WO2023146343A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2023146343A1
WO2023146343A1 PCT/KR2023/001269 KR2023001269W WO2023146343A1 WO 2023146343 A1 WO2023146343 A1 WO 2023146343A1 KR 2023001269 W KR2023001269 W KR 2023001269W WO 2023146343 A1 WO2023146343 A1 WO 2023146343A1
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substituted
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deuterium
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김민준
홍성길
이성재
김주호
문현진
박성주
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주식회사 엘지화학
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Definitions

  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has 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, a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • the present invention provides a compound represented by Formula 1 below:
  • L 1 and L 2 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; Or a substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms of N, O and S,
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl; A substituted or unsubstituted C 3-60 aliphatic ring group; Or a substituted or unsubstituted C 2-60 heterocyclic group containing one or more heteroatoms of N, O and S;
  • Ar 1 and Ar 2 are not substituted or unsubstituted fluorenyl
  • R 1 to R 5 is unsubstituted or deuterium-substituted phenanthryl, the other is a substituent represented by Formula 2 below, and the others are each independently hydrogen or deuterium,
  • L 3 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or a substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms of N, O and S,
  • Ar 3 is substituted or unsubstituted biphenylyl; Substituted or unsubstituted naphthyl; A substituted or unsubstituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,
  • R 2 is unsubstituted phenanthryl and R 4 is a substituent represented by Formula 2
  • Ar 3 is substituted biphenylyl, substituted naphthyl, substituted phenanthryl, substituted or unsubstituted di benzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. .
  • the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.
  • FIG. 1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5 and a cathode 6.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and an example of an organic light emitting element composed of a cathode 6 is shown.
  • substituted or unsubstituted means deuterium; halogen group; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing at least one of N, O and S atoms, or substituted or unsubstit
  • a substituent in which two or more substituents are linked may be a biphenylyl group. That is, the biphenylyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • substituted or unsubstituted means “unsubstituted or selected from the group consisting of deuterium, halogen, cyano, C 1-10 alkyl, C 1-10 alkoxy and C 6-20 aryl.
  • substituted with one or more substituents are substituted with one or more substituents; or “unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, phenyl and naphthyl.
  • substituted with one or more substituents may be understood as “substituted with one to the maximum number of substitutable hydrogens.”
  • substituted with one or more substituents may be understood as “substituted with 1 to 5 substituents” or “substituted with 1 or 2 substituents”.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.
  • the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a substituent of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.
  • a substituted or unsubstituted silyl group means -Si(Z 1 )(Z 2 )(Z 3 ), where Z 1 , Z 2 and Z 3 are each independently hydrogen, deuterium, substituted or unsubstituted substituted C 1-60 alkyl, substituted or unsubstituted C 1-60 haloalkyl, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 2-60 haloalkenyl, or substituted or unsubstituted may be C 6-60 aryl.
  • Z 1 , Z 2 and Z 3 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-10 alkyl, substituted or unsubstituted C 1-10 haloalkyl, substituted or unsubstituted C 1-10 haloalkyl, or substituted or unsubstituted C 6-20 aryl.
  • silyl group examples include 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. Not limited.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • examples of the halogen group include fluoro, chloro, bromo, or iodo.
  • the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5 -methylhexy
  • 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 one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.
  • the aliphatic group refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound containing only carbon as a ring-forming atom and having no aromaticity, and includes both monocyclic or condensed polycyclic compounds. understood to be inclusive.
  • the carbon number of the aliphatic ring group is 3 to 60.
  • the number of carbon atoms of the cycloalkyl group is 3 to 30.
  • the number of carbon atoms of the cycloalkyl group is 3 to 20.
  • Examples of such aliphatic groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spiro hydrocarbon groups, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds, and the like. can be heard
  • examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • bridged hydrocarbon group examples include bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, decalinyl, etc., but is not limited thereto.
  • examples of the spiro ring hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecanyl, but are not limited thereto.
