WO2024091024A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2024091024A1
WO2024091024A1 PCT/KR2023/016753 KR2023016753W WO2024091024A1 WO 2024091024 A1 WO2024091024 A1 WO 2024091024A1 KR 2023016753 W KR2023016753 W KR 2023016753W WO 2024091024 A1 WO2024091024 A1 WO 2024091024A1
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한수진
윤정민
윤희경
이재탁
허동욱
홍성길
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주식회사 엘지화학
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    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • H10K50/00—Organic light-emitting devices
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Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • an organic light-emitting device is a light-emitting device using an organic semiconductor material and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material.
  • Organic light-emitting devices can be broadly divided into two types according to their operating principles as follows. First, excitons are formed in the organic layer by photons flowing into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as current sources (voltage sources). It is a type of light emitting device. The second type is a light-emitting device that applies voltage or current to two or more electrodes to inject holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes, and operates by the injected electrons and holes.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and for example, it consists of a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. You can lose.
  • this organic light-emitting device when a voltage is applied between two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.
  • These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function.
  • charge transport materials such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function.
  • color of light emitting there are blue, green, and red light emitting materials, and yellow and orange light emitting materials needed to realize better natural colors.
  • a host/dopant system can be used as a luminescent material.
  • the principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light.
  • the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
  • the materials that make up the organic layer within the device such as hole injection material, hole transport material, light-emitting material, electron suppressor material, electron transport material, and electron injection material, must be stable and efficient materials. As this is supported by , the development of new materials continues to be required.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • A is a heteroaryl group containing a 6-membered ring containing N substituted with a substituted or unsubstituted aryl group
  • B is a heteroaryl group containing a 6-membered ring containing N substituted with a substituted or unsubstituted aryl group
  • L is a direct bond, or a substituted or unsubstituted arylene group
  • One of Q1 and Q2 is an aryl group having 6 to 30 carbon atoms, and the other is hydrogen or an aryl group having 6 to 30 carbon atoms,
  • one of Q1 and Q2 is hydrogen
  • the remainder is one or more substituents selected from deuterium, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group. It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
  • both Q1 and Q2 are aryl groups having 6 to 30 carbon atoms
  • the aryl group having 6 to 30 carbon atoms is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted Or, it is substituted or unsubstituted with one or more substituents selected from unsubstituted heteroaryl groups.
  • the compound of the present invention can be used as a material for the organic layer of an organic light-emitting device.
  • an organic light-emitting device including the compound of the present invention an organic light-emitting device with high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the electron transport layer of the organic light-emitting device, intramolecular Due to its high polarity, the effect of electron transfer is high, making it possible to manufacture organic light-emitting devices with long-life characteristics.
  • the compound of the present invention has two or more substituted heterocycles containing an N-containing 6-membered ring with electron transport properties, and is adjacent to the ortho position of phenyl, resulting in structural distortion, so that the electron transport ability can be adjusted in various ways. there is.
  • FIG. 1 and 2 show examples of organic light-emitting devices according to the present invention.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group (-CN); silyl group; boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
  • a substituent group in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
  • the silyl group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
  • the boron group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, and octyl groups.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine groups include methylamine groups; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc.
  • N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • N-arylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group.
  • N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as examples of the alkyl groups described above.
  • the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc.
  • examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.
  • 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30.
  • heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group, etc. However, it is not limited to these.
  • the arylene group is the same as defined for the aryl group, except that it is a divalent group.
  • heteroarylene group is the same as defined for the heteroaryl group, except that it is a divalent group.
  • Formula 1 is Formula 1-1 or 1-2 below.
  • A, B, L, Q1, and Q2 are as defined in Formula 1.
  • Formula 1 is Formula 1-3 below.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group. Or, it combines with an adjacent group to form a substituted or unsubstituted ring,
  • a and b are integers from 1 to 5
  • R1 is the same or different
  • R2 is the same or different.
  • Formula 1 is Formula 1-4 below.
  • One of X1 to X3 is N, and the others are N or CR, respectively,
  • R is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
  • One of X4 to X8 is N, and the others are N or CR1, respectively,
  • R1 is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or is substituted or unsubstituted by combining with adjacent substituents. forms a ring
  • A is pyridine, pyrimidine, triazine, quinoline, quinazoline, or quinoxaline,
  • pyridine, pyrimidine, triazine, quinoline, quinazoline, or quinoxaline are each independently substituted with deuterium, nitrile group, nitro group, halogen group, or substituted or unsubstituted aryl group with substituted or unsubstituted alkyl group.
  • B is pyridine, pyrimidine, or triazine
  • the pyridine, pyrimidine, or triazine are each independently deuterium, nitrile group, nitro group, halogen group, or substituted or unsubstituted. It is substituted with a substituted alkyl group or with an unsubstituted aryl group.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, halogen group, alkyl group of 1 to 10 carbon atoms, aryl group of 6 to 30 carbon atoms. group, or a heteroaryl group having 3 to 30 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted benzene ring.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, F, Cl, methyl group, ethyl group, propyl group, terbutyl group, phenyl group. , a naphthyl group, anthracene group, biphenyl group, carbazole group, dibenzofuran group, or dibenzothiophene group, or is combined with an adjacent group to form a benzene ring.
  • A is a triazine substituted with an aryl group, a pyrimidine substituted with an aryl group, a pyridine substituted with an aryl group, or a quinazole group substituted with an aryl group.
  • A is a triazine, pyrimidine, pyridine, or quinazole group, and the substituents are substituted with deuterium or with an unsubstituted aryl group having 6 to 30 carbon atoms.
  • B is a triazine substituted with an aryl group, a pyrimidine substituted with an aryl group, a pyridine substituted with an aryl group, or a quinazole group substituted with an aryl group.
  • B is a triazine, pyrimidine, pyridine, or quinazole group, and the substituents are substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a direct bond, or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium.
  • L is a direct bond, a phenyl group substituted or unsubstituted with deuterium, or a divalent naphthalene group substituted or unsubstituted with deuterium.
  • L is a direct bond, a phenylene group, or a divalent naphthalene group.
  • one of Q1 and Q2 is an aryl group having 6 to 30 carbon atoms, and the other is hydrogen or an aryl group having 6 to 30 carbon atoms,
  • the remainder is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from deuterium, nitro group, halogen group, alkyl group, aryl group, and heteroaryl group,
  • both Q1 and Q2 are aryl groups having 6 to 30 carbon atoms
  • the aryl group having 6 to 30 carbon atoms is substituted with one or more substituents selected from deuterium, nitrile group, nitro group, halogen group, alkyl group, aryl group, and heteroaryl group. or unsubstituted.
  • the other is a phenyl group, naphthyl group, phenanthrene group, fluoranthene group, or phenanthrene group
  • the substituent is deuterium, nitro group, F , an alkyl group with 1 to 10 carbon atoms, a haloalkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms that is unsubstituted or substituted with deuterium and an alkyl group with 1 to 10 carbon atoms. It's a relief.
  • Q1 and Q2 are a phenyl group, naphthyl group, phenanthrene group, fluoranthene group, or phenanthrene group
  • the substituent is deuterium, nitro group, nitrile group, F, and has 1 to 10 carbon atoms. is substituted or unsubstituted with an alkyl group, a haloalkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms that is substituted or unsubstituted with deuterium and an alkyl group with 1 to 10 carbon atoms.
  • the substituent is a deuterium group, a nitrile group, F, a methyl group, or a methyl group substituted with F. , terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, carbazole group substituted or unsubstituted with deuterium, benzothiazole group, benzoxazole group, or benz substituted or unsubstituted with ethyl group. It is substituted or unsubstituted with an imidazole group.
  • the substituent is deuterium, F, methyl group, F-substituted methyl group, terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, deuterium-substituted or unsubstituted carbazole group, benzothiazole group, benzoxazole group, or ethyl group. Or, it is substituted or unsubstituted with an unsubstituted benzimidazole group.
  • the phenyl group is a deuterium group, a nitrile group, F, a methyl group, or a methyl group substituted with F.
  • the naphthyl group, phenanthrene group, fluoranthene group, and phenanthrene group are unsubstituted.
  • the phenyl group is deuterium, F, methyl group, F-substituted methyl group, terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, deuterium-substituted or unsubstituted carbazole group, benzothiazole group, benzoxazole group, or ethyl group. or substituted or unsubstituted with an unsubstituted benzimidazole group,
  • the naphthyl group, phenanthrene group, fluoranthene group, and phenanthrene group are unsubstituted.
  • Formula 1 is one of the structural formulas below.
  • Substituents of the compound of Formula 1 may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.
  • the organic light emitting device includes a first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising 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 contains the above-described compound.
  • the organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
  • the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • 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 layer that simultaneously performs hole injection and hole transport, 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 to this and may include fewer or more organic material layers.
  • the organic material layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers includes the compound of Formula 1.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of Formula 1.
  • the electron injection and transport layer includes the compound of Formula 1 and a metal complex.
  • the organic material layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport, and one or more of the layers contains the compound of Formula 1. Includes.
  • the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound of Formula 1.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is an anode.
  • the structure of the organic light emitting device of the present invention may have the same structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound of Formula 1 may be included in the organic layer 3.
  • an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and transport layer (8), and a cathode (4) are sequentially stacked on a substrate (1).
  • the structure of the light emitting device is illustrated. In this structure, the compound of Formula 1 is included in the electron injection and transport layer (8).
  • the organic light emitting device deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • An anode is formed by depositing a layer on top of a hole injection layer, a hole transport layer, a layer that performs both hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a group consisting of a layer that performs both electron transport and electron injection. It can be manufactured by forming an organic material layer containing one or more selected layers and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure.
  • the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
  • the anode is an electrode that injects holes
  • the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • anode materials that can be used in the present invention 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); Combination of metal and oxide 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 are included, but are not limited to these.
  • the cathode is an electrode that injects electrons
  • the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer.
  • Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage.
  • HOMO highest occupied
  • the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
  • the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
  • R300 to R308 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or combines with an adjacent group to form a substituted or unsubstituted ring,
  • r301 and r302 are each integers from 1 to 4,
  • r303 and r304 are each integers from 1 to 3,
  • R301 is 2 or more, R301 is the same or different from each other,
  • R302 is 2 or more, R302 is the same or different from each other,
  • R303 is 2 or more, R303 is the same or different from each other,
  • R304 is the same or different from each other.
  • R301 to R304 are hydrogen.
  • R300 is a substituted or unsubstituted aryl group.
  • R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R300 is a phenyl group.
  • R305 to R308 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R305 to R308 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R305 to R308 are the same as or different from each other, and are each independently a phenyl group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.
  • the formula HI-1 is represented by the following compound.
  • the hole transport layer may play a role in facilitating the transport of holes.
