WO2021194261A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2021194261A1
WO2021194261A1 PCT/KR2021/003658 KR2021003658W WO2021194261A1 WO 2021194261 A1 WO2021194261 A1 WO 2021194261A1 KR 2021003658 W KR2021003658 W KR 2021003658W WO 2021194261 A1 WO2021194261 A1 WO 2021194261A1
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차용범
전상영
홍성길
조우진
김민준
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주식회사 엘지화학
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Priority to CN202180023657.8A priority Critical patent/CN115397816A/zh
Publication of WO2021194261A1 publication Critical patent/WO2021194261A1/fr

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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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole blocking layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron It may be formed of an injection layer or the like.
  • a voltage when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
  • an organic light emitting diode using a solution process has been developed instead of a conventional deposition process.
  • all organic light emitting device layers were coated with a solution process to develop an organic light emitting device, but the current technology has limitations, so only HIL, HTL, and EML are processed in the solution process in the regular structure, and the subsequent process is the conventional deposition process.
  • the present invention provides a novel material for an organic light emitting device that can be used in an organic light emitting device and can be deposited by a solution process at the same time.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1):
  • A is a benzene ring fused with two adjacent rings
  • R 1 is each independently hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C 1-60 alkyl; substituted or unsubstituted C 1-60 alkoxy; substituted or unsubstituted C 2-60 alkenyl; substituted or unsubstituted C 2-60 alkynyl; substituted or unsubstituted C 3-60 cycloalkyl; substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • R 2 are each independently substituted or unsubstituted C 6-60 aryl
  • R 3 is of Formula 2, the rest is hydrogen or deuterium,
  • L is a single bond; substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • each X is independently N, or CH, provided that at least one of X is N,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • n1 is an integer from 0 to 6
  • n2 is an integer from 0 to 2.
  • the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises a compound represented by the formula (1). to provide.
  • the compound represented by Formula 1 described above may be used as a material for an organic layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.
  • the compound represented by the above formula (1) can be applied to a solution process, and hole suppression, hole injection, hole transport, hole injection and transport, light emission, electron suppression, electron transport, electron injection, or electron injection and transport material can be used as
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , a hole blocking layer 4 , and a cathode 5 .
  • FIG. 2 is a substrate (1), an anode (2), a hole injection layer (6), a hole transport layer (7), an electron blocking layer (8), a light emitting layer (3), a hole blocking layer (4), an electron injection and transport layer ( 9), and an example of an organic light emitting device including a cathode 5 is shown.
  • substituted or unsubstituted refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, etc. can be
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothioph
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group.
  • heteroaryl among heteroarylamines the description of the above-described heterocyclic group may be applied.
  • the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group.
  • the description of the above-described aryl group may be applied except that arylene is a divalent group.
  • the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents.
  • the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.
  • the present invention provides a compound represented by the above formula (1).
  • a hetero ring including one or more N is bonded to a specific position of the parent nucleus structure in which a benzene ring is further fused to fluorene including A, which is a benzene ring, thereby forming an organic light emitting device using the same.
  • characteristics can be improved.
  • the compound represented by Chemical Formula 1 uses a polycyclic aromatic core in which a plurality of aromatic rings are connected and includes a specific substituent, thereby increasing molecular rigidity to exhibit better light emitting properties and increasing thermal stability. and, thereby, can improve quantum efficiency and lifetime.
  • Chemical Formula 1 the compound represented by Chemical Formula 1 may be represented by Chemical Formulas 3 to 5 according to a structure in which fluorene including A, which is a benzene ring, and an additional benzene ring are fused to each other.
  • R 1 , R 2 , R 3 , n1 , and n2 are as defined in Formula 1 above.
  • the compound represented by Formula 1 may be represented by any one of Formulas 6 to 11 below.
  • R 1 , R 2 , L, X, Ar 1 , Ar 2 , n1 , and n2 are as defined in Formula 1 above.
  • A is a benzene ring fused with two adjacent rings.
  • each R 1 is hydrogen, deuterium, halogen, or cyano, or substituted or unsubstituted C 1-20 alkyl, or C 1-12 alkyl, or C 1-6 alkyl, or substituted or unsubstituted C 1-20 alkoxy, or C 1-12 alkoxy, or C 1-6 alkoxy, or substituted or unsubstituted C 2-20 alkenyl, or C 2-12 alkenyl, or C 2-6 alkenyl or substituted or unsubstituted C 2-20 alkynyl, or C 2-12 alkynyl, or C 2-6 alkynyl, or substituted or unsubstituted C 3-30 cycloalkyl, or C 3-25 cycloalkyl, or C 3-20 cycloalkyl, or C 3-12 cycloalkyl, or substituted or unsubstituted C 6-30 aryl, or C 6-28 aryl, or C 6-25 aryl, or C 6- 18 aryl
  • each R 1 is independently hydrogen; heavy hydrogen; halogen; cyano; substituted or unsubstituted C 1-6 alkyl; substituted or unsubstituted C 1-6 alkoxy; substituted or unsubstituted C 2-6 alkenyl; substituted or unsubstituted C 2-6 alkynyl; substituted or unsubstituted C 3-12 cycloalkyl; substituted or unsubstituted C 6-12 aryl; Or it may be a C 4-12 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
