Compound and organic light emitting device comprising same

Abstract

The present specification relates to a compound of Formula 1 and an organic light-emitting device containing the same.

Description

Technology Field

[0001] This specification relates to a compound and an organic light-emitting device containing the same. Background Technology

[0002] In this specification, an organic light-emitting device refers to a light-emitting device utilizing an organic semiconductor material, which requires the exchange of holes and / or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly classified into two types based on their operating principles as follows. The first is a light-emitting device in which excitons are formed in an organic layer by photons introduced into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are each transferred to different electrodes to be used as current sources (voltage sources). The second is a light-emitting device in which holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and the device operates based on the injected electrons and holes.

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron suppression layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, a wide viewing angle, and high contrast.

[0004] Materials used as organic layers in organic light-emitting diodes can be classified according to their function 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. Light-emitting materials are classified according to their emission color into blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials necessary to achieve better natural colors.

[0005] In addition, a host / dopant system can be used as a light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap and superior luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated from the host are transported to the dopant to emit high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0006] In order to fully exhibit the excellent characteristics of the aforementioned organic light-emitting diode, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, so the development of new materials is continuously required. Prior art literature

[0007] International Patent Publication No. 2017-126443 The problem to be solved

[0008] The present specification describes a compound and an organic light-emitting device containing the same. means of solving the problem

[0009] One embodiment of the present specification provides a compound of the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0014] Ar1 is the following chemical formula 2 or 3, and

[0015] [Chemical Formula 2]

[0016]

[0017] [Chemical Formula 3]

[0018]

[0019] In the above chemical formula 2,

[0020] X1 is N connected to NR, O, S, CR1R2, L1, or CR1 connected to L1, and

[0021] X2 to X5 are the same or different from each other and are each independently connected to N, CR3, or L1, and are C.

[0022] R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can combine with adjacent substituents to form a substituted or unsubstituted ring, and

[0023] However, X1 is NR, or at least one of X2 to X5 is N, and

[0024] X1 is N connected to L1, or CR1 connected to L1, or any one of X2 to X5 is C connected to L1, and

[0025] In the above chemical formula 3,

[0026] Y1 is O or S, and

[0027] Y2 and Y3 are equal to or different from each other, and each is independently N or CR4, and

[0028] Y4 to Y7 C that are the same or different from each other and each independently connected to N, CR5, or L1, and

[0029] Any one of Y4 to Y7 is C connected to L1, and

[0030] R4 and R5 are the same or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can bond with adjacent substituents to form a substituted or unsubstituted ring, and

[0031] Ar2 is the following chemical formula 4, and

[0032] [Chemical Formula 4]

[0033]

[0034] In the above chemical formula 4,

[0035] X6 to X11 are the same or different from each other and are each C that independently combines with N, CR6, or L2, and

[0036] Any one of X6 to X11 is C that combines with L2, and at least one of the remainder is N, and

[0037] R6 can be a deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can bond with adjacent substituents to form a substituted or unsubstituted ring.

[0038] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises the aforementioned compound. Effects of the invention

[0039] The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long lifespan characteristics can be obtained. Furthermore, when the compound of the present invention is included in the electron transport layer of an organic light-emitting device, the high intramolecular polarization results in a high electron transfer effect, thereby enabling the manufacture of an organic light-emitting device having long lifespan characteristics. Brief explanation of the drawing

[0040] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention. Specific details for implementing the invention

[0041] The present specification will be described in more detail below.

[0042] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0043] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0044] Examples of substituents in this specification are described below, but are not limited thereto.

[0045] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0046] In this specification, the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of 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 group, or substituted with a substituent in which two or more of the exemplified substituents are connected, or not having any substituents. For example, “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 it may be interpreted as a substituent in which two phenyl groups are connected.

[0047] Examples of the above substituents are described below, but are not limited thereto.

[0048] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0049] In the present specification, the silyl group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, etc. Specifically, the silyl group includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0050] In the present specification, the boron group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the boron group may be a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, etc., but is not limited thereto.

[0051] In the present specification, the alkyl group may be a straight chain or a branched chain, and while the number of carbon atoms is not particularly limited, it is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto.

[0052] In this specification, the amine group may be selected from the group consisting of -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group; and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group; 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., are included, but are not limited thereto.

[0053] In this specification, an N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.

[0054] In this specification, the N-aryl heteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group.

[0055] In this specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group.

