WO2014092431A1 - Nouveau composé, et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé, et dispositif électroluminescent organique le comprenant Download PDF

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WO2014092431A1
WO2014092431A1 PCT/KR2013/011402 KR2013011402W WO2014092431A1 WO 2014092431 A1 WO2014092431 A1 WO 2014092431A1 KR 2013011402 W KR2013011402 W KR 2013011402W WO 2014092431 A1 WO2014092431 A1 WO 2014092431A1
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group
formula
aryl
compound
alkyl
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심재의
이인혁
백영미
신진용
박호철
이창준
이은정
김태형
이재훈
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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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
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    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
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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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two 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
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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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Definitions

  • the present invention relates to a novel compound and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material included in 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 according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
  • a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.
  • 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.
  • anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
  • a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1).
  • X 1 to X 3 are each independently CR 2 or N, wherein at least one is N,
  • R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine is selected from the pingi, C 6 ⁇ C 60 aryl phosphine oxide group, and the group consisting of
  • A is selected from the group consisting of hydrogen, a C 6 ⁇ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms,
  • L is selected from the group consisting of a single bond, a C 6 ⁇ C 60 arylene group and a heteroarylene group having 5 to 60 nuclear atoms, n is an integer of 0 to 3,
  • Cy 1 is a compound represented by the following formula (2),
  • Y 1 to Y 4 are each independently CR 5 or N, and one of Y 1 and Y 2 , Y 2 and Y 3, and Y 3 and Y 4 forms a condensed ring represented by the following Formula 3,
  • the dotted line means a site where condensation occurs with the compound of Formula 2, and Y 5 to Y 8 are each independently CR 6 or N,
  • Z 1 and Z 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein at least One is N (Ar 1 ),
  • R 3 to R 6 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear hetero atoms 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group and C 6 ⁇ C 60 It is selected from the group consisting of an arylamine group,
  • Ar 1 to Ar 5 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 Aryloxy group of ⁇ C 60 , C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 An arylphosphine group of ⁇ C 60 , a C 6 ⁇ C 60 arylphosphine oxide group and a C 6 ⁇
  • the aryl group and heteroaryl group of A are each independently deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group (preferably C 1 ⁇ C 10 alkyl group), C 2 ⁇ C 40 Alkenyl groups (preferably C 2 to C 10 alkenyl groups), C 2 to C 40 alkynyl groups (preferably C 2 to C 10 alkynyl groups), C 3 to C 40 cycloalkyl groups (preferably A C 3 -C 18 cycloalkyl group), a heterocycloalkyl group having 3 to 40 nuclear atoms (preferably a heterocycloalkyl group having 3 to 18 nuclear atoms), and an aryl group having a C 6 -C 40 (preferably C 6 An aryl group of -C 18 ), a heteroaryl group of 5 to 40 nuclear atoms (preferably a heteroaryl group of 5 to 18 nuclear atoms), an alkyloxy group of C 1 to C 40 (preferably C 1 to) C
  • Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group (preferably C 1 An alkyl group of ⁇ C 10 ), an alkenyl group of C 2 ⁇ C 40 (preferably an alkenyl group of C 2 ⁇ C 10 ), an alkynyl group of C 2 ⁇ C 40 (preferably an alkynyl group of C 2 ⁇ C 10 ) C 3 -C 40 cycloalkyl group (preferably
  • L is connected to any one of Z 1 , Z 2 , R 3 , R 4 and Y 1 to Y 8 of Formula 2 to which Formula 3 is attached.
  • Alkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl and the like.
  • Alkenyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl and the like.
  • Alkynyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
  • Non-limiting examples thereof include ethynyl, 2-propynyl and the like.
  • Cycloalkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon).
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and preferably at least one carbon in the ring, preferably 1 To 3 carbons are substituted with a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • Aryl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms alone or in combination of two or more rings.
  • the two or more rings may be attached in a simple or condensed form with each other.
  • Non-limiting examples thereof include phenyl, biphenyl, triphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, indenyl and the like.
  • Heteroaryl used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 Carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Alkyloxy used in the present invention means a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Can be. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Aryloxy used in the present invention means a monovalent functional group represented by R'O-, wherein R 'is an aryl having 6 to 60 carbon atoms.
  • R ' is an aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkylsilyl used in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • arylamine is substituted with aryl having 6 to 60 carbon atoms. Amine.
  • the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention is an anode; cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer comprises a compound represented by Chemical Formula 1 Provided is a light emitting device.
  • the organic material layer including the compound represented by Chemical Formula 1 is selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, and is preferably a light emitting layer.
  • the compound represented by Chemical Formula 1 may be used as a phosphorescent host of the emission layer.
  • novel compound of the present invention forms a basic skeleton by combining an indene derivative including nitrogen (N) and an indole fusion compound, and is represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 of the present invention not only has excellent phosphorescence properties, but also has excellent electron and / or hole transporting ability, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron, which is an organic material layer of an organic EL device. It can be used as the material of any one of the injection layer. Preferably it can be used as a material of any one of a hole injection layer, a hole transport layer and a light emitting layer, more preferably a material (especially a phosphorescent host) of the light emitting layer.
  • the compound represented by Chemical Formula 1 of the present invention is a combination of an indene derivative and an indole fusion compound into which various substituents are introduced, and has a bipolar characteristic, so that the balance of holes and electron mobility is controlled.
  • the recombination efficiency of the electrons can be improved, thereby exhibiting excellent phosphorescence characteristics.
  • the compound represented by Formula 1 of the present invention has a wide energy bandgap (sky blue ⁇ red) as the energy level is controlled by introducing various substituents into the basic skeleton consisting of an indene derivative containing nitrogen (N) and an indole fusion compound ) Therefore, when the compound of Formula 1 of the present invention is used in an organic electroluminescent device, the phosphorescence property of the device may be improved, and the hole injection ability and / or hole transport ability, the luminous efficiency, the driving voltage and the lifetime characteristics may be improved. .
  • the compound represented by the general formula (1) of the present invention has a significant increase in molecular weight due to the various substituents introduced in the basic skeleton, thereby improving the glass transition temperature, which is a conventional organic electroluminescent device material (for example, CBP [4,4-dicarbazolybiphenyl]) may have a higher thermal stability.
