WO2022177358A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2022177358A1
WO2022177358A1 PCT/KR2022/002440 KR2022002440W WO2022177358A1 WO 2022177358 A1 WO2022177358 A1 WO 2022177358A1 KR 2022002440 W KR2022002440 W KR 2022002440W WO 2022177358 A1 WO2022177358 A1 WO 2022177358A1
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허동욱
윤정민
한미연
이재탁
박호윤
홍성길
윤희경
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주식회사 엘지화학
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Priority to CN202280008102.0A priority Critical patent/CN116685587A/zh
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Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • an organic light emitting device is a light emitting device using an organic semiconductor material, and requires the exchange of holes and/or electrons between the electrode and the organic semiconductor material.
  • the organic light emitting diode can be roughly divided into two types as follows according to the principle of operation. First, excitons are formed in the organic material layer by photons flowing into the device from an external light source, the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes and used as a current source (voltage source). It is a type of light emitting device.
  • the second is a light emitting device of a type that applies a voltage or current to two or more electrodes to inject holes and/or electrons into an organic semiconductor material layer forming an interface with the electrodes, and operates by the injected electrons and holes.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc.
  • Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as organic layers in organic light emitting devices may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron suppression materials, hole suppression materials, electron transport materials, electron injection materials, etc. according to their functions. have.
  • the light-emitting material includes blue, green, and red light-emitting materials depending on the light-emitting color, and yellow and orange light-emitting materials required to realize a better natural color.
  • a host/dopant system may be used as a light emitting material.
  • the principle is that when a small amount of a dopant having a smaller energy band gap and excellent luminous efficiency than the host constituting the light emitting layer is mixed in the light emitting layer in a small amount, excitons generated from the host are transported to the dopant to emit light with high efficiency.
  • the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
  • a material constituting an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, a hole suppressing material, an electron transporting material, an electron injection material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, a hole suppressing material, an electron transporting material, an electron injection material, etc.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • Ar1 is substituted or unsubstituted naphthalene, in which -L1-Ar2 is bonded to positions 1 and 8, or -L1-Ar2 is bonded to positions 1 and 3;
  • L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Ar2 is the following formula (2),
  • Y1 and Y2 are the same as or different from each other, each independently N or CR2,
  • R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted a cyclic heteroaryl group,
  • Ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
  • L1-Ar2 in parentheses are the same as or different from each other.
  • the first electrode a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the compound of the present invention can be used as a material for an organic layer of an organic light emitting device.
  • an organic light emitting device is manufactured by including the compound of the present invention, an organic light emitting device having high efficiency, low voltage and long lifespan characteristics can be obtained. It is possible to manufacture an organic light emitting device.
  • FIG 1 and 2 show an example of an organic light emitting device according to the present invention.
  • naphthalene is substituted at Nos. 1, 3, or 1, 8 to control the injection rate of electrons by maintaining an appropriate distance between molecules in forming a deposition film when manufacturing an organic light emitting device, so that an organic light emitting device is manufactured In this case, an organic light emitting device having a high lifespan can be manufactured.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position in which the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; nitrile group (-CN); silyl group; boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted amine group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heteroaryl group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the silyl group may be represented by the formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not
  • the boron group may be represented by the formula of -BY4Y5, wherein Y4 and Y5 are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, a phenyl boron group, and the like.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 1 to 10 carbon atoms.
  • the phosphine oxide group is specifically a diphenylphosphine oxide group; Dinaphthyl phosphine oxide group, and the like, but is not limited thereto.
  • the amine group is -NH 2 ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; N-phenylnaphthylamine 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;
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the above-described alkyl group.
  • the alkyl thiooxy group includes a methyl thiooxy group; ethyl thiooxy group; tert-butyl thiooxy group; hexyl thiooxy group; octylthiooxy group and the like, and examples of the alkylsulfoxy group include mesyl; ethyl sulfoxy group; propyl sulfoxy group; Butyl sulfoxy group and the like, but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, 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 an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the heteroaryl group is a cyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and the like.