[0056] In this specification, the alkyl groups among the alkylamine groups, N-arylalkylamine groups, alkylthioxy groups, alkyl sulfoxy groups, and N-alkylheteroarylamine groups are the same as the examples of alkyl groups described above. Specifically, alkylthioxy groups include methylthioxy groups; ethylthioxy groups; tert-butylthioxy groups; hexylthioxy groups; octylthioxy groups, etc., and alkyl sulfoxy groups include methyl sulfoxy groups; ethyl sulfoxy groups; propyl sulfoxy groups; butyl sulfoxy groups, etc., but are not limited thereto.

[0057] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included but are not limited thereto.

[0058] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the 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.

[0059] In the present specification, the heteroaryl group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. Examples of heteroaryl groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, etc.

[0060] In this specification, the arylene group is as defined in the aryl group, except that it is a divalent group.

[0061] In this specification, the heteroarylene group is as defined in the heteroaryl group, except that it is a divalent group.

[0062] In the present specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6.

[0063] [Chemical Formula 1-1]

[0064]

[0065] [Chemical Formula 1-2]

[0066]

[0067] [Chemical Formula 1-3]

[0068]

[0069] [Chemical Formula 1-4]

[0070]

[0071] [Chemical Formula 1-5]

[0072]

[0073] [Chemical Formula 1-6]

[0074]

[0075] In the above chemical formulas 1-1 to 1-6, L1, L2, Ar1, and Ar2 are as defined in chemical formula 1.

[0076] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0077] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0078] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0079] According to one embodiment of the present specification, L1 and L2 are the same 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.

[0080] According to one embodiment of the present specification, L1 and L2 are the same 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.

[0081] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and each independently, directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent phenanthrene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted It is a divalent benzimidazole group, or a substituted or unsubstituted divalent benzoxazole group.

[0082] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted divalent benzoxazole group.

[0083] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, or a substituted or unsubstituted divalent terphenyl group.

[0084] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted divalent benzoxazole group.

[0085] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a substituted or unsubstituted divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent pyrene group, a divalent carbazole group, a divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a divalent dibenzofuran group, a dibenzothiophen group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.

[0086] According to one embodiment of the present specification, L1 and L2 are the same 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 carbazole group, a divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a divalent dibenzofuran group, a divalent dibenzothiophen group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.

[0087] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, or a divalent terphenyl group.

[0088] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond, a divalent carbazole group, a divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a divalent dibenzofuran group, a divalent dibenzothiophene group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.

[0089] According to one embodiment of the present specification, L1 and L2 are directly coupled.

[0090] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a phenylene group, a substituted or unsubstituted divalent naphthyl group, a divalent biphenyl group, or a divalent terphenyl group.

[0091] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a divalent carbazole group, a divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a divalent dibenzofuran group, a divalent dibenzothiophen group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.

[0092] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently phenylene groups.

[0093] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently divalent naphthyl groups.

[0094] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently divalent biphenyl groups.

[0095] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently divalent terphenyl groups.

[0096] According to one embodiment of the present specification, L1 is a direct connection.

[0097] According to one embodiment of the present specification, L1 is a phenylene group.

[0098] According to one embodiment of the present specification, L1 is a divalent naphthyl group.

[0099] According to one embodiment of the present specification, L1 is a divalent biphenyl group.

[0100] According to one embodiment of the present specification, L1 is a divalent terphenyl group.

[0101] According to one embodiment of the present specification, L2 is a direct coupling.

[0102] According to one embodiment of the present specification, L2 is a phenylene group.

[0103] According to one embodiment of the present specification, L2 is a divalent naphthyl group.

[0104] According to one embodiment of the present specification, L2 is a divalent biphenyl group.

[0105] According to one embodiment of the present specification, L2 is a divalent terphenyl group.

[0106] According to one embodiment of the present specification, X1 is NR.

[0107] According to one embodiment of the present specification, X1 is O.

[0108] According to one embodiment of the present specification, X1 is S.

[0109] According to one embodiment of the present specification, X1 is CR1R2.

[0110] According to one embodiment of the present specification, X1 is CR1 combined with L.

[0111] According to one embodiment of the present specification, X2 is N.

[0112] According to one embodiment of the present specification, X3 is N.

[0113] According to one embodiment of the present specification, X4 is N.

[0114] According to one embodiment of the present specification, X5 is N.

[0115] According to one embodiment of the present specification, X2 is CR3.

[0116] According to one embodiment of the present specification, X3 is CR3.

[0117] According to one embodiment of the present specification, X4 is CR3.

[0118] According to one embodiment of the present specification, X5 is CR3.

[0119] According to one embodiment of the present specification, X2 is C combined with L.

[0120] According to one embodiment of the present specification, X3 is C combined with L.

[0121] According to one embodiment of the present specification, X4 is C combined with L.

[0122] According to one embodiment of the present specification, X5 is C combined with L.