  • each R 1 may be hydrogen, deuterium, C 1-6 alkyl, or C 6-12 aryl. Preferably, each R 1 may be hydrogen or deuterium. Also, all of R 1 may be hydrogen.
  • n1 and n2 may each be an integer of 0 to 2, or 0 or 1.
  • R 2 may be each substituted or unsubstituted C 6-30 aryl, or C 6-28 aryl, C 6-25 aryl, C 6-18 aryl, or C 6-12 aryl.
  • R 2 since the compound represented by Formula 1 according to the present invention has a core structure in which R 2 is an aryl group, thermal stability of the material is increased, so that when applied to an organic light emitting device, long life characteristics can be remarkably improved.
  • each R 2 may be a substituted or unsubstituted C 6-12 aryl.
  • each R 2 may be phenyl, biphenyl, or naphthyl.
  • all of R 2 may be phenyl.
  • L is a single bond; Or it may be a substituted or unsubstituted C 6-25 arylene.
  • L is a single bond; or phenylene, biphenylrylene, terphenylrylene, quaterphenylrylene, or naphthylene, anthracenylene, fluorenylene, phenathrenylene, pyrenylene, or triphenylrylene.
  • L is a single bond; Or it may be one represented by any one selected from the group consisting of:
  • one or two of X may be N, the other may be CH, or all of X may be N.
  • Ar 1 and Ar 2 are each substituted or unsubstituted C 6-30 aryl, or C 6-28 aryl, or C 6-25 aryl, or any one selected from the group consisting of N, O and S It may be a substituted or unsubstituted C 5-30 heteroaryl containing more than one heteroatom, or a C 8-20 heteroaryl, or a C 12-18 heteroaryl heteroaryl.
  • Ar 1 and Ar 2 are each phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, fluorenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolylyl can
  • Ar 1 and Ar 2 may each be represented by any one selected from the group consisting of the following.
  • the compound represented by Chemical Formula 1 may be prepared by a preparation method as shown in Scheme 1 below.
  • the manufacturing method may be more specific in the Synthesis Examples to be described later.
  • R 1 , R 2 , L, X, Ar 1 , Ar 2 , n1 , and n2 are as defined in Formula 1 above, and one of Q 1 is BO 2 C 2 (CH 3 ) 4 , or B(OH) 2 , the remainder is hydrogen or deuterium, Q 2 is a halogen group, preferably Cl, Br, or I.
  • Scheme 1 is a reaction in which a heterocyclic ring containing one or more N is introduced at a specific position of the parent nucleus structure in which a benzene ring is fused to fluorene including A, which is a benzene ring.
  • one of Q 1 is a pinacolborane group, BO 2 C 2 (CH 3 ) 4 , or a boronic acid group, B(OH) 2 , and includes a benzene ring A
  • a polycyclic compound in which a benzene ring is further fused to fluorene and a heterocyclic compound containing Q 2 as a halogen group and at least one N are reacted with a palladium catalyst (Pd catalyst) in the presence of a base.
  • Pd catalyst palladium catalyst
  • a pinacolborone group BO 2 C 2 (CH 3 ) 4 , or B(OH) 2 among polycyclic compounds in which a benzene ring is fused to fluorene including a benzene ring A is Q It is to introduce a heterocyclic carbazole group containing one or more N at the 1st position.
  • Q 1 is BO 2 C 2 (CH 3 ) 4
  • Q 2 may be chlorine.
  • Specific reaction conditions of Scheme 1 may be performed with reference to known reactions known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.
  • the base component is potassium carbonate (K 2 CO 3 ), cesium carbonate (Cs 2 CO 3 ), potassium acetate (KOAc), sodium tert-butoxide (sodium tert- butoxide, NaOtBu), or N,N-diisopropylethylamine (N,N-diisopropylethylamine, EtN(iPr) 2 ).
  • the palladium catalyst includes tetrakis(triphenylphosphine)palladium (0), tris(dibenzylideneacetone)dipalladium (0) (tris(dibenzylideneacetone)-dipalladium (0), Pd 2 (dba) 3 ), bis(tri-(tert-butyl)phosphine)palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu 3 ) 2 ) , bis(dibenzylideneacetone)palladium (0) (bis(dibenzylideneacetone)palladium (0), Pd(dba) 2 ), Pd(PPh 3 ) 4 ) or palladium(II) acetate, Pd (OAc) 2 ) and the like can be used.
  • the palladium catalyst is tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), Pd(PPh 3 ) 4 ), bis(tri-(tert-butyl)phosphine) palladium (0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu 3 ) 2 ), or bis(dibenzylideneacetone)palladium (0) (bis(dibenzylideneacetone)palladium ( 0), Pd(dba) 2 ).
  • the present invention provides an organic light emitting device including the compound represented by Formula 1 above.
  • the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a hole injection layer, a hole transport layer, or a layer that injects and transports holes at the same time, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 including compounds.
  • the organic material layer may include an electron blocking layer, the electron blocking layer includes the compound represented by the formula (1).
  • the organic material layer may include a light emitting layer, the light emitting layer includes the compound represented by Formula 1 above.
  • the organic material layer may include a hole blocking layer, the hole blocking layer includes the compound represented by the formula (1).
  • the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Formula 1 above.
  • the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons includes the compound represented by Formula 1 above.
  • the organic layer may include a light emitting layer and an electron transport layer
  • the electron transport layer may include a compound represented by Formula 1 above.
  • the thickness of the organic material layer including the compound of Formula 1 is 10 ⁇ to 500 ⁇ .
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , a hole blocking layer 4 , and a cathode 5 .
  • the compound represented by Formula 1 may be included in the hole blocking layer.
  • the compound represented by Formula 1 may be included in one or more of the hole injection layer, the light emitting layer, the hole blocking layer, and the electron injection and transport layer. Specifically, the compound represented by Formula 1 may be included in the hole blocking layer.
