WO2021125648A1 - Nouveau composé, et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé, et élément électroluminescent organique l'utilisant Download PDF

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WO2021125648A1
WO2021125648A1 PCT/KR2020/017665 KR2020017665W WO2021125648A1 WO 2021125648 A1 WO2021125648 A1 WO 2021125648A1 KR 2020017665 W KR2020017665 W KR 2020017665W WO 2021125648 A1 WO2021125648 A1 WO 2021125648A1
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서상덕
정민우
이정하
한수진
박슬찬
황성현
이동훈
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주식회사 엘지화학
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Priority to CN202080034253.4A priority Critical patent/CN113795488A/zh
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    • 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
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • 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 material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and 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.
  • 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):
  • X 1 to X 3 are each independently N or CH, provided that at least one of X 1 to X 3 is N,
  • Y is O or S
  • Z 1 to Z 4 are each independently CR 4 , or two adjacent groups of Z 1 to Z 4 together represent the structure of Formula 2 below,
  • Ar 1 to Ar 5 are each independently substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S;
  • R 1 to R 4 are 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,
  • a and b are each independently an integer of 1 to 3
  • c is an integer from 1 to 4,
  • W is O, S, CR 6 R 6 ' or NR 7 ,
  • R 5 are 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 6 , R 6 ′, and R 7 are each independently hydrogen; substituted or unsubstituted C 1-60 alkyl; Or a substituted or unsubstituted C 6-60 aryl,
  • d is an integer from 1 to 4,
  • At least one of Ar 1 to Ar 5 and R 1 to R 5 is substituted with one or more deuterium, or at least one of R 1 to R 5 is deuterium.
  • the compound represented by Chemical 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 Chemical 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 (7), 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; cyano 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 heteroaryl containing one or
  • 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 or 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.
  • halogen groups are 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 having aromaticity. 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 phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and the like, but is not limited thereto.
  • heteroaryl is a heteroaryl containing 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.
  • heteroaryl 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, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyzinyl group
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the examples 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 regarding heteroaryl described above 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 heteroaryl described above 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 heterocycle is not a monovalent group, and the description of the above-described heteroaryl 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 may be substituted with 4 or more deuterium.
  • at least one of Ar 1 to Ar 5 , and R 1 to R 5 in Formula 1 is substituted with deuterium, or at least one of R 1 to R 5 becomes deuterium, so that 4 or more in the compound, or 5 or more, or 6 or more, or 8 or more, or 10 or more, and may contain up to 26 deuterium.
  • At least one of Ar 1 to Ar 5 is phenyl, biphenyl, or phenyl substituted with 5 deuterium, and the rest are each independently unsubstituted C 6-30 aryl; Or it may be an unsubstituted C 5-30 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
  • At least one of Ar 1 to Ar 5 is phenyl, biphenyl, or phenyl substituted with 5 deuterium, and the rest are each independently unsubstituted, phenyl, dibenzofuranyl or dibenzothiophenyl.
  • any one, or two, or three of Ar 1 to Ar 5 is phenyl substituted with 5 deuterium, and the rest are each independently unsubstituted, phenyl, biphenyl, dibenzofuranyl or dibenzothiophenyl.
  • a and b are each independently an integer of 2 or 3, and c is an integer of 3 or 4.
  • a 3
  • b 3
  • Ar 4 3
  • c 4
  • any one of Ar 1 and Ar 2 is phenyl substituted with 5 deuterium, and the remainder is unsubstituted phenyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, Ar 3 to Ar 5 may each independently be an unsubstituted phenyl, a and b may be an integer of 2 or 3, respectively, and c may be an integer of 3 or 4.
  • both Ar 1 and Ar 2 are phenyl substituted with 5 deuterium
  • Ar 3 to Ar 5 are each independently unsubstituted phenyl
  • a and b are each 2 or It is an integer of 3
  • c may be an integer of 3 or 4.
  • Ar 1 and Ar 2 are both unsubstituted phenyl, at least one of Ar 3 and Ar 4 is phenyl substituted with 5 deuterium, and the rest are unsubstituted phenyl, a and b are each independently an integer of 2 or 3, but a and b are not 3 at the same time, and c may be an integer of 4.