[0123] According to one embodiment of the present specification, X1 is O, any one of X2 to X5 is N, and the remainder is CR3.

[0124] According to one embodiment of the present specification, X1 is O, any two of X2 to X5 are N, and the remainder is CR3.

[0125] According to one embodiment of the present specification, X1 is O, any three of X2 to X5 are N, and the remainder is CR3.

[0126] According to one embodiment of the present specification, X1 is O, and X2 to X5 are N.

[0127] According to one embodiment of the present specification, X1 is S, any one of X2 to X5 is N, and the remainder is CR3.

[0128] According to one embodiment of the present specification, X1 is S, any two of X2 to X5 are N, and the remainder is CR3.

[0129] According to one embodiment of the present specification, X1 is S, any three of X2 to X5 are N, and the remainder is CR3.

[0130] According to one embodiment of the present specification, X1 is S, and X2 to X5 are N.

[0131] According to one embodiment of the present specification, X1 is CR1R2, any one of X2 to X5 is N, and the remainder is CR3.

[0132] According to one embodiment of the present specification, X1 is CR1R2, any two of X2 to X5 are N, and the remainder is CR3.

[0133] According to one embodiment of the present specification, X1 is CR1R2, any three of X2 to X5 are N, and the remainder is CR3.

[0134] According to one embodiment of the present specification, X1 is CR1 combined with L, and X2 to X5 are N.

[0135] According to one embodiment of the present specification, X1 is NR, any one of X2 to X5 is N, and the remainder is CR3.

[0136] According to one embodiment of the present specification, X1 is NR, any two of X2 to X5 are N, and the remainder is CR3.

[0137] According to one embodiment of the present specification, X1 is NR, any three of X2 to X5 are N, and the remainder is CR3.

[0138] According to one embodiment of the present specification, X1 is NR, and X2 to X5 are CR3.

[0139] According to one embodiment of the present specification, X1 is N or CR1 combined with L.

[0140] According to one embodiment of the present specification, X2 and X3 are CR3, and adjacent R3s are bonded to each other to form a ring substituted with or unsubstituted alkyl groups or unsubstituted aryl groups.

[0141] According to one embodiment of the present specification, X3 and X4 are CR3, and adjacent R3s are bonded to each other to form a ring substituted with or unsubstituted alkyl groups or unsubstituted aryl groups.

[0142] According to one embodiment of the present specification, X4 and X5 are CR3, and adjacent R3s are bonded to each other to form a ring substituted with or unsubstituted alkyl groups or unsubstituted aryl groups.

[0143] According to one embodiment of the present specification, at least one of X2 to X5 is N.

[0144] According to one embodiment of the present specification, Y1 is O.

[0145] According to one embodiment of the present specification, Y1 is S.

[0146] According to one embodiment of the present specification, Y2 is N.

[0147] According to one embodiment of the present specification, Y2 is CR4.

[0148] According to one embodiment of the present specification, Y3 is N.

[0149] According to one embodiment of the present specification, Y3 is CR4.

[0150] According to one embodiment of the present specification, Y2 and Y3 are N.

[0151] According to one embodiment of the present specification, Y2 and Y3 are CR4.

[0152] According to one embodiment of the present specification, Y2 is N and Y3 is CR4.

[0153] According to one embodiment of the present specification, Y3 is N and Y2 is CR4.

[0154] According to one embodiment of the present specification, at least one of Y2 to Y7 is N.

[0155] According to one embodiment of the present specification, three of the Y4 to Y7 are CR5, and the remaining one is C that combines with L.

[0156] According to one embodiment of the present specification, three of the Y4 to Y7 are N, and the remaining one is C combined with L.

[0157] According to one embodiment of the present specification, Y4 is C connected to L1.

[0158] According to one embodiment of the present specification, Y5 is C connected to L1.

[0159] According to one embodiment of the present specification, Y6 is C connected to L1.

[0160] According to one embodiment of the present specification, Y7 is C connected to L1.

[0161] According to one embodiment of the present specification, Ar1 is any one of the following structural formulas, and the following structural formulas are substituted or unsubstituted.

[0162]

[0163] According to one embodiment of the present specification, R and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, an unsubstituted alkyl group, or an unsubstituted aryl group, or are bonded to adjacent substituents to form a ring substituted with or unsubstituted alkyl groups or unsubstituted aryl groups.

[0164] According to one embodiment of the present specification, R and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, or anthracene group; and are combined with adjacent substituents to form a ring substituted or unsubstituted with a methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, or anthracene group.

[0165] According to one embodiment of the present specification, R and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, or naphthyl group; and are combined with adjacent substituents to form an aromatic hydrocarbon ring substituted or unsubstituted with a methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, or naphthyl group.

