WO2024005486A1 - Composé et élément électroluminescent organique le comprenant - Google Patents

Composé et élément électroluminescent organique le comprenant Download PDF

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WO2024005486A1
WO2024005486A1 PCT/KR2023/008866 KR2023008866W WO2024005486A1 WO 2024005486 A1 WO2024005486 A1 WO 2024005486A1 KR 2023008866 W KR2023008866 W KR 2023008866W WO 2024005486 A1 WO2024005486 A1 WO 2024005486A1
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김민준
서상덕
이성재
전현수
홍성길
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주식회사 엘지화학
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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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 made up of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device. For example, it consists of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer. You can lose.
  • this organic light-emitting device when a voltage is applied between the 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 is 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 the light there are blue, green, and red light emitting materials, as well as yellow and orange light emitting materials needed to achieve 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.
  • L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Ar1 and Ar2 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,
  • Ar3 is of the formula 2 below,
  • One of Y1 to Y12 is N, one of the others is C that combines with L3, the others are the same or different from each other and are each independently N or CR1,
  • R1 is hydrogen or deuterium
  • Y11 is CR1.
  • a first electrode a second electrode provided opposite the first electrode; and an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the above-mentioned compounds.
  • 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 having narrow half width, high efficiency, low voltage, and long lifespan characteristics can be obtained.
  • 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 substituents.
  • 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.
  • halogen groups 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, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, diphenyl 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 an aryl group and a heteroaryl group are substituted at the N of the amine 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 it 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 above, except that it is a divalent group.
  • heteroarylene group is the same as defined for the heteroaryl group above, except that it is a divalent group.
  • Formula 1 is any one of the following Formulas 1-1 to 1-6.
  • Formula 2 is any one of the following structures.
  • the dotted line refers to the portion that binds to L3.
  • At least one of Y1 to Y12 is N.
  • one of Y1 to Y12 is N.
  • one of Y1 to Y4 is N.
  • one of Y5 to Y10 is N.
  • one of Y1 to Y12 is N, the other is C that combines with L3, and the remainder is CR1.
  • one of Y1 to Y12 is N, the other is C combining with L3, the remainder is CR1, and R1 is hydrogen or deuterium.
  • Y1 is N.
  • Y2 is N.
  • Y3 is N.
  • Y4 is N.
  • Y5 is N.
  • Y6 is N.
  • Y7 is N.
  • Y8 is N.
  • Y9 is N.
  • Y10 is N.
  • Y11 is N.
  • Y12 is N.
  • Y1 is N
  • one of Y2 to Y12 is C that combines with L3
  • the other is CR1.
  • Y2 is N, Y1, and one of Y3 to Y12 is C that combines with L3, and the other is CR1.
  • Y3 is N
  • one of Y1, Y2, and Y4 to Y12 is C that combines with L3, and the other is CR1.
  • Y4 is N
  • Y5 to Y12 is C that combines with L3
  • the other is CR1.
  • Y5 is N
  • Y1 to Y4 is C that combines with L3
  • the other is CR1.
  • Y6 is N
  • Y7 to Y12 is C that combines with L3
  • the other is CR1.
  • Y7 is N
  • one of Y1 to Y6, and Y8 to Y12 is C that combines with L3, and the other is CR1.
  • Y8 is N
  • one of Y1 to Y7, and Y9 to Y12 is C that combines with L3, and the other is CR1.
  • Y9 is N
  • one of Y1 to Y8 and Y10 to Y12 is C combining with L3
  • the other and Y10 are CR1.
  • Y10 is N
  • one of Y1 to Y9, Y11 and Y12 is C that combines with L3, and the other is CR1.
  • Y11 is N
  • Y1 to Y10 one of Y1 to Y10
  • Y12 is C that combines with L3, and the other is CR1.