  • the hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
  • At least one of X'1 to X'6 is N, and the remainder is CH,
  • R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
  • X'1 to X'6 are N.
  • R309 to R314 are nitrile groups.
  • the formula HT-1 is represented by the following compound.
  • the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
  • R400 to R402 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • L402 are the same or different from each other, and each independently represents a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • R400 to R402 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R400 and R401 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R400 and R401 are the same or different from each other, and are each independently a phenyl group or a diphenylfluorene group.
  • R402 is a carbazole group substituted or unsubstituted with a phenyl group.
  • the formula HT-2 is selected from the following compounds.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron suppressing layer may be made of the spiro compound described above or a material known in the art.
  • the light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material.
  • the light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • An organic light-emitting device includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following formula H as a host material.
  • L21 and L22 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R21 to R28 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar21 and Ar22 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R21 to R28 are the same as or different from each other, and are each independently hydrogen or deuterium.
  • Ar21 and Ar22 are different from each other.
  • Ar21 and Ar22 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • Ar21 and Ar22 are naphthyl groups.
  • L21 and L22 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or it is a substituted or unsubstituted dibenzothiophene group.
  • the formula H is represented by the following compound.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium).
  • phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
  • the dopant includes, but is not limited to, a compound represented by the following formula D-1.
  • T1 to T6 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • t5 and t6 are each integers from 1 to 4,
  • t5 is 2 or more, the 2 or more T5 are the same or different from each other,
  • the 2 or more T6s are the same or different from each other.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; a nitrile group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • T1 to T6 are the same as or different from each other, and are each independently hydrogen; isopropyl group; A phenyl group substituted with a methyl group; Or it is a dibenzofuran group.
  • Formula D-1 is represented by the following compound.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer may play a role in facilitating the transport of electrons.
  • the electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals.
  • fluorenone anthraquinodimethane
  • diphenoquinone diphenoquinone
  • thiopyran dioxide oxazole
  • oxadiazole triazole
  • imidazole imidazole
  • perylenetetracarboxylic acid
  • the electron injection and transport layer may serve to simultaneously inject and transport electrons.
  • the layer can be formed using an electron transport material and an electron injection material.
  • metal complex compounds 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
  • Q1, Q2, A and B are as defined in Formula 1 above.
  • compound 1-b 50 g, 100.8 mmol
  • bis(pinacolato)diboron 25.6 g, 100.8 mmol
  • potassium acetate 64.2 g, 302.4 mmol
  • palladium dibenzylidene acetone palladium 1.7 g, 3 mmol
  • compound 1-c 50 g, 85.1 mmol
  • 2-chloro-4,6-diphenyl-1,3,5-triazine 22.8 g, 85.1 mmol
  • potassium carbonate 35.3 g, 255.3 mmol
  • tetrakistriphenyl-phosphinopalladium 2.9 g, 2.6 mmol
  • a glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following compound HI-A was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • hole injection layer hexanitrile hexaazatriphenylene (HAT, 50 ⁇ ) of the following formula and HT-A (600 ⁇ ) of the following compound were sequentially vacuum deposited to form a hole transport layer.
  • HAT hexanitrile hexaazatriphenylene
  • the following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to a film thickness of 200 ⁇ on the hole transport layer to form a light emitting layer.
  • Compound 1 prepared in Synthesis Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited at a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 360 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10.
  • An organic light emitting device was manufactured by maintaining -7 to 5 ⁇ 10 -8 torr.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound 1 in Experimental Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound 1 in Experimental Example 1.
  • the compounds ET-1 to ET-6 used in Table 1 below are as follows.
  • the driving voltage, luminous efficiency, and color coordinates were measured at a current density of 10 mA/cm 2 , and the luminance was 90% of the initial luminance at a current density of 20 mA/cm 2.
  • the time to become (T 90 ) was measured. The results are shown in Table 1 below.
  • the organic light-emitting device using the compound represented by Formula 1 of the present invention exhibits excellent characteristics in terms of voltage, efficiency, and/or lifespan (T 90 ).
  • the organic light-emitting device containing the compound of Formula 1 of the present invention has two or more heterocycles containing an N-containing 6-membered ring with electron transport properties. Therefore, the electron transport ability can be adjusted in various ways. Therefore, it was confirmed that the organic light-emitting device showed significantly better properties in terms of efficiency and lifespan than an organic light-emitting device using a compound with one N-containing ring substituted.
  • the organic light-emitting device containing the compound of Formula 1 of the present invention has a heterocycle containing an N-containing 6-membered ring with electron transport properties. Since it is adjacent to the ortho position of phenyl, structural distortion occurs, which is advantageous for electron transport. Therefore, the heterocycle containing an N-containing 6-membered ring has a higher voltage than the organic light emitting device using meta and para phenyl. It was confirmed that it showed significantly excellent characteristics in terms of efficiency and lifespan.
  • A is heteroaryl containing an unsubstituted N-containing 6-membered ring.
  • Experimental Examples 1 to 14 of the present invention are different in that A and B are heteroaryl groups containing an N-containing 6-membered ring substituted with an aryl group.

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Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compounds and organic light-emitting devices containing them
본 출원은 2022년 10월 26일 한국특허청에 제출된 한국 특허 출원 제10-2022-0139484 호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0139484 filed with the Korea Intellectual Property Office on October 26, 2022, the entire contents of which are incorporated herein by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. This specification relates to compounds and organic light-emitting devices containing the same.
본 명세서에서, 유기 발광 소자란 유기 반도체 물질을 이용한 발광 소자로서, 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다. 유기 발광 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 발광 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 발광 소자이다.In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly divided into two types according to their operating principles as follows. First, excitons are formed in the organic layer by photons flowing into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as current sources (voltage sources). It is a type of light emitting device. The second type is a light-emitting device that applies voltage or current to two or more electrodes to inject holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes, and operates by the injected electrons and holes.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자억제층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트 등의 특성을 갖는 것으로 알려져 있다.In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and for example, it consists of a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. You can lose. In the structure of this organic light-emitting device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows. These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공 주입 재료, 정공 수송 재료, 전자 억제 물질, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료가 있다.Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function. Depending on the color of light emitting, there are blue, green, and red light emitting materials, and yellow and orange light emitting materials needed to realize better natural colors.
또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도펀트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
전술한 유기 발광 소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공 주입 물질, 정공 수송 물질, 발광 물질, 전자 억제 물질, 전자 수송 물질, 전자 주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되므로 새로운 재료의 개발이 계속 요구되고 있다.In order to fully demonstrate the excellent characteristics of the above-described organic light-emitting device, the materials that make up the organic layer within the device, such as hole injection material, hole transport material, light-emitting material, electron suppressor material, electron transport material, and electron injection material, must be stable and efficient materials. As this is supported by , the development of new materials continues to be required.
본 명세서에는 화합물 및 이를 포함하는 유기 발광 소자가 기재된다. Disclosed herein are compounds and organic light-emitting devices containing the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2023016753-appb-img-000001
Figure PCTKR2023016753-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
A는 치환 또는 비치환된 아릴기로 치환된 N을 포함하는 6원 고리를 포함하는 헤테로아릴기이고, A is a heteroaryl group containing a 6-membered ring containing N substituted with a substituted or unsubstituted aryl group,
B는 치환 또는 비치환된 아릴기로 치환된 N을 포함하는 6원 고리를 포함하는 헤테로아릴기이고,B is a heteroaryl group containing a 6-membered ring containing N substituted with a substituted or unsubstituted aryl group,
L은 직접결합, 또는 치환 또는 비치환된 아릴렌기이고,L is a direct bond, or a substituted or unsubstituted arylene group,
Q1 및 Q2 중 하나는 탄소수 6 내지 30의 아릴기이고, 나머지는 수소 또는 탄소수 6 내지 30의 아릴기이고,One of Q1 and Q2 is an aryl group having 6 to 30 carbon atoms, and the other is hydrogen or an aryl group having 6 to 30 carbon atoms,
Q1 및 Q2 중 하나가 수소인 경우, 나머지는 중수소, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로아릴기 중 선택되는 하나 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이고, When one of Q1 and Q2 is hydrogen, the remainder is one or more substituents selected from deuterium, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group. It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Q1 및 Q2가 모두 탄소수 6 내지 30의 아릴기일 때, 상기 탄소수 6 내지 30의 아릴기는 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로아릴기 중 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.When both Q1 and Q2 are aryl groups having 6 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted Or, it is substituted or unsubstituted with one or more substituents selected from unsubstituted heteroaryl groups.
본 발명의 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 본 발명의 화합물을 포함하여 유기 발광 소자를 제조하는 경우, 고효율, 저전압 및 장수명 특성을 갖는 유기 발광 소자를 얻을 수 있으며, 본 발명의 화합물을 유기 발광 소자의 전자 수송층에 포함하는 경우, 분자 내 분극성이 높아 전자전달의 효과가 높아서 장수명 특성을 가지는 유기 발광 소자를 제조할 수 있다.The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When manufacturing an organic light-emitting device including the compound of the present invention, an organic light-emitting device with high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the electron transport layer of the organic light-emitting device, intramolecular Due to its high polarity, the effect of electron transfer is high, making it possible to manufacture organic light-emitting devices with long-life characteristics.
본 발명의 화합물은 전자 수송 특성을 가진 N함유 6원 고리를 포함하는 헤테로고리가 2개 이상으로 치환 되어있고, 페닐의 오쏘 위치에 이웃하고 있어 구조적 뒤틀림이 발생하여 전자 수송 능력이 다양하게 조절할 수 있다. The compound of the present invention has two or more substituted heterocycles containing an N-containing 6-membered ring with electron transport properties, and is adjacent to the ortho position of phenyl, resulting in structural distortion, so that the electron transport ability can be adjusted in various ways. there is.
도 1 및 2는 본 발명에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 show examples of organic light-emitting devices according to the present invention.
[부호의 설명][Explanation of symbols]
1: 기판1: substrate
2: 양극2: anode
3: 유기물층3: Organic layer
4: 음극4: cathode
5: 정공주입층5: Hole injection layer
6: 정공수송층6: Hole transport layer
7: 발광층7: Light-emitting layer
8: 전자주입 및 수송층8: Electron injection and transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, this specification will be described in more detail.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in this specification are described below, but are not limited thereto.
상기 "치환" 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기(-CN); 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 도 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group (-CN); silyl group; boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the above substituents are described below, but are not limited thereto.
본 명세서에 있어서, 상기 할로겐기의 예로는 불소(F), 염소(Cl), 브롬(Br) 또는 요오드(I)가 있다.In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
본 명세서에 있어서, 상기 실릴기는 중수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기 등으로 치환 또는 비치환될 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
본 명세서에 있어서, 상기 붕소기는 중수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기로 치환 또는 비치환될 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, tert-부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, and octyl groups.