[0166] According to one embodiment of the present specification, R and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, or naphthyl group; and are combined with adjacent substituents to form a benzene ring substituted or unsubstituted with a methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, or naphthyl group.

[0167] According to one embodiment of the present specification, R and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, or naphthyl group; and are combined with adjacent substituents to form a naphthalene ring substituted or unsubstituted with a methyl group, ethyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, or naphthyl group.

[0168] According to one embodiment of the present specification, Ar1 is a benzimidazole group substituted or unsubstituted with an alkyl or aryl group, an imidazole group substituted or unsubstituted with an alkyl or aryl group, a benzoxazole group substituted or unsubstituted with an alkyl or aryl group, an oxadiazole group substituted or unsubstituted with an alkyl or aryl group, or a benzothiazole group substituted or unsubstituted with an alkyl or aryl group.

[0169] According to one embodiment of the present specification, Ar1 is a benzimidazole group, an imidazole group, a benzoxazole group, an oxadiazole group, or a benzothiazole group, and

[0170] The above benzimidazole group, imidazole group, benzoxazole group, oxadiazole group, or benzothiazole group is substituted or unsubstituted with a methyl group, ethyl group, propyl group, isopropyl group, terbutyl group, phenyl group, biphenyl group, naphthyl group, or terphenyl group.

[0171] According to one embodiment of the present specification, the Ar1 is any one of the following structures.

[0172]

[0173] According to one embodiment of the present specification, any one of X6 to X11 is C that is coupled to L2, at least one of the remainder is N, and the remainder is CR6.

[0174] According to one embodiment of the present specification, any one of X6 to X11 is C that is coupled to L2, at least two of the remainder are N, and the remainder is CR6.

[0175] According to one embodiment of the present specification, any one of X6 to X11 is C that is coupled to L2, at least three of the remainder are N, and the remainder is CR6.

[0176] According to one embodiment of the present specification, among X6 to X11, X6 is N, one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0177] According to one embodiment of the present specification, among X6 to X11, X7 is N, one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0178] According to one embodiment of the present specification, among X6 to X11, X8 is N, one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0179] According to one embodiment of the present specification, among X6 to X11, X9 is N, any one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0180] According to one embodiment of the present specification, among X6 to X11, X10 is N, one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0181] According to one embodiment of the present specification, among X6 to X11, X11 is N, any one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0182] According to one embodiment of the present specification, among X6 to X11, X6 and X8 are N, one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0183] According to one embodiment of the present specification, among X6 to X11, X6 and X7 are N, one of the remainder is C that combines with L2, and the remainder is CR6.

[0184] According to one embodiment of the present specification, among X6 to X11, X6 and X9 are N, one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0185] According to one embodiment of the present specification, among X6 to X11, X6, X8, and X10 are N, any one of the remainder is C that is coupled to L2, and the remainder is CR6.

[0186] According to one embodiment of the present specification, the R6 may be a deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or may be bonded to an adjacent substituent to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

[0187] According to one embodiment of the present specification, the R6 may be a deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms, or may bond with an adjacent substituent to form a ring having 6 to 20 carbon atoms.

[0188] According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group.

[0189] According to one embodiment of the present specification, Ar2 is a pyridine group substituted or unsubstituted with an aryl group, a pyrimidine group substituted or unsubstituted with an aryl group, or a triazine group substituted or unsubstituted with an aryl group.

[0190] According to one embodiment of the present specification, the Ar2 is a pyridine group, a pyrimidine group, or a triazine group, and the pyridine group, pyrimidine group, or triazine group is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

[0191] According to one embodiment of the present specification, the Ar2 is a pyridine group, a pyrimidine group, or a triazine group, and the pyridine group, pyrimidine group, or triazine group is substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0192] According to one embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.

[0193]

[0194]

[0195]

[0196] The substituents of the compound of Chemical Formula 1 above may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0197] In addition, by introducing various substituents into a core structure having the structure described above, compounds possessing the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0198] In addition, the organic light-emitting device according to the present invention comprises a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the aforementioned compound.

[0199] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0200] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0201] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure comprising, as an organic layer, a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, a light-emitting layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0202] In the organic light-emitting device of the present invention, the organic layer may include one or more layers among an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more layers among the layers may include a compound represented by the chemical formula 1.

[0203] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the chemical formula 1.

[0204] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises a compound of Formula 1 and a metal complex.

[0205] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises the compound of Formula 1 and lithium quinolate.

[0206] In the organic light-emitting device of the present invention, the electron injection and transport layer may include a compound of Formula 1 and a metal complex in a weight ratio of 1:10 to 10:1.