  • Y12 is N
  • one of Y1 to Y11 is C that combines with L3
  • the remainder and Y11 are CR1.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, Divalent phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent carbazole group, A divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a dibenzofuran group, a dibenzothiophene group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or It is a divalent benzoxazole group.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond or an arylene group having 6 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms.
  • L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent anthracene group, It is a divalent phenanthrene group, a divalent fluorene group, a divalent triphenylene group, or a divalent pyrene group.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
  • L1 to L3 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
  • L1 to L3 are direct bonds.
  • L1 to L3 are phenylene groups.
  • L1 to L3 are divalent naphthyl groups.
  • L1 to L3 are divalent biphenyl groups.
  • L1 and L2 are the same as each other and are a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are the same as each other and are a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L1 and L2 are the same as each other, and are a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, 2 Divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, divalent thiophene group , a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L1 and L2 are different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, and a divalent Phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, It is a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 and L2 are different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
  • L1 and L2 are a direct bond.
  • L1 and L2 are phenylene groups.
  • L1 and L2 are divalent naphthyl groups.
  • L1 and L2 are divalent biphenyl groups.
  • L1 is a direct bond.
  • L1 is a phenylene group.
  • L1 is a divalent naphthyl group.
  • L1 is a divalent biphenyl group.
  • L2 is a direct bond.
  • L2 is a phenylene group.
  • L2 is a divalent naphthyl group.
  • L2 is a divalent biphenyl group.
  • L3 is a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L3 is a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L3 is a direct bond, or an arylene group having 6 to 30 carbon atoms.
  • L3 is a direct bond, or an arylene group having 6 to 20 carbon atoms.
  • L3 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent pyrene group, 2 divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, dibenzofuran group, dibenzothiophene group, divalent furan group, divalent thiophene group, divalent benzimi It is a polyazole group or a divalent benzoxazole group.
  • L3 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
  • L3 is a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
  • L3 is a direct bond.
  • L3 is a phenylene group, a divalent naphthyl group, a divalent biphenyl group, or a divalent terphenyl group.
  • L3 is a phenylene group, a divalent naphthyl group, or a divalent biphenyl group.
  • L3 is a direct bond.
  • L3 is a phenylene group.
  • L3 is a direct bond, or a substituted or unsubstituted phenylene group.
  • L3 is a direct bond or an unsubstituted phenylene group.
  • L3 is a direct bond or a phenylene group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. .
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. .
  • Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or provided with an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms; Or it is a heteroaryl group having 3 to 20 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms; Or it is a heteroaryl group having 3 to 20 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 15 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a triphenylene group, a phenanthrene group, an anthracene group, and a carbon number.
  • Carbazole group dibenzofuran group, dibenzothiophene group, triazine group, pyrimidine group, quinazoline group, quinoline group, quinoxaline group, benzonaphthofuran group, benzoline group, substituted or unsubstituted with 6 to 15 aryl groups It is a naphthothiophene group, a benzoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a benzofuropyridine group, or a benzothiopyridine group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a triphenylene group, a phenanthrene group, and a carbon number of 6 to 15. It is a carbazole group, dibenzofuran group, dibenzothiophene group, benzonaphthofuran group, benzonaphthothiophene group, benzoquinoline group, benzofuropyridine group, or benzothiopyridine group substituted or unsubstituted with an aryl group. .
  • Ar1 and Ar2 are the same as or different from each other, and are each independently substituted with a phenyl group, biphenyl group, naphthyl group, terphenyl group, fluoranthene group, triphenylene group, phenanthrene group, or phenyl group. It is an unsubstituted carbazole group, dibenzofuran group, dibenzothiophene group, benzonaphthofuran group, benzonaphthothiophene group, benzoquinoline group, benzofuropyridine group, or benzothiopyridine group. Items of the present specification According to the embodiment, R1 is hydrogen or deuterium.
  • R1 is hydrogen
  • R1 is deuterium
  • 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 means 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 represented by Formula 1 can do.
  • 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 may include the compound represented by Formula 1.
