que des propriétés telles que l'efficacité électroluminescente, la tension d'attaque et la durée de vie de l'élément peuvent être améliorées.
PCT/KR2013/011957 2012-12-26 2013-12-20 Composé organique et élément électroluminescent organique comprenant ce composé WO2014104663A1 (fr)

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KR1020120152964A KR101548040B1 (ko) 2012-12-26 2012-12-26 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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USRE47654E1 (en) 2010-01-15 2019-10-22 Idemitsu Koasn Co., Ltd. Organic electroluminescence device

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US10968226B2 (en) * 2017-06-23 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices

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JP2006193729A (ja) * 2004-12-14 2006-07-27 Xerox Corp インドロカルバゾール残基を含む化合物、ならびにそのような化合物を含む電子デバイス及び薄膜トランジスタ
WO2011099451A1 (fr) * 2010-02-12 2011-08-18 新日鐵化学株式会社 Élément électroluminescent organique
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USRE47654E1 (en) 2010-01-15 2019-10-22 Idemitsu Koasn Co., Ltd. Organic electroluminescence device

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KR20140084413A (ko) 2014-07-07

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