본 명세서에 있어서, 상기 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기; 디메틸아민기; 에틸아민기; 디에틸아민기; 페닐아민기; 나프틸아민기; 바이페닐아민기; 안트라세닐아민기; 9-메틸안트라세닐아민기; 디페닐아민기; 디톨릴아민기; N-페닐톨릴아민기; 트리페닐아민기; N-페닐바이페닐아민기; N-페닐나프틸아민기; N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기; N-페닐페난트레닐아민기; N-바이페닐페난트레닐아민기; N-페닐플루오레닐아민기; N-페닐터페닐아민기; N-페난트레닐플루오레닐아민기; N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., but is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, N-arylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
본 명세서에 있어서, 알킬아민기, N-아릴알킬아민기, 알킬티옥시기, 알킬술폭시기, N-알킬헤테로아릴아민기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기; 에틸티옥시기; tert－부틸티옥시기; 헥실티옥시기; 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실; 에틸술폭시기; 프로필술폭시기; 부틸술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as examples of the alkyl groups described above. Specifically, the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc., and examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필기, 사이클로부틸기, 사이클로펜틸기, 사이클로헥실기, 사이클로헵틸기, 사이클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐렌기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 헤테로아릴기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로고리기의 예로는 피리딘기, 피롤기, 피리미딘기, 피리다지닐기, 퓨란기, 티오펜기, 이미다졸기, 피라졸기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group, etc. However, it is not limited to these.
본 명세서에 있어서, 상기 아릴렌기는 2가기인 것을 제외하고, 상기 아릴기에서 정의한 바와 같다.In the present specification, the arylene group is the same as defined for the aryl group, except that it is a divalent group.
본 명세서에 있어서, 상기 헤테로아릴렌기는 2가기인 것을 제외하고, 상기 헤테로아릴기에서 정의한 바와 같다.In the present specification, the heteroarylene group is the same as defined for the heteroaryl group, except that it is a divalent group.
본 명세서에 있어서, 상기 화학식 1은 아래 화학식 1-1 또는 1-2이다.In this specification, Formula 1 is Formula 1-1 or 1-2 below.
[화학식 1-1][Formula 1-1]
Figure PCTKR2023016753-appb-img-000002
Figure PCTKR2023016753-appb-img-000002
[화학식 1-2][Formula 1-2]
Figure PCTKR2023016753-appb-img-000003
Figure PCTKR2023016753-appb-img-000003
상기 화학식 1-1 및 1-2에 있어서, 상기 A, B, L, Q1 및 Q2는 상기 화학식 1에서 정의한 것과 같다.In Formulas 1-1 and 1-2, A, B, L, Q1, and Q2 are as defined in Formula 1.
본 명세서에 있어서, 상기 화학식 1은 아래 화학식 1-3이다.In this specification, Formula 1 is Formula 1-3 below.
[화학식 1-3][Formula 1-3]
Figure PCTKR2023016753-appb-img-000004
Figure PCTKR2023016753-appb-img-000004
상기 화학식 1-3에 있어서, 상기 A, B, 및 L는 상기 화학식 1에서 정의한 것과 같고, In Formula 1-3, A, B, and L are as defined in Formula 1,
R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 결합하여 치환 또는 비치환된 고리를 형성하고,R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group. Or, it combines with an adjacent group to form a substituted or unsubstituted ring,
a 및 b는 1 내지 5의 정수이고,a and b are integers from 1 to 5,
a가 2 이상일 때, R1은 서로 같거나 상이하고,When a is 2 or more, R1 is the same or different,
b가 2 이상일 때, R2는 서로 같거나 상이하다.When b is 2 or more, R2 is the same or different.
본 명세서에 있어서, 상기 화학식 1은 아래 화학식 1-4이다.In this specification, Formula 1 is Formula 1-4 below.
[화학식 1-4][Formula 1-4]
Figure PCTKR2023016753-appb-img-000005
Figure PCTKR2023016753-appb-img-000005
상기 화학식 1-4에 있어서, 상기 L, Q1, 및 Q2는 상기 화학식 1에서 정의한 것과 같고,In Formula 1-4, L, Q1, and Q2 are as defined in Formula 1,
X1 내지 X3 중 하나는 N이고, 나머지는 각각 N 또는 CR이고,One of X1 to X3 is N, and the others are N or CR, respectively,
R은 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고,R is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
X4 내지 X8 중 하나는 N이고, 나머지는 각각 N 또는 CR1이고,One of X4 to X8 is N, and the others are N or CR1, respectively,
R1은 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 치환기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R1 is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or is substituted or unsubstituted by combining with adjacent substituents. forms a ring
본 명세서의 일 실시상태에 따르면, 상기 A는 피리딘, 피리미딘, 트리아진, 퀴놀린, 퀴나졸린, 또는 퀴녹살린이고,According to an exemplary embodiment of the present specification, A is pyridine, pyrimidine, triazine, quinoline, quinazoline, or quinoxaline,
상기 피리딘, 피리미딘, 트리아진, 퀴놀린, 퀴나졸린, 또는 퀴녹살린은 각각 독립적으로 중수소, 니트릴기, 니트로기, 할로겐기, 또는 치환 또는 비치환된 알킬기로 치환 또는 비치환된 아릴기로 치환된다.The pyridine, pyrimidine, triazine, quinoline, quinazoline, or quinoxaline are each independently substituted with deuterium, nitrile group, nitro group, halogen group, or substituted or unsubstituted aryl group with substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 B는 피리딘, 피리미딘, 또는 트리아진이고, 상기 피리딘, 피리미딘, 또는 트리아진은 각각 독립적으로 중수소, 니트릴기, 니트로기, 할로겐기, 또는 치환 또는 비치환된 알킬기로 치환 또는 비치환된 아릴기로 치환된다.According to an exemplary embodiment of the present specification, B is pyridine, pyrimidine, or triazine, and the pyridine, pyrimidine, or triazine are each independently deuterium, nitrile group, nitro group, halogen group, or substituted or unsubstituted. It is substituted with a substituted alkyl group or with an unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로, 수소, 중수소, 니트릴기, 니트로기, 할로겐기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기이거나, 인접한 기와 결합하여 치환 또는 비치환된 벤젠고리를 형성한다. According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, halogen group, alkyl group of 1 to 10 carbon atoms, aryl group of 6 to 30 carbon atoms. group, or a heteroaryl group having 3 to 30 carbon atoms, or is combined with an adjacent group to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로, 수소, 중수소, 니트릴기, 니트로기, F, Cl, 메틸기, 에틸기, 프로필기, 터부틸기, 페닐기, 나프틸기, 안트라센기, 비페닐기, 카바졸기, 디벤조퓨란기, 또는 디벤조티오펜기이거나, 인접한 기와 결합하여 벤젠고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, F, Cl, methyl group, ethyl group, propyl group, terbutyl group, phenyl group. , a naphthyl group, anthracene group, biphenyl group, carbazole group, dibenzofuran group, or dibenzothiophene group, or is combined with an adjacent group to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A는 아릴기로 치환된 트리아진, 아릴기로 치환된 피리미딘, 아릴기로 치환된 피리딘, 또는 아릴기로 치환된 퀴나졸기이다. According to an exemplary embodiment of the present specification, A is a triazine substituted with an aryl group, a pyrimidine substituted with an aryl group, a pyridine substituted with an aryl group, or a quinazole group substituted with an aryl group.
본 명세서의 일 실시상태에 따르면, A는 트리아진, 피리미딘, 피리딘, 또는 퀴나졸기이고, 상기 치환기들은 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기로 치환된다.According to an exemplary embodiment of the present specification, A is a triazine, pyrimidine, pyridine, or quinazole group, and the substituents are substituted with deuterium or with an unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, B는 아릴기로 치환된 트리아진, 아릴기로 치환된 피리미딘, 아릴기로 치환된 피리딘, 또는 아릴기로 치환된 퀴나졸기이다. According to an exemplary embodiment of the present specification, B is a triazine substituted with an aryl group, a pyrimidine substituted with an aryl group, a pyridine substituted with an aryl group, or a quinazole group substituted with an aryl group.