  • the substituent derived from the hydrogenated derivative of the aromatic hydrocarbon compound refers to a substituent derived from a compound in which hydrogen is added to some of the unsaturated bonds of the monocyclic or polycyclic aromatic hydrocarbon compound, and examples of such a substituent include 1 H -indenyl , 2 H -indenyl, 4 H -indenyl, 2,3-dihydro-1 H -indenyl, 1,4-dihydronaphthalenyl, 1,2,3,4-tetrahydronaphthalenyl, 6,7,8,9-tetrahydro-5 H -benzo [7] annulenyl (6,7,8,9-tetrahydro-5 H -benzo [7] annulenyl), 6,7-dihydro-5 H - Benzocycloheptenyl, etc., but is not limited thereto.
  • an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound having aromaticity while containing only carbon as a ring-forming atom, and the number of carbon atoms is not particularly limited, but preferably has 6 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenylyl group, a terphenylyl group, etc. as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • a heterocyclic group refers to a monovalent substituent derived from a monocyclic or condensed polycyclic compound further including one or more heteroatoms selected from O, N, Si, and S in addition to carbon as a ring-forming atom.
  • the number of carbon atoms of the heterocyclic group is 2 to 60 carbon atoms.
  • the heterocyclic group has 2 to 30 carbon atoms.
  • the heterocyclic group has 2 to 20 carbon atoms. Examples of such a heterocyclic group include a heteroaryl group, a substituent derived from a hydrogenated derivative of a heteroaromatic compound, and the like.
  • the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound further including at least one heteroatom selected from N, O, and S in addition to carbon as a ring-forming atom, and refers to a substituent having aromaticity. do.
  • the number of carbon atoms of the heteroaryl group is 2 to 60 carbon atoms.
  • the heteroaryl group has 2 to 30 carbon atoms.
  • the heteroaryl group has 2 to 20 carbon atoms.
  • heteroaryl group examples include a thiophenyl group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, and a triazinyl group.
  • the substituent derived from the hydrogenated derivative of the heteroaromatic compound refers to a substituent derived from a compound in which hydrogen is added to some of the unsaturated bonds of the monocyclic or polycyclic heteroaromatic compound, and examples of such substituents include 1,3-di Hydroisobenzofuranyl (1,3-dihydroisobenzofuranyl), 2,3-dihydrobenzofuranyl (2,3-dihydrobenzofuranyl), 1,3-dihydrobenzo[ c ]thiophenyl (1,3-dihydrobenzo[ c ]thiophenyl), 2,3-dihydro[ b ]thiophenyl (2,3-dihydro[ b ]thiophenyl), and the like, but are not limited thereto.
  • an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, and an aryl group among arylsilyl groups are 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 examples of the above-mentioned alkyl group.
  • the description of the above-described heteroaryl may be applied to the heteroaryl among heteroarylamines.
  • the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of heteroaryl described above may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents.
  • the heterocyclic group 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.
  • deuterated or substituted with deuterium means that at least one of substitutable hydrogens in a compound, a divalent linking group, or a monovalent substituent is substituted with deuterium.
  • unsubstituted or substituted with deuterium or “substituted or unsubstituted with deuterium” means “unsubstituted or substituted with one to the maximum number of deuterium hydrogen atoms”.
  • the term “unsubstituted or deuterium-substituted phenanthryl” means “unsubstituted or deuterium-substituted phenanthryl", considering that the maximum number of deuterium-substituted hydrogens in the phenanthryl structure is 9, “unsubstituted or deuterium-substituted phenanthryl” It can be understood in the sense of "substituted phenanthryl”.
  • deuterated structure means a compound of any structure in which at least one hydrogen is substituted with deuterium, a divalent linking group, or a monovalent substituent.
  • a deuterated structure of phenyl may be understood to refer to monovalent substituents of all structures in which at least one substitutable hydrogen in a phenyl group is substituted with a deuterium as follows.
