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WO2021230689A1 - Nouveau composé et élément électroluminescent organique le comprenant - Google Patents

Nouveau composé et élément électroluminescent organique le comprenant Download PDF

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WO2021230689A1
WO2021230689A1 PCT/KR2021/006036 KR2021006036W WO2021230689A1 WO 2021230689 A1 WO2021230689 A1 WO 2021230689A1 KR 2021006036 W KR2021006036 W KR 2021006036W WO 2021230689 A1 WO2021230689 A1 WO 2021230689A1
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김민준
이동훈
차용범
서상덕
김동희
김서연
이다정
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LG Chem Ltd
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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
    • 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
    • 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
    • C07D405/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • 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
    • C07D409/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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 injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron It may be formed of an injection layer or the like.
  • 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.
  • 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):
  • Y is O or S
  • 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 a 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 3
  • R 2 is of Formula 2, and the rest is hydrogen or deuterium;
  • L is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
  • X is N, or CH, provided that at least two or more of X are N;
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
  • 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 the compound represented by Formula 1 above; 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 Formula 1 described above may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
  • FIG. 2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (6), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light emitting device including a cathode 4 are 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 aryl phosphine 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
  • 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 of the carbonyl group is not particularly limited, but it is preferably from 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 examples of the above-described alkenyl groups.
  • 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).
  • the compound represented by Formula 1 is a fluoranthene ring and a heterocyclic ring containing two or more N is bonded to a specific position of the parent nucleus structure in which a bicyclic heterocyclic ring containing O or S is condensed. It is possible to improve the characteristics of the organic light emitting device.
  • the compound represented by Formula 1 uses a polycyclic aromatic core that connects a plurality of aromatic rings, thereby increasing molecular rigidity, increasing stability with respect to electrons and holes, and can exhibit better light emitting properties, thereby Due to this, quantum efficiency and lifetime can be improved.
  • the compound represented by Formula 1 may be represented by Formula 1-1 or 1-2, depending on a specific position at which a heterocyclic ring containing two or more N is bonded:
  • Y, R 1 , n1, n2, L, X, Ar 1 and Ar 2 are as defined in Formula 1 above.
  • Formula 1-1 Y is O or S.
  • Formula 1-2 Y is O or S.
  • R 1 is each 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 substituted or unsubstituted C 6-30 aryl, or C 6-28 aryl, or C 6- 25 aryl, or C 6-20
  • each of 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.
  • L is a single bond; or substituted or unsubstituted C 6-30 arylene, or C 6-28 arylene, or C 6-25 arylene, or C 6-20 arylene.
  • L is a single bond; or phenylene, biphenylrylene, terphenylrylene, quaterphenylrylene, or naphthylene.
  • L is a single bond; Or it may be one represented by any one selected from the group consisting of:
  • Formula 1-1, and Formula 1-2 two of X may be N, the remainder 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 C 6-20 aryl; or substituted or unsubstituted C 3-30 heteroaryl, or C 5-28 heteroaryl, or C 5-25 heteroaryl, containing any one or more heteroatoms selected from the group consisting of N, O and S; or C 6-20 heteroaryl, or C 12-18 heteroaryl.
  • Ar 1 and Ar 2 are each phenyl, naphthyl substituted phenyl, dibenzofuranyl substituted phenyl, dibenzothiophenyl substituted phenyl, carbazolyl substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenyl substituted carbazolyl.
  • Ar 1 and Ar 2 may be phenyl, naphthyl substituted phenyl, biphenyl, naphthyl, or phenyl substituted naphthyl, preferably phenyl, biphenyl, or naphthyl.
  • the compound represented by Chemical Formula 1 may be prepared by a preparation method such as Scheme 1 or Scheme 2 below.
  • the manufacturing method may be more specific in the Synthesis Examples to be described later.
  • Y, R 1 , R 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, more preferably Cl;
  • Y, R 1 , R 2 , n1, and n2 are as defined in Formula 1 above, and one of Q 3 is a halogen group, preferably Cl, Br, or I, and more preferably is Cl, the remainder of Q 3 is hydrogen or deuterium, and Q 4 is BO 2 C 2 (CH 3 ) 4 , or B(OH) 2 .