본 명세서의 일 실시상태에 따르면, B는 트리아진, 피리미딘, 피리딘, 또는 퀴나졸기이고, 상기 치환기들은 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, B is a triazine, pyrimidine, pyridine, or quinazole group, and the substituents are substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 중수소로 치환 또는 비치환된 페닐기, 또는 중수소로 치환 또는 비치환된 2가의 나프탈렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, a phenyl group substituted or unsubstituted with deuterium, or a divalent naphthalene group substituted or unsubstituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L은 직접결합, 페닐렌기, 또는 2가의 나프탈렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond, a phenylene group, or a divalent naphthalene group.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2 중 하나는 탄소수 6 내지 30의 아릴기이고, 나머지는 수소 또는 탄소수 6 내지 30의 아릴기이고,According to an exemplary embodiment of the present specification, one of Q1 and Q2 is an aryl group having 6 to 30 carbon atoms, and the other is hydrogen or an aryl group having 6 to 30 carbon atoms,
Q1 및 Q2 중 하나가 수소인 경우, 나머지는 중수소, 니트로기, 할로겐기, 알킬기, 아릴기, 및 헤테로아릴기 중 선택되는 하나 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이고, When one of Q1 and Q2 is hydrogen, the remainder is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from deuterium, nitro group, halogen group, alkyl group, aryl group, and heteroaryl group,
Q1 및 Q2가 모두 탄소수 6 내지 30의 아릴기일 때, 상기 탄소수 6 내지 30의 아릴기는 중수소, 니트릴기, 니트로기, 할로겐기, 알킬기, 아릴기, 및 헤테로아릴기 중 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.When both Q1 and Q2 are aryl groups having 6 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms is substituted with one or more substituents selected from deuterium, nitrile group, nitro group, halogen group, alkyl group, aryl group, and heteroaryl group. or unsubstituted.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2 중 하나가 수소일 때, 나머지는 페닐기, 나프틸기, 페난트렌기, 플루오란텐기, 또는 페난트렌기이고, 상기 치환기는 중수소, 니트로기, F, 탄소수 1 내지 10의 알킬기, 탄소수 1 내지 10의 할로알킬기, 탄소수 3 내지 10의 시클로알킬기, 또는 중수소 및 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, when one of Q1 and Q2 is hydrogen, the other is a phenyl group, naphthyl group, phenanthrene group, fluoranthene group, or phenanthrene group, and the substituent is deuterium, nitro group, F , an alkyl group with 1 to 10 carbon atoms, a haloalkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms that is unsubstituted or substituted with deuterium and an alkyl group with 1 to 10 carbon atoms. It's a relief.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2는 페닐기, 나프틸기, 페난트렌기, 플루오란텐기, 또는 페난트렌기일 때, 상기 치환기는 중수소, 니트로기, 니트릴기, F, 탄소수 1 내지 10의 알킬기, 탄소수 1 내지 10의 할로알킬기, 탄소수 3 내지 10의 시클로알킬기, 또는 중수소 및 탄소수 1 내지 10의 알킬기로 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, when Q1 and Q2 are a phenyl group, naphthyl group, phenanthrene group, fluoranthene group, or phenanthrene group, the substituent is deuterium, nitro group, nitrile group, F, and has 1 to 10 carbon atoms. is substituted or unsubstituted with an alkyl group, a haloalkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms that is substituted or unsubstituted with deuterium and an alkyl group with 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2는 페닐기, 나프틸기, 페난트렌기, 플루오란텐기, 또는 페난트렌기일 때, 상기 치환기는 중수소, 니트릴기, F, 메틸기, F로 치환된 메틸기, 터부틸기, 디벤조퓨란기, 디벤조티오펜기, 아다만틸기, 니트로기, 중수소로 치환 또는 비치환된 카바졸기, 벤조티아졸기, 벤조옥사졸기, 또는 에틸기로 치환 또는 비치환된 벤즈이미다졸기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, when Q1 and Q2 are a phenyl group, a naphthyl group, a phenanthrene group, a fluoranthene group, or a phenanthrene group, the substituent is a deuterium group, a nitrile group, F, a methyl group, or a methyl group substituted with F. , terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, carbazole group substituted or unsubstituted with deuterium, benzothiazole group, benzoxazole group, or benz substituted or unsubstituted with ethyl group. It is substituted or unsubstituted with an imidazole group.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2 중 하나가 수소일 때, 나머지는 페닐기, 나프틸기, 페난트렌기, 플루오란텐기, 또는 페난트렌기일 때, 상기 치환기는 중수소, F, 메틸기, F로 치환된 메틸기, 터부틸기, 디벤조퓨란기, 디벤조티오펜기, 아다만틸기, 니트로기, 중수소로 치환 또는 비치환된 카바졸기, 벤조티아졸기, 벤조옥사졸기, 또는 에틸기로 치환 또는 비치환된 벤즈이미다졸기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, when one of Q1 and Q2 is hydrogen and the other is a phenyl group, naphthyl group, phenanthrene group, fluoranthene group, or phenanthrene group, the substituent is deuterium, F, methyl group, F-substituted methyl group, terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, deuterium-substituted or unsubstituted carbazole group, benzothiazole group, benzoxazole group, or ethyl group. Or, it is substituted or unsubstituted with an unsubstituted benzimidazole group.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2는 페닐기, 나프틸기, 페난트렌기, 플루오란텐기, 또는 페난트렌기일 때, 상기 페닐기는 중수소, 니트릴기, F, 메틸기, F로 치환된 메틸기, 터부틸기, 디벤조퓨란기, 디벤조티오펜기, 아다만틸기, 니트로기, 중수소로 치환 또는 비치환된 카바졸기, 벤조티아졸기, 벤조옥사졸기, 또는 에틸기로 치환 또는 비치환된 벤즈이미다졸기로 치환 또는 비치환되고, According to an exemplary embodiment of the present specification, when Q1 and Q2 are a phenyl group, a naphthyl group, a phenanthrene group, a fluoranthene group, or a phenanthrene group, the phenyl group is a deuterium group, a nitrile group, F, a methyl group, or a methyl group substituted with F. , terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, carbazole group substituted or unsubstituted with deuterium, benzothiazole group, benzoxazole group, or benz substituted or unsubstituted with ethyl group. Substituted or unsubstituted with an imidazole group,
상기 나프틸기, 페난트렌기, 플루오란텐기, 및 페난트렌기는 비치환된다.The naphthyl group, phenanthrene group, fluoranthene group, and phenanthrene group are unsubstituted.
본 명세서의 일 실시상태에 따르면, 상기 Q1 및 Q2 중 하나가 수소일 때, 나머지는 페닐기, 나프틸기, 페난트렌기, 플루오란텐기, 또는 페난트렌기일 때, 상기 페닐기는 중수소, F, 메틸기, F로 치환된 메틸기, 터부틸기, 디벤조퓨란기, 디벤조티오펜기, 아다만틸기, 니트로기, 중수소로 치환 또는 비치환된 카바졸기, 벤조티아졸기, 벤조옥사졸기, 또는 에틸기로 치환 또는 비치환된 벤즈이미다졸기로 치환 또는 비치환되고, According to an exemplary embodiment of the present specification, when one of Q1 and Q2 is hydrogen and the other is a phenyl group, naphthyl group, phenanthrene group, fluoranthene group, or phenanthrene group, the phenyl group is deuterium, F, methyl group, F-substituted methyl group, terbutyl group, dibenzofuran group, dibenzothiophene group, adamantyl group, nitro group, deuterium-substituted or unsubstituted carbazole group, benzothiazole group, benzoxazole group, or ethyl group. or substituted or unsubstituted with an unsubstituted benzimidazole group,
상기 나프틸기, 페난트렌기, 플루오란텐기, 및 페난트렌기는 비치환된다.The naphthyl group, phenanthrene group, fluoranthene group, and phenanthrene group are unsubstituted.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 아래 구조식 중 어느 하나이다. According to an exemplary embodiment of the present specification, Formula 1 is one of the structural formulas below.
Figure PCTKR2023016753-appb-img-000006
Figure PCTKR2023016753-appb-img-000006
Figure PCTKR2023016753-appb-img-000007
Figure PCTKR2023016753-appb-img-000007
Figure PCTKR2023016753-appb-img-000008
Figure PCTKR2023016753-appb-img-000008
Figure PCTKR2023016753-appb-img-000009
Figure PCTKR2023016753-appb-img-000009
Figure PCTKR2023016753-appb-img-000010
Figure PCTKR2023016753-appb-img-000010
Figure PCTKR2023016753-appb-img-000011
Figure PCTKR2023016753-appb-img-000011
Figure PCTKR2023016753-appb-img-000012
Figure PCTKR2023016753-appb-img-000012
Figure PCTKR2023016753-appb-img-000013
Figure PCTKR2023016753-appb-img-000013
Figure PCTKR2023016753-appb-img-000014
Figure PCTKR2023016753-appb-img-000014
Figure PCTKR2023016753-appb-img-000015
Figure PCTKR2023016753-appb-img-000015
Figure PCTKR2023016753-appb-img-000016
Figure PCTKR2023016753-appb-img-000016
Figure PCTKR2023016753-appb-img-000017
Figure PCTKR2023016753-appb-img-000017
상기 화학식 1의 화합물의 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.Substituents of the compound of Formula 1 may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송용 물질, 발광층 물질 및 전자 수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.In addition, by introducing various substituents into the core structure of the above structure, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic material layer can be synthesized. You can.
또한, 본 발명에 따른 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 전술한 화합물을 포함하는 것을 특징으로 한다.Additionally, the organic light emitting device according to the present invention includes a first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising 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 contains the above-described compound.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound 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. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 정공주입 및 정공수송을 동시에 하는 층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층 또는 더 많은 수의 유기물층을 포함할 수 있다.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. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자수송층, 전자주입층, 및 전자주입 및 수송 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1의 화합물을 포함한다.In the organic light emitting device of the present invention, the organic material layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers includes the compound of Formula 1.
또 하나의 유기 발광 소자에서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층이 상기 화학식 1의 화합물을 포함한다.In another organic light emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of Formula 1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 금속 착체를 포함한다.In the organic light emitting device of the present invention, the electron injection and transport layer includes the compound of Formula 1 and a metal complex.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층, 정공수송층 및 정공주입과 정공수송을 동시에 하는 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1의 화합물을 포함한다.In the organic light emitting device of the present invention, the organic material layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport, and one or more of the layers contains the compound of Formula 1. Includes.
또 하나의 유기 발광 소자에서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함할 수 있고, 상기 정공수송층 또는 정공주입층이 상기 화학식 1의 화합물을 포함할 수 있다.In another organic light emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound of Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
(1) 양극/정공수송층/발광층/음극(1) Anode/hole transport layer/light emitting layer/cathode
(2) 양극/정공주입층/정공수송층/발광층/음극(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) 양극/정공주입층/정공버퍼층/정공수송층/발광층/음극(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) 양극/정공수송층/발광층/전자수송층/음극(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) 양극/정공수송층/발광층/전자수송층/전자주입층/음극(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/음극(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/음극(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /음극(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) 양극/ 정공수송층/전자억제층/발광층/전자수송층/음극(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) 양극/ 정공수송층/전자억제층/발광층/전자수송층/전자주입층/음극(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) 양극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/음극(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13)양극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/전자주입 층/음극(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(14) 양극/정공수송층/발광층/정공억제층/전자수송층/음극(14) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode
(15) 양극/정공수송층/발광층/ 정공억제층/전자수송층/전자주입층/음극(15) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode
(16) 양극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/음극(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode
(17)양극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/전자주입 층/음극(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode
(18)양극/정공주입층/정공수송층/전자억제층/발광층/정공저지층/전자주입및 수송층/음극(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode
본 발명의 유기 발광 소자의 구조는 도 1 및 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present invention may have the same structure as shown in FIGS. 1 and 2, but is not limited thereto.
도 1에는 기판(1) 위에 양극(2), 유기물층(3) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 상기 유기물층(3)에 포함될 수 있다.Figure 1 illustrates the structure of an organic light-emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In this structure, the compound of Formula 1 may be included in the organic layer 3.
도 2에는 기판(1) 위에 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자주입 및 수송층(8), 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 상기 전자주입 및 수송층(8)에 포함된다. In Figure 2, an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron injection and transport layer (8), and a cathode (4) are sequentially stacked on a substrate (1). The structure of the light emitting device is illustrated. In this structure, the compound of Formula 1 is included in the electron injection and transport layer (8).
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 정공수송 및 정공주입을 동시에 하는 층, 발광층, 전자수송층, 전자주입층, 및 전자수송 및 전자주입을 동시에하는 층으로 이루어진 군으로부터 선택된 1층 이상을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다. For example, the organic light emitting device according to the present invention deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. An anode is formed by depositing a layer on top of a hole injection layer, a hole transport layer, a layer that performs both hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a group consisting of a layer that performs both electron transport and electron injection. It can be manufactured by forming an organic material layer containing one or more selected layers and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공주입층, 정공수송층, 발광층 및 전자수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
상기 양극은 정공을 주입하는 전극으로, 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO, Indium Tin Oxide), 인듐아연 산화물(IZO, Indium Zinc Oxide)과 같은 금속 산화물; ZnO : Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention 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); Combination of metal and oxide 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 are included, but are not limited to these.