[0207] In the organic light-emitting device of the present invention, the electron injection and transport layer may include a compound of Formula 1 and a metal complex in a weight ratio of 1:5 to 5:1.

[0208] In the organic light-emitting device of the present invention, the electron injection and transport layer may include a compound of Formula 1 and a metal complex in a weight ratio of 1:3 to 3:1.

[0209] In the organic light-emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate in a weight ratio of 1:10 to 10:1.

[0210] In the organic light-emitting device of the present invention, 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.

[0211] In the organic light-emitting device of the present invention, 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.

[0212] In the organic light-emitting device of the present invention, the organic layer comprises a hole-blocking layer, and the hole-blocking layer comprises a compound of Formula 1.

[0213] In the organic light-emitting device of the present invention, the organic layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs hole injection and hole transport simultaneously, and one or more layers among the layers may include a compound represented by the chemical formula 1.

[0214] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1.

[0215] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0216] According to another embodiment, the first electrode is a negative electrode and the second electrode is a positive electrode.

[0217] (1) Anode / hole transport layer / emissive layer / cathode

[0218] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0219] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0220] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0221] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0222] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0223] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0224] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0225] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0226] (10) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0227] (11) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0228] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0229] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0230] (14) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0231] (15) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0232] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0233] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0234] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / hole blocking layer / electron injection and transport layer / cathode

[0235] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

[0236] FIG. 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially stacked on a substrate (1). In such a structure, a compound represented by the chemical formula 1 may be included in the organic layer (3).

[0237] For example, an organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer comprising one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a layer that performs hole transport and hole injection simultaneously, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that performs electron transport and electron injection simultaneously, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0238] The above organic 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. In addition, the above organic layer may be manufactured with fewer layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0239] The above-mentioned anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0240] The above-mentioned cathode is an electrode for injecting electrons, and as the cathode material, it is preferable to have a material with a low work function to facilitate electron injection, typically an 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; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0241] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is a material capable of receiving holes well from the anode at low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, there is an advantage of preventing the driving voltage from rising to improve the movement of holes because the thickness of the hole injection layer is too thick.

[0242] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0243] [Chemical Formula HI-1]

[0244]

[0245] In the above chemical formula HI-1,

[0246] L301 to L303 are the same or different from each other, and each is independently a directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0247] R301 to R303 are the same or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0248] According to one embodiment of the present specification, R301 to R303 are the same or different from one another and are selected from the group consisting of an independently substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0249] According to one embodiment of the present specification, R301 to R303 are the same or different from one another and are each independently selected from the group consisting of a substituted or unsubstituted carbazole group; a substituted or unsubstituted phenyl group; a biphenyl group; and combinations thereof.

[0250] According to one embodiment of the present specification, L301 to L303 are the same or different from one another and are each independently a direct bond; an arylene group; or a heteroarylene group.

[0251] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0252]

[0253] The hole transport layer described above can play a role in facilitating the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0254] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0255] [Chemical Formula HT-2]

[0256]

[0257] In the above chemical formula HT-2,

[0258] R315 to R317 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0259] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0260] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0261] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0262] According to one embodiment of the present specification, the R317 is any one selected from the group consisting of a substituted or unsubstituted carbazole group; a substituted or unsubstituted phenyl group; a biphenyl group; and combinations thereof.

[0263] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0264]

[0265] A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0266] An electron suppression layer may be provided between the hole transport layer and the light-emitting layer. The electron suppression layer may use the aforementioned spiro compound or a material known in the art.

[0267] The above-mentioned light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible light region 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, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene groups, rubrene, etc.

[0268] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0269] According to one embodiment of the present specification, the host comprises a compound represented by the following chemical formula H-1, but is not limited thereto.

[0270] [Chemical Formula H-1]

[0271]

[0272] In the above chemical formula H-1,

[0273] L20 and L21 are identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, and

[0274] Ar20 and Ar21 are identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0275] R2O1 is hydrogen; deuterium; a 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, and

[0276] r201 is an integer from 1 to 8, and if r201 is 2 or more, the 2 or more R201s are the same or different from each other.

[0277] In one embodiment of the present specification, L20 and L21 are identical or different from each other and are each independently directly bonded; 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.

[0278] In one embodiment of the present specification, L20 and L21 are identical or different from each other and are each independently directly bonded; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a dibenzofuran group; or a dibenzothiophene group.

[0279] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.

[0280] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and 4 rings; or substituted or unsubstituted heterocyclic groups having 6 to 20 carbon atoms and 4 rings.