  • Scheme 1 and Scheme 2 introduce a heteroaryl substituent containing at least two or more N at a specific position in the parent nucleus structure in which a fluoranthene ring and a bicyclic heterocyclic ring containing O or S are condensed.
  • a leaving group such as BO 2 C 2 (CH 3 ) 4 , or B(OH) 2
  • the compound of Formula 1 can be prepared according to Scheme 1.
  • the BO 2 C 2 (CH 3 ) 4 , or a leaving group such as B(OH) 2 is bonded to an intermediate compound including a heteroaryl substituent containing at least two or more N, according to Scheme 2, Formula 1 compounds can be prepared.
  • one of Q 1 is a pinacolborane group, BO 2 C 2 (CH 3 ) 4 , or a boronic acid group, B(OH) 2 , and a fluoranthene ring.
  • a polycyclic compound in which a bicyclic heterocyclic ring containing O or S is condensed, and a heterocyclic compound containing Q 2 as a halogen group and at least two or more N are prepared by a palladium catalyst (Pd) in the presence of a base. reaction with a catalyst).
  • a pinacolborone group BO 2 C 2 (CH 3 ) 4 , or B(OH) in a polycyclic compound in which a fluoranthene ring and a bicyclic heterocycle including O or S are condensed ) 2 is to introduce a heteroaryl group containing at least two or more N at the position of Q 1 .
  • 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 a synthesis example to be described later.
  • one of Q 3 is a halogen group, and a polycyclic compound in which a fluoranthene ring and a bicyclic heterocyclic ring including O or S are condensed, and BO 2 C 2 (CH 3 ) ) 4 , or a boronic acid group, B(OH) 2 , which is Q 4 , and a heterocyclic compound containing at least two or more N is reacted with a palladium catalyst (Pd catalyst) in the presence of a base It is done by doing Through this reaction, a heteroaryl group containing at least two or more N is introduced at the Q 3 position, which is a halogen group, of a polycyclic compound in which a fluoranthene ring and a bicyclic hetero ring containing O or S are condensed will be.
  • Pd catalyst palladium catalyst
  • Q 3 may be chlorine
  • Q 4 may be BO 2 C 2 (CH 3 ) 4 .
  • Specific reaction conditions of Scheme 2 may be performed with reference to known reactions known in the art. The manufacturing method may be more specific in a synthesis example to be described later.
  • the base component is potassium carbonate (K 2 CO 3 ), sodium bicarbonate (NaHCO 3 ), cesium carbonate (Cs 2 CO 3 ), sodium acetate (sodium acetate, NaOAc), potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), sodium ethoxide (NaOEt), or triethylamine (Et 3) N), N,N-diisopropylethylamine (N,N-diisopropylethylamine, EtN(iPr) 2 ) and the like may be used.
  • 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 is tetrakis (triphenylphosphine) palladium (0) (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 (palladium(II) acetate, Pd(OA
  • 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 ).
  • tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), Pd(PPh 3 ) 4 ) may be used as a catalyst
  • bis(tri- (tert-butyl)phosphine)palladium (0) bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu 3 ) 2 )
  • Pd(P-tBu 3 ) 2 bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu 3 ) 2
  • equivalent means molar equivalent
  • 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 suppression 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 layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 The compounds shown are included.
  • the organic layer may include an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.
  • the organic layer may include an emission layer, and the emission layer includes the compound represented by Formula 1 above.
  • the light emitting layer further includes a dopant compound.
  • the light emitting layer includes the compound of Formula 1 and a dopant.
  • the light emitting layer includes the compound of Formula 1 and a dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 1:1.
  • the light emitting layer includes the compound of Formula 1 and the dopant, and the compound of Formula 1 and the dopant in a content ratio of 100:1 to 2:1.
  • the light emitting layer includes the compound of Formula 1 and the dopant, and the compound of Formula 1 and the dopant in a content ratio of 100:1 to 5:1.
  • the dopant is a metal complex.
  • the dopant is an iridium-based metal complex.
  • the organic material layer includes an emission layer
  • the emission layer includes a dopant
  • the dopant material is selected from the following structural formulas.
  • the structures specified above are not limited to dopant compounds.