상기 음극은 전자를 주입하는 전극으로, 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
상기 정공주입층은 양극으로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이며, 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 정공주입층의 두께는 1 내지 150nm일 수 있다. 상기 정공주입층의 두께가 1nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공주입층의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는것을 방지할 수 있는 이점이 있다.The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2023016753-appb-img-000018
Figure PCTKR2023016753-appb-img-000018
상기 화학식 HI-1에 있어서,In the formula HI-1,
R300 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R300 to R308 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or combines with an adjacent group to form a substituted or unsubstituted ring,
r301 및 r302는 각각 1 내지 4의 정수이고,r301 and r302 are each integers from 1 to 4,
r303 및 r304는 각각 1 내지 3의 정수이며,r303 and r304 are each integers from 1 to 3,
상기 r301이 2 이상인 경우, 상기 R301은 서로 같거나 상이하고,When r301 is 2 or more, R301 is the same or different from each other,
상기 r302가 2 이상인 경우, 상기 R302는 서로 같거나 상이하며,When r302 is 2 or more, R302 is the same or different from each other,
상기 r303이 2 이상인 경우, 상기 R303은 서로 같거나 상이하고,When r303 is 2 or more, R303 is the same or different from each other,
상기 r304가 2 이상인 경우, 상기 R304는 서로 같거나 상이하다.When r304 is 2 or more, R304 is the same or different from each other.
본 명세서의 일시상태에 따르면, 상기 R301 내지 R304는 수소이다.According to the provisional status of this specification, R301 to R304 are hydrogen.
본 명세서의 일시상태에 따르면, 상기 R300은 치환 또는 비치환된 아릴기이다.According to the provisional status of the present specification, R300 is a substituted or unsubstituted aryl group.
본 명세서의 일시상태에 따르면, 상기 R300은 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to the provisional status of the present specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일시상태에 따르면, 상기 R300은 페닐기이다.According to the provisional status of the present specification, R300 is a phenyl group.
*본 명세서의 일 실시상태에 따르면, 상기 R305 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.*According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 R305 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R305 내지 R308은 서로 같거나 상이하고, 각각 독립적으로 페닐기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and are each independently a phenyl group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HI-1 is represented by the following compound.
Figure PCTKR2023016753-appb-img-000019
Figure PCTKR2023016753-appb-img-000019
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
[화학식 HT-1][Formula HT-1]
Figure PCTKR2023016753-appb-img-000020
Figure PCTKR2023016753-appb-img-000020
상기 화학식 HT-1에 있어서,In the formula HT-1,
X'1 내지 X'6 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of X'1 to X'6 is N, and the remainder is CH,
R309 내지 R314은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 X'1 내지 X'6는 N이다.According to an exemplary embodiment of the present specification, X'1 to X'6 are N.
본 명세서의 일 실시상태에 따르면, 상기 R309 내지 R314는 니트릴기다.According to an exemplary embodiment of the present specification, R309 to R314 are nitrile groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HT-1 is represented by the following compound.
Figure PCTKR2023016753-appb-img-000021
Figure PCTKR2023016753-appb-img-000021
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-2로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
[화학식 HT-2][Formula HT-2]
Figure PCTKR2023016753-appb-img-000022
Figure PCTKR2023016753-appb-img-000022
상기 화학식 HT-2에 있어서,In the formula HT-2,
R400 내지 R402는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R400 to R402 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
L402는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이다.L402 are the same or different from each other, and each independently represents a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 R400 내지 R402는 서로 같거나 상이하고, 각가 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R400 to R402 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R400 및 R401는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접한 기와 서로 결합하여 알킬기로 치환된 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R400 and R401 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R400 및 R401는 서로 같거나 상이하고, 각각 독립적으로 페닐기 또는 디페닐플루오렌기이다.According to an exemplary embodiment of the present specification, R400 and R401 are the same or different from each other, and are each independently a phenyl group or a diphenylfluorene group.
본 명세서의 일 실시상태에 따르면, 상기 R402는 페닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, R402 is a carbazole group substituted or unsubstituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-2는 하기 화합물들 선택된다.According to an exemplary embodiment of the present specification, the formula HT-2 is selected from the following compounds.
Figure PCTKR2023016753-appb-img-000023
Figure PCTKR2023016753-appb-img-000023
정공수송층과 발광층 사이에 전자억제층이 구비될 수 있다. 상기 전자억제층은 전술한 스피로 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다.An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron suppressing layer may be made of the spiro compound described above or a material known in the art.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 발광층을 포함하고, 상기 발광층은 호스트 물질로 하기 화학식 H로 표시되는 화합물을 포함한다.An organic light-emitting device according to an exemplary embodiment of the present specification includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following formula H as a host material.
[화학식 H][Formula H]
Figure PCTKR2023016753-appb-img-000024
Figure PCTKR2023016753-appb-img-000024
상기 화학식 H에 있어서,In the formula H,
L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L21 and L22 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R21 내지 R28은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R21 to R28 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar21 and Ar22 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
본 명세서의 일 실시상태에 있어서, 상기 R21 내지 R28은 서로 동일하거나 상이하고, 각각 독립적으로 수소 또는 중수소이다.In an exemplary embodiment of the present specification, R21 to R28 are the same as or different from each other, and are each independently hydrogen or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 상이하다.In an exemplary embodiment of the present specification, Ar21 and Ar22 are different from each other.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 나프틸기이다.In an exemplary embodiment of the present specification, Ar21 and Ar22 are naphthyl groups.
본 명세서의 일 실시상태에 있어서, 상기 L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 비페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 2가의 디벤조퓨란기; 또는 치환 또는 비치환된 2가의 디벤조티오펜기이다.In an exemplary embodiment of the present specification, L21 and L22 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or it is a substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H는 하기 화합물로 표시된다.In one embodiment of the present specification, the formula H is represented by the following compound.
Figure PCTKR2023016753-appb-img-000025
Figure PCTKR2023016753-appb-img-000025
발광층이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.When the light-emitting layer emits red light, the light-emitting dopants include PIQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium). ), phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these. If the light-emitting layer emits green light, a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant. However, it is not limited to this. If the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 하기 화학식 D-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following formula D-1.
[화학식 D-1][Formula D-1]
Figure PCTKR2023016753-appb-img-000026
Figure PCTKR2023016753-appb-img-000026
상기 화학식 D-1에 있어서,In Formula D-1,
T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,T1 to T6 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
t5 및 t6은 각각 1 내지 4의 정수이며,t5 and t6 are each integers from 1 to 4,
상기 t5가 2 이상인 경우, 상기 2 이상의 T5는 서로 같거나 상이하고,When t5 is 2 or more, the 2 or more T5 are the same or different from each other,
상기 t6가 2 이상인 경우, 상기 2 이상의 T6는 서로 같거나 상이하다.When the t6 is 2 or more, the 2 or more T6s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 니트릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; a nitrile group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 T1 내지 T6은 서로 같거나 상이하고, 각각 독립적으로 수소; 이소프로필기; 메틸기로 치환된 페닐기; 또는 디벤조퓨란기이다.According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; isopropyl group; A phenyl group substituted with a methyl group; Or it is a dibenzofuran group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 D-1는 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.
Figure PCTKR2023016753-appb-img-000027
Figure PCTKR2023016753-appb-img-000027
전자수송층과 발광층 사이에 정공억제층이 구비될 수 있으며, 당 기술분야에 알려져 있는 재료가 사용될 수 있다.A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 할 수 있다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1 내지 50nm일 수 있다. 전자수송층의 두께가 1nm 이상이면, 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자수송층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.The electron transport layer may play a role in facilitating the transport of electrons. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
상기 전자주입 및 수송층은 전자 주입 및 수송을 동시에 하는 역할을 할 수 있다. 전자 수송 물질 및 전자 주입 물질을 이용하여 층을 형성할 수 있다.The electron injection and transport layer may serve to simultaneously inject and transport electrons. The layer can be formed using an electron transport material and an electron injection material.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compounds 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
상기 정공차단층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The method for producing the compound of Formula 1 and the production of organic light-emitting devices using the same will be described in detail in the examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
하기 반응식에 있어서, 치환기의 종류 및 개수는 당업자가 공지된 출발물질을 적절히 선택함에 따라 다양한 종류의 중간체를 합성할 수 있다. 반응 종류 및 반응 조건은 당기술분야에 알려져 있는 것들이 이용될 수 있다. In the following reaction formula, various types of intermediates can be synthesized by appropriately selecting starting materials known to those skilled in the art regarding the type and number of substituents. Reaction types and reaction conditions known in the art can be used.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The method for producing the compound of Formula 1 and the production of organic light-emitting devices using the same will be described in detail in the examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
하기 반응식에 있어서, 치환기의 종류 및 개수는 당업자가 공지된 출발물질을 적절히 선택함에 따라 다양한 종류의 중간체를 합성할 수 있다. 반응 종류 및 반응 조건은 당기술분야에 알려져 있는 것들이 이용될 수 있다. In the following reaction formula, various types of intermediates can be synthesized by appropriately selecting starting materials known to those skilled in the art regarding the type and number of substituents. Reaction types and reaction conditions known in the art can be used.
Figure PCTKR2023016753-appb-img-000028
Figure PCTKR2023016753-appb-img-000028
상기 Q1, Q2, A 및 B는 상기 화학식 1에서 정의한 것과 같다.Q1, Q2, A and B are as defined in Formula 1 above.
본 명세서의 실시예에 기재된 제조식과 상기 중간체들을 통상의 기술상식을 바탕으로 적절히 조합하면, 본 명세서에 기재되어 있는 상기 화학식 1의 화합물들을 모두 제조할 수 있다. By appropriately combining the production formulas described in the Examples of this specification and the intermediates based on common technical knowledge, all of the compounds of Formula 1 described in this specification can be prepared.
[합성예] [Synthesis example]
합성예 1: 화합물 1의 합성Synthesis Example 1: Synthesis of Compound 1
Figure PCTKR2023016753-appb-img-000029
Figure PCTKR2023016753-appb-img-000029
단계 1) 화합물 1-a의 합성Step 1) Synthesis of Compound 1-a
질소 분위기에서 1-브로모-4-클로로-2-아이오도벤젠(50 g, 157.6 mmol)와 페닐보론산(19.2 g, 157.6mmol)를 테트라하이드로퓨란 1000ml에 넣고 교반 및 환류하였다. 이 후 소듐카보네이트(50.1 g, 472.7mmol)를 물 50ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(5.5 g, 4.7mmol)을 투입하였다. 1시간 반응 후 상온으로 식인 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 톨루엔 20배 843 mL에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 톨루엔과 에틸아세테이트재결정을 통해 흰색의 고체 화합물 1-a(35.8g, 85%, MS: [M+H]+ = 268.6)을 제조하였다.In a nitrogen atmosphere, 1-bromo-4-chloro-2-iodobenzene (50 g, 157.6 mmol) and phenylboronic acid (19.2 g, 157.6 mmol) were added to 1000 ml of tetrahydrofuran, stirred and refluxed. Afterwards, sodium carbonate (50.1 g, 472.7 mmol) was dissolved in 50 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (5.5 g, 4.7 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 843 mL of 20 times toluene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate to prepare white solid compound 1-a (35.8 g, 85%, MS: [M+H]+ = 268.6).