  • the “deuterium substitution rate” or “degree of deuteration” of a compound is the number of deuterium atoms substituted for the total number of hydrogen atoms that may exist in the compound (the sum of the number of hydrogen atoms that can be substituted with deuterium atoms and the number of deuterium atoms that are substituted in the compound). means that the ratio is calculated as a percentage. Therefore, when the "deuterium substitution rate” or “degree of deuteration” of a compound is referred to as "K%", it means that K% of hydrogen substitutable with deuterium in the compound is substituted with deuterium.
  • the "deuterium substitution rate” or “deuteration degree” is MALDI-TOF MS (Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin -Layer Chromatography/Mass Spectrometry) or GC/MS (Gas Chromatography/Mass Spectrometry) can be used to measure according to a commonly known method.
  • the "deuterium substitution rate” or “degree of deuteration” is obtained by calculating the number of deuterium substituted in the compound through MALDI-TOF MS analysis, and then replacing the total number of hydrogens that may exist in the compound. It can be obtained by calculating the ratio of the number of deuterium atoms as a percentage.
  • the present invention provides a compound represented by Formula 1 above.
  • the compound represented by Formula 1 has a structure in which a specific substituent (biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl) is substituted together with a phenanthryl group and an amino group on a benzene ring.
  • a specific substituent biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl
  • the compound represented by Formula 1 does not have substituted or unsubstituted fluorenyl such as fluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl as a substituent of an amino group.
  • the compound represented by Formula 1 having such a structure can effectively block electron movement to the hole transport layer compared to compounds having a different structure, so it can be used as a material for the electron blocking layer, and also contributes to the stabilization of excitons and at the same time gives a red color. It has excellent energy transfer ability to the dopant and can be used as a host material.
  • an organic light emitting device employing the compound may exhibit a lower driving voltage than an organic light emitting device employing a compound having a substituent different from that of the present application, and may simultaneously improve efficiency and lifetime characteristics.
  • R 1 is unsubstituted or phenanthryl substituted with deuterium
  • one of R 2 , R 3 , R 4 and R 5 is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or phenanthryl substituted with deuterium, one of R 1 , R 3 , R 4 and R 5 is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium; or
  • R 3 is unsubstituted or deuterium-substituted phenanthryl, one of R 1 , R 2 , R 4 and R 5 is a substituent represented by Formula 2, and the others may each independently be hydrogen or deuterium.
  • R 1 is unsubstituted or deuterium-substituted phenanthryl
  • R 2 is a substituent represented by Formula 2
  • R 3 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 1 is unsubstituted or deuterium-substituted phenanthryl, R 3 is a substituent represented by Formula 2, R 2 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 1 is unsubstituted or deuterium-substituted phenanthryl, R 4 is a substituent represented by Formula 2, R 2 , R 3 and R 5 are each independently hydrogen or deuterium;
  • R 1 is unsubstituted or deuterium-substituted phenanthryl, R 5 is a substituent represented by Formula 2, R 2 , R 3 and R 4 are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or deuterium-substituted phenanthryl, R 1 is a substituent represented by Formula 2, R 3 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or deuterium-substituted phenanthryl, R 3 is a substituent represented by Formula 2, R 1 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or deuterium-substituted phenanthryl, R 4 is a substituent represented by Formula 2, R 1 , R 3 and R 5 are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or deuterium-substituted phenanthryl, R 5 is a substituent represented by Formula 2, R 1 , R 3 and R 4 are each independently hydrogen or deuterium;
  • R 3 is unsubstituted or deuterium-substituted phenanthryl, R 1 is a substituent represented by Formula 2, R 2 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 3 is unsubstituted or deuterium-substituted phenanthryl, R 2 is a substituent represented by Formula 2, R 1 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 3 is unsubstituted or deuterium-substituted phenanthryl
  • R 4 is a substituent represented by Formula 2
  • R 1 , R 2 and R 5 are each independently hydrogen or deuterium; or
  • R 3 is unsubstituted or deuterium-substituted phenanthryl
  • R 5 is a substituent represented by Formula 2
  • R 1 , R 2 and R 4 may each independently represent hydrogen or deuterium.