  • the present invention is not limited thereto.
  • 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.
  • Chemical Formula 1 is represented by Chemical Formula 1-1 below, Chemical Formula 1-1 or Chemical 1-2.
  • L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Ar4 is the following formula (2),
  • Y1 and Y2 are the same as or different from each other, each independently N or CR2,
  • R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted a cyclic heteroaryl group,
  • Ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
  • R3 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group , a substituted or unsubstituted phosphine oxide group, or a substituted or unsubstituted heteroaryl group,
  • a is an integer from 0 to 6, and when a is 2 or more, R3 is the same as or different from each other.
  • X is O or S.
  • X is O.
  • X is S.
  • X is NR1.
  • Chemical Formula 2 is represented by the following Chemical Formula 2-1.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number 3 to 30 It is a heteroarylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C3 to C20 It is a heteroarylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted C6 to C15 arylene group, or a substituted or unsubstituted C3 to C15 It is a heteroarylene group.
  • L1 and L2 are the same as or different from each other, and each independently represents 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 or different from each other, and each independently represents 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 or different from each other, and each independently represents a direct bond, an arylene group having 6 to 15 carbon atoms, or a heteroarylene group having 3 to 15 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted 2 A valent terphenyl group, a substituted or unsubstituted divalent naphthalene group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent phenanthrene group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted a divalent pyridine group, a substituted or unsubstituted divalent triazine group, or a substituted or unsubstituted divalent carbazole group.
  • L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent biphenyl group.
  • L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a phenylene group, or a divalent biphenylene group.
  • L1 and L2 are the same as each other and are a direct bond, a phenylene group, or a divalent biphenylene group.
  • L1 and L2 are different from each other and each independently represent a direct bond, a phenylene group, or a divalent biphenylene group.
  • L1 is a direct bond or a phenylene group.
  • L1 is a direct bond
  • L1 is phenylene
  • L1 is divalent biphenylene.
  • L2 is a direct bond, or a phenylene group.
  • L2 is a direct bond
  • L2 is phenylene
  • L2 is divalent biphenylene.
  • Y1 and Y2 are N.
  • Y1 and Y2 are CR2.
  • Y1 is N
  • Y2 is CR2.
  • Y2 is N
  • Y1 is CR2.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or an unsubstituted silyl group, or a substituted or unsubstituted heteroaryl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted A silyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a silyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 30 carbon atoms It is an aryl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, Or a substituted or unsubstituted C 3 to C 30 heteroaryl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or aryl having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms group, or a heteroaryl group having 3 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or aryl having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms group, or a heteroaryl group having 3 to 20 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; methyl group; ethyl group; Profile group; butyl group; a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; biphenyl group; terphenyl group; naphthyl group; carbazole group; triazine group; pyrimidine group; pyridine group; dibenzofuran group; or a dibenzothiophene group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; methyl group; ethyl group; Profile group; butyl group; a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a terbutyl group; biphenyl group; terphenyl group; naphthyl group; carbazole group; triazine group; pyrimidine group; pyridine group; dibenzofuran group; or a dibenzothiophene group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; or a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a terbutyl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; or a phenyl group unsubstituted or substituted with a methyl group, an isopropyl group, or a terbutyl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; or a phenyl group unsubstituted or substituted with a methyl group or an isopropyl group.
  • R3 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted an aryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, or a substituted or unsubstituted heteroaryl group.
  • R3 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C3 to C30 of a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • R3 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C3 to C20 of a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
  • R3 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or 3 carbon atoms. to 30 is a heteroaryl group.
  • R3 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
  • R3 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
  • R3 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 3 to 15 carbon atoms.
  • R3 is hydrogen, deuterium, methyl group, ethyl group, propyl group, terbutyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridine group, pyrimidine group, triazine group, dibenzo a furan group, a dibenzothiophene group, or a carbazole group.
  • R3 is hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a terbutyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
  • R3 is hydrogen or deuterium.