단계 2) 화합물 1-b의 합성Step 2) Synthesis of Compound 1-b
질소 분위기에서 화합물 1-a(50 g, 186.9 mmol)와 (2-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산(66 g, 186.9mmol)를 테트라하이드로퓨란 1000ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(77.5 g, 560.6mmol)를 물77 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(6.5 g, 5.6mmol)을 투입하였다. 1시간 반응 후 상온으로 식인 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 톨루엔 20배 1854 mL에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 톨루엔과 에틸아세테이트재결정을 통해 흰색의 고체 화합물 1-b(64.9g, 70%, MS: [M+H]+ = 497.3)을 제조하였다.Compound 1-a (50 g, 186.9 mmol) and (2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (66 g, 186.9 mmol) in a nitrogen atmosphere. was added to 1000 ml of tetrahydrofuran, stirred and refluxed. Afterwards, potassium carbonate (77.5 g, 560.6 mmol) was dissolved in 77 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 5.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 1854 mL of 20 times toluene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate to prepare white solid compound 1-b (64.9 g, 70%, MS: [M+H]+ = 497.3).
단계 3) 화합물 1-c의 합성Step 3) Synthesis of Compound 1-c
질소 분위기에서 화합물 1-b(50 g, 100.8 mmol)와 비스(피나콜라토)디보론(25.6 g, 100.8mmol)를 1,4-다이옥산 1000ml에 넣고 교반 및 환류하였다. 이 후 포타슘아세테이트(64.2 g, 302.4mmol)를투입하고 충분히 교반한 후 팔라듐디벤질리덴아세톤팔라듐(1.7 g, 3mmol) 을 투입하였다. 5시간 반응 후 상온으로 식인 후 유기층을 필터처리하여 염을 제거한 후 걸러진 유기층을 증류하였다. 이를 다시 클로로포름 10 배 592 mL에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에탄올재결정을 통해 흰색의 고체 화합물 1-c(29.6g, 50%, MS: [M+H]+ = 588.5)을 제조하였다.In a nitrogen atmosphere, compound 1-b (50 g, 100.8 mmol) and bis(pinacolato)diboron (25.6 g, 100.8 mmol) were added to 1000 ml of 1,4-dioxane, stirred and refluxed. Afterwards, potassium acetate (64.2 g, 302.4 mmol) was added, stirred sufficiently, and then palladium dibenzylidene acetone palladium (1.7 g, 3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again dissolved in 592 mL of 10 times chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethanol to prepare white solid compound 1-c (29.6 g, 50%, MS: [M+H]+ = 588.5).
단계 4) 화합물 1의 합성Step 4) Synthesis of Compound 1
질소 분위기에서 화합물 1-c(50 g, 85.1 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진(22.8 g, 85.1mmol)를 테트라하이드로퓨란 1000ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(35.3 g, 255.3mmol)를 물35 ml에 녹여 투입하고 충분히 교반한 후 테트라키스트리페닐-포스피노팔라듐(2.9 g, 2.6mmol)을 투입하였다. 2시간 반응 후 상온으로 식인 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 톨루엔 20배 1179 mL에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 톨루엔과 에틸아세테이트재결정을 통해 흰색의 고체 화합물 1(45.4g, 77%, MS: [M+H]+ = 693.8)을 제조하였다.In a nitrogen atmosphere, compound 1-c (50 g, 85.1 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (22.8 g, 85.1 mmol) were added to 1000 ml of tetrahydrofuran and stirred. It refluxed. Afterwards, potassium carbonate (35.3 g, 255.3 mmol) was dissolved in 35 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (2.9 g, 2.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 1179 mL of 20 times toluene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate to prepare white solid Compound 1 (45.4 g, 77%, MS: [M+H]+ = 693.8).
합성예 2: 화합물 2의 합성Synthesis Example 2: Synthesis of Compound 2
Figure PCTKR2023016753-appb-img-000030
Figure PCTKR2023016753-appb-img-000030
합성예 1에서, 페닐보론산을 나프탈렌-1-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 2(MS[M+H]+= 743.9)을 제조하였다.In Synthesis Example 1, compound 2 (MS[M+H] + = 743.9) was prepared in the same manner as that of compound 1, except that phenylboronic acid was changed to naphthalen-1-ylboronic acid. .
합성예 3: 화합물 3의 합성Synthesis Example 3: Synthesis of Compound 3
Figure PCTKR2023016753-appb-img-000031
Figure PCTKR2023016753-appb-img-000031
합성예 1에서, 페닐보론산을 나프탈렌-2-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 3(MS[M+H]+= 743.9)을 제조하였다.In Synthesis Example 1, Compound 3 (MS[M+H] + = 743.9) was prepared in the same manner as that of Compound 1, except that phenylboronic acid was changed to naphthalen-2-ylboronic acid. .
합성예 4: 화합물 4의 합성Synthesis Example 4: Synthesis of Compound 4
Figure PCTKR2023016753-appb-img-000032
Figure PCTKR2023016753-appb-img-000032
합성예 1에서, 페닐보론산을 페난트렌-9-일보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 4(MS[M+H]+= 793.9)을 제조하였다.In Synthesis Example 1, Compound 4 (MS[M+H] + = 793.9) was prepared using the same method as that of Compound 1, except that phenylboronic acid was changed to phenanthrene-9-ylboronic acid. did.
합성예 5: 화합물 5의 합성Synthesis Example 5: Synthesis of Compound 5
Figure PCTKR2023016753-appb-img-000033
Figure PCTKR2023016753-appb-img-000033
합성예 1에서, (2-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산 및 2-클로로-4,6-디페닐-1,3,5-트리아진을 (2-(4,6-디페닐피리미딘-2-일)페닐)보론산 및 2-클로로-4,6-디페닐피리미딘으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 5(MS[M+H]+= 691.9)을 제조하였다.In Synthesis Example 1, (2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid and 2-chloro-4,6-diphenyl-1,3,5 -Compound 1, except that triazine was changed to (2-(4,6-diphenylpyrimidin-2-yl)phenyl)boronic acid and 2-chloro-4,6-diphenylpyrimidine. Compound 5 (MS[M+H] + = 691.9) was prepared using the same manufacturing method.
합성예 6: 화합물 6의 합성Synthesis Example 6: Synthesis of Compound 6
Figure PCTKR2023016753-appb-img-000034
Figure PCTKR2023016753-appb-img-000034
합성예 1에서, 페닐보론산, (2-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산 및 2-클로로-4,6-디페닐-1,3,5-트리아진을 플루오란텐-8-일보론산, (2-(2,6-디페닐피리미딘-4-일)페닐)보론산 및 4-클로로-2,6-디페닐피리미딘으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 6(MS[M+H]+= 815.4)을 제조하였다.In Synthesis Example 1, phenylboronic acid, (2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid and 2-chloro-4,6-diphenyl-1 , 3,5-triazine is combined with fluoranthen-8-ylboronic acid, (2-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid and 4-chloro-2,6-diphenylpyri. Compound 6 (MS[M+H] + = 815.4) was prepared in the same manner as that of compound 1, except that it was changed to midine.
합성예 7: 화합물 7의 합성Synthesis Example 7: Synthesis of Compound 7
Figure PCTKR2023016753-appb-img-000035
Figure PCTKR2023016753-appb-img-000035
합성예 1에서, 페닐보론산을 (페닐-d5)보론산으로 변경하여 사용한 것을 제외하고는, 화합물 4의 제조 방법과 동일한 제조 방법으로 화합물 7(MS[M+H]+= 698.3)을 제조하였다.In Synthesis Example 1, compound 7 (MS[M+H] + = 698.3) was prepared using the same manufacturing method as that of compound 4, except that phenylboronic acid was changed to (phenyl-d5)boronic acid. did.
합성예 8: 화합물 8의 합성Synthesis Example 8: Synthesis of Compound 8
Figure PCTKR2023016753-appb-img-000036
Figure PCTKR2023016753-appb-img-000036
합성예 1에서, 페닐보론산 및 2-클로로-4,6-디페닐-1,3,5-트리아진을 나프탈렌-2-일보론산 및 2-클로로-4-페닐-6-(페닐-d5)-1,3,5-트리아진으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 8(MS[M+H]+= 748.3)을 제조하였다.In Synthesis Example 1, phenylboronic acid and 2-chloro-4,6-diphenyl-1,3,5-triazine were reacted with naphthalen-2-ylboronic acid and 2-chloro-4-phenyl-6-(phenyl-d5 Compound 8 (MS[M+H] + = 748.3) was prepared in the same manner as that of Compound 1, except that it was changed to )-1,3,5-triazine.
합성예 9: 화합물 9의 합성Synthesis Example 9: Synthesis of Compound 9
Figure PCTKR2023016753-appb-img-000037
Figure PCTKR2023016753-appb-img-000037
합성예 1에서, 1-브로모-4-클로로-2-아이오도벤젠을 4-브로모-1-클로로-2-아이오도벤젠으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 9(MS[M+H]+= 693.3)을 제조하였다.In Synthesis Example 1, the same method for preparing Compound 1 was used, except that 1-bromo-4-chloro-2-iodobenzene was changed to 4-bromo-1-chloro-2-iodobenzene. Compound 9 (MS[M+H] + = 693.3) was prepared using the preparation method.
합성예 10: 화합물 10의 합성Synthesis Example 10: Synthesis of Compound 10
Figure PCTKR2023016753-appb-img-000038
Figure PCTKR2023016753-appb-img-000038
합성예 1에서, 1-브로모-4-클로로-2-아이오도벤젠 및 보론산을 4-브로모-1-클로로-2-아이오도벤젠 및 (4-(아다만탄-1-일)보론산으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 10(MS[M+H]+= 827.4)을 제조하였다.In Synthesis Example 1, 1-bromo-4-chloro-2-iodobenzene and boronic acid were reacted with 4-bromo-1-chloro-2-iodobenzene and (4-(adamantan-1-yl) Compound 10 (MS[M+H] + = 827.4) was prepared using the same manufacturing method as that of Compound 1, except that it was changed to boronic acid.