  • Ar 1 and Ar 2 are each unsubstituted phenyl
  • Ar 5 is phenyl substituted with 5 deuterium
  • a and b are both an integer of 3
  • c is 3 It can be an integer.
  • X 1 to X 3 may be N.
  • R 1 to R 4 may each independently be hydrogen or deuterium.
  • R 5 may be hydrogen or deuterium.
  • W is O, S, CR 6 R 6 ' or NR 7 , wherein, preferably, R 6 and R 6 ' are each independently unsubstituted C 1-30 alkyl, and R 7 may be unsubstituted C 6-30 aryl. More preferably, both R 6 and R 6 ′ may be methyl, and R 7 may be phenyl.
  • the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 1-1 to 1-7:
  • X 1 to X 3 , Y, Ar 1 to Ar 5 , R 1 to R 5 , a to d are as defined above,
  • e is an integer from 1 to 4,
  • f is an integer of 1 or 2.
  • Ar 1 to Ar 5 are each independently unsubstituted, phenyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, R 1 and R 2 are both hydrogen, R 3 and R 4 are hydrogen or deuterium, but the total number of R 3 and R 4 being deuterium is 6 or more, more preferably 6 to 8.
  • a and b are each independently an integer of 2 or 3
  • c is an integer of 3 or 4
  • e is an integer of 4.
  • Ar 1 to Ar 5 are each independently unsubstituted, phenyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, R 1 and R 2 is all hydrogen, and R 3 to R 5 are each independently hydrogen or deuterium, and the total number of R 3 to R 5 is deuterium is 5 or more, more preferably 5 to 10.
  • a and b are each independently an integer of 2 or 3
  • c and d are each independently an integer of 3 or 4
  • f is an integer of 2.
  • Ar 1 to Ar 5 are each independently unsubstituted, phenyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, R 1 and R 2 is each independently hydrogen or deuterium, R 3 to R 5 are all hydrogen, and the total number of R 1 and R 2 is deuterium is 4 or more, more preferably 4 to 6, respectively.
  • a and b are each independently an integer of 2 or 3
  • c and d are each independently an integer of 3 or 4
  • f is an integer of 2.
  • the compound represented by Formula 1 may be any one selected from the group consisting of the following compounds:
  • the compound represented by Formula 1 may be prepared by, for example, a preparation method as shown in Scheme 1 below.
  • X 1 to X 3 , Y, Ar 1 to Ar 5 , R 1 to R 5 , and a to d are as defined in Formula 1 above, and X is halogen, preferably chloro or bromo.
  • Scheme 1 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • 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. .
  • 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, 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 It may include the indicated compound.
  • the organic layer may include an electron blocking layer
  • the electron blocking layer may include a compound represented by Formula 1 above.
  • the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons
  • the electron transport layer, the electron injection layer, or a layer that simultaneously transports and injects electrons is represented by the above formula It may include a compound represented by 1.
  • the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer and a light emitting layer, and any one or more selected from the group consisting of the hole injection layer, the hole transport layer and the electron blocking layer is a compound represented by Formula 1 may include.
  • the organic layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be used as a host material in the emission layer, and more specifically, the compound represented by Formula 1 may be used as a green host used in the emission layer of the organic light emitting device.
  • the emission layer may include two or more types of hosts, and when the emission layer includes two or more types of hosts, at least one of the hosts may be a compound represented by Formula 1 above.
  • the light emitting layer may further include a compound represented by the following Chemical Formula 3:
  • Ar 6 and Ar 7 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
  • R 8 and R 9 are each independently hydrogen; heavy hydrogen; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 alkyl; substituted or unsubstituted C 3-60 cycloalkyl; substituted or unsubstituted C 2-60 alkenyl; substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
  • p and q are each independently an integer of 0 to 7.
  • Ar 6 and Ar 7 are each independently selected from substituted or unsubstituted C 6-20 aryl; Or it may be a substituted or unsubstituted C 5-20 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S, more preferably phenyl, biphenyl, terphenyl, naphthyl , dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
  • R 8 and R 9 are each independently hydrogen; or phenyl.
  • p and q may each independently be 0 or 1.