  • R3 is hydrogen
  • Ar2 and Ar4 are the same as each other.
  • Ar2 and Ar4 are different from each other.
  • Ar3 is 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.
  • Ar3 is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C3-C20 heteroaryl group.
  • Ar3 is a substituted or unsubstituted C6 to C15 aryl group, or a substituted or unsubstituted C3 to C15 heteroaryl group.
  • Ar3 is an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
  • Ar3 is an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
  • Ar3 is an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 3 to 15 carbon atoms.
  • Ar3 is an aryl group having 6 to 15 carbon atoms that is unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group; or a C 3 to C 15 heteroaryl group unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group.
  • Ar3 is an aryl group having 6 to 15 carbon atoms that is unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group; or a C 3 to C 15 heteroaryl group unsubstituted or substituted with an alkyl group.
  • Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzimidazole group, or a benzoxazole group;
  • the phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, pyrimidine group, pyridine group, triazine group, carbazole group, thiophene group, furan group, dibenzofuran group , a dibenzothiophene group, a benzimidazole group, or a benzoxazole group is unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group or a heteroaryl group.
  • Ar3 is a phenyl group, a biphenyl group, a naphthyl group, a furan group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group
  • the phenyl group, a biphenyl group, a naphthyl group , a furan group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group is unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group.
  • Ar3 is a phenyl group, a biphenyl group, a naphthyl group, a furan group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group
  • the phenyl group, a biphenyl group, a naphthyl group , furan group, pyridine group, dibenzofuran group, dibenzothiophene group, or carbazole group is CN, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or 3 to carbon atoms It is unsubstituted or substituted with a heteroaryl group of 30.
  • Ar3 is a phenyl group unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group; a biphenyl group unsubstituted or substituted with CN, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group; naphthyl group; furan group; a pyridine group unsubstituted or substituted with an alkyl group; dibenzofuran group; dibenzothiophene group; or a carbazole group.
  • Ar3 is CN, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms phenyl group; a biphenyl group unsubstituted or substituted with CN, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms; naphthyl group; furan group; a pyridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; dibenzofuran group; dibenzothiophene group; or a carbazole group.
  • Ar3 is CN, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms phenyl group; CN, or a biphenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; naphthyl group; furan group; a pyridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; dibenzofuran group; dibenzothiophene group; or a carbazole group.
  • Ar3 is a phenyl group unsubstituted or substituted with CN, a methyl group, a terbutyl group, a methoxy group, a naphthyl group, or a carbazole group; CN, or a biphenyl group unsubstituted or substituted with a methyl group; naphthyl group; furan group; a pyridine group unsubstituted or substituted with a methyl group; dibenzofuran group; dibenzothiophene group; or a carbazole group.
  • L1-Ar2 in parentheses of Formula 1 are the same as each other.
  • L1-Ar2 in parentheses of Formula 1 are different from each other
  • Chemical Formula 1 may be represented by any one of the following structures.
  • 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 to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer of the organic material layer includes the compound described above.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.
  • 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 coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers or a larger number of organic material layers.
  • the organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers is represented by Formula 1 compounds may be included.
  • 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 above.
  • the organic material layer may include at least one of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and at least one of the layers is represented by Formula 1 compounds may be included.
  • the organic material layer includes a layer that simultaneously injects and transports electrons, and the layer that simultaneously injects and transports electrons includes the compound of Formula 1 above.
  • the organic material layer includes an electron injection layer, and the electron injection layer includes the compound of Formula 1 above.
  • the organic material layer includes an electron transport layer
  • the electron transport layer includes the compound of Formula 1 above.
  • the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate.
  • the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate in a weight ratio of 9:1 to 1:9.
  • the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate in a weight ratio of 6:4 to 4:6.
  • the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate in a weight ratio of 1:1.
  • 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 above.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.
  • the emission layer includes a host and a dopant, and may include an additional material.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 60:40.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2 , but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 2 , an organic material layer 3 , and a second electrode 4 are sequentially stacked on a substrate 1 .
