WO2021251661A1 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2021251661A1
WO2021251661A1 PCT/KR2021/006624 KR2021006624W WO2021251661A1 WO 2021251661 A1 WO2021251661 A1 WO 2021251661A1 KR 2021006624 W KR2021006624 W KR 2021006624W WO 2021251661 A1 WO2021251661 A1 WO 2021251661A1
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light emitting
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서상덕
김민준
김영석
김동희
오중석
김서연
이다정
최승원
심재훈
이동훈
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주식회사 엘지화학
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Priority to CN202180004646.5A priority Critical patent/CN114144402B9/zh
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Definitions

  • the present invention relates to a novel compound and an organic light emitting device using 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, 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 It lights up when it falls back to the ground state.
  • Patent Document 0001 Korean Patent Publication No. 10-2013-073537
  • 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 is NR′, O or S, wherein R′ is hydrogen, deuterium, substituted or unsubstituted C 1-10 alkyl or substituted or unsubstituted C 6-30 aryl;
  • L is a single bond or a substituted or unsubstituted C 6-60 arylene
  • Ar 1 is substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
  • Ar 2 and Ar 3 are each independently substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 2-60 hetero atom including one or more hetero atoms selected from the group consisting of N, O and S aryl,
  • R 1 and R 2 are each independently one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 6-60 aryl, or N, O and S It is a substituted or unsubstituted C 2-60 heteroaryl containing more than one hetero atom,
  • n are each independently an integer of 0 to 4.
  • 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 of the organic material layers includes the compound of the present invention as described above.
  • 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 the above formula (1) 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 suppression layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9) and an example of an organic light-emitting device including a cathode 4 .
  • substituted or unsubstituted refers to deuterium (D); halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a 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
  • 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.
  • 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 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.
  • it 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 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 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 number of carbon atoms in the alkyl group is 1 to 10. 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 heteroaryl group includes at least one of O, N, Si and S as a heterogeneous element, and is a heterocyclic group having aromaticity, the number of carbon atoms being not particularly limited, but having 2 to 60 carbon atoms desirable.
  • heteroaryl 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 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.
  • the description of the heterocyclic group described above for heteroaryl among heteroarylamines 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 following formula (1):
  • the amine group (*-LN(Ar 2 )(Ar 3 )) is connected to any one carbon of 1, 2, 3, 4, 5, 6, 7, and 8.
  • X is NR′, O or S, wherein R′ is hydrogen, deuterium, substituted or unsubstituted C 1-10 alkyl or substituted or unsubstituted C 6-30 aryl;
  • L is a single bond or a substituted or unsubstituted C 6-60 arylene
  • Ar 1 is substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
  • Ar 2 and Ar 3 are each independently substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 2-60 hetero atom including one or more hetero atoms selected from the group consisting of N, O and S aryl,
  • R 1 and R 2 are each independently one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 6-60 aryl, or N, O and S It is a substituted or unsubstituted C 2-60 heteroaryl containing more than one hetero atom,
  • n are each independently an integer of 0 to 4.
  • the compound represented by Formula 1 is a compound represented by Formula 1-1 or 1-8 below:
  • X, L, Ar 1 , Ar 2 , Ar 3 , R 1 , R 2 , m and n are as defined above.
  • R' is hydrogen, deuterium, phenyl, biphenylyl or naphthyl. More preferably, R' is phenyl.
  • L is a single bond, phenylene, biphenylylene or naphthylene.
  • Ar 1 is phenyl, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofu Ranyl or dibenzothiophenyl. They are each independently substituted or unsubstituted with one or more deuterium (D).
  • D deuterium
  • phenyl, biphenylyl, naphthyl or dibenzofuranyl unsubstituted or substituted with one or more deuteriums.
  • Ar 2 and Ar 3 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenyl fluorenyl, dibenzofuranyl or dibenzothiophenyl.
  • R 1 and R 2 are each independently hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl or dibenzothiophenyl.
  • n and n are each independently an integer from 0 to 3. More preferably, m and n are each independently 0 or 1.
  • the compound represented by Formula 1 may be any one selected from the group consisting of:
  • the compound represented by Chemical Formula 1 according to the present invention includes a phenanthrooxazole, phenanthrothiazole and phenantropyrazole core structure, and these structures have high electrical conductivity and high electron density at the same time.
  • the condensed structure has rigid characteristics, so it is easy to transfer intermolecular charges, and in particular, an additional amine substituent is connected thereto, so it has excellent hole transport ability. Through such excellent intermolecular stacking and charge transport ability, it is possible to realize fast hole current characteristics.
  • the compound according to the present invention when the compound according to the present invention is applied to the p-type host of the hole transport layer, the electron blocking layer (electron suppression layer), and the light emitting layer that mainly transports holes in the organic electroluminescent device, it will greatly contribute to low voltage driving and improvement of efficiency and lifespan.