  • the electron injection and transport layer includes the compound of Formula 1 and a metal complex.
  • the electron injection and transport layer includes the compound of Formula 1 and lithium quinolate.
  • the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:10 to 10:1.
  • the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:5 to 5:1.
  • the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:3 to 3:1.
  • the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate at a weight ratio of 1:10 to 10:1.
  • the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate in a weight ratio of 1:5 to 5:1.
  • the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate in a weight ratio of 1:3 to 3:1.
  • the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound of Formula 1.
  • 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 is represented by the formula (1) It may contain compounds.
  • 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 represented by Formula 1.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of Formula 1 as a host.
  • the light emitting layer includes a host and a dopant.
  • the light emitting layer may include one or more types of hosts.
  • the light emitting layer may include one or more types of dopants.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99.9:0.1 to 70:30.
  • the light emitting layer includes a host and a dopant at a mass ratio of 99.9:0.1 to 80:20.
  • the light emitting layer includes a host and a dopant at a mass ratio of 99.9:0.1 to 85:15.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99.9:0.1 to 90:10.
  • 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 FIG. 1, 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 represented by Formula 1 may be included in the organic layer 3.
  • an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron injection and transport layer The structure of an organic light emitting device in which the cathode 10) and the cathode 4 are sequentially stacked is illustrated. In this structure, the compound represented by Formula 1 may be included in the light-emitting 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 which a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection are selected from the group consisting of 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.
  • 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 is 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.
  • R402 is a phenyl group substituted with a carbazole group or an arylamine group; Biphenyl group substituted with carbazole group or arylamine 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 each independently represents an aryl group substituted or unsubstituted by an alkyl group.
  • R400 and R401 are the same or different from each other, and are each independently a phenyl group, a biphenyl group, or a dimethylfluorene group.
  • L402 is a phenylene group.
  • the formula HI-1 is selected from the following compounds.
  • the hole injection layer includes a compound represented by the following formula HI-2, but is not limited thereto.
  • X'1 to X'3 are the same or different from each other and are each independently hydrogen, deuterium, or halogen group,
  • R309 to R314 are the same as 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 a substituted or unsubstituted heteroaryl group,
  • x1' to x3' are each integers from 1 to 4, and when they are 2 or more, the substituents in parentheses are the same or different from each other.
  • X'1 to X'3 are halogen groups.
  • X'1 to X'3 are F or Cl.
  • X'1 to X'3 are F.
  • R309 to R314 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted amine group.
  • R309 to R314 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or nitrile.
  • R309 to R314 are nitrile groups.
  • the formula HI-2 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 chemical formula HT-2, but is not limited thereto.
  • R403 to R406 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,
  • L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • l403 is an integer from 1 to 3, and if l403 is 2 or more, L403 is the same or different from each other.
  • R403 to R406 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.
  • R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.
  • R403 to R406 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, or a naphthyl group.
  • R403 to R406 are the same or different from each other, and each independently represents a phenyl group.
  • L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.
  • L403 is a divalent carbazole group unsubstituted or substituted with a phenylene group, a divalent biphenyl group, or an aryl group.
  • L403 is a divalent carbazole group substituted with a naphthyl 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 blocking layer may be made of the spiro compound described above or a material known in the art.
  • the electron blocking layer includes, but is not limited to, a compound represented by the following formula EB-1.
  • R318 to R320 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 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,
  • r318 is an integer from 1 to 5, and when r318 is 2 or more, 2 or more of R318 are the same or different from each other,
  • r319 is an integer of 1 to 5, and when r319 is 2 or more, 2 or more R319s are the same or different from each other.
  • R320 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R320 is a phenyl group, a biphenyl group, or a phenanthrene group.
  • R318 and R319 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.
  • R318 and R319 are the same or different from each other, and are each independently a phenyl group, a biphenyl group, or a phenanthrene group.