  • R 1 is unsubstituted or deuterium-substituted phenanthryl, R 3 is a substituent represented by Formula 2, R 2 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 1 is unsubstituted or deuterium-substituted phenanthryl, R 4 is a substituent represented by Formula 2, R 2 , R 3 and R 5 are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or deuterium-substituted phenanthryl, R 3 is a substituent represented by Formula 2, R 1 , R 4 and R 5 are each independently hydrogen or deuterium;
  • R 2 is unsubstituted or deuterium-substituted phenanthryl, R 4 is a substituent represented by Formula 2, R 1 , R 3 and R 5 are each independently hydrogen or deuterium;
  • R 3 is unsubstituted or deuterium-substituted phenanthryl
  • R 4 is a substituent represented by Formula 2
  • R 1 , R 2 and R 5 are each independently hydrogen or deuterium; or
  • R 3 is unsubstituted or deuterium-substituted phenanthryl
  • R 5 is a substituent represented by Formula 2
  • R 1 , R 2 and R 4 are each independently hydrogen or deuterium.
  • L 1 and L 2 are each independently a single bond; A substituted or unsubstituted C 6-20 arylene; Or a substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms selected from N, O and S.
  • L 1 and L 2 are each independently a single bond; C 6-20 arylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl and naphthyl; Or it may be C 2-20 heteroarylene containing one heteroatom of O and S unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl and naphthyl.
  • L 1 and L 2 may each independently represent a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, or substituted or unsubstituted naphthylene.
  • L 1 and L 2 are each independently a single bond, phenylene, naphthylphenylene, biphenyldiyl, naphthylene, or phenylnaphthylene;
  • phenylene, naphthylphenylene, biphenyldiyl, naphthylene and phenylnaphthylene may be unsubstituted or substituted with deuterium.
  • L 1 and L 2 may each independently be a single bond, or any one selected from the group consisting of or a deuterated structure thereof:
  • At least one of L 1 and L 2 may be a single bond.
  • L 1 and L 2 may be the same as each other. or L 1 and L 2 may be different.
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-20 aryl; A substituted or unsubstituted C 3-20 aliphatic ring group; Or a substituted or unsubstituted C 2-60 heterocyclic group containing at least one heteroatom selected from N, O, and S.
  • Ar 1 and Ar 2 are each independently C 6-20 aryl which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, phenyl and naphthyl.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, dihydroindenyl, tetrahydronaphthyl, tetrahydrobenzo[7]anulenyl, adamantyl , dibenzofuranyl, or dibenzothiophenyl;
  • Ar 1 and Ar 2 may be substituted or unsubstituted.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetra hydronaphthyl, 6,7,8,9-tetrahydro-5H-benzo[7]anulenyl, adamantyl, dibenzofuranyl, or dibenzothiophenyl;
  • Ar 1 and Ar 2 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, phenyl, and naphthyl.
  • Ar 1 and Ar 2 may each independently be any one selected from the group consisting of, or a deuterated structure thereof, but is not limited thereto:
  • Ar 1 and Ar 2 may be different.
  • Ar 1 and Ar 2 may be identical to each other.
  • L 1 -Ar 1 and L 2 -Ar 2 may be identical to each other.
  • L 1 -Ar 1 and L 2 -Ar 2 can be different.
  • R 1 to R 5 may be any one substituent selected from the group consisting of a1 to a5 below:
  • n is an integer from 0 to 9;
  • one of R 1 to R 5 is any one substituent selected from the group consisting of a2, a3 and a5.
  • L 3 is a single bond; A substituted or unsubstituted C 6-20 arylene; Or a substituted or unsubstituted C 2-20 heteroarylene containing one heteroatom of O and S.