[0281] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and each independently comprises: a phenyl group substituted or unsubstituted with a deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with a deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. Or it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0282] In one embodiment of the present specification, the Ar20 and Ar21 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophen group; or a naphthobenzothiophen group.

[0283] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0284] According to one embodiment of the present specification, R201 is hydrogen.

[0285] According to one embodiment of the present specification, the formula H-1 is represented by the following compound.

[0286]

[0287] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0288] According to one embodiment of the present specification, the dopant comprises a compound represented by the following chemical formula D-1, but is not limited thereto.

[0289] [Chemical Formula D-1]

[0290]

[0291] In the above chemical formula D-1,

[0292] T1 to T6 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0293] t5 and t6 are integers from 1 to 4, respectively, and

[0294] If the above t5 is 2 or more, the above 2 or more T5s are the same or different from each other, and

[0295] If the above t6 is 2 or more, the above 2 or more T6s are the same or different from each other.

[0296] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; 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.

[0297] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0298] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a phenyl group; a phenyl group substituted with a halogen group; or a phenyl group substituted with deuterium.

[0299] According to one embodiment of the present specification, the formula D-1 is represented by the following compound.

[0300]

[0301] A hole suppression layer may be provided between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0302] The electron transport layer described above can facilitate the transport of electrons. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility, is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the deterioration of electron transport characteristics, and if it is 50 nm or less, there is an advantage in preventing the driving voltage from rising to improve electron transport due to the electron transport layer being too thick.

[0303] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0304] The above 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, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited to these.

[0305]

[0306] The hole blocking layer described above is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc. are used, but are not limited thereto.

[0307] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0308] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0309] The method for preparing the compound of Chemical Formula 1 above and the preparation of an organic light-emitting device using them will be specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0310] In the following reaction scheme, various types of intermediates can be synthesized by appropriately selecting known starting materials regarding the types and number of substituents. The types and conditions of the reaction and reaction conditions known in the art may be utilized.

[0311] [Reaction Equation 1]

[0312]

[0313] In the above reaction scheme 1, the remaining definitions excluding Y are as previously defined, and Y is a halogen group, preferably a bromo group or a chloro group.

[0314] The above reaction is a carbon substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the carbon substitution reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples described below.

[0315] By appropriately combining the manufacturing formulas described in the embodiments of this specification and the intermediates based on common technical knowledge, all of the compounds of Formula 1 described in this specification can be produced.

[0316] [Synthetic Example]

[0317] Synthesis Example 1: Preparation of Compound E1

[0318]

[0319] Under a nitrogen atmosphere, E1-A (20 g, 57.7 mmol) and E1-B (25.1 g, 57.7 mmol) were added to 400 ml of Diox and stirred and refluxed. Subsequently, tripotassium phosphate (36.7 g, 173 mmol) dissolved in 37 ml of water was added and stirred thoroughly, after which dibenzylideneacetone palladium (1 g, 1.7 mmol) and tricyclohexylphosphine (1 g, 3.5 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1072 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was used to prepare the yellow solid compound E1 (5.4 g, 15%) through recrystallization with chloroform and ethyl acetate.

[0320] MS: [M+H] + = 620

[0321] Synthesis Example 2: Preparation of Compound E2

[0322]

[0323] Compound E2 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the above reaction scheme.

[0324] MS: [M+H] + = 646

[0325] Synthesis Example 3: Preparation of Compound E3

[0326]

[0327] Compound E3 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0328] MS: [M+H] + = 631

[0329] Synthesis Example 4: Preparation of Compound E4

[0330]

[0331] Compound E4 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the above reaction scheme.

[0332] MS: [M+H] + = 604

[0333] Synthesis Example 5: Preparation of Compound E5

[0334]

[0335] Compound E5 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0336] MS: [M+H] + = 654

[0337] Synthesis Example 6: Preparation of Compound E6

[0338]

[0339] Compound E6 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0340] MS: [M+H] + = 706

[0341] Synthesis Example 7: Preparation of Compound E7

[0342]

[0343] Compound E7 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0344] MS: [M+H] + = 604

[0345] Synthesis Example 8: Preparation of Compound E8

[0346]

[0347] Compound E8 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0348] MS: [M+H] + = 707

[0349] Synthesis Example 9: Preparation of Compound E9

[0350]

[0351] Compound E9 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0352] MS: [M+H] + = 679

[0353] Synthesis Example 10: Preparation of Compound E10

[0354]

[0355] Compound E10 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0356] MS: [M+H] + = 654

[0357] Synthesis Example 11: Preparation of Compound E11

[0358]

[0359] Compound E11 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0360] MS: [M+H] + = 680

[0361] Synthesis Example 12: Preparation of Compound E12

[0362]

[0363] Compound E12 was prepared using the same method as the preparation method of Synthesis Example 1, except that each starting material was prepared as per the reaction scheme above.