합성예 11: 화합물 11의 합성Synthesis Example 11: Synthesis of Compound 11
Figure PCTKR2023016753-appb-img-000039
Figure PCTKR2023016753-appb-img-000039
합성예 1에서, 1-브로모-4-클로로-2-아이오도벤젠, (2-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산 및 2-클로로-4,6-디페닐-1,3,5-트리아진을 4-브로모-1-클로로-2-아이오도벤젠, (2-(4,6-디페닐피리미딘-2-일)페닐)보론산 및 2-클로로-4-(디벤조[b,d]티오펜-4-일)-6-페닐-1,3,5-트리아진으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 11(MS[M+H]+= 798.3)을 제조하였다.In Synthesis Example 1, 1-bromo-4-chloro-2-iodobenzene, (2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid and 2 -Chloro-4,6-diphenyl-1,3,5-triazine is 4-bromo-1-chloro-2-iodobenzene, (2-(4,6-diphenylpyrimidin-2-yl ) phenyl) boronic acid and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine, except that it is used as a compound. Compound 11 (MS[M+H] + = 798.3) was prepared using the same preparation method as that of 1.
합성예 12: 화합물 12의 합성Synthesis Example 12: Synthesis of Compound 12
Figure PCTKR2023016753-appb-img-000040
Figure PCTKR2023016753-appb-img-000040
합성예 1에서, 1-브로모-4-클로로-2-아이오도벤젠, 페닐보론산 및 2-클로로-4,6-디페닐-1,3,5-트리아진을 4-브로모-1-클로로-2-아이오도벤젠, (3-(9H-카바졸-9-일)페닐)보론산 및 2-클로로-4,6-디페닐피리미딘으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 12(MS[M+H]+= 857.3)을 제조하였다.In Synthesis Example 1, 1-bromo-4-chloro-2-iodobenzene, phenylboronic acid and 2-chloro-4,6-diphenyl-1,3,5-triazine were reacted with 4-bromo-1. -Compound 1, except that it was changed to chloro-2-iodobenzene, (3-(9H-carbazol-9-yl)phenyl)boronic acid, and 2-chloro-4,6-diphenylpyrimidine. Compound 12 (MS[M+H] + = 857.3) was prepared using the same manufacturing method as that of .
합성예 13: 화합물 13의 합성Synthesis Example 13: Synthesis of Compound 13
Figure PCTKR2023016753-appb-img-000041
Figure PCTKR2023016753-appb-img-000041
합성예 1에서, 2-클로로-4,6-디페닐-1,3,5-트리아진을 2-(2-클로로페닐)-4,6-디페닐-1,3,5-트리아진으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 13(MS[M+H]+=769.3)을 제조하였다.In Synthesis Example 1, 2-chloro-4,6-diphenyl-1,3,5-triazine is converted to 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 13 (MS[M+H] + =769.3) was prepared using the same preparation method as that of Compound 1, except that it was used in modification.
합성예 14: 화합물 14의 합성Synthesis Example 14: Synthesis of Compound 14
Figure PCTKR2023016753-appb-img-000042
Figure PCTKR2023016753-appb-img-000042
합성예 1에서, 1-브로모-4-클로로-2-아이오도벤젠, (2-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산 및 2-클로로-4,6-디페닐-1,3,5-트리아진을 1-브로모-4-클로로-2,3-디아이오도벤젠, (2-(4-페닐퀴나졸린-2-일)페닐)보론산 및 9-(4-클로로-6-페닐-1,3,5-트리아진-2-일)-9H-카바졸으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 14(MS[M+H]+= 831.3)을 제조하였다.In Synthesis Example 1, 1-bromo-4-chloro-2-iodobenzene, (2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid and 2 -Chloro-4,6-diphenyl-1,3,5-triazine is combined with 1-bromo-4-chloro-2,3-diiodobenzene, (2-(4-phenylquinazolin-2-yl) The same method for preparing compound 1 was used except that it was changed to phenyl)boronic acid and 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole. Compound 14 (MS[M+H] + = 831.3) was prepared using the preparation method.
실험예 1Experimental Example 1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 HI-A를 600Å의 두께로 열 진공증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식의 헥사니트릴 헥사아자트리페닐렌(hexaazatriphenylene; HAT, 50Å) 및 하기 화합물 HT-A(600Å)를 순차적으로 진공증착하여 정공수송층을 형성하였다.On the ITO transparent electrode prepared in this way, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, 50Å) of the following formula and HT-A (600Å) of the following compound were sequentially vacuum deposited to form a hole transport layer.
이어서, 상기 정공수송층 위에 막 두께 200Å으로 하기 화합물 BH와 BD를 25:1의 중량비로 진공증착하여 발광층을 형성하였다.Subsequently, the following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to a film thickness of 200 Å on the hole transport layer to form a light emitting layer.
상기 발광층 위에 합성예 1에서 제조한 화합물 1과 하기 화합물 [LiQ](Lithiumquinolate)를 1:1 중량비로 진공증착하여 360Å의 두께로 전자주입 및 수송층을 형성하였다. 상기 전자주입 및 수송층 위에 순차적으로 10Å 두께로 리튬 플루오라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다.On the emitting layer, Compound 1 prepared in Synthesis Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited at a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 360 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
Figure PCTKR2023016753-appb-img-000043
Figure PCTKR2023016753-appb-img-000043
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.9 Å/sec를 유지하였고, 음극의 리튬 플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착 시 진공도는 1 × 10-7 ~ 5 × 10-8 torr를 유지하여, 유기 발광 소자를 제작하였다. In the above process, the deposition rate of organic matter was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 × 10. An organic light emitting device was manufactured by maintaining -7 to 5 × 10 -8 torr.
실험예 2 내지 14Experimental Examples 2 to 14
실험예 1의 화합물 1 대신 하기 표 1의 화합물을 사용한 것을 제외하고는 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound 1 in Experimental Example 1.
비교 실험예 1 내지 6Comparative Experimental Examples 1 to 6
실험예 1의 화합물 1 대신 하기 표 1의 화합물을 사용한 것을 제외하고는 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 ET-1 내지 ET-6의 화합물은 하기와 같다.An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound 1 in Experimental Example 1. The compounds ET-1 to ET-6 used in Table 1 below are as follows.
Figure PCTKR2023016753-appb-img-000044
Figure PCTKR2023016753-appb-img-000044
상기 실험예 및 비교실험예에서 제조한 유기 발광 소자에 대하여, 10 mA/cm2의 전류밀도에서 구동 전압, 발광 효율 및 색좌표를 측정하였고, 20 mA/cm2의 전류밀도에서 초기 휘도 대비 90%가 되는 시간(T90)을 측정하였다. 그 결과를 하기 표 1에 나타내었다.For the organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples, the driving voltage, luminous efficiency, and color coordinates were measured at a current density of 10 mA/cm 2 , and the luminance was 90% of the initial luminance at a current density of 20 mA/cm 2. The time to become (T 90 ) was measured. The results are shown in Table 1 below.
화합물
(전자주입 및 수송층)compound
(Electron injection and transport layer) 		전압
(V@10mA/cm2)Voltage
(V@10mA/cm 2 ) 		효율
(cd/A@10mA/cm2)efficiency
(cd/A@10mA/cm 2 ) 		색좌표
(x,y)Color coordinates
(x,y) 		T90
(hr@20mA/cm2) T90
(hr@20mA/cm 2 )
실험예 1Experimental Example 1 화합물1Compound 1 3.153.15 4.254.25 (0.136, 0.112)(0.136, 0.112) 180180
실험예 2Experimental Example 2 화합물2Compound 2 3.203.20 4.384.38 (0.136, 0.111)(0.136, 0.111) 177177
실험예 3Experimental Example 3 화합물3Compound 3 3.193.19 4.444.44 (0.136, 0.112)(0.136, 0.112) 198198
실험예 4Experimental Example 4 화합물4Compound 4 3.253.25 4.194.19 (0.136, 0.111)(0.136, 0.111) 169169
실험예 5Experimental Example 5 화합물5Compound 5 3.093.09 4.214.21 (0.136, 0.111)(0.136, 0.111) 172172
실험예 6Experimental Example 6 화합물6Compound 6 3.223.22 4.394.39 (0.136, 0.111)(0.136, 0.111) 159159
실험예 7Experimental Example 7 화합물7Compound 7 3.153.15 4.254.25 (0.136, 0.112)(0.136, 0.112) 220220
실험예 8Experimental Example 8 화합물8Compound 8 3.193.19 4.464.46 (0.136, 0.111)(0.136, 0.111) 240240
실험예 9Experimental Example 9 화합물9Compound 9 3.173.17 4.274.27 (0.136, 0.112)(0.136, 0.112) 171171
실험예 10Experimental Example 10 화합물10Compound 10 3.263.26 4.264.26 (0.136, 0.111)(0.136, 0.111) 165165
실험예 11Experimental Example 11 화합물11Compound 11 3.053.05 4.784.78 (0.136, 0.111)(0.136, 0.111) 158158
실험예 12Experimental Example 12 화합물12Compound 12 3.293.29 4.664.66 (0.136, 0.111)(0.136, 0.111) 160160
실험예 13Experimental Example 13 화합물 13Compound 13 3.233.23 4.284.28 (0.136, 0.111)(0.136, 0.111) 189189
실험예 14Experimental Example 14 화합물 14Compound 14 3.263.26 4.54.5 (0.136, 0.111)(0.136, 0.111) 177177
비교실험예 1Comparative Experiment Example 1 ET-1ET-1 4.934.93 3.013.01 (0.136, 0.111)(0.136, 0.111) 9191
비교실험예 2Comparative Experiment Example 2 ET-2ET-2 4.884.88 3.053.05 (0.136, 0.111)(0.136, 0.111) 9595
비교실험예 3Comparative Experiment Example 3 ET-3ET-3 4.754.75 3.083.08 (0.136, 0.112)(0.136, 0.112) 9999
비교실험예 4Comparative Experiment Example 4 ET-4ET-4 5.135.13 3.193.19 (0.136, 0.111)(0.136, 0.111) 5454
비교실험예 5Comparative Experiment Example 5 ET-5ET-5 5.555.55 2.782.78 (0.136, 0.112)(0.136, 0.112) 4545
비교실험예 6Comparative Experiment Example 6 ET-6ET-6 5.255.25 2.852.85 (0.136, 0.111)(0.136, 0.111) 5959
상기 표 1에 기재된 바와 같이, 본 발명의 화학식 1로 표시되는 화합물을 사용한 유기 발광 소자의 경우, 전압, 효율 및/또는 수명(T90)에서 우수한 특성을 나타내는 것을 확인하였다.상기 표 1의 실험예 1 내지 14과 비교실험예 1 및 2을 비교하면, 본 발명의 화학식 1의 화합물을 포함하는 유기 발광소자는 전자 수송 특성을 가진 N함유 6원 고리를 포함하는 헤테로고리가 2개 이상으로 치환되어 있어 전자 수송 능력이 다양하게 조절할 수 있다. 따라서 N함유 고리가 1개 치환된 화합물을 사용한 유기 발광 소자보다 효율 및 수명 면에서 현저히 우수한 특성을 보임을 확인할 수 있었다. As shown in Table 1, it was confirmed that the organic light-emitting device using the compound represented by Formula 1 of the present invention exhibits excellent characteristics in terms of voltage, efficiency, and/or lifespan (T 90 ). Experiments in Table 1 above Comparing Examples 1 to 14 and Comparative Experiment Examples 1 and 2, the organic light-emitting device containing the compound of Formula 1 of the present invention has two or more heterocycles containing an N-containing 6-membered ring with electron transport properties. Therefore, the electron transport ability can be adjusted in various ways. Therefore, it was confirmed that the organic light-emitting device showed significantly better properties in terms of efficiency and lifespan than an organic light-emitting device using a compound with one N-containing ring substituted.
