WO2015093813A2 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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WO2015093813A2
WO2015093813A2 PCT/KR2014/012387 KR2014012387W WO2015093813A2 WO 2015093813 A2 WO2015093813 A2 WO 2015093813A2 KR 2014012387 W KR2014012387 W KR 2014012387W WO 2015093813 A2 WO2015093813 A2 WO 2015093813A2
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substituted
unsubstituted
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aryl
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WO2015093813A3 (fr
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이용환
김영배
이창준
신진용
김태형
백영미
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주식회사 두산
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    • 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
    • C07D487/22—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 four or more hetero 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
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
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    • 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
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    • 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
    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
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    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • 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
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    • 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
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • 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 a novel organic compound that is excellent in thermal stability due to a high glass transition temperature, and can improve the luminous efficiency of the device by improving the binding force between holes and electrons.
  • 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:
  • Y 1 and Y 2 are the same as or different from each other, and each independently a single bond, or in the group consisting of O, S, N (R 13 ) and C (R 14 ) (R 15 )
  • X 1 to X 4 are the same as or different from each other, and each independently C (R 16 ) or N,
  • Y 1 and Y 2 are hydrogen, wherein X 1 and X 3 are the same or different from each other, and are each independently C (R 16 ) or N, and X 2 and X 4 are the same as each other. Or different and are C (R 16 ) 2 or N (Ar 2 );
  • Ar 1 is 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, a 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 an unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstit
  • R 1 to R 16 and Ar 2 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
  • cycloalkyl group of ⁇ C 40 a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atom
  • R 1 to R 16 Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group of Ar 1 and Ar 2 , cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron
  • the group, the arylphosphine group, the arylphosphine oxide group and the 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 to 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 cycloalkyl
  • 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, wherein at least one of the at least one organic layer comprises the compound.
  • 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 comprises the compound.
  • the organic material layer containing the compound is preferably a light emitting layer.
  • 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.
  • novel compounds according to the present invention are condensed with each other by two arylamine moieties bonded to carbon positions 2 and 3 of the carbazole moiety to form an octagonal ring to form a basic skeleton.
  • the compound represented by the 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 compound represented by Formula 1 has a strong electron donating due to the carbazole moiety and the arylamine moiety which are strong electron donating groups (EDGs). Therefore, when an electron withdrawing group (EWG) having strong electron absorption in the basic skeleton is introduced as a substituent, the entire molecule has a bipolar characteristic, and the binding force between holes and electrons can be increased. Therefore, when the compound of Chemical Formula 1 is applied to the organic EL device, the phosphorescence property of the device may be improved compared to the conventional CBP, and the hole injection and / or transport capacity, the luminous efficiency, the driving voltage, and the lifespan characteristics may be improved. have.
  • EWG electron withdrawing group
  • the compound of Chemical Formula 1 may have an energy level controlled according to the substituents, thereby having a wide band gap (sky blue to red), and thus not only a light emitting layer material but also a hole transporting layer material, a hole injection layer material, and the like. May also be applied.
  • the compound represented by the formula (1) by introducing a variety of aromatic ring (aromatic ring) substituents to the basic skeleton, the molecular weight of the compound can be significantly increased to improve the glass transition temperature, thereby higher than the conventional CBP May have thermal stability.
  • the compound of Formula 1 may not only improve the thermal stability of the compound itself due to the basic skeleton, it is also effective in suppressing the crystallization of the organic layer containing the compound of Formula 1. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve durability and lifespan 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.
  • the dotted line represents a bond or a non-bond.
  • Y 1 and Y 2 are the same as or different from each other, and each independently a single bond, or consist of O, S, N (R 13 ) and C (R 14 ) (R 15 ). It is selected from the group, Preferably it is a single bond or it may be O or S.
  • X 1 to X 4 are the same as or different from each other, and each independently C (R 16 ) or N. However, when there are a plurality of C (R 16 ), they are the same or different from each other.
  • X 1 and X 3 are the same as or different from each other, and are each independently C (R 16 ) or N, X 2 and X 4 are the same as or different from each other, and C (R 16 ) 2 or N (Ar 2 ) to be. However, when there are a plurality of C (R 16 ), they are the same or different from each other.
  • R 1 to R 16 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium (D), 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
  • R 1 to R 16 and Ar 2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C 6 ⁇ C 40 aryl group, and a substituted or unsubstituted nuclear atom of 5 to 40 It may be selected from the group consisting of heteroaryl groups, or may be combined with adjacent groups to form a condensed ring, aromatic ring or heteroaromatic ring.
  • R 1 to R 15 and Ar 2 are all hydrogen
  • R 16 is selected from the group consisting of hydrogen and a substituted or unsubstituted C 6 to C 40 aryl group (eg phenyl group), or adjacent to A C 6 to C 12 condensed aromatic ring (e.g., a condensed benzene ring, etc.), a condensed heteroaromatic ring having 5 to 9 nuclear atoms (e.g., a condensed benzofuran ring), an aromatic ring of C 6 to C 12 (Eg, a phenyl group) or a heteroaromatic ring having 5 to 9 nuclear atoms.
  • a substituted or unsubstituted C 6 to C 40 aryl group eg phenyl group
  • a C 6 to C 12 condensed aromatic ring e.g., a condensed benzene ring, etc.
  • a condensed heteroaromatic ring having 5 to 9 nuclear atoms e
  • both X 1 and X 2 are C (R 16 ), or both X 3 and X 4 are C (R 16 ), a plurality of R 16 are bonded to each other to condense a benzene ring, a condensed benzofuran ring or a phenyl group. Can be formed.
  • Ar 1 is 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, a 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 an unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstit
  • Ar 1 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, and a substituted or unsubstituted C 6 ⁇ C 40 arylamine It may be selected from the group consisting of groups.
  • R 1 to R 16 , Ar 1 and Ar 2 may be each independently selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto. .
  • Ar 1 may be more preferably selected from the group consisting of the following substituents A1 to A67.
  • Examples of the compound represented by Chemical Formula 1 according to the present invention include a compound represented by the following Chemical Formulas 2 to 8, but are not limited thereto.
  • Y 1 and Y 2 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of O, S, N (R 13 ) and C (R 14 ) (R 15 ),
  • X 1 to X 4 are the same as or different from each other, and each independently C (R 16 ) or N,
  • X 1 and X 3 are the same as or different from each other, and each independently C (R 16 ) or N, X 2 and X 4 are the same as or different from each other, and C (R 16 ) 2 or N (Ar 2 ),
  • R 1 to R 16 , Ar 1 and Ar 2 are the same as defined in Chemical Formula 1.
  • Formula 1 according to the present invention is a compound represented by the following formula 6 to formula 15, but is not limited thereto.
  • Y 1 and Y 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (R 13 ) and C (R 14 ) (R 15 ),
  • X 1 to X 4 are the same as or different from each other, and each independently C (R 16 ) or N,
  • R 1 to R 16 and Ar 1 are the same as defined in Chemical Formula 1.
  • Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto.
  • 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 fused 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 fused form to 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 Interpret as included.
  • 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
  • Fused ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • the present invention is an organic electroluminescent device comprising a compound represented by the above-described formula (1), preferably a compound represented by any one of formulas 2 to 5, more preferably a compound represented by any one of formulas 6 to 15 to provide.
  • the organic electroluminescent device includes an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer.
  • a compound represented by Formula 1 preferably a compound represented by any one of Formulas 2 to 5, and more preferably a compound represented by any one of Formulas 6 to 15.
  • 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, 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 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 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 described above 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.
  • 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, 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.
  • Compound C-7 (Compound C7) was carried out in the same manner as in Synthesis Example 1, except that (4-bromophenyl) triphenylsilane (23.01 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1. 14.94 g, yield: 39%) was obtained.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • Example 2 Except for using the compounds C-2 to C-19 synthesized in Synthesis Examples 2 to 19 instead of the compound C-1 used as a light emitting host material in Example 1, the same as in Example 1 To produce a green organic EL device.
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C-1 as a light emitting host material when forming the emission layer.
  • the structure of CBP used is as follows.
  • the green organic EL device of Examples 1 to 19 using the compounds C-1 to C-19 as the light emitting layer material compared to the green organic EL device of Comparative Example 1 using the conventional CBP, It can be seen that the excellent performance in terms of driving voltage.