  • L 3 is a single bond; It may be C 6-20 arylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl and naphthyl.
  • L 3 can be a single bond or substituted or unsubstituted phenylene.
  • L 3 may be a single bond or unsubstituted or deuterium-substituted phenylene.
  • Ar 3 is substituted or unsubstituted biphenylyl; Substituted or unsubstituted naphthyl; A substituted or unsubstituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,
  • R 2 is unsubstituted phenanthryl and R 4 is a substituent represented by Formula 2
  • Ar 3 is substituted biphenylyl, substituted naphthyl, substituted phenanthryl, substituted or unsubstituted di benzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • substituents of biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, and substituted dibenzothiophenyl are selected from the group consisting of deuterium, halogen, cyano, C 1-10 alkyl and C 6-20 aryl. One or more substituents may be selected.
  • Ar 3 is biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or substituted dibenzothiophenyl;
  • Ar 3 is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, and C 6-20 aryl;
  • biphenylyl substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, and C 6-20 aryl;
  • naphthyl substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, and C 6-20 aryl;
  • phenanthryl substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, and C 6-20 aryl;
  • dibenzofuranyl unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-4 alkyl, and C 6-20 aryl; or
  • Ar 3 is biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl;
  • Ar 3 is unsubstituted or substituted with one or more deuterium, one phenyl, one biphenylyl, or one naphthyl;
  • biphenylyl substituted with 1 to 9 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl;
  • naphthyl substituted with 1 to 7 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl;
  • phenanthryl substituted with 1 to 9 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl;
  • dibenzofuranyl unsubstituted or substituted with 1 to 7 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl; or
  • dibenzothiophenyl which is unsubstituted or substituted with 1 to 7 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl.
  • Ar 3 may be any one selected from the group consisting of;
  • Q is deuterium, phenyl, biphenylyl, or naphthyl
  • n1 is an integer from 0 to 7;
  • n2 is an integer from 0 to 4.
  • n3 is an integer from 0 to 5;
  • m4 is an integer from 0 to 9;
  • Ar 3 may be any one selected from the group consisting of:
  • Q is deuterium, phenyl, biphenylyl, or naphthyl
  • n1 is an integer from 0 to 7;
  • n5 is an integer from 1 to 7;
  • n6 is an integer from 0 to 4.
  • n 1
  • n6+m7 is an integer from 1 to 9;
  • n8 is an integer from 1 to 9;
  • n1 is an integer from 0 to 7;
  • n2 is an integer from 0 to 4.
  • n3 is an integer from 0 to 5;
  • m4 is an integer from 0 to 9;
  • n1, m2, m3 and m4 may each independently be 0 or 1.
  • R 2 is unsubstituted phenanthryl
  • R 4 is a substituent represented by Formula 2, and Q is deuterium
  • n1 is an integer from 0 to 7;
  • n5 is an integer from 1 to 7;
  • n6 is an integer from 0 to 4.
  • n 1
  • n6+m7 is an integer from 1 to 9;
  • n8 is an integer from 1 to 9;
  • n 1
  • m6+m7 can be 1 or 2.
  • the compound may be represented by any one of Formulas 1-1 to 1-6:
  • p is an integer from 0 to 3;
  • A is a substituent represented by any one of the following formulas a1 to a5,
  • n is an integer from 0 to 9;
  • L 1 to L 3 and Ar 1 to Ar 3 are as defined in Formula 1 above;
  • Ar 3 is substituted biphenylyl; substituted naphthyl, substituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiophenyl.
  • the compound may contain no deuterium or one or more deuterium atoms.
  • the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound is 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, Alternatively, it may be 90% or more and 100% or less.
  • the compound may contain no deuterium or 1 to 50 deuterium atoms. More specifically, the compound does not contain deuterium, or at least 1, at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, or at least 9 More than 50, 40 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 13 or less , 12 or less, 11 or less, or 10 or less deuterium.