  • the compound represented by Formula 3 may be selected from the group consisting of the following compounds:
  • the weight ratio of the compound represented by Formula 1 to the compound represented by Formula 3 is 10:90 to 90:10, more preferably is 20:80 to 80:20, 30:70 to 70:30 or 40:60 to 60:40.
  • 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.
  • the organic layer may include at least one of a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer, and the electron injection layer and the electron transport layer are electron injection layers. and a single layer of the transport layer.
  • 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 one or more 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 organic light emitting device in which the electron injection and transport layer is formed of a single layer is illustrated in FIG. 2
  • the electron injection layer and the electron transport layer may be sequentially stacked on the hole blocking layer as separate layers.
  • 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 it can be prepared by 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 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.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • 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 preferred. 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 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 a layer placed between the hole transport layer and the emission layer in order to prevent electrons injected from the cathode from passing to the hole transport layer without recombination in the emission layer, and is also called an electron blocking layer.
  • a material having an electron affinity smaller than that of the electron transport layer is preferable for the electron suppressing layer.
  • the compound represented by Formula 1 may be included as a material for the electron blocking 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, etc.
  • 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 a layer interposed between the electron transport layer and the emission layer to prevent the holes injected from the anode from passing to the electron transport layer without recombination in the emission layer, and is also called a hole blocking layer.
  • a material having high ionization energy is preferable for the hole blocking layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer.
  • an electron transport material a material that can receive electrons from the cathode and transfer them to the light emitting layer is suitable. 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, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • Examples of the metal complex compound 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. It is not limited to this.
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • 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.
  • compound 1-1 (15.0g, 48.1mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (14.4g, 52.9mmol) were added to 300ml of THF Stirred and refluxed.
  • potassium carbonate (K 2 CO 3 ) (26.6g, 192.2mmol) (26.6g, 192.2mmol) was dissolved in 80ml of water (H 2 O) and thoroughly stirred, followed by tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) ( 1.7 g, 1.4 mmol) was added.
  • step 2 of Synthesis Example 1 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine to 2-chloro-4,6-diphenyl-1,3,5-triazine
  • compound 6-1 (15.0 g, 29.9 mmol) and phenylboronic acid (4.0 g, 32.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (16.5g, 119.7mmol) was dissolved in 50ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.0g, 0.9mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • step 2 of Synthesis Example 1 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine was added to 2-([1,1'-biphenyl]-3-yl)-4 -chloro-6-phenyl-1,3,5-triazine, and in step 3, 9H-carbazole was changed to 9H-carbazole-1,3,4,5,6,8-d6.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • 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.
  • the following HT-A compound and the following PD compound were thermally vacuum-deposited in a weight ratio of 95:5 to a thickness of 100 ⁇ , and then only the following HT-A compound was deposited to a thickness of 1150 ⁇ , hole injection A layer and a hole transport layer were sequentially formed.
  • the following HT-B compound was thermally vacuum deposited to a thickness of 450 ⁇ to form an electron blocking layer.
  • compound 1 prepared above and the compound GD below were vacuum-deposited in a weight ratio of 85:15 to a thickness of 400 ⁇ to form a light emitting layer.
  • the following ET-A compound was vacuum-deposited to a thickness of 50 ⁇ to form a hole blocking layer.
  • the following ET-B compound and the following Liq compound were thermally vacuum-deposited in a weight ratio of 2:1 to a thickness of 250 ⁇ , and then LiF and magnesium were vacuum-deposited to a thickness of 30 ⁇ in a weight ratio of 1:1.
  • an electron transport layer and an electron injection layer were sequentially formed.
  • magnesium and silver were deposited to a thickness of 160 ⁇ in a weight ratio of 1:4 to form a cathode, thereby manufacturing an organic light emitting diode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the negative electrode was 0.3 ⁇ /sec
  • the deposition rate of silver and magnesium was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 2 ⁇ 10 -7 to 5 ⁇ 10 -6 torr was maintained, an organic light emitting device 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 Compound 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were mixed and used instead of Compound 1.
  • the mixing ratio of the compounds means the weight ratio
  • the compounds PGH-1 and PGH-2 are as follows, respectively.
  • 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 Compound 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were mixed and used instead of Compound 1.
  • the mixing ratio of the compounds means the weight ratio
  • the compounds GH-A, GH-D, PGH-1 and PGH-2 are the same as described above.