  • This device characteristic improvement has a great effect on securing stability and improving performance due to high temperature exposure in the panel manufacturing process.
  • the compound represented by Formula 1 may be prepared through the following Reaction Scheme 1:
  • variables other than X are as defined above, and each X is independently halogen, preferably chloro or bromo.
  • the present invention provides an organic light emitting device comprising 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 layer of the organic material layer 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, 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 indicated compounds 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 electron transport layer, an electron injection layer, or a layer that transports and injects electrons at the same time, and the electron transport layer, the electron injection layer, or a layer that simultaneously transports and injects electrons is represented by the above formula
  • the compound represented by 1 is included.
  • the organic layer includes a hole injection layer, a hole transport layer, an electron suppression layer, and a light emitting layer, and at least one selected from these 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 compound represented by the following formula (2) in addition to the compound represented by the formula (1).
  • two or more hosts are used in the light emitting layer, and one of the hosts is a compound of Formula 1 herein, and preferably a compound of Formula 1 and Formula 2 is used as a host compound at the same time.
  • a 1 and A 2 are each independently a benzene ring or a naphthalene ring,
  • Ar′ 1 is a substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S, provided that Ar′ 1 includes at least one N,
  • L′ 1 is a single bond, substituted or unsubstituted C 6-60 arylene or substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of N, O and S ego,
  • R′ 1 and R′ 2 are each independently hydrogen, deuterium, 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 substituted or unsubstituted C 2-60 containing one or more heteroatoms selected from the group consisting of N, O and S heteroaryl;
  • o and p are each independently an integer from 0 to 4.
  • the compound represented by Formula 2 is a compound represented by the following Formulas 2-1 to 2-4:
  • L′ 1 , Ar′ 1 , R′ 1 , R′ 2 , o and p are as defined above.
  • L′ 1 is a single bond, phenylene, biphenylrylene, naphthylene, carbazolylene, 9-phenyl-9H-carbazolylene, dibenzofuranylene or dibenzothiophenylene.
  • Ar′ 1 is any one selected from the group consisting of:
  • each X' is independently CH or N, provided that at least one of them is N;
  • each R" is independently phenyl, biphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl or 9-phenyl- 9H-carbazolyl.
  • R' 1 and R' 2 are each independently hydrogen, deuterium, phenyl, biphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, benzocarbazole- 5-yl, benzocarbazol-7-yl, benzocarbazol-11-yl, 9-phenyl-9H-carbazolyl, 5-phenyl-5H-benzocarbazolyl, 7-phenyl-7H-benzocarbazolyl or 11 -phenyl-11H-benzocarbazolyl.
  • the compound represented by Formula 2 is any one selected from the group consisting of:
  • 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 diode 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 electron transport layer, and the electron injection 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 diode according to the present invention 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
  • 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 coating 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 multi-layered 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.
  • 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 lower than that of the electron transport layer is preferable for the electron suppressing 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 heterocyclic compound containing compound.
  • 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, periflanthene, and the like, 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 include, but are not limited to, an iridium complex and a platinum complex.
  • 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, 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 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.
  • 5-bromo-2-phenylphenanthro[9,10-d]oxazole (15.0 g, 40.1 mmol) and bis(pinacolato)diboron (11.2 g, 44.1 mmol) were refluxed in 300 ml of 1,4-dioxane and stirred. . After that, potassium acetate (5.9g, 60.1mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.7g, 1.2mmol) and tricyclohexylphosphine (0.7g, 2.4mmol) were added.
  • compound 3-1 (15.0 g, 35.6 mmol) and N-(4-chlorophenyl)-N-phenylnaphthalen-2-amine (12.9 g, 39.2 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (19.7g, 142.4mmol) was dissolved in 60ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.2g, 1.1mmol) was added. After the reaction for 8 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • compound 9-1 (15.0 g, 22.5 mmol) and phenylboronic acid (3.0 g, 24.7 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (12.4g, 89.9mmol) was dissolved in 37ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • compound 10-1 (15.0 g, 22.5 mmol) and phenylboronic acid (3.0 g, 24.7 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (12.4g, 89.9mmol) was dissolved in 37ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) 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.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was placed in distilled water dissolved in detergent and washed with ultrasonic waves.
  • Fischer Co.'s DeconTM CON705 product was used as the detergent, and distilled water secondarily filtered with a 0.22 ⁇ m sterilizing filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed for 10 minutes each with a solvent of isopropyl alcohol, acetone, and methanol, and then transported to a plasma cleaner after drying.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A and LG-101 were sequentially thermally vacuum deposited to a thickness of 650 ⁇ and 50 ⁇ , respectively, to form a hole injection layer.
  • the following EB-A as an electron blocking layer (electron suppression layer) was thermally vacuum deposited to a thickness of 50 ⁇ .
  • BH-A and BD-A were vacuum-deposited to a thickness of 200 ⁇ in a weight ratio of 96:4 as a light emitting layer.
  • HB-A as a hole blocking layer to a thickness of 50 ⁇ and a compound represented by ET-A and Liq as an electron transport layer to a thickness of 310 ⁇ in a weight ratio of 1:1 were thermally vacuum-deposited, followed by vacuum deposition of the following Liq compound to a thickness of 5 ⁇ .
  • An electron injection layer was formed by vapor deposition.
  • magnesium and silver were sequentially deposited at a weight ratio of 10:1 to a thickness of 220 ⁇ and aluminum to a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light emitting diode.
  • a glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was placed in distilled water dissolved in detergent and washed with ultrasonic waves.
  • the detergent DeconTM CON705 of Fischer Co. was used, and as distilled water, distilled water that was secondarily filtered with a 0.22 ⁇ m sterilizing filter manufactured by Millipore Co. was used.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed for 10 minutes each with a solvent of isopropyl alcohol, acetone, and methanol, and then transported to a plasma cleaner after drying.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A and LG-101 were sequentially thermally vacuum deposited to a thickness of 800 ⁇ and 50 ⁇ , respectively, to form a hole injection layer. Thereafter, HT-A as a hole transport layer was vacuum deposited to a thickness of 800 ⁇ , and then EB-A as an electron blocking layer was thermally vacuum deposited to a thickness of 600 ⁇ . As a light emitting layer, RH-A and RD-A were vacuum-deposited to a thickness of 400 ⁇ in a weight ratio of 98:2. Then, as an electron transport and injection layer, the following ET-B and Liq were thermally vacuum-deposited at a ratio of 1:1 to a thickness of 360 ⁇ , followed by vacuum deposition of Liq to a thickness of 5 ⁇ .
  • magnesium and silver were sequentially deposited at a ratio of 10:1 to a thickness of 220 ⁇ and aluminum to a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light emitting diode.
  • Substrate 2 Anode

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant.
PCT/KR2021/006624 2020-06-11 2021-05-27 Nouveau composé et dispositif électroluminescent organique le comprenant WO2021251661A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114394982A (zh) * 2022-01-28 2022-04-26 武汉天马微电子有限公司 一种有机化合物、包含其的oled器件及其应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20240071307A (ko) 2022-11-15 2024-05-22 듀폰스페셜티머터리얼스코리아 유한회사 복수 종의 호스트 재료, 유기 전계 발광 화합물, 및 이를 포함하는 유기 전계 발광 소자

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120052936A (ko) * 2009-06-18 2012-05-24 바스프 에스이 전계 발광 소자를 위한 정공 수송 물질로서의 페난트로아졸 화합물
KR101486096B1 (ko) * 2007-03-29 2015-01-23 바스프 에스이 헤테로시클릭 가교된 바이페닐
KR101556098B1 (ko) * 2006-09-14 2015-10-01 시바 홀딩 인크 헤테로사이클릭 브릿징된 바이페닐 및 ｏｌｅｄ에서의 이의 용도
WO2018058494A1 (fr) * 2016-09-30 2018-04-05 Dow Global Technologies Llc Composé organique et dispositif électronique comprenant une couche organique contenant le composé organique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101497133B1 (ko) 2011-12-23 2015-02-27 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101556098B1 (ko) * 2006-09-14 2015-10-01 시바 홀딩 인크 헤테로사이클릭 브릿징된 바이페닐 및 ｏｌｅｄ에서의 이의 용도
KR101486096B1 (ko) * 2007-03-29 2015-01-23 바스프 에스이 헤테로시클릭 가교된 바이페닐
KR20120052936A (ko) * 2009-06-18 2012-05-24 바스프 에스이 전계 발광 소자를 위한 정공 수송 물질로서의 페난트로아졸 화합물
WO2018058494A1 (fr) * 2016-09-30 2018-04-05 Dow Global Technologies Llc Composé organique et dispositif électronique comprenant une couche organique contenant le composé organique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TSAI MING-SHAN, HSU YING-CHAN, LIN JIANN T., CHEN HUNG-CHENG, HSU CHAO-PING: "Organic Dyes Containing 1 H -Phenanthro[9,10- d ]imidazole Conjugation for Solar Cells", THE JOURNAL OF PHYSICAL CHEMISTRY C, AMERICAN CHEMICAL SOCIETY, US, vol. 111, no. 50, 1 December 2007 (2007-12-01), US , pages 18785 - 18793, XP055879339, ISSN: 1932-7447, DOI: 10.1021/jp075653h *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114394982A (zh) * 2022-01-28 2022-04-26 武汉天马微电子有限公司 一种有机化合物、包含其的oled器件及其应用

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