  • the compound represented by Formula 1 can be prepared by, for example, a preparation method as shown in Reaction Scheme 1 below:
  • X is halogen, preferably bromo or chloro, and descriptions of the remaining substituents are as defined above.
  • the compound represented by Formula 1 may be prepared by an amine substitution reaction of reactants A1 and A2.
  • the amine substitution reaction is preferably performed under a palladium catalyst and a base, and a reactor for the reaction may be changed to a reactor known in the art. This 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 one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. .
  • the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer or an electron blocking layer.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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, a light emitting layer, an electron transport layer, and an electron injection layer as organic material layers.
  • the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.
  • the organic material layer may include a light emitting layer, and in this case, the organic material layer including the compound may be a light emitting layer.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer, wherein the organic material layer including the compound may be a light emitting layer or a hole transport layer.
  • the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron injection and transport layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron blocking layer.
  • the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron injection and transport layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron blocking layer.
  • the organic light emitting device according to the present invention has a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. may be minor.
  • the organic light emitting device according to the present invention has an inverted type organic layer in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate, wherein the first electrode is a cathode and the second electrode is an anode. It may be a light emitting element.
  • FIGS. 1 and 2 the structure of an 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 composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5 and a cathode 6.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer or the electron blocking layer.
  • the organic light emitting device according to the present invention may be manufactured with materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1. 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 physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode
  • PVD physical vapor deposition
  • depositing a metal or a metal oxide having conductivity or an alloy thereof depositing a metal or a metal oxide having conductivity or an alloy thereof on the 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
  • 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 Chemical Formula 1 may be formed as 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
  • the cathode material a material having a high work function is generally preferable so that holes can be smoothly injected into the organic material layer.
  • the cathode material include metals such as vanadium, chromium, copper, zinc, and 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 so as to easily inject electrons into the organic material layer.
  • Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer
  • a compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, anthraquinone, and polyaniline and polythiophene-based conductive polymers, 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.
  • the hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer, and has high hole mobility. material is suitable.
  • As the hole transport material a compound represented by Formula 1, an arylamine-based organic material, a conductive polymer, or a block copolymer having both conjugated and non-conjugated parts may be used, but is not limited thereto.
  • the electron blocking layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase the probability of hole-electron coupling, thereby increasing the efficiency of the organic light emitting device.
  • the electron blocking layer includes an electron blocking material, and examples of the electron blocking material include a compound represented by Chemical Formula 1 or an arylamine-based organic material, but is not limited thereto.
  • 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-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • a host material the compound represented by Chemical Formula 1 may be used.
  • the host material may further include a condensed aromatic ring derivative or a heterocyclic compound other than the compound represented by Formula 1 above.
  • 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, etc., but are not limited thereto.
  • the organic material layer containing the compound is a light emitting layer.
  • the light emitting layer includes the compound represented by Formula 1 as a host material
  • the light emitting layer may further include a compound represented by Formula 3 below:
  • R 11 to R 14 are each independently hydrogen; heavy hydrogen; cyano; halogen; or substituted or unsubstituted C 1-60 alkyl, or two adjacent R 11 to R 14 bond to each other to form a substituted or unsubstituted benzene ring fused with the adjacent ring;
  • R 15 to R 18 is a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heterocyclic group containing one or more heteroatoms of N, O, and S, and the others are each independently hydrogen; heavy hydrogen; cyano; halogen; or a substituted or unsubstituted C 1-60 alkyl;
  • L 11 is a single bond; or a substituted or unsubstituted C 6-60 arylene;
  • Ar 11 and Ar 12 are each independently a substituted or unsubstituted C 6-60 aryl; A substituted or unsubstituted C 3-60 aliphatic ring group; or a substituted or unsubstituted C 2-60 heterocyclic group containing at least one heteroatom selected from N, O and S.