  • the compound represented by Formula 1 may be included in the organic material layer 3 .
  • the compound represented by Formula 1 may preferably be included in the electron injection and transport layer 9 .
  • the organic light emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate.
  • a PVD physical vapor deposition
  • a hole injection layer a hole transport layer, a layer that transports and injects holes at the same time
  • a light emitting layer an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection.
  • an organic material layer including one or more selected layers it may be manufactured by depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto, and may have a single layer structure.
  • the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.
  • the anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer.
  • the hole injection material holes can be well injected from the anode at a low voltage.
  • the molecular orbital is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
  • the hole injection layer may have a thickness of 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.
  • the hole transport layer may serve to facilitate hole transport.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable.
  • Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the hole transport layer includes a compound represented by the following Chemical Formula HT-1, but is not limited thereto.
  • At least one of X'1 to X'6 is N, the rest are CH,
  • R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring is formed by bonding with an adjacent group.
  • X'1 to X'6 are N.
  • R309 to R314 are nitrile groups.
  • 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.
  • R315 to R317 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of a combination thereof, or a substituted or unsubstituted ring by combining with an adjacent group,
  • r315 is an integer of 1 to 5, and when r315 is 2 or more, 2 or more of R315 are the same as or different from each other,
  • r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same as or different from each other.
  • R317 is a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.
  • R317 is a carbazole group; phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.
  • R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R315 and R316 are the same as or different from each other, and are each independently a phenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.
  • Chemical Formula HT-2 is represented by the following compound.
  • An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron-blocking layer may be the aforementioned spiro compound or a material known in the art.
  • the light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compounds
  • compounds of the benzoxazole, benzthiazole and benzimidazole series Poly(p-phenylenevinylene) (PPV)-based polymers
  • spiro compounds polyfluorene, rubrene, and the like, but is not limited thereto.
  • Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the host includes a compound represented by the following Chemical Formula H-1, but is not limited thereto.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R201 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r201 is an integer of 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; divalent dibenzofuran group; or a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C6-C20 monocyclic to 4-ring heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted or substituted
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • R201 is hydrogen
  • Formula H-1 is represented by the following compound.
  • the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • the present invention is not limited thereto.
  • the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA),
  • a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.
  • T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • t5 and t6 are each an integer of 1 to 4,
  • t5 is 2 or more, the 2 or more T5 are the same as or different from each other,
  • t6 is 2 or more
  • the 2 or more T6 are the same as or different from each other.
  • T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or 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 each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a nitrile group or a linear or branched alkyl group having 1 to 30 carbon atoms; or 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 each independently hydrogen; isopropyl group; a phenyl group substituted with a nitrile group; or a phenyl group substituted with a methyl 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 a material known in the art may be used.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • 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 that the electron transport characteristics can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be
  • the electron injection layer may serve to facilitate electron injection.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.
  • the compound represented by Formula 1 may be prepared by, for example, a preparation method such as Scheme 1 or 2 or 3 below, and other compounds may be prepared similarly.
  • Z is a halogen group or -SO 3 C 4 F 9 , preferably Z is a chloro group, a bromo group, or -SO 3 C It is 4F9 .
  • Reaction Schemes 1 to 3 are Suzuki coupling reactions, which are preferably performed in the presence of a palladium catalyst and a base, and the reactor for Suzuki coupling reaction can be changed as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • E1-A (20 g, 69.9 mmol) and E1-B (48.8 g, 139.8 mmol) were placed in 400 ml of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (29 g, 209.8 mmol) was dissolved in 29 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (2.4 g, 2.1 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • E5-A (20 g, 50.1 mmol) and E5-B (17.5 g, 50.1 mmol) were placed in 400 ml of Diox, stirred and refluxed.
  • potassium triphosphate (31.9 g, 150.4 mmol) was dissolved in 32 ml of water, and after stirring sufficiently, dibenzylideneacetone palladium (0.9 g, 1.5 mmol) and tricyclohexylphosphine (0.8 g, 3 mmol) were added. was put in. After the reaction for 5 hours, the resulting solid was filtered after cooling to room temperature.
  • Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E10 was prepared in the same manner as in Preparation Example 1-5, except that each starting material was prepared as in the above reaction scheme.
  • Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E12 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.
  • Compound E13 was prepared in the same manner as in Preparation Example 1-5, except that each starting material was prepared as in the above reaction scheme.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following compound HI-A was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • a first hole transport layer and a second hole transport layer were formed by sequentially vacuum-depositing 50 ⁇ of the HAT compound and 60 ⁇ of the HT-A compound on the hole injection layer.
  • the following BH compound and BD compound were vacuum-deposited at a weight ratio of 25:1 to a thickness of 200 ⁇ on the second hole transport layer to form a light emitting layer.
  • the compound E1 prepared above and the compound LiQ below were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 350 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.9 ⁇ /sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 ⁇ /sec, and the deposition rate of aluminum was 2 ⁇ /sec, and the vacuum degree during deposition was By maintaining 1 * 10 -7 torr to 5 * 10 -5 torr, an organic light emitting device was manufactured.
  • An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compounds E2 to E13 of Table 1 were used instead of compound E1 of Example 1-1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-13 in Table 1 below were used instead of compound E1 of Example 1-1.
  • the compounds ET-1 to ET-13 are as follows.
  • the compound represented by Formula 1 according to the present specification may be used in an organic material layer capable of simultaneously performing electron injection and electron transport of the organic light emitting device.
  • the organic light emitting device including the compound of Formula 1 according to the present specification includes a compound in which Ar 1 is phenyl. It was confirmed that the organic light emitting device showed significantly superior characteristics in terms of efficiency and lifespan.
  • the organic light emitting device including the compound of Formula 1 according to the present specification is -L1 to naphthalene -Ar2 is more efficient than an organic light emitting device including a compound substituted at 1,2, 1,4, 1,7, 1,5, 2,7, 2,6, 1,6 It was confirmed that it showed remarkably excellent properties.
  • the organic light emitting device including the compound of Formula 1 according to the present specification is superior to the organic light emitting device including the compound in which Ar1 is anthracene. It was confirmed that the characteristics were remarkably excellent in terms of efficiency.

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  • Spectroscopy & Molecular Physics (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2022/002440 2021-02-19 2022-02-18 Composé et dispositif électroluminescent organique le comprenant WO2022177358A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07109451A (ja) * 1993-10-13 1995-04-25 Ricoh Co Ltd 電界発光素子
KR20050029712A (ko) * 2003-09-22 2005-03-28 히로세 엔지니어링 가부시키가이샤 발광 화합물 및 발광 소자
KR20070027522A (ko) * 2004-03-25 2007-03-09 호도가야 가가쿠 고교 가부시키가이샤 피리딜기로 치환된 옥사디아졸환 구조를 갖는 화합물 및유기 전계 발광 소자
CN101434602A (zh) * 2008-12-16 2009-05-20 淮海工学院 含有载流子传输基团的化合物及其制备方法
KR20210004849A (ko) * 2019-07-05 2021-01-13 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2974937C (fr) 2015-03-25 2023-09-05 National Cancer Center Agent therapeutique contre le cancer du canal choledoque

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07109451A (ja) * 1993-10-13 1995-04-25 Ricoh Co Ltd 電界発光素子
KR20050029712A (ko) * 2003-09-22 2005-03-28 히로세 엔지니어링 가부시키가이샤 발광 화합물 및 발광 소자
KR20070027522A (ko) * 2004-03-25 2007-03-09 호도가야 가가쿠 고교 가부시키가이샤 피리딜기로 치환된 옥사디아졸환 구조를 갖는 화합물 및유기 전계 발광 소자
CN101434602A (zh) * 2008-12-16 2009-05-20 淮海工学院 含有载流子传输基团的化合物及其制备方法
KR20210004849A (ko) * 2019-07-05 2021-01-13 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

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