  • a conventional organic electroluminescent device material for example, CBP [4,4-dicarbazolybiphenyl]
  • the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic light emitting device, and further, the lifespan of the organic light emitting device can maximize the performance of the full color organic light emitting panel.
  • X 1 to X 3 of the indene derivative containing nitrogen (N) are each independently CR 2 or N, wherein at least one is preferably nitrogen (N), It is more preferable that all are nitrogen (N).
  • the indene derivative containing nitrogen (N) Is preferably selected from the group consisting of the structures represented by S-1 to S-7, and among them, S-7 which is a triazolopyridine derivative is most preferred.
  • S-7 which is a triazolopyridine derivative is most preferred.
  • R 2 is as defined above, and a plurality of R 2 may be the same as or different from each other.
  • R 1 and R 2 are each independently hydrogen, C 6 ⁇ C 60 aryl group (preferably C 6 ⁇ C 25 aryl group), 5 to 5 nuclear atoms Selected from the group consisting of 60 heteroaryl groups (preferably heteroaryl groups having 5 to 32 nuclear atoms) and arylamine groups having C 6 to C 60 (preferably arylamine groups having C 6 to C 20 ) It is preferable, and it is more preferable that it is hydrogen.
  • R 1 and R 2 and A bonded to the indene derivative may be each independently selected from the group consisting of hydrogen or a structure (substituent) represented by A1 to A70.
  • Cy 1 is preferably selected from the group consisting of compounds represented by the following Formulas 2a to 2f.
  • Z 1 , Z 2, and R 3 to R 6 are the same as defined above.
  • the plurality of R 5 may be the same or different from each other, a plurality of R 6 may be the same or different from each other.
  • L connecting the selected compound is a single bond or phenylene.
  • Z 1 and Z 2 are preferably both N (Ar 1 ), and are bonded to Ar 1 and Z 2 of N (Ar 1 ) bonded to Z 1 .
  • N 1 of Ar (Ar 1) which may be the same or different from each other.
  • Ar 1 is hydrogen, C 6 ⁇ C 60 aryl group (preferably C 6 ⁇ C 18 aryl group) and the number of nuclear atoms 5 It is preferably selected from the group consisting of a heteroaryl group of 60 to 60 (preferably a heteroaryl group having 5 to 18 nuclear atoms).
  • the linking position (bonding position) of L and the compound represented by Formula 2 is not particularly limited, but is connected to any one of Z 1 and Z 2 of Formula 2 to which Formula 3 is bound. It is desirable to be.
  • the compound represented by the formula (1) of the present invention is preferably a compound represented by the following formula (4) or formula (5).
  • A, L, Cy 1 , R 1 and n are as defined above, and a plurality of R 1 are the same as or different from each other.
  • Such a compound represented by Formula 1 of the present invention may be specifically exemplified by the following compounds (1 to 70), but is not limited thereto.
  • Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • the organic electroluminescent device comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It is characterized by including a compound represented by the formula (1).
  • the organic material layer including the compound represented by Chemical Formula 1 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.
  • the organic material layer including the compound of Formula 1 may be a hole injection layer, a hole transport layer or a light emitting layer, more preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device according to the present invention may contain a host material (preferably a phosphorescent host material), in which case, the compound represented by Chemical Formula 1 may be used as the host material.
  • a host material preferably a phosphorescent host material
  • the compound represented by Chemical Formula 1 may be used as the host material.
  • the hole transporting ability is increased to increase the bonding force between the holes and the electrons in the light emitting layer, efficiency (luminescence efficiency and power efficiency), lifetime, luminance, driving voltage, etc.
  • An excellent organic electroluminescent device can be provided.
  • the structure of the organic electroluminescent device according to the present invention is not particularly limited and may be formed of 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.
  • the electron injection layer may be further stacked on the electron transport layer.
  • the organic electroluminescent device according to the present invention may not only have a structure in which an anode, at least one organic material layer, and a cathode are sequentially stacked, but also have a structure in which an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the material that can be used as the anode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, 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 and the like can be used.
  • metals such as vanadium, chromium, copper, zinc, 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
  • the material that can be used as the cathode included in the organic EL device according to the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, Tin or metals such as lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the compound represented by Chemical Formula 1 may be any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, preferably a hole injection layer, a hole transport layer and Except for use in any one of the light emitting layers, more preferably the light emitting layer, it can be made using materials and methods known in the art.
  • the material usable as the substrate included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples may include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
  • Such an organic electroluminescent device of the present invention may be manufactured by a method known in the art, wherein the light emitting layer included in the organic material layer may be manufactured 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.
  • Ar and Ar 'in Schemes 1 and 2 are C 6 ⁇ C 60 aryl group, X is a halogen group.
  • EtOH / MeOH (1: 1, 1.5 L) mixed solvent was added to 180.5 g (2.60 mol) of hydroxylamine hydrochloride. 271 mL (1.56 mol) of N, N-Diisopropylethylamine was added to the reaction solution, and the mixture was stirred for 1 hour. 158 g (0.52 mol) of 1- (3-bromo-pyridine-2-yl) -3-carboethoxy-thiourea synthesized above was added thereto, and the temperature was gradually raised to reflux for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered off. The filtrate was distilled under reduced pressure and the resulting solid was filtered. The obtained solid product was combined, washed with purified water, EtOH / MeOH mixed solvent, n-hexane, and warmed to obtain 91 g (yield 82%) of the title compound.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / NPB (20 nm) / Compound 8, 32, 40, 51, 64, 69 + 10% (piq) 2 Ir (acac) (30nm) /
  • a red organic electroluminescent device was manufactured by stacking BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of compound 8 as a light-emitting host material when forming the light-emitting layer.
  • the red organic electroluminescent devices (Examples 1 to 6) using the compound of the present invention in the light emitting layer have a driving voltage and a red organic electroluminescent device (comparative example) using the conventional CBP in the light emitting layer. It can be seen that the excellent performance in terms of current efficiency.
  • the compound represented by Formula 1 according to the present invention may be applied to an organic material layer, preferably a light emitting layer of the organic electroluminescent device because of excellent thermal stability and phosphorescence properties. That is, when the light emitting layer of the organic electroluminescent device includes the compound represented by Chemical Formula 1 as a phosphorescent host material, the efficiency (light emitting efficiency and power efficiency), lifetime, brightness and driving of the device compared to the case of including a conventional host material The voltage can be improved, and furthermore, the performance and lifetime of the full color organic electroluminescent panel can be greatly improved.