  • the formula EB-1 is represented by the following compound.
  • 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
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)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.
  • a metal complex may be used as the dopant.
  • the dopant may be an iridium complex.
  • the dopant is represented by any one of the compounds below.
  • the structure specified above is not limited to the dopant 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 hole blocking layer includes a compound of the following formula HB-1: do.
  • At least one of Z1 to Z3 is N, and the others are CH,
  • L601 and L602 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,
  • Ar601 to Ar603 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.
  • L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 and L602 are the same as or different from each other, and are each independently a phenylene group; Biphenylylene group; Or it is a naphthylene group.
  • Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. .
  • Ar601 to Ar603 are phenyl groups or triphenylene groups.
  • the formula HB-1 is represented by the following compound.
  • 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 group, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, These include, but are not limited to, metal complex compounds and nitrogen-containing five-membered ring derivatives.
  • the electron injection and transport layer includes a compound of the following formula EI-1.
  • At least one of Z11 to Z13 is N, the others are CH,
  • At least one of Z14 to Z16 is N, the rest are CH,
  • L701 is directly coupled; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar701 to Ar704 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,
  • l701 is an integer from 1 to 4, and when l701 is plural, L701 is the same or different from each other.
  • L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L701 is a phenylene group; Biphenylylene group; Or it is a naphthylene group.
  • L701 is a phenylene group; Or it is a naphthylene group.
  • Ar701 to Ar704 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. .
  • Ar701 to Ar704 are phenyl groups.
  • the formula EI-1 is represented by the following compound.
  • 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 blocks 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.
  • Trz3 (15g, 35.9mmol) and sub2 (13.4g, 37.7mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.9g, 107.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following HI-1 compound was formed as a hole injection layer to a thickness of 1150 ⁇ , and the following A-1 compound was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer with a film thickness of 800 ⁇ .
  • the following EB-1 compound was vacuum deposited to a film thickness of 150 ⁇ on the hole transport layer to form an electron blocking layer.
  • Compound 1 as a host and Compound Dp-7 as a dopant were vacuum deposited on the EB-1 deposition film at a weight ratio of 98:2 to form a red light-emitting layer with a thickness of 400 ⁇ .
  • the following HB-1 compound was vacuum deposited to a film thickness of 30 ⁇ on the light emitting layer to form a hole blocking layer.
  • the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer at a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 2X10 -7 ⁇
  • An organic light emitting device was manufactured by maintaining 5X10 -6 torr.
  • An organic light-emitting device was manufactured in the same manner as Example 1, except that the compound of Formula 1 shown in Table 1 was used as the host of the light-emitting layer in the organic light-emitting device of Example 1.
  • An organic light-emitting device was manufactured in the same manner as Example 1, except that the comparative example compound listed in Table 2 was used as the host of the light-emitting layer in the organic light-emitting device of Example 1.
  • the red organic light-emitting devices of Examples 1 to 43 used widely used conventional materials except for the light-emitting layer material, and had a structure using compound [EB-1] as an electron blocking layer and Dp-7 as a red dopant.
  • Comparative Examples 1 to 3 used compounds in which Y9 was N and Y10 was C bonded to L3, or Y12 was N and Y11 was C bonded to L3.
  • Comparative Example 4 used a compound containing pyrimidine instead of triazine.
  • Comparative Examples 5 and 6 used compounds where R was a substituent other than hydrogen or deuterium.
  • the driving voltage of Examples 1 to 43 is reduced and the efficiency and lifespan are increased compared to Comparative Examples 1 to 6.
  • the reason for the improvement in driving voltage and increase in efficiency and lifespan is that when the compound of the present invention is used as a host, energy is better transferred to the red dopant in the red light-emitting layer compared to the comparative example compound. there was.

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Abstract

La présente invention concerne un composé de formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2023/008866 2022-06-27 2023-06-26 Composé et élément électroluminescent organique le comprenant WO2024005486A1 (fr)

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