  • two adjacent R 11 to R 14 combine with each other to form a benzene ring unsubstituted or substituted with deuterium fused with the adjacent ring, and the others may be hydrogen or deuterium.
  • R 15 to R 18 is a substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing one or more heteroatoms selected from N, O and S, and the others are each independently hydrogen; heavy hydrogen; cyano; halogen; Or it may be a substituted or unsubstituted C 1-10 alkyl.
  • R 15 to R 18 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and the others may each independently be hydrogen or deuterium.
  • R 15 is substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R 16 , R 17 and R 18 are each independently hydrogen; heavy hydrogen; cyano; halogen; or C 1-10 alkyl.
  • R 15 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • R 16 , R 17 and R 18 may each independently be hydrogen or deuterium.
  • R 16 is substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R 15 , R 17 and R 18 are each independently hydrogen; heavy hydrogen; cyano; halogen; or C 1-10 alkyl.
  • R 16 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • R 15 , R 17 and R 18 may each independently be hydrogen or deuterium.
  • R 17 is substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R 15 , R 16 and R 18 are each independently hydrogen; heavy hydrogen; cyano; halogen; or C 1-10 alkyl.
  • R 17 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • R 15 , R 16 and R 18 may each independently be hydrogen or deuterium.
  • R 18 is substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R 15 , R 16 and R 17 are each independently hydrogen; heavy hydrogen; cyano; halogen; or C 1-10 alkyl.
  • R 18 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • R 15 , R 16 and R 17 may each independently be hydrogen or deuterium.
  • L 11 is a single bond; Or it may be a substituted or unsubstituted C 6-20 arylene.
  • L 11 may be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, or substituted or unsubstituted naphthylene.
  • Ar 11 and Ar 12 are each independently substituted or unsubstituted C 6-20 aryl; Or a substituted or unsubstituted C 2-20 heteroaryl containing one or more heteroatoms selected from N, O and S.
  • Ar 11 and Ar 12 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted naphthyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
  • the compound represented by Chemical Formula 3 may be represented by any one of the following Chemical Formulas 3-1 to 3-4:
  • each R' is independently deuterium, halogen, or cyano
  • r is an integer from 0 to 4.
  • s is an integer from 0 to 6;
  • R 15 to R 18 , L 11 , Ar 11 and Ar 12 are as defined in Formula 3 above.
  • the compound represented by Formula 3 may be any one selected from the group consisting of the following compounds:
  • X' is halogen, preferably bromo or chloro, and descriptions of the remaining substituents are as defined above.
  • the compound represented by Chemical Formula 3 may be prepared by an amine substitution reaction of reactants B1 and B2.
  • the amine substitution reaction is preferably performed under a palladium catalyst and a base, and a reactor for the reaction may be changed to a reactor known in the art. This manufacturing method may be more specific in Preparation Examples to be described later.
  • the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 3 in the light emitting layer may be included in a weight ratio of 1:99 to 99:1.
  • the compound represented by Formula 1 and the compound represented by Formula 3 in the light emitting layer are 30:70 to 70: It is more preferable that it is included in a weight ratio of 30, a weight ratio of 40:60 to 60:40, or a weight ratio of 50:50.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc.
  • styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein 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.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the following compounds may be used as the dopant material, but are not limited thereto:
  • the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling layers that play a role.
  • the hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound having an electron withdrawing group such as a phosphine oxide derivative may be used, but is not limited thereto.
  • the electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting the received electrons to the light emitting layer, and is formed on the light emitting layer or the hole blocking layer.
  • an electron injecting and transporting material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable.
  • specific electron injection and transport materials include Al complexes of 8-hydroxyquinoline; Complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives, etc., but are not limited thereto.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds , or may be used together with nitrogen-containing 5-membered ring derivatives, etc., but is not limited thereto.
  • the electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer.
  • the electron transport layer is formed on the light emitting layer or the hole blocking layer, and the above-described electron injection and transport material may be used as an electron transport material included in the electron transport layer.