상기 표 1의 실험예 1 내지 14과 비교실험예 3 및 4를 비교하면, 본 발명의 화학식 1의 화합물을 포함하는 유기 발광소자는 전자 수송 특성을 가진 N함유 6원 고리를 포함하는 헤테로고리가 페닐의 오쏘 위치로 이웃하고 있어 구조적 뒤틀림이 발생하여 전자 수송에 유리하다. 따라서, N함유 6원 고리를 포함하는 헤테로고리가 페닐의 메타 및 파라로 사용한 유기 발광 소자보다 전압. 효율 및 수명면에서 현저히 우수한 특성을 보임을 확인할 수 있었다.Comparing Experimental Examples 1 to 14 of Table 1 and Comparative Experimental Examples 3 and 4, the organic light-emitting device containing the compound of Formula 1 of the present invention has a heterocycle containing an N-containing 6-membered ring with electron transport properties. Since it is adjacent to the ortho position of phenyl, structural distortion occurs, which is advantageous for electron transport. Therefore, the heterocycle containing an N-containing 6-membered ring has a higher voltage than the organic light emitting device using meta and para phenyl. It was confirmed that it showed significantly excellent characteristics in terms of efficiency and lifespan.
비교실험예 5 및 6의 경우, A가 비치환된 N함유 6원고리를 포함하는 헤테로아릴이다. 본 발명의 실험예 1 내지 14는 A와 B가 아릴기로 치환된 N함유 6원 고리를 포함하는 헤테로아릴기인 점이 상이하다. In Comparative Experiment Examples 5 and 6, A is heteroaryl containing an unsubstituted N-containing 6-membered ring. Experimental Examples 1 to 14 of the present invention are different in that A and B are heteroaryl groups containing an N-containing 6-membered ring substituted with an aryl group.
본 발명의 화합물들을 사용하는 실험예 1 내지 14의 경우, 비교실험예 5 및 6보다 저전압, 고효율, 장수명의 특성을 보임을 알 수 있다.It can be seen that Experimental Examples 1 to 14 using the compounds of the present invention showed lower voltage, higher efficiency, and longer lifespan characteristics than Comparative Experimental Examples 5 and 6.

Claims (10)

  1. 하기 화학식 1의 화합물: Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023016753-appb-img-000045
    Figure PCTKR2023016753-appb-img-000045
    상기 화학식 1에 있어서,In Formula 1,
    A는 치환 또는 비치환된 아릴기로 치환된 N을 포함하는 6원 고리를 포함하는 헤테로아릴기이고, A is a heteroaryl group containing a 6-membered ring containing N substituted with a substituted or unsubstituted aryl group,
    B는 치환 또는 비치환된 아릴기로 치환된 N을 포함하는 6원 고리를 포함하는 헤테로아릴기이고,B is a heteroaryl group containing a 6-membered ring containing N substituted with a substituted or unsubstituted aryl group,
    L은 직접결합, 또는 치환 또는 비치환된 아릴렌기이고,L is a direct bond, or a substituted or unsubstituted arylene group,
    Q1 및 Q2 중 하나는 탄소수 6 내지 30의 아릴기이고, 나머지는 수소 또는 탄소수 6 내지 30의 아릴기이고,One of Q1 and Q2 is an aryl group having 6 to 30 carbon atoms, and the other is hydrogen or an aryl group having 6 to 30 carbon atoms,
    Q1 및 Q2 중 하나가 수소인 경우, 나머지는 중수소, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로아릴기 중 선택되는 하나 이상의 치환기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이고, When one of Q1 and Q2 is hydrogen, the remainder is one or more substituents selected from deuterium, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group. It is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted,
    Q1 및 Q2가 모두 탄소수 6 내지 30의 아릴기일 때, 상기 탄소수 6 내지 30의 아릴기는 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로아릴기 중 선택되는 하나 이상의 치환기로 치환 또는 비치환된다.When both Q1 and Q2 are aryl groups having 6 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted Or, it is substituted or unsubstituted with one or more substituents selected from unsubstituted heteroaryl groups.
  2. 청구항 1에 있어서, 상기 화학식 1은 아래 화학식 1-1 또는 1-2인 것인 화합물:The compound according to claim 1, wherein the formula 1 is the formula 1-1 or 1-2 below:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2023016753-appb-img-000046
    Figure PCTKR2023016753-appb-img-000046
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2023016753-appb-img-000047
    Figure PCTKR2023016753-appb-img-000047
    상기 화학식 1-1 및 1-2에 있어서, 상기 A, B, L, Q1 및 Q2는 상기 화학식 1에서 정의한 것과 같다.In Formulas 1-1 and 1-2, A, B, L, Q1, and Q2 are as defined in Formula 1.
  3. 청구항 1에 있어서, 상기 화학식 1은 아래 화학식 1-3인 것인 화합물:The compound according to claim 1, wherein the formula 1 is the formula 1-3 below:
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2023016753-appb-img-000048
    Figure PCTKR2023016753-appb-img-000048
    상기 화학식 1-3에 있어서, 상기 A, B, 및 L는 상기 화학식 1에서 정의한 것과 같고, In Formula 1-3, A, B, and L are as defined in Formula 1,
    R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 결합하여 치환 또는 비치환된 고리를 형성하고,R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group. Or, it combines with an adjacent group to form a substituted or unsubstituted ring,
    a 및 b는 1 내지 5의 정수이고,a and b are integers from 1 to 5,
    a가 2 이상일 때, R1은 서로 같거나 상이하고,When a is 2 or more, R1 is the same or different,
    b가 2 이상일 때, R2는 서로 같거나 상이하다.When b is 2 or more, R2 is the same or different.
  4. 청구항 1에 있어서, 상기 화학식 1은 아래 화학식 1-4인 것인 화합물:The compound according to claim 1, wherein the formula 1 is the formula 1-4 below:
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2023016753-appb-img-000049
    Figure PCTKR2023016753-appb-img-000049
    상기 화학식 1-4에 있어서, 상기 L, Q1, 및 Q2는 상기 화학식 1에서 정의한 것과 같고,In Formula 1-4, L, Q1, and Q2 are as defined in Formula 1,
    X1 내지 X3 중 하나는 N이고, 나머지는 각각 N 또는 CR이고,One of X1 to X3 is N, and the others are N or CR, respectively,
    R은 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고,R is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
    X4 내지 X8 중 하나는 N이고, 나머지는 각각 N 또는 CR1이고,One of X4 to X8 is N, and the others are N or CR1, respectively,
    R1은 중수소, 니트릴기, 니트로기, 할로겐기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 치환기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R1 is deuterium, nitrile group, nitro group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or is substituted or unsubstituted by combining with adjacent substituents. forms a ring
  5. 청구항 1에 있어서, 상기 A는 피리딘, 피리미딘, 트리아진, 퀴놀린, 퀴나졸린, 또는 퀴녹살린이고,The method of claim 1, wherein A is pyridine, pyrimidine, triazine, quinoline, quinazoline, or quinoxaline,
    상기 피리딘, 피리미딘, 트리아진, 퀴놀린, 퀴나졸린, 또는 퀴녹살린은 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기로 치환된 것인 화합물.The pyridine, pyrimidine, triazine, quinoline, quinazoline, or quinoxaline is each independently substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  6. 청구항 1에 있어서, 상기 B는 피리딘, 피리미딘, 또는 트리아진이고, 상기 피리딘, 피리미딘, 또는 트리아진은 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기로 치환된 것인 화합물.The compound according to claim 1, wherein B is pyridine, pyrimidine, or triazine, and the pyridine, pyrimidine, or triazine are each independently substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  7. 청구항 3에 있어서, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로, 수소, 중수소, 니트릴기, 니트로기, 할로겐기, 탄소수 1 내지 10의 알킬기, 탄소수 6 내지 30의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기인 것인 화합물.The method of claim 3, wherein R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group with 1 to 10 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a carbon number. A compound having 3 to 30 heteroaryl groups.
  8. 청구항 1에 있어서, 상기 화학식 1은 아래 화합물 중 어느 하나인 것인 화합물: The method according to claim 1, wherein Formula 1 is any one of the following compounds:
    Figure PCTKR2023016753-appb-img-000050
    Figure PCTKR2023016753-appb-img-000050
    Figure PCTKR2023016753-appb-img-000051
    Figure PCTKR2023016753-appb-img-000051
    Figure PCTKR2023016753-appb-img-000052
    Figure PCTKR2023016753-appb-img-000052
    Figure PCTKR2023016753-appb-img-000053
    Figure PCTKR2023016753-appb-img-000053
    Figure PCTKR2023016753-appb-img-000054
    Figure PCTKR2023016753-appb-img-000054
    Figure PCTKR2023016753-appb-img-000055
    Figure PCTKR2023016753-appb-img-000055
    Figure PCTKR2023016753-appb-img-000056
    Figure PCTKR2023016753-appb-img-000056
    Figure PCTKR2023016753-appb-img-000057
    Figure PCTKR2023016753-appb-img-000057
    Figure PCTKR2023016753-appb-img-000058
    Figure PCTKR2023016753-appb-img-000058
    Figure PCTKR2023016753-appb-img-000059
    Figure PCTKR2023016753-appb-img-000059
    Figure PCTKR2023016753-appb-img-000060
    Figure PCTKR2023016753-appb-img-000060
    Figure PCTKR2023016753-appb-img-000061
    Figure PCTKR2023016753-appb-img-000061
  9. 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 8 중 어느 한 항에 따른 화합물을 포함하는 유기 발광 소자.first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising 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 according to any one of claims 1 to 8. .
  10. 청구항 9에 있어서, 상기 유기물층은 전자수송층, 전자주입층, 및 전자주입 및 수송 층 중 1층 이상을 포함하고, 상기 층들 중 1층 이상이 상기 화합물을 포함하는 유기 발광 소자.The organic light-emitting device of claim 9, wherein the organic material layer includes one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers includes the compound.
PCT/KR2023/016753 2022-10-26 2023-10-26 Compound and organic light-emitting device comprising same WO2024091024A1 (en)

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