[0364] MS: [M+H] + = 705

[0365] [Experimental Example]

[0366] Experimental Example 1

[0367] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0368] A hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å on the ITO transparent electrode prepared in this way. A hole transport layer was formed by sequentially vacuum depositing hexaazatriphenylene (HAT, 50 Å) of the following chemical formula and the following compound HT-A (600 Å) on the hole injection layer.

[0369] Next, a light-emitting layer was formed by vacuum depositing the following compounds BH and BD in a weight ratio of 25:1 on the hole transport layer with a film thickness of 200 Å.

[0370] On the above-mentioned light-emitting layer, compound E1 prepared in Synthesis Example 1 and the following compound [LiQ] (Lithium quinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron transport and injection layer with a thickness of 360 Å. On the above-mentioned electron transport and injection layer, lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1,000 Å were sequentially deposited to form a cathode.

[0371]

[0372] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, while the deposition rates for lithium fluoride and aluminum at the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 1 × 10⁻⁶ -7 ~ 5 × 10 -8 An organic light-emitting diode was fabricated by maintaining torr.

[0373] Experimental Examples 2 to 12

[0374] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1, except that the compound of Table 1 below was used instead of compound E1 of Experimental Example 1.

[0375] Comparative Experiment Examples 1 to 16

[0376] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1, except that the compounds in Table 1 below were used instead of compound E1 of Experimental Example 1. The compounds ET-1 to ET-16 used in Table 1 below are as follows.

[0377]

[0378] For the organic light-emitting diodes prepared in the above experimental and comparative experimental examples, 10 mA / cm 2 The driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA / cm². 2 The time (T) when the brightness reaches 90% of the initial brightness at the current density 90) was measured. The results are shown in Table 1 below.

[0379] Compound (electron transport and injection layer) Voltage (V@10mA / cm²) 2 ) Efficiency (cd / A @ 10mA / cm²) 2 ) Color coordinates (x,y) T 90 (hr@20mA / cm 2 ) Experimental Example 1 E1 3.95 4.31 (0.136, 0.112) 191 Experimental Example 2 E2 4.07 4.40 (0.136, 0.111) 160 Experimental Example 3 E3 3.91 4.42 (0.136, 0.112) 174 Experimental Example 4 E4 3.87 4.44 (0.136, 0.111) 170 Experimental Example 5 E5 3.95 4.28 (0.136, 0.111) 214 Experimental Example 6 E6 4.11 4.23 (0.136, 0.111) 227 Experimental Example 7 E7 3.79 4.48 (0.136, 0.112) 151 Experimental Example 8 E8 3.94 4.55 (0.136, 0.111) 137 Experimental Example 9 E9 3.86 4.50 (0.136, 0.112) 158 Experimental Example 10 E10 3.94 4.44 (0.136, 0.111) 164 Experimental Example 11 E11 4.22 4.21 (0.136, 0.111) 238 Experimental Example 12 E12 4.51 4.00 (0.136, 0.111) 345 Comparative Experiment Example 1 ET-1 4.03 2.72 (0.136, 0.111) 46 Comparative Experiment Example 2 ET-2 4.15 2.77 (0.136, 0.111) 39 Comparative Experiment Example 3 ET-3 3.99 2.79 (0.136, 0.112) 42 Comparative Experiment Example 4 ET-4 3.95 2.80 (0.136, 0.111) 41 Comparative Experiment Example 5 ET-5 4.03 2.69 (0.136, 0.112) 51 Comparative Experiment Example 6 ET-6 4.19 2.67 (0.136, 0.111) 54 Comparative Experiment Example 7 ET-7 3.87 2.82 (0.136, 0.111) 36 Comparative Experiment Example 8 ET-8 4.02 2.86 (0.136, 0.111) 33 Comparative Experiment Example 9 ET-9 3.94 2.83 (0.136, 0.112) 38 Comparative Experiment Example 10 ET-10 4.02 2.80 (0.136, 0.111) 39 Comparative Experiment Example 11 ET-11 4.30 2.66 (0.136, 0.112) 57 Comparative Experiment Example 12 ET-12 4.60 2.52 (0.136, 0.111) 83 Comparative Experiment Example 13 ET-13 4.42 2.62 (0.136, 0.111) 72 Comparative Experiment Example 14 ET-14 4.68 2.57 (0.136, 0.111) 108 Comparative Experiment Example 15 ET-15 4.59 2.52 (0.136, 0.112) 130 Comparative Experiment Example 16 ET-16 4.55 2.60 (0.136, 0.111) 142

[0380] As described in Table 1 above, for an organic light-emitting diode using a compound represented by Formula 1 of the present invention, voltage, efficiency, and / or lifetime (T 90 It was confirmed that it exhibits excellent characteristics in ).