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

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé dans une couche organique, et de façon plus préférable, dans une couche émettant de la lumière du dispositif électroluminescent organique. Ainsi, l'efficacité d'émission de lumière, la tension de commande, la durée de vie de service, etc. du dispositif électroluminescent organique peuvent être améliorées.
PCT/KR2013/011402 2012-12-10 2013-12-10 Nouveau composé, et dispositif électroluminescent organique le comprenant WO2014092431A1 (fr)

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KR1020120142824A KR101601354B1 (ko) 2012-12-10 2012-12-10 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2012-0142824 2012-12-10

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KR102198515B1 (ko) * 2014-12-23 2021-01-05 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102307236B1 (ko) * 2014-12-23 2021-10-01 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR101965928B1 (ko) * 2015-06-29 2019-04-04 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102587382B1 (ko) * 2016-04-29 2023-10-12 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102617613B1 (ko) * 2016-10-24 2023-12-27 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180046152A (ko) 2016-10-27 2018-05-08 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN111848604B (zh) * 2019-04-25 2022-02-11 上海钥熠电子科技有限公司 有机电致发光材料及其应用
CN112300152B (zh) * 2019-07-25 2021-11-19 南京高光半导体材料有限公司 新型双极性绿色磷光主体材料及含有该材料的oled发光器件

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KR20110048838A (ko) * 2009-11-03 2011-05-12 제일모직주식회사 유기광전소자용 조성물, 이를 이용한 유기광전소자 및 이를 포함하는 표시장치
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KR20130076080A (ko) * 2011-12-28 2013-07-08 이-레이 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 카바졸 유도체, 이를 이용한 유기 전기발광 소자 및 그 제조방법

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