  • the organic 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, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, the electron injection layer, or a layer that simultaneously injects and transports electrons is represented by Formula 1 The compounds shown are included.
  • the organic layer may include a light emitting layer and a hole transport layer, and the light emitting layer or the hole transport layer may include a compound represented by Formula 1 above.
  • 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 , and a cathode 4 .
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the electron suppression layer, the light emitting layer, the hole blocking layer, and the electron injection and transport layer.
  • the compound represented by Formula 1 may be included in the light emitting layer or the hole transport layer, for example, may be included as a host material of the light emitting 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.
  • a material that can be used as a cathode is deposited thereon. can do.
  • 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, 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 for 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 on 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. It is preferable that 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.
  • HOMO highest occupied molecular orbital
  • 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.
  • organic substances anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports them to 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 compound according to the present invention is used as the host material.
  • 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.
  • styrylamine compound a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more 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.
  • 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.
  • an iridium-based metal complex is used as the dopant material.
  • the light emitting layer may be a red light emitting layer, and when the compound according to the present invention is used as a host material, stability for electrons and holes is increased, and energy transfer from the host to the red dopant is well achieved, the driving voltage of the organic light emitting device, It is possible to improve luminous efficiency and lifespan characteristics.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. do. 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.
  • suitable 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, perylene tetracarboxylic 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 according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Compound b-2 was synthesized in the same manner as in the preparation method of compound a-2, except that compound b-3 was used instead of compound a-3.
  • K 2 CO 3 potassium carbonate
  • compound d-3 was synthesized in the same manner as in the preparation method of compound a-3 described above.
  • compound d-1 was synthesized in the same manner as in the preparation method of compound a-1 described above.
  • a glass substrate coated with a thin film of 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 washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transferred to a vacuum evaporator.
  • the following compound HI-1 was thermally vacuum deposited to a thickness of 1150 ⁇ to form a hole injection layer, but the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following compound HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ⁇ .
  • the following compound EB-1 was vacuum-deposited to a film thickness of 150 ⁇ on the hole transport layer to form an electron blocking layer.
  • the following compound 1 and the following compound Dp-7 were vacuum-deposited in a weight ratio of 98:2 on the EB-1 deposited layer to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed by vacuum-depositing the following compound HB-1 to a thickness of 30 ⁇ on the light emitting layer. Then, on the hole blocking layer, the following compound ET-1 and the following compound LiQ were vacuum-deposited in a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 ⁇ .
  • 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.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 ⁇ /sec, and the deposition rate of aluminum was 2 ⁇ /sec, and the vacuum degree during deposition was By maintaining 2x10 -7 to 5x10 -6 torr, an organic light emitting diode was manufactured.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that Compounds 2 to 29 described in Table 1 were used instead of Compound 1 in the organic light emitting device of Example 1, respectively.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1.
  • the compound of -12 is as follows.
  • the lifetime T95 means the time it takes for the luminance to decrease from the initial luminance (6000 nits) to 95%.
  • the compound represented by Formula 1 that is, a fluoranthene ring and a bicyclic heterocyclic ring containing O or S, is condensed with N at a specific position in the parent nucleus structure of 2
  • the organic light emitting devices of Examples 1 to 29 in which a compound having a specific polycyclic structure including at least two heteroaryl substituents is used in the light emitting layer is C-1, C-2, C-3, C-4, C-5 , C-6, C-7, C-8, C-9, C-10, C-11, and the driving voltage was significantly higher than that of the organic light-emitting devices of Comparative Examples 1 to 12 prepared using the compounds of C-12 It was lowered, and it was found that energy transfer from the host to the red dopant was well done, as it was also seen that the efficiency was greatly increased.
  • the organic light emitting devices of Examples 1 to 29 can significantly improve lifespan characteristics while maintaining high efficiency. It can be determined that this is because the compound of the example according to the present invention has higher stability to electrons and holes than the compound of the comparative example. In conclusion, it can be confirmed that when the compound of the present invention is used as a host for the red light emitting layer, the driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diode can be improved.
  • Substrate 2 Anode

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Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant.
PCT/KR2021/006036 2020-05-13 2021-05-13 Nouveau composé et élément électroluminescent organique le comprenant Ceased WO2021230689A1 (fr)

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