[0381] Specifically, the compound represented by Chemical Formula 1 of the present invention is characterized by having an N-containing ring group represented by Chemical Formula 2 connected to a benzene ring containing a cyano group through a linker, and the two N-containing ring groups in the molecule increase electron mobility, thereby increasing the efficiency of the organic light-emitting device, and the inclusion of one cyano group in the molecule controls electron injection characteristics, thereby increasing the lifespan of the organic light-emitting device.

[0382] When comparing Experimental Examples 1 to 12 and Comparative Experimental Examples 1 to 13 in Table 1 above, it was confirmed that the organic light-emitting device containing the compound of Formula 1 of the present invention has a structure containing a benzene ring substituted with a cyano group, and thus exhibits significantly superior characteristics in terms of efficiency and lifespan compared to an organic light-emitting device using a compound that does not contain a cyano group.

[0383] When comparing Experimental Examples 1 to 12 and Comparative Experimental Examples 14 to 16 of Table 1 above, it was confirmed that the organic light-emitting device containing the compound of Formula 1 of the present invention exhibits significantly superior characteristics in terms of efficiency compared to organic light-emitting devices using compounds substituted with carbazole and benzonaphthofuran compounds. Explanation of the symbols

[0384] 1: Substrate 2: Anode 3: Organic layer 4: Cathode 5: Hole injection layer 6: Precision Transport Layer 7: Emissive layer 8: Electron injection and transport layer

Claims

Claim 1 Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above Chemical Formula 1, L1 and L2 are the same or different from each other and each independently are a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and Ar1 is the following Chemical Formula 2 or 3, [Chemical Formula 2] [Chemical Formula 3] In the above formula 2, X1 is NR, O, S, N connected to CR1R2 or L1, or CR1 connected to L1; X2 to X5 are the same or different from each other and are each independently C connected to N, CR3, or L1; R, R1, and R2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can form a substituted or unsubstituted ring by bonding with adjacent substituents; R3 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or an unsubstituted aryl group, or can form a substituted or unsubstituted ring by bonding with adjacent substituents, provided that X1 is NR, or at least one of X2 to X5 is N, X1 is N connected to L1 or CR1 connected to L1, or any one of X2 to X5 is C connected to L1; and in the above formula 3, Y1 is O or S, and Y2 and Y3 are each They are the same or different, each independently N or CR4, and Y4 to Y7 are C is the same or different from each other and is independently connected to N, CR5, or L1, any one of Y4 to Y7 is C connected to L1, R4 and R5 are the same or different from each other and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can bond with adjacent substituents to form a substituted or unsubstituted ring, and Ar2 is the following Chemical Formula 4, [Chemical Formula 4] In the above chemical formula 4, X6 to X11 are the same or different from each other and are each independently C bonded to N, CR6, or L2, any one of X6 to X11 is C bonded to L2, and at least one of the remainder is N, and R6 is deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can bond with adjacent substituents to form a substituted or unsubstituted ring. Claim 2 A compound according to claim 1, wherein L1 and L2 are the same or different from each other and each independently have a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms. Claim 3 A compound according to claim 1, wherein any one of X6 to X11 is C bonded to L2, at least one of the remainder is N, and the remainder is CR6. Claim 4 A compound according to claim 1, wherein at least one of X2 to X5 is N. Claim 5 A compound according to claim 1, wherein at least one of Y2 to Y7 is N. Claim 6 A compound according to claim 1, wherein R, R1, and R2 are the same or different from each other and each independently is hydrogen, deuterium, an unsubstituted alkyl group, or an unsubstituted aryl group, or is bonded to an adjacent substituent to form a ring substituted with or unsubstituted alkyl groups or unsubstituted aryl groups. Claim 7 A compound according to claim 1, wherein Ar1 is a benzimidazole group substituted or unsubstituted with an alkyl or aryl group, an imidazole group substituted or unsubstituted with an alkyl or aryl group, a benzoxazole group substituted or unsubstituted with an alkyl or aryl group, an oxadiazole group substituted or unsubstituted with an alkyl or aryl group, or a benzothiazole substituted or unsubstituted with an alkyl or aryl group. Claim 8 A compound according to claim 1, wherein Ar2 is a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group. Claim 9 A compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, L1, L2, Ar1, and Ar2 are as defined in chemical formula 1. Claim 10 A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: Claim 11 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 10. Claim 12 An organic light-emitting device according to claim 11, wherein the organic layer may comprise 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 comprises the compound.

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