  • the organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the compound represented by Formula 1 has excellent solubility in a solvent used for the solution coating method, and thus it is easy to apply the solution coating method.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.
  • the solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and for example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o - Chlorine solvents, such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such
  • the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy in the above range.
  • the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.
  • the present invention provides a method of forming a functional layer using the above-described coating composition. Specifically, coating the coating composition according to the present invention as described above in a solution process; and heat-treating the coated coating composition.
  • the heat treatment temperature in the heat treatment step is preferably 150 °C to 230 °C.
  • the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour.
  • the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode
  • anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect with respect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • a compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • a hole transport material a material capable of transporting holes from the anode or hole injection layer to the light emitting layer and transferring them to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron blocking layer is formed on the hole transport layer, specifically, the electron blocking layer is provided in contact with the light emitting layer, preventing excessive movement of electrons to increase the hole-electron coupling probability, thereby improving the efficiency of the organic light emitting device means the layer that does
  • the electron-blocking layer is preferably a material having low mobility with respect to electrons so that electrons do not move in the light-emitting layer.
  • the light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is a substituted or unsubstituted derivative.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the hole blocking layer is formed on the light emitting layer, specifically, the hole blocking layer is provided in contact with the light emitting layer, preventing excessive movement of holes and increasing the hole-electron coupling probability, thereby improving the efficiency of the organic light emitting device.
  • layer means.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may generally be formed under the same conditions as the hole injection layer.
  • the compound according to the present invention is used as the hole blocking layer material.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. Specifically, the electron transport layer is provided in contact with the hole blocking layer.
  • the electron transport material in the electron transport layer a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material as used in accordance with the prior art.
  • cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer.
  • a compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 angstrom ( ⁇ , angstrom) was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a hole injection layer was formed by thermally vacuum-depositing a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode.
  • a hole transport layer was formed by vacuum-depositing a compound (1150 ⁇ ) represented by the following formula HT1 on the hole injection layer. Then, the compound of EB1 was vacuum-deposited to a film thickness of 50 ⁇ on the hole transport layer to form an electron blocking layer.
  • the compound represented by the following Chemical Formula BH and the compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25:1 to a thickness of 200 ⁇ on the electron blocking layer to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing the compound represented by Compound 1 synthesized in Synthesis Example 1 to a film thickness of 50 ⁇ on the light emitting layer.
  • the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 310 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 ⁇ /sec, and the deposition rate of aluminum was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 2x10.
  • -7 to 5x10 -6 torr an organic light emitting diode was manufactured.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound of Synthesis Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound of Synthesis Example 1.
  • the compounds of HB1, HB2, HB3, HB4, HB5, HB6, HB7, HB8, HB9, HB10, HB11, and HB12 used in Table 1 are as follows.
  • T 95 means the time (hr) at which the luminance becomes 95% of the initial luminance (1600 nit).
  • the compound represented by Formula 1 that is, one or more N is included at a specific position in the parent nucleus structure in which a benzene ring is fused to fluorene including A, which is a benzene ring.
  • Examples 1 to 10 in which a compound having a specific polycyclic structure to which a hetero ring is bonded, was used as a hole blocking layer, exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device.
  • the organic light emitting diodes of Examples 1 to 10 using the compound represented by Formula 1 according to the present invention HB1, HB2, HB3, HB4, HB5, HB6, HB7, HB8, HB9, HB10, HB11, HB12
  • Substrate 2 Anode

Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant : une première électrode; une seconde électrode disposée à l'opposé de la première électrode ; et une ou plusieurs couches organiques disposées entre la première électrode et la seconde électrode, les couches organiques comprenant un nouveau composé.
PCT/KR2021/003658 2020-03-26 2021-03-24 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2021194261A1 (fr)

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KR20190038254A (ko) * 2017-09-29 2019-04-08 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20200127628A (ko) * 2019-05-03 2020-11-11 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치

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KR20200127628A (ko) * 2019-05-03 2020-11-11 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치

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