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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 And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

La présente invention porte sur un composé représenté par la formule (1) ci-dessous et sur un dispositif électroluminescent organique le comprenant. Le composé représenté par la formule (1) ci-dessous est inclus dans au moins une couche organique, de préférence une couche luminescente, et, de ce fait, l'efficacité lumineuse, la tension de commande, la durée de vie, etc. d'un dispositif peuvent être améliorées.
PCT/KR2014/012387 2013-12-17 2014-12-16 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2015093813A2 (fr)

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KR1020130157473A KR101622811B1 (ko) 2013-12-17 2013-12-17 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2013-0157473 2013-12-17

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017086729A1 (fr) * 2015-11-20 2017-05-26 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, matériau organique électroluminescent et dispositif organique électroluminescent les comprenant
WO2017188672A1 (fr) * 2016-04-28 2017-11-02 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102677628B1 (ko) 2015-11-20 2024-06-25 듀폰스페셜티머터리얼스코리아 유한회사 유기 전계 발광 화합물, 유기 전계 발광 재료, 및 이를 포함하는 유기 전계 발광 소자
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
KR102370068B1 (ko) * 2016-04-28 2022-03-07 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102306983B1 (ko) * 2019-06-24 2021-09-30 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070114562A (ko) * 2006-05-29 2007-12-04 삼성에스디아이 주식회사 유기 발광 소자 및 이를 구비한 평판 표시 장치
KR20110043342A (ko) * 2009-10-21 2011-04-27 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20120104246A (ko) * 2009-11-14 2012-09-20 메르크 파텐트 게엠베하 전자 소자용 재료
KR20130093207A (ko) * 2012-02-14 2013-08-22 덕산하이메탈(주) 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자장치

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070114562A (ko) * 2006-05-29 2007-12-04 삼성에스디아이 주식회사 유기 발광 소자 및 이를 구비한 평판 표시 장치
KR20110043342A (ko) * 2009-10-21 2011-04-27 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20120104246A (ko) * 2009-11-14 2012-09-20 메르크 파텐트 게엠베하 전자 소자용 재료
KR20130093207A (ko) * 2012-02-14 2013-08-22 덕산하이메탈(주) 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자장치

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017086729A1 (fr) * 2015-11-20 2017-05-26 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, matériau organique électroluminescent et dispositif organique électroluminescent les comprenant
CN108368120A (zh) * 2015-11-20 2018-08-03 罗门哈斯电子材料韩国有限公司 有机电致发光化合物、有机电致发光材料及包含其的有机电致发光装置
WO2017188672A1 (fr) * 2016-04-28 2017-11-02 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
CN109071556A (zh) * 2016-04-28 2018-12-21 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
CN109071556B (zh) * 2016-04-28 2022-04-05 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置

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