WO2021020928A2

WO2021020928A2 - Polycyclic compound and organic light-emitting element comprising same

Info

Publication number: WO2021020928A2
Application number: PCT/KR2020/010123
Authority: WO
Inventors: 김명곤; 금수정; 김경희; 홍완표
Original assignee: 주식회사 엘지화학
Priority date: 2019-07-31
Filing date: 2020-07-31
Publication date: 2021-02-04
Also published as: WO2021020928A3

Abstract

The present specification relates to a polycyclic compound and an organic light-emitting element comprising same.

Description

Polycyclic compound and organic light-emitting device comprising the same

The present specification relates to a polycyclic compound and an organic light emitting device including the same.

This application is for Korean Patent Application No. 10-2019-0093157 filed with the Korean Intellectual Property Office on July 31, 2019, Korean Patent Application No. 10-2019-0156836 filed with the Korean Intellectual Property Office on November 29, 2019, and 2020. It claims the interest of the filing date of the Korean Patent Application No. 10-2020-0065269 filed with the Korean Intellectual Property Office on May 29, the entire contents of which are incorporated herein.

In the present specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires an exchange of holes and/or electrons between an electrode and an organic semiconductor material. The organic light emitting device can be divided into two types as follows according to the operating principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these 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 in which holes and/or electrons are injected into an organic semiconductor material layer that forms an interface with the electrode by applying voltage or current to two or more electrodes, and operates by the injected electrons and holes.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made 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, the organic material layer is composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. I can lose. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic light emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light-emitting device may be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, electron injection materials, and the like, according to their functions. The light-emitting material includes blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.

In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host that mainly constitutes the light emitting layer is mixed with the light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, electron injection materials, etc., are stable and efficient materials. As it is supported by, the development of new materials is continuously required.

[Prior Technical Literature] (Patent Literature 1) International Patent Publication No. 2017-126443

In the present specification, a compound and an organic light emitting device including the same are described.

The present specification provides a polycyclic compound represented by the following formula (100).

[Chemical Formula 100]

In Formula 100,

R1 and R301 are the same as or different from each other, and each independently deuterium; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

x101 is 1 or 2,

Cy3 and Cy4 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocycle, or a ring in which two or more rings selected from the group are fused,

R302 is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n1 is an integer of 1 to 3, n301 is an integer of 1 to 4, n302 is an integer of 0 to 10,

When n1, n301 and n302 are each 2 or more, the substituents in parentheses are the same as or different from each other,

At least one of Cy3 and Cy4 is one selected from Formulas A-1 to A-3,

In the formulas A-1 to A-3,

The dotted line is the position connected to Formula 100,

Q1 is O; S; Or C(R118)(R119),

R101 to R104, R118 and R119 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

x11 is 1 or 2,

n101 is an integer from 0 to 7, n102 is an integer from 0 to 11, n103 is an integer from 0 to 4, n104 is an integer from 0 to 5,

When n101 to n104 are each 2 or more, the substituents in parentheses are the same as or different from each other,

At least one of the aliphatic rings contained in Formula 100 is selected from the following structures,

In the above structure,

The dotted double line is the condensed position,

R105 to R114 are the same as or different from each other, and each independently, a substituted or unsubstituted alkyl group,

R115 to R117 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n115 is an integer of 0 to 2, n116 and n117 are each an integer of 0 to 4,

When n115 to n117 are each 2 or more, the substituents in parentheses are the same as or different from each other.

Further, according to an exemplary embodiment of the present invention, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned polycyclic compound.

The compound of the present invention can be used as a material for an organic material layer of an organic light emitting device. In the case of manufacturing an organic light emitting device including the compound of the present invention, an organic light emitting device having high efficiency, low voltage and long life characteristics can be obtained, and when the compound of the present invention is included in the light emitting layer of the organic light emitting device, a high color gamut is achieved. Eggplant can manufacture an organic light emitting device.

1 and 2 show an example of an organic light emitting device according to the present invention.

3 to 7 show systems of Examples 2-1 to 2-5, respectively.

8 and 9 show systems of Comparative Examples 2-1 and 2-2, respectively.

[Explanation of code]

1: substrate

2: anode

3: light emitting layer

4: cathode

5: first hole injection layer

6: second hole injection layer

7: hole transport layer

8: electron blocking layer

9: first electron transport layer

10: second electron transport layer

11: Electron injection layer

Hereinafter, the present specification will be described in more detail.

The present specification provides a compound represented by the following formula (100). When the compound represented by the following Chemical Formula 100 is used in the organic material layer of the organic light-emitting device, the efficiency and lifetime characteristics of the organic light-emitting device are improved. In particular, conventional compounds having a high sublimation temperature have low stability of the compound, resulting in a problem that the efficiency and life of the device decrease when applied to a device, but the compound represented by the following formula 100 is an aliphatic hydrocarbon ring substituted with an alkyl group in the molecule ( Specifically, by including a cycloalkene ring), it has a low sublimation temperature and thus has high stability, so that when applied to a device, a device having excellent efficiency and long life characteristics can be obtained.

In addition, the compound represented by the following formula (100) contains a cycloalkene ring in the molecule, so that the solubility is increased and thus can be applied to a solution process.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

In the present specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

Examples of the substituent in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the 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, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group (-CN); Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, "a substituent to 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 to which two phenyl groups are connected.

In the present specification, the connection of two or more substituents means that hydrogen of any one substituent is substituted with another substituent. For example, an isopropyl group and a phenyl group are connected

or

It may be a substituent of.

In the present specification, the connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are Includes connections. For example, two phenyl groups and isopropyl groups are connected

or

It may be a substituent of. The same applies to those in which four or more substituents are connected.

In the present specification, the dotted line means a site bonded or condensed to another substituent or bonding portion.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, 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 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, etc., but is not limited thereto. Does not.

In the present specification, 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 specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. 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. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 4 carbon atoms. Specific examples of the alkyl group 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.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; Alkylarylamine group; Arylamine group; Arylheteroarylamine group; It may be selected from the group consisting of an alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In the case of an arylamine group, the number of carbon atoms is 6 to 60. According to another exemplary embodiment, the arylamine group has 6 to 40 carbon atoms. Specific examples of the amine group include 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; N-biphenylfluorenylamine group; N-(4-(tert-butyl)phenyl)-N-phenylamine group; N,N-bis(4-(tert-butyl)phenyl)amine group; N,N-bis(3-(tert-butyl)phenyl)amine group, and the like, but are not limited thereto.

In the present specification, the alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group, the arylalkylamine group, the alkylthioxy group, the alkylsulfoxy group, and the alkylheteroarylamine group is the same as the example of the alkyl group described above. Specifically, the alkyl thioxy group is a methyl thioxy group; Ethyl thioxy group; tert-butyl thioxy group; Hexylthioxy group; Octylthioxy group and the like, and examples of the alkyl sulfoxy group include mesyl; Ethyl sulfoxy group; Propyl sulfoxy group; Butyl sulfoxy group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 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 cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Cychloroalkyl groups include monocyclic groups as well as bicyclic groups such as bridgeheads, fused rings, and spiro rings. 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.

In the present specification, cycloalkene is a cyclic group that has a double bond in a hydrocarbon ring, but is not aromatic, and the number of carbons is not particularly limited, but may be 3 to 60 carbon atoms, and according to an exemplary embodiment, 3 to May be 30. Cycloalkene includes not only monocyclic groups, but also bicyclic groups such as bridgehead, fused ring, and spiro. Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, and cyclohexene, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group 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. In the present specification, the substituted aryl group includes a form in which an aliphatic ring is condensed with an aryl group.

In the present specification, the alkylaryl group refers to an aryl group substituted with an alkyl group, and a substituent other than the alkyl group may be further connected.

In the present specification, the arylalkyl group refers to an alkyl group substituted with an aryl group, and a substituent other than the alkyl group may be further connected.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of 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 a hexa Hydrocarbazole group and the like, but are not limited to these. In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or condensed rings of aromatic and aliphatic, and may be selected from examples of the heterocyclic group.

In the present specification, the aromatic hydrocarbon ring refers to a hydrocarbon ring in which pi electrons are completely conjugated and planar, and the description of the aryl group may be applied except that it is divalent.

In the present specification, the aliphatic hydrocarbon ring is a structure bonded in a ring shape, and refers to a ring that is not aromatic. Examples of the aliphatic hydrocarbon ring include cycloalkyl or cycloalkane, and the description of the cycloalkyl group or cycloalkenyl group described above may be applied except for divalent. Further, the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring condensed with an aromatic ring.

In the present specification, the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring form a condensed ring.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other. In addition, substituent groups (total of 4) connected to two consecutive carbons in the aliphatic ring can also be interpreted as "adjacent" groups.

In the present specification, the meaning of "adjacent groups bonded to each other to form a ring" among substituents refers to a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups to each other; Or it means to form a substituted or unsubstituted heterocycle.

In the present specification, the condensed hydrocarbon ring may be monovalent or divalent. Specifically, when Cy3 and Cy4 are condensed hydrocarbon rings in the present formula, the condensed hydrocarbon ring corresponds to a monovalent group.

[Chemical Formula 100]

In an exemplary embodiment of the present specification, the aliphatic ring contained in Chemical Formula 100 is selected from the following structures.

In the above structure,

The dotted double line is the condensed position,

n115 is an integer of 0 to 2, n116 and n117 are each an integer of 0 to 4,

When n115 is 2, R115 is the same as or different from each other. When n116 is 2 or more, R116 is the same as or different from each other. When n117 is 2 or more, R117 is the same as or different from each other.

In the present specification, the aliphatic ring included in Formula 100 is 1) an aliphatic hydrocarbon ring formed by bonding of two R301s to each other, 2) a cyclopentene ring when x101 is 1, 3) a cyclopentene ring when x101 is 2 It means at least one of the hexene ring, 4) an aliphatic hydrocarbon ring included in Cy3, and 5) an aliphatic hydrocarbon ring included in Cy5.

In the exemplary embodiment of the present specification, R105 to R114 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R105 to R114 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, R105 to R114 are methyl groups.

In the exemplary embodiment of the present specification, R115 and R116 are the same as or different from each other, and each independently, hydrogen; Or deuterium.

In the exemplary embodiment of the present specification, R117 is hydrogen or deuterium, or four adjacent R117s combine with each other to form a substituted or unsubstituted benzene ring.

In the exemplary embodiment of the present specification, R117 is hydrogen or deuterium, or four adjacent R117s combine with each other to form a benzene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R117 is hydrogen or deuterium, or four adjacent R117s are bonded to each other to form a benzene ring.

In an exemplary embodiment of the present specification, all aliphatic rings included in Chemical Formula 100 are selected from the above structures,

In the exemplary embodiment of the present specification, R301 is the same as or different from each other, and each independently, deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, and two adjacent R301s are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In an exemplary embodiment of the present specification, R301 is deuterium; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 60 carbon atoms, and two adjacent R301s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R301 is deuterium; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 40 carbon atoms, and two adjacent R301s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R301 is deuterium; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Substituted or unsubstituted substituted or unsubstituted C6-C30 hetero with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group Cyclic group; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent to which two or more groups selected from the group are connected, and an aliphatic hydrocarbon ring having 5 or 6 carbon atoms is condensed or uncondensed, 6 carbon atoms Arylamine group of to 60; Or an arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group, and two adjacent R301s are An aliphatic hydrocarbon ring having 5 to 30 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms, or a substituent connected with two or more groups selected from the group. To form.

In an exemplary embodiment of the present specification, R301 is a methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Dimethylfluorenyl group; Dibenzofuran group; Dibenzothiophene group; A hexahydrocarbazole group unsubstituted or substituted with a methyl group, tert-butyl group, phenyl group, tolyl group, tert-butylphenyl group or tetramethyltetrahydronaphthalene group; A diphenylamine group substituted or unsubstituted with a methyl group or a tert-butyl group and condensed or non-condensed with a cyclohexene; N-phenyl-N-dibenzofuranamine group unsubstituted or substituted with a methyl group or a tert-butyl group; Or N-phenyl-N-dibenzothiophenamine group unsubstituted or substituted with a methyl group or a tert-butyl group.

In an exemplary embodiment of the present specification, R302 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, R302 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C10 alkyl group.

In an exemplary embodiment of the present specification, R302 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In an exemplary embodiment of the present specification, R302 is hydrogen; heavy hydrogen; Or a methyl group.

In an exemplary embodiment of the present specification, n302 is 2 or more, and two or four of the plurality of R302s are methyl groups.

In an exemplary embodiment of the present specification, Chemical Formula 100 is represented by any one of Chemical Formulas 1 to 3.

[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

R1, Cy3, Cy4 and n1 are as defined in Chemical Formula 100,

R3 and R4 are the same as or different from each other, and each independently, deuterium; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R2, R5, R6, and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n3 and n4 are each an integer of 1 to 4, n2, n5 and n6 are each an integer of 0 to 10, n8 is an integer of 0 to 8,

When n2 to n6 and n8 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocycle, or a ring in which two or more rings selected from the group are fused,

At least one of Cy3 and Cy4 is one selected from Formulas A-1 to A-3 below.

In the formulas A-1 to A-3,

The dotted line is the position connected to Formula 100,

Q1 is O; S; Or C(R118)(R119),

x11 is 1 or 2,

When n101 to n104 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest are substituted or unsubstituted aromatic hydrocarbon rings.

In the exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the remainder is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

In the exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest is a substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest is from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms. It is an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected substituents or a substituent to which two or more groups selected from the group are connected.

In the exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest are from the group consisting of deuterium, an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms. It is a monocyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with one or more selected substituents or a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest is substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an arylalkyl group having 7 to 50 carbon atoms. Or an unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, at least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the remainder is a phenyl group, a biphenyl group, or a terphenyl group, and the phenyl group, biphenyl group, or terphenyl group is a methyl group , Isopropyl group, tert-butyl group, or 2-phenylpropan-2-yl group (2-phenylpropan-2-yl) substituted or unsubstituted.

In the exemplary embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently, is selected from Formulas A-1 to A-3.

In the exemplary embodiment of the present specification, R118 and R119 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R118 and R119 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R118 and R119 are methyl groups.

In an exemplary embodiment of the present specification, R101 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R101 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R101 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In an exemplary embodiment of the present specification, R101 is hydrogen; heavy hydrogen; Or tert-butyl group.

In an exemplary embodiment of the present specification, R102 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or four adjacent R102 bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In an exemplary embodiment of the present specification, R102 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or four adjacent R 102 bonds to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R102 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or four adjacent R102s are bonded to each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, R102 is hydrogen; heavy hydrogen; Or it is a methyl group, or four adjacent R102 combine with each other to form a benzene ring.

In an exemplary embodiment of the present specification, n102 is 2 or more, and two or four of the plurality of R102s are methyl groups.

In the exemplary embodiment of the present specification, R103 and R104 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, adjacent two R103; Or two adjacent R104s are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In the exemplary embodiment of the present specification, R103 and R104 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or two adjacent R103; Or two adjacent R104s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R103 and R104 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or two adjacent R103; Or two adjacent R104s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the alkyl group or aryl group of R103 and R104 includes one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms; Alternatively, two or more groups selected from the group may be substituted with a linked substituent.

In the exemplary embodiment of the present specification, the alkyl group or aryl group of R103 and R104 may be substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 7 to 50 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, two adjacent R103; Or the aliphatic hydrocarbon ring formed by bonding of two adjacent R104s to each other is at least one substituent selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms; Alternatively, two or more groups selected from the group may be substituted with a linked substituent.

In the exemplary embodiment of the present specification, R103 and R104 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A C 1 to C 6 alkyl group unsubstituted or substituted with deuterium or a C 6 to C 20 aryl group; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms, or two adjacent R103; Or two adjacent R104s are bonded to each other to form an aliphatic hydrocarbon ring having 5 or 6 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R103 and R104 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group, or two adjacent R103; Alternatively, two adjacent R104s are bonded to each other to form a cyclopentene ring substituted or unsubstituted with a methyl group, or a cyclohexene ring unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, R103 is hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group.

In an exemplary embodiment of the present specification, R104 is hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group, or two adjacent R104s are bonded to each other to form a cyclopentene ring unsubstituted or substituted with a methyl group, or a cyclohexene ring unsubstituted or substituted with a methyl group.

When n101 is 2 or more. R101 is the same as or different from each other. When n102 is 2 or more, R102 is the same as or different from each other. When n103 is 2 or more. R103 is the same as or different from each other. When n104 is 2 or more, R104 is the same as or different from each other.

In the exemplary embodiment of the present specification, Cy3 and Cy4 are the same as or different from each other, and each independently, is selected from the following groups A-11 to A-14, and at least one of Cy3 and Cy4 is the following groups A-11 to A It is selected from -13.

[Group A-11]

[Group A-12]

[Group A-13]

[Group A-14]

In the above groups A-11 to A-14,

The dotted line is the position connected to Formula 100,

Q1 is O; S; Or C(R118)(R119),

R41 to R43, R46 to R50, R53 to R55, R118 and R119 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R45, R51 and R52 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

n41, n43 and n44 are each an integer of 0 to 7, n42, n49 and n50 are each an integer of 0 to 5,

When n41 to n44, n49 and n50 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, R41 may be applied to the description of R101 described above.

In an exemplary embodiment of the present specification, R41 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R41 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R41 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In an exemplary embodiment of the present specification, R41 is hydrogen; heavy hydrogen; Or tert-butyl group.

In the exemplary embodiment of the present specification, the description of R102 described above may be applied to R42 to R44.

In the exemplary embodiment of the present specification, R42 and R43 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R42 and R43 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R42 and R43 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In the exemplary embodiment of the present specification, R42 and R43 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a methyl group.

In an exemplary embodiment of the present specification, R44 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or four adjacent R44 bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In an exemplary embodiment of the present specification, R44 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or four adjacent R 44 bonds to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R44 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or four adjacent R44s are bonded to each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, R44 is hydrogen; heavy hydrogen; Or a methyl group, or four adjacent R44s are bonded to each other to form a benzene ring.

In one embodiment of the present specification, the descriptions of R103 and R104 described above may be applied to R45 to R49.

In the exemplary embodiment of the present specification, R46 to R50 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R46 to R50 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R46 to R50 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the alkyl group or aryl group of R46 to R50 is one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms; Alternatively, two or more groups selected from the group may be substituted with a linked substituent.

In the exemplary embodiment of the present specification, the alkyl group or aryl group of R46 to R50 may be substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 7 to 50 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, the aliphatic hydrocarbon ring formed by bonding of two adjacent R49 or two adjacent R50 to each other is at least one substituent selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms; Alternatively, two or more groups selected from the group may be substituted with a linked substituent.

In the exemplary embodiment of the present specification, R46 to R50 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A C 1 to C 6 alkyl group unsubstituted or substituted with deuterium or a C 6 to C 20 aryl group; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms, or two adjacent R49; Or two adjacent R50s are bonded to each other to form an aliphatic hydrocarbon ring having 5 or 6 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R46 to R50 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group, or two adjacent R49; Alternatively, two adjacent R50s are bonded to each other to form a cyclopentene ring unsubstituted or substituted with a methyl group or a cyclohexene ring unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, R45 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, R45 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C10 alkyl group.

In an exemplary embodiment of the present specification, R45 is hydrogen; heavy hydrogen; Or deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms, or an alkyl group having 1 to 10 carbon atoms substituted with a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, R45 is hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; Or 2-phenylpropan-2-yl group (2-phenylpropan-2-yl).

In the exemplary embodiment of the present specification, R51 and R52 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, R51 and R52 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C10 alkyl group.

In the exemplary embodiment of the present specification, R51 and R52 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms, or an alkyl group having 1 to 10 carbon atoms substituted with a substituent to which two or more groups selected from the group are connected.

In the exemplary embodiment of the present specification, R51 and R52 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; Or 2-phenylpropan-2-yl group (2-phenylpropan-2-yl).

In the exemplary embodiment of the present specification, the group A-12 is selected from the following group A-12-1.

[Group A-12-1]

In the above group A-12-1,

The definition of R42 to R44 is as defined in group A-12,

n421, n431 and n441 are each an integer of 0 to 3, and when n421, n431 and n441 are each 2 or more, the substituents in parentheses are the same or different from each other.

When n41 is 2 or more, R41 is the same as or different from each other. When n42 is 2 or more, R42 is the same as or different from each other. When n43 is 2 or more, R43 is the same as or different from each other. When n44 is 2 or more, R44 is the same as or different from each other. When n49 is 2 or more, R49 is the same as or different from each other. When n50 is 2 or more, R50 is the same as or different from each other.

In an exemplary embodiment of the present specification, R1 is deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group.

In an exemplary embodiment of the present specification, R1 is deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted heterocyclic group; Or -N(R211)(R212).

In an exemplary embodiment of the present specification, R1 is deuterium; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted N-containing heterocyclic group having 2 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 is deuterium; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted C 2 to C 20 N-containing heterocyclic group; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 40 carbon atoms.

In an exemplary embodiment of the present specification, R1 is deuterium; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted N-containing heterocyclic group having 2 to 30 carbon atoms; Or -N(R211)(R212).

In an exemplary embodiment of the present specification, R1 is deuterium; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted C 2 to C 20 N-containing heterocyclic group; Or -N(R211)(R212).

In an exemplary embodiment of the present specification, R1 is deuterium; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Deuterium, an N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent to which two or more groups selected from the group are connected, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or uncondensed, 6 carbon atoms Arylamine group of to 60; Or an arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group.

In an exemplary embodiment of the present specification, R1 is deuterium; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An N-containing heterocyclic group having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms; An arylamine group having 6 to 40 carbon atoms, unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms and condensed or uncondensed with an aliphatic hydrocarbon ring having 5 or 6 carbon atoms; Or an arylheteroarylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium.

In the exemplary embodiment of the present specification, R1 is a methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; A hexahydrocarbazole group unsubstituted or substituted with a methyl group, tert-butyl group, phenyl group, tolyl group, tert-butylphenyl group or tetramethyltetrahydronaphthalene group; A diphenylamine group in which a methyl group, an isopropyl group, or a tert-butyl group is substituted or unsubstituted, and a cyclopentene or cyclohexene is condensed or non-condensed; N-phenyl-N-dibenzofuranamine group; Or N-phenyl-N-dibenzothiophenamine group.

In the exemplary embodiment of the present specification, R211 and R212 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R211 and R212 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In the exemplary embodiment of the present specification, R211 and R212 are the same as or different from each other, each independently substituted or unsubstituted with deuterium or an alkyl group having 1 to 10 carbon atoms, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or non-condensed An aryl group having 6 to 30 carbon atoms; Or a C2 to C30 heterocyclic group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group.

In the exemplary embodiment of the present specification, R211 and R212 are the same as or different from each other, each independently substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms, and an aliphatic hydrocarbon ring having 5 or 6 carbon atoms is condensed or non-condensed An aryl group having 6 to 20 carbon atoms; Or it is a C6-C20 heterocyclic group substituted or unsubstituted with deuterium or a C1-C6 alkyl group.

In the exemplary embodiment of the present specification, R211 and R212 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, a methyl group, or a tert-butyl group; A tetrahydronaphthalene group unsubstituted or substituted with a methyl group; Dibenzofuran group; Or a dibenzothiophene group.

In the exemplary embodiment of the present specification, R1 is an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or uncondensed, 6 Arylamine group of to 60; Arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Or the following formula Het1.

[Chemical Formula Het1]

In the formula Het1,

The dotted line is the position connected to Chemical Formula 100,

R203 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group,

n205 is an integer from 0 to 12, and when n205 is 2 or more, R205 is the same as or different from each other.

In the exemplary embodiment of the present specification, R203 and R204 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, R203 and R204 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C10 alkyl group.

In the exemplary embodiment of the present specification, R203 and R204 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In an exemplary embodiment of the present specification, R203 and R204 are methyl groups.

In an exemplary embodiment of the present specification, R205 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R205 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R205 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or a substituent connected with two or more groups selected from the group.

In an exemplary embodiment of the present specification, R205 is hydrogen; heavy hydrogen; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or deuterium or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

The substituted aryl group of R205 also includes an aliphatic hydrocarbon ring condensed.

In an exemplary embodiment of the present specification, R205 is hydrogen; heavy hydrogen; Methyl group, tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Or a tetrahydronaphthalene group unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 60 carbon atoms.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 40 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 40 carbon atoms.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms; Or -N(R211)(R212).

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 20 carbon atoms; Or -N(R211)(R212).

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Substituted or unsubstituted substituted or unsubstituted C6-C30 hetero with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group Cyclic group; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent to which two or more groups selected from the group are connected, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or uncondensed, 6 carbon atoms Arylamine group of to 60; Or an arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, deuterium; A C 1 to C 6 alkyl group unsubstituted or substituted with deuterium or a C 6 to C 20 aryl group; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; A C6-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group, a C6-C20 aryl group, or a C7-C30 alkylaryl group; An arylamine group having 6 to 40 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; Or an arylheteroarylamine group having 2 to 40 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently, a methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Dimethylfluorenyl group; Dibenzofuran group; Dibenzothiophene group; A hexahydrocarbazole group unsubstituted or substituted with a methyl group, tert-butyl group, phenyl group, tolyl group, tert-butylphenyl group or tetramethyltetrahydronaphthalene group; A diphenylamine group substituted or unsubstituted with a methyl group or a tert-butyl group and condensed or non-condensed with a cyclohexene; N-phenyl-N-dibenzofuranamine group unsubstituted or substituted with a methyl group or a tert-butyl group; Or N-phenyl-N-dibenzothiophenamine group unsubstituted or substituted with a methyl group or a tert-butyl group.

In an exemplary embodiment of the present specification, two adjacent R3s combine with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In the exemplary embodiment of the present specification, two adjacent R3s are bonded to each other to form an aliphatic hydrocarbon ring having 5 to 30 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, two adjacent R3s are bonded to each other to form an aliphatic hydrocarbon ring having 5 to 20 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, two adjacent R3s are bonded to each other to form an aliphatic hydrocarbon ring having 5 or 6 carbon atoms unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R2, R5, R6 and R8 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In the exemplary embodiment of the present specification, R2, R5, R6 and R8 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R2, R5, R6 and R8 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or two adjacent substituents bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 5 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R2, R5, R6 and R8 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a methyl group, adjacent two R2; Two adjacent R5s; Or, two adjacent R6 bonds to each other to form a benzene ring.

In an exemplary embodiment of the present specification, n2 is 4 or more, and 4 of the plurality of R2s are methyl groups.

In an exemplary embodiment of the present specification, n5 is 4 or more, and 4 of the plurality of R5 are methyl groups.

In an exemplary embodiment of the present specification, n6 is 4 or more, and 4 of the plurality of R6 are methyl groups.

In an exemplary embodiment of the present specification, n8 is 2 or more, and two or four of the plurality of R8s are methyl groups.

In an exemplary embodiment of the present specification, n1 is 1.

In an exemplary embodiment of the present specification, n3 is 1.

In an exemplary embodiment of the present specification, n4 is 1.

When n2 is 2 or more, R2 is the same as or different from each other. When n5 is 2 or more, r5 is the same as or different from each other. When n6 is 2 or more, R6 is the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 100 is represented by any one of Chemical Formulas 101 to 109 below.

[Formula 101]

[Formula 102]

[Chemical Formula 103]

[Formula 104]

[Chemical Formula 105]

[Chemical Formula 106]

[Chemical Formula 107]

[Formula 108]

[Formula 109]

In Formulas 101 to 109,

Cy3 and Cy4 are as defined in Chemical Formula 100,

R22, R31, G1, G2 and Y1 to Y6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R21 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

At least one of G1 and G2 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

n22 and n31 are each an integer of 0 to 2, y1 and y5 are each an integer of 0 to 4, y2 to y4 and y6 are each an integer of 0 to 6,

When n22, n31 and y1 to y6 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, the description of R1 described above may be applied to R21.

In the exemplary embodiment of the present specification, R21 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group.

In an exemplary embodiment of the present specification, R21 is deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted heterocyclic group; Or -N(R211)(R212).

In the exemplary embodiment of the present specification, R21 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted N-containing heterocyclic group having 2 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 60 carbon atoms.

In the exemplary embodiment of the present specification, R21 is an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Deuterium, an N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent to which two or more groups selected from the group are connected, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or uncondensed, 6 carbon atoms Arylamine group of to 60; Or an arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group.

In the exemplary embodiment of the present specification, R21 is an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An N-containing heterocyclic group having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms; An arylamine group having 6 to 40 carbon atoms, unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms and condensed or uncondensed with an aliphatic hydrocarbon ring having 5 or 6 carbon atoms; Or an arylheteroarylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium.

In the exemplary embodiment of the present specification, R21 is a methyl group unsubstituted or substituted with deuterium; Isopropyl group; tert-butyl group; A hexahydrocarbazole group unsubstituted or substituted with a methyl group, tert-butyl group, phenyl group, tolyl group, tert-butylphenyl group or tetramethyltetrahydronaphthalene group; A diphenylamine group in which a methyl group, an isopropyl group, or a tert-butyl group is substituted or unsubstituted, and a cyclopentene or cyclohexene is condensed or non-condensed; N-phenyl-N-dibenzofuranamine group; Or N-phenyl-N-dibenzothiophenamine group.

In the exemplary embodiment of the present specification, R21 is an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Deuterium, an N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group; Or -N(R211)(R212).

In the exemplary embodiment of the present specification, R21 is an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or uncondensed, 6 Arylamine group of to 60; Arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Or the above formula Het1.

In an exemplary embodiment of the present specification, R22 is hydrogen; Or deuterium.

In an exemplary embodiment of the present specification, R31 is hydrogen; Or deuterium.

In the exemplary embodiment of the present specification, the description of R3 and R4 described above may be applied to G1 and G2.

In an exemplary embodiment of the present specification, at least one of G1 and G2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, at least one of G1 and G2 is deuterium; A substituted or unsubstituted alkyl group; A substituted or unsubstituted heterocyclic group; Or -N(R211)(R212).

In an exemplary embodiment of the present specification, at least one of G1 and G2 is one or more substituents selected from the group consisting of deuterium and an aryl group having 6 to 30 carbon atoms, or 1 carbon number unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected. An alkyl group of to 10; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Substituted or unsubstituted substituted or unsubstituted C6-C30 hetero with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group Cyclic group; Substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent to which two or more groups selected from the group are connected, and an aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed or uncondensed, 6 carbon atoms Arylamine group of to 60; Or an arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group.

In an exemplary embodiment of the present specification, at least one of G1 and G2 is an alkyl group having 1 to 6 carbon atoms unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; A C6-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group, a C6-C20 aryl group, or a C7-C30 alkylaryl group; An arylamine group having 6 to 40 carbon atoms, unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms and condensed or uncondensed with an aliphatic hydrocarbon ring having 5 or 6 carbon atoms; Or an arylheteroarylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, at least one of G1 and G2 is a methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); A phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; Dimethylfluorenyl group; Dibenzofuran group; Dibenzothiophene group; A hexahydrocarbazole group unsubstituted or substituted with a methyl group, tert-butyl group, phenyl group, tolyl group, tert-butylphenyl group or tetramethyltetrahydronaphthalene group; A diphenylamine group in which a methyl group, an isopropyl group, or a tert-butyl group is substituted or unsubstituted, and a cyclopentene or cyclohexene is condensed or non-condensed; N-phenyl-N-dibenzofuranamine group; Or N-phenyl-N-dibenzothiophenamine group.

In an exemplary embodiment of the present specification, at least one of G1 and G2 is one or more substituents selected from the group consisting of deuterium and an aryl group having 6 to 30 carbon atoms, or 1 carbon number unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected. An alkyl group of to 10; An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Substituted or unsubstituted substituted or unsubstituted C6-C30 hetero with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group Cyclic group; Or -N(R211)(R212).

In an exemplary embodiment of the present specification, any one of G1 and G2 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, and the other is hydrogen or deuterium.

In an exemplary embodiment of the present specification, any one of G1 and G2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylheteroarylamine group having 6 to 60 carbon atoms, and the other is hydrogen or deuterium.

In the exemplary embodiment of the present specification, any one of G1 and G2 is an alkyl group having 1 to 6 carbon atoms unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; A C6-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group, a C6-C20 aryl group, or a C7-C30 alkylaryl group; An arylamine group having 6 to 40 carbon atoms, unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms and condensed or uncondensed with an aliphatic hydrocarbon ring having 5 or 6 carbon atoms; Or an arylheteroarylamine group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium, and the other is hydrogen or deuterium.

In the exemplary embodiment of the present specification, any one of G1 and G2 is an alkyl group having 1 to 6 carbon atoms unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; A C6-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group, a C6-C20 aryl group, or a C7-C30 alkylaryl group; Or -N(R211)(R212), and the other is hydrogen or deuterium.

In the exemplary embodiment of the present specification, Y1 to Y6 are the same as or different from each other, and each independently, hydrogen; Or deuterium, or four adjacent Y3; Or, four adjacent Y6s are bonded to each other to form a benzene ring.

In an exemplary embodiment of the present specification, Chemical Formula 103 is represented by Chemical Formula 103-1 or 103-2 below.

In Formulas 103-1 and 103-2,

The definitions of G1, G2, Cy3, Cy4, R21, R22, R31, n22 and n31 are as defined in Chemical Formula 103.

In the exemplary embodiment of the present specification, Chemical Formula 107 is represented by Chemical Formula 107-1 or 107-2 below.

In Formulas 107-1 and 107-2,

The definitions of Y5, Cy3, Cy4, R21, R22, n22 and y5 are as defined in Chemical Formula 107.

In the exemplary embodiment of the present specification, Chemical Formula 108 is represented by Chemical Formula 108-1 or 108-2 below.

In Formulas 108-1 and 108-2,

The definitions of Y4, Cy3, Cy4, R21, R22, n22 and y4 are as defined in Chemical Formula 108.

In the exemplary embodiment of the present specification, Chemical Formula 109 is represented by any one of Chemical Formulas 109-1 to 109-3 below.

In Formulas 109-1 to 109-3,

The definitions of Cy3, Cy4, R21, R22 and n22 are as defined in Chemical Formula 109.

In an exemplary embodiment of the present specification, Chemical Formula 100 is represented by any one of Chemical Formulas 201 to 209 below.

[Formula 201]

[Formula 202]

[Formula 203]

[Formula 204]

[Formula 205]

[Formula 206]

[Formula 207]

[Chemical Formula 208]

[Chemical Formula 209]

In Formulas 201 to 209,

Q1 is as defined in Chemical Formula 100,

Cy5 to Cy7 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocycle, or a ring in which two or more rings selected from the group are fused,

R22, R31 to R38, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

x1 to x3 are each 1 or 2,

n22, n31, n36 and n37 are each an integer of 0 to 2, n32 and n35 are each an integer of 0 to 4, n33 is an integer of 0 to 5, n34 and n38 are each an integer of 0 to 3,

When n22 and n31 to n38 are each 2 or more, the substituents in parentheses are the same as or different from each other,

Cy11 to Cy13 are the same as or different from each other, and each independently, is selected from the following structures,

In the above structure,

The dotted double line is the condensed position,

R121 to R123 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; Or a substituted or unsubstituted heterocyclic group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n121 is an integer of 0 to 2, n122 and n123 are each an integer of 0 to 4, when n121 to n123 are each 2 or more. The substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, the description of R115 to R117 described above is applied to R121 to R123.

In the exemplary embodiment of the present specification, R121 and R122 are the same as or different from each other, and each independently, hydrogen; Or deuterium.

In the exemplary embodiment of the present specification, R123 is hydrogen or deuterium, or four adjacent R117s combine with each other to form a substituted or unsubstituted benzene ring.

In the exemplary embodiment of the present specification, R123 is hydrogen or deuterium, or four adjacent R117s are bonded to each other to form a benzene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R123 is hydrogen or deuterium, or four adjacent R117s are bonded to each other to form a benzene ring.

In the exemplary embodiment of the present specification, Cy11 to Cy13 are the same as or different from each other, and each independently, is selected from the following structures.

In the exemplary embodiment of the present specification, the description of R103 described above may be applied to R32.

In the exemplary embodiment of the present specification, the description of R104 described above may be applied to R33.

In the exemplary embodiment of the present specification, R32 and R33 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or two adjacent R32; Or two adjacent R33s are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In the exemplary embodiment of the present specification, R32 and R33 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or two adjacent R32; Or, two adjacent R33s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R32 and R33 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or two adjacent R32; Or two adjacent R33s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the alkyl group or aryl group of R32 and R33 includes at least one substituent selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms; Alternatively, two or more groups selected from the group may be substituted with a linked substituent.

In the exemplary embodiment of the present specification, the alkyl group or aryl group of R32 and R33 may be substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 7 to 50 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, two adjacent R32; Or the aliphatic hydrocarbon ring formed by bonding of two adjacent R 33 to each other is at least one substituent selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms; Alternatively, two or more groups selected from the group may be substituted with a linked substituent.

In the exemplary embodiment of the present specification, R32 and R33 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A C 1 to C 6 alkyl group unsubstituted or substituted with deuterium or a C 6 to C 20 aryl group; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms, or two adjacent R32; Or two adjacent R33s are bonded to each other to form an aliphatic hydrocarbon ring having 5 or 6 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R32 and R33 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group, or two adjacent R32; Alternatively, two adjacent R33s are bonded to each other to form a cyclopentene ring substituted or unsubstituted with a methyl group, or a cyclohexene ring unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, R32 is hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group.

In an exemplary embodiment of the present specification, R33 is hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); Or a phenyl group unsubstituted or substituted with a tert-butyl group, or two adjacent R33s are bonded to each other to form a cyclopentene ring unsubstituted or substituted with a methyl group, or a cyclohexene ring unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, the description of R101 described above may be applied to R34 and R35.

In the exemplary embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In the exemplary embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or tert-butyl group.

In the exemplary embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; Or deuterium.

In the exemplary embodiment of the present specification, the description of R102 described above may be applied to R38.

In an exemplary embodiment of the present specification, R38 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R38 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R38 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C6 alkyl group.

In an exemplary embodiment of the present specification, R38 is hydrogen; heavy hydrogen; Or a methyl group.

In the exemplary embodiment of the present specification, the description of Cy3 and Cy4 described above may be applied to Cy5 to Cy7.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently is a substituted or unsubstituted aromatic hydrocarbon ring selected from Formulas A-1 to A-3.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms selected from Formulas A-1 to A-3.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently, a substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms selected from Formulas A-1 to A-3 to be.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently, is selected from the above Chemical Formulas A-1 to A-3, or deuterium, an alkyl group having 1 to 6 carbon atoms, and having 6 to 20 carbon atoms It is a monocyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups or a substituent connected with two or more groups selected from the group.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently, is selected from Formulas A-1 to A-3, or deuterium, an alkyl group having 1 to 10 carbon atoms, or 7 to 50 carbon atoms It is a monocyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms unsubstituted or substituted with an arylalkyl group of.

In an exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently, is selected from Formulas A-1 to A-3, or is a phenyl group, a biphenyl group, or a terphenyl group, and the phenyl group, biphenyl group Or the terphenyl group is substituted or unsubstituted with a methyl group, isopropyl group, tert-butyl group, or 2-phenylpropan-2-yl group.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently, is selected from Formulas A-1 to A-3.

In the exemplary embodiment of the present specification, Cy5 to Cy7 are the same as or different from each other, and each independently, is selected from the groups A-11 to A-14.

In the exemplary embodiment of the present specification, in Chemical Formula 103, Cy4 is

And R44 is hydrogen or deuterium, G2 is a tert-butyl group, R21 is a methyl group, and Cy3 is a substituted phenyl group,

There are two or more substituents linked to the phenyl group of Cy3.

In the exemplary embodiment of the present specification, in Chemical Formula 205, Cy11 and Cy13 are each

And, when G2 is a tert-butyl group, R21 is a methyl group, and Cy7 is a substituted phenyl group,

There are two or more substituents linked to the phenyl group of Cy7.

In the exemplary embodiment of the present specification, Chemical Formula 103 excludes the case of including two tert-butyl groups as a substituent included in G2 or/and Cy3. That is, when G2 in Formula 103 is a tert-butyl group, it may be included, and when there is one tert-butyl group among the substituents connected to Cy3 in Formula 103, it may be included, and among the substituents connected to Cy3 in Formula 103, Cases with three tert-butyl groups may also be included. However, the case where G2 in Formula 103 is a tert-butyl group and one tert-butyl group among the substituents connected to Cy3 is excluded. In addition, the case of having two tert-butyl groups among the substituents connected to Cy3 of Chemical Formula 103 is also excluded.

In the exemplary embodiment of the present specification, Chemical Formula 205 is excluded from the case of including two tert-butyl groups as a substituent included in G2 or/and Cy7. That is, when G2 in Formula 205 is a tert-butyl group, it may be included, and when there is one tert-butyl group among the substituents connected to Cy7 in Formula 205, it may be included, and among the substituents connected to Cy7 in Formula 205, Cases with three tert-butyl groups may also be included. However, the case where G2 in Formula 205 is a tert-butyl group and one tert-butyl group among the substituents connected to Cy7 is excluded. In addition, the case of having two tert-butyl groups among the substituents connected to Cy7 of Formula 205 is also excluded.

In an exemplary embodiment of the present specification, the above-described chemical formula excludes the following compounds.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following structures.

The substituent of the compound of Formula 1 may be bonded by a method known in the art, and the type, position, or number of the substituent may be changed according to techniques known in the art.

The conjugation length and the energy band gap of the compound are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.

In addition, by introducing various substituents into the core structure of the above-described structure, a compound having the inherent characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used for the hole injection layer material, the hole transport material, the light emitting layer material and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material that satisfies the conditions required by each organic material layer. I can.

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, etc., 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 multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers or a greater number of organic material layers.

In the organic light emitting device of the present invention, 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 above. It may contain a compound.

In another organic light emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by Formula 1 above.

In the organic light emitting device of the present invention, 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 above. It may contain a compound.

In another organic light emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above. As an example, the compound represented by Formula 1 may be included as a dopant of the emission layer.

In the exemplary embodiment of the present specification, the organic light-emitting device is a green organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

According to the exemplary embodiment of the present specification, the organic light-emitting device is a red organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

In another exemplary embodiment, the organic light-emitting device is a blue organic light-emitting device in which the emission layer includes the compound represented by Formula 1 as a dopant.

As another example, the organic material layer including the compound represented by Formula 1 may include the compound represented by Formula 1 as a dopant, and may include an organic compound such as an anthracene compound as a host.

As another example, the organic material layer including the heterocyclic compound represented by Formula 1 may include the compound represented by Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.

In another exemplary embodiment, the organic material layer comprising the heterocyclic compound represented by Formula 1 includes the compound represented by Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or A metal compound may be included as a dopant.

As another example, the organic material layer including the compound represented by Formula 1 includes the compound represented by Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and can be used together with an iridium-based (Ir) dopant. have.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes the polycyclic compound described above as a dopant of the emission layer, and a compound represented by the following Formula H as a host of the emission layer.

[Formula H]

In the formula H,

L21 and L22 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 heteroarylene group,

Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R201 and R202 are the same as or different from each other, and each independently 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,

n202 is an integer from 0 to 7, and when n202 is 2 or more, R202 is the same as or different from each other.

In the exemplary embodiment of the present specification, L21 and L22 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 heteroarylene group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently, a direct bond; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently, a direct bond; A phenylene group unsubstituted or substituted with deuterium; Biphenylylene group unsubstituted or substituted with deuterium; A naphthylene group unsubstituted or substituted with deuterium; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar21 and Ar22 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.

In the exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently, a substituted or unsubstituted monocyclic to 4 ring aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic to 4 ring heterocyclic group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently, a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In the exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently, 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 dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently, a phenyl group unsubstituted or substituted with deuterium; Biphenyl group unsubstituted or substituted with deuterium; Terphenyl group; A naphthyl group unsubstituted or substituted with deuterium; Phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.

In the exemplary embodiment of the present specification, any one of Ar21 and Ar22 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted heterocyclic group, and Ar22 is a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R201 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 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 heterocyclic group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R201 is hydrogen; heavy hydrogen; Fluorine; A substituted or unsubstituted C 1 to C 10 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 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 heterocyclic group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R201 is hydrogen; 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.

In the exemplary embodiment of the present specification, R201 is hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R201 is hydrogen; A substituted or unsubstituted monocyclic to 4 ring aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic to 4 ring heterocyclic group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R201 is hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In the exemplary embodiment of the present specification, R201 is hydrogen; heavy hydrogen; 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 a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 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 with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R201 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.

[0366] According to an exemplary embodiment of the present specification, R202 is hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, four or more of R202 are deuterium.

According to an exemplary embodiment of the present specification, R202 is hydrogen.

According to an exemplary embodiment of the present specification, R202 is deuterium.

In the exemplary embodiment of the present specification, when the compound represented by Formula H is substituted with deuterium, hydrogen at a position where it can be substituted is substituted with deuterium by 30% or more. In another exemplary embodiment, in the structure of Formula H, 40% or more of hydrogen at a replaceable position is substituted with deuterium. In another exemplary embodiment, in the structure of Formula H, hydrogen at a position where it can be substituted is substituted by at least 60% of deuterium.

In another exemplary embodiment, in the structure of Formula H, at least 80% of hydrogen at a replaceable position is substituted with deuterium. In another exemplary embodiment, in the structure of Formula H, 100% of hydrogen at a replaceable position is substituted with deuterium.

In the exemplary embodiment of the present specification, the compound represented by Formula H is any one selected from the following compounds.

In the exemplary embodiment of the present specification, the emission layer includes the polycyclic compound described above as a dopant of the emission layer, and the compound represented by Formula H as a host of the emission layer.

In the exemplary embodiment of the present specification, when the emission layer includes a host and a dopant, the content of the dopant may be selected from 0.01 to 10 parts by weight based on 100 parts by weight of the emission layer, but is not limited thereto.

In the exemplary embodiment of the present specification, the emission layer includes a host and a dopant, and the host and the dopant are 99:1 to 1:99 weight ratio, preferably 99:1 to 70:30 weight ratio, even more preferably 99 It includes in a weight ratio of :1 to 90:10.

The light emitting layer may further include a host material, and the host may include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and may be a mixture of two or more thereof, but are not limited thereto.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes at least one dopant and a host.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two or more mixed dopants and a host.

According to an exemplary embodiment of the present specification, at least one of the two or more mixed dopants includes Formula 1, and the host includes a compound represented by Formula H. At least one of the two or more mixed dopants includes Formula 1, and the other may use a conventionally known dopant material, but is not limited thereto.

According to an exemplary embodiment of the present specification, at least one of the two or more mixed dopants includes the formula 1, and the rest of the boron-based compounds, pyrene-based compounds, and delayed fluorescent compounds different from those of the formula 1 are used. However, it is not limited thereto.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes one or more types of hosts.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two or more mixed hosts.

According to an exemplary embodiment of the present specification, at least one of the two or more mixed hosts is a compound represented by Formula H.

According to an exemplary embodiment of the present specification, the two or more kinds of mixed hosts are different from each other, and each independently, is a compound represented by Formula H.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two kinds of mixed hosts.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes a mixed host of two types, the two types of mixed hosts are different from each other, and the two types of hosts are represented by Formula H. It is a compound that becomes.

According to an exemplary embodiment of the present specification, the organic material layer includes a first host including an emission layer and represented by Chemical Formula H; And a second host represented by Formula H, wherein the first host and the second host are different from each other.

According to an exemplary embodiment of the present specification, the first host: the second host is included in a weight ratio of 95:5 to 5:95, and preferably is included in a weight ratio of 70:30 to 30:70.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes at least one host and a dopant.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes at least one host and a dopant, the host includes a compound represented by Formula H, and the dopant is the formula It includes the compound represented by 1.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two or more mixed hosts and a dopant.

According to an exemplary embodiment of the present specification, at least one of the two or more mixed hosts includes the compound represented by Formula H, and the dopant includes the compound represented by Formula 1 above.

In the present specification, the two or more kinds of mixed hosts are different from each other.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two kinds of mixed hosts and a dopant.

According to an exemplary embodiment of the present specification, the two kinds of mixed hosts are different from each other, and each independently includes a compound represented by Chemical Formula H, and the dopant includes a compound represented by Chemical Formula 1.

According to an exemplary embodiment of the present specification, the organic material layer includes a first host including an emission layer and represented by Chemical Formula H; A second host represented by Formula H; And a dopant represented by Formula 1, wherein the first host and the second host are different from each other.

According to an exemplary embodiment of the present specification, the organic material layer uses at least one host and at least one dopant, the at least one host comprises a compound represented by Formula H, and the at least one dopant is the It includes a compound represented by Formula 1.

According to an exemplary embodiment of the present specification, the organic material layer may use two or more types of mixed hosts and two or more types of mixed dopants, and the two or more types of mixed hosts may use the same material as described above, and the two or more types of mixed host may be used. The dopant may use the same material as described above.

In the exemplary embodiment of the present specification, the maximum emission peak of the emission layer including the polycyclic compound represented by Chemical Formula 100 is 380 nm to 500 nm. That is, the light emitting layer containing the polycyclic compound described above is a blue light emitting layer.

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The structure of the organic light-emitting device of the present invention may have the following structures (1) to (18), but is not limited thereto.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Anode

(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Electron transport layer/Anode

(9) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Electron transport layer/Electron injection layer/Anode

(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Blocking Layer/Electron Transport Layer/Anode

(15) Anode/Hole transport layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(16) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode

(17) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(18) Anode/Hole injection layer/Hole transport layer/Electron blocking layer/Light emitting layer/Hole blocking layer/Electron injection and transport layer/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.

1 illustrates a structure of an organic light-emitting device in which a light emitting layer 3 and a cathode 4 are sequentially stacked on a substrate 1 and an anode 2. In such a structure, the compound represented by Formula 1 may be included in the emission layer 3.

2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, a light emitting layer 3, and a second hole injection layer 6 on the substrate 1 and the anode 2 The structure of an organic light-emitting device in which the first electron transport layer 9, the second electron transport layer 10, the electron injection layer 11, and the cathode 4 are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 may be included in the emission layer 3.

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. Is deposited to form an anode, and on it After forming an organic material layer including one or more selected layers, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, 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, an emission layer, an electron transport layer, etc., but is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.

The anode is an electrode for injecting holes, and a material having a large work function is preferably used as the anode material to facilitate hole injection into an organic material layer. Specific examples of the cathode material 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of 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; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and may have a single-layer or multi-layer structure. The hole injection material is a material capable of injecting holes well from the anode at a low voltage, It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it. In one embodiment of the present specification, the hole injection layer has a multilayer structure of two or more layers.

The hole transport layer may serve to facilitate transport of holes. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. As the electron blocking layer, the aforementioned spiro compound or a material known in the art may be used.

The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding 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 compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopants include 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), but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distillbenzene (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.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer serves to facilitate transport of electrons, and may have a single layer or multilayer structure. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing 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. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage to be able to. In one embodiment of