  • the organic light emitting devices prepared in Examples and Comparative Examples were stored in an oven at 110° C. for 30 minutes and heat-treated, and then voltage, efficiency, and lifetime (T95) were measured by applying a current, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
  • At least one deuterium is substituted in a structure in which a nitrogen-containing heterocycle serving as an electron acceptor and a carbazole derivative serving as an electron donor are connected through dibenzofuran or dibenzothiophene.
  • a nitrogen-containing heterocycle serving as an electron acceptor and a carbazole derivative serving as an electron donor are connected through dibenzofuran or dibenzothiophene.
  • the nitrogen-containing heterocyclic ring is substituted in the 1st position of the dibenzofuran/dibenzothiophene
  • the carbazole derivative is substituted in the 6th position, respectively, and they are bonded in opposite directions to each other.
  • LUMO is positioned over the nitrogen-containing heterocycle and dibenzofuran/dibenzothiophene
  • HOMO is positioned over the carbazole derivative and dibenzofuran/dibenzothiophene.
  • the position of is divided so that hole transport and electron transport occur in each unit, so it is advantageous for charge transport.
  • the substitution of deuterium in this structure lowers vibrational energy, thereby increasing the stability of the material and helping to prevent problems in energy transfer to the dopant even in an unstable triplet state. Therefore, as in the above Examples, it can be confirmed that the compound represented by Formula 1 exhibits more improved effects in terms of low voltage, high efficiency, and long life compared to the compound applied in Comparative Example when applied as a host of an organic light emitting device. have. In particular, this improvement effect is advantageous even when forming an exciplex by using it as a host together with the compound represented by Formula 3, and it can be confirmed that the characteristic effects of low voltage, high efficiency, and long life are greater.

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Abstract

La présente invention concerne un nouveau composé, et un élément électroluminescent organique l'utilisant.
PCT/KR2020/017665 2019-12-19 2020-12-04 Nouveau composé, et élément électroluminescent organique l'utilisant WO2021125648A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4074706A1 (fr) * 2021-04-16 2022-10-19 LG Display Co., Ltd. Composé hétérocyclique deutéré et dispositif électroluminescent organique le comprenant et composition pour une couche organique de dispositif électroluminescent organique
WO2023055177A1 (fr) * 2021-10-01 2023-04-06 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130130236A (ko) * 2011-05-03 2013-12-02 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하는 유기 전계 발광 소자
KR20180045798A (ko) * 2016-10-25 2018-05-04 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20180061076A (ko) * 2016-11-29 2018-06-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20190024926A (ko) * 2019-02-21 2019-03-08 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20190138615A (ko) * 2018-06-05 2019-12-13 상하이 니켐 파인 케미컬 컴퍼니 리미티드 유기 전자 소자용 조성물 및 이를 이용한 유기 전자 소자

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법
CN103664909B (zh) * 2013-12-10 2015-02-25 京东方科技集团股份有限公司 联咔唑类衍生物及制备方法、应用和有机发光器件
KR20150135123A (ko) * 2014-05-23 2015-12-02 롬엔드하스전자재료코리아유한회사 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
WO2018174678A1 (fr) * 2017-03-24 2018-09-27 희성소재(주) Composé hétérocyclique et élément électroluminescent organique le comprenant
KR102231197B1 (ko) * 2018-07-27 2021-03-23 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130130236A (ko) * 2011-05-03 2013-12-02 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하는 유기 전계 발광 소자
KR20180045798A (ko) * 2016-10-25 2018-05-04 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20180061076A (ko) * 2016-11-29 2018-06-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20190138615A (ko) * 2018-06-05 2019-12-13 상하이 니켐 파인 케미컬 컴퍼니 리미티드 유기 전자 소자용 조성물 및 이를 이용한 유기 전자 소자
KR20190024926A (ko) * 2019-02-21 2019-03-08 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4074706A1 (fr) * 2021-04-16 2022-10-19 LG Display Co., Ltd. Composé hétérocyclique deutéré et dispositif électroluminescent organique le comprenant et composition pour une couche organique de dispositif électroluminescent organique
WO2023055177A1 (fr) * 2021-10-01 2023-04-06 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant

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