  • the electron injection layer is formed on the electron transport layer, and examples of electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiophyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like can be used.
  • electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiophyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methan
  • 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. It is not limited to this.
  • 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 light emitting efficiency.
  • the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • a glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water.
  • ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • the following compound HI-1 was formed to a thickness of 1150 ⁇ as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%.
  • a hole transport layer having a thickness of 800 ⁇ was formed by vacuum depositing the following HT-1 compound on the hole injection layer. Then, the compound 1 prepared in Synthesis Example 1 was vacuum deposited to form a film thickness of 150 ⁇ on the hole transport layer to form an electron blocking layer.
  • the following RH-1 compound as a host and the following Dp-7 compound as a dopant were vacuum-deposited on the electron blocking layer in a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed on the light emitting layer by vacuum depositing the HB-1 compound to a film thickness of 30 ⁇ . Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • a negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride on the anode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum level during deposition was 2 ⁇ 10 -7 to 5 ⁇ 10 -6 torr was maintained.
  • 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.
  • Example 1 In the organic light-emitting device of Example 1, the following compound EB-1 was used instead of Compound 1 as an electron blocking layer, RH-1 was used as a first host instead of single host RH-1 as a host, and the compounds listed in Table 2 were used as a second host. Thus, an organic light emitting device was manufactured in the same manner as in Example 1, except that the first host and the second host were used in a weight ratio of 1:1.
  • An organic light emitting device was manufactured in the same manner as in Comparative 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. At this time, the structures of comparative compounds C-1 to C-6 are as follows.
  • the EB-1 compound was used instead of Compound 1 as an electron blocking layer, RH-1 was used as a first host instead of a single host RH-1 as a host, and the compounds listed in Table 2 were used as a second host.
  • an organic light emitting device was manufactured in the same manner as in Example 1, except that the first host and the second host were used in a weight ratio of 1:1.
  • the lifetime T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the organic light emitting device of the example using the compound represented by Formula 1 as a host material of the electron blocking layer or the light emitting layer is the organic light emitting device of the comparative example using a compound having a structure different from this. It can be seen that compared to the reduced driving voltage and improved efficiency and lifespan characteristics. Through this, the compound represented by Formula 1 can not only effectively block the movement of electrons to the hole transport layer, but also can balance the charge between the hosts well, contribute to the stabilization of excitons, and at the same time, energy transfer ability to the red dopant You can check this excellence.
  • substrate 2 anode
  • hole transport layer 4 light emitting layer

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
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  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2023/001269 2022-01-28 2023-01-27 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2023146343A1 (fr)

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KR20180082124A (ko) * 2017-01-10 2018-07-18 에스에프씨 주식회사 고효율을 갖는 유기 발광 소자
KR20190116941A (ko) * 2018-04-05 2019-10-15 주식회사 엘지화학 카바졸계 화합물 및 이를 포함하는 유기 발광 소자
KR102094830B1 (ko) * 2018-11-30 2020-03-30 에스에프씨 주식회사 다환 방향족 유도체 화합물 및 이를 이용한 유기발광소자
CN111440156A (zh) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 一种发光辅助材料、其制备方法及有机电致发光器件

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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

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
KR20140096182A (ko) * 2012-05-02 2014-08-04 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20180082124A (ko) * 2017-01-10 2018-07-18 에스에프씨 주식회사 고효율을 갖는 유기 발광 소자
KR20190116941A (ko) * 2018-04-05 2019-10-15 주식회사 엘지화학 카바졸계 화합물 및 이를 포함하는 유기 발광 소자
KR102094830B1 (ko) * 2018-11-30 2020-03-30 에스에프씨 주식회사 다환 방향족 유도체 화합물 및 이를 이용한 유기발광소자
CN111440156A (zh) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 一种发光辅助材料、其制备方法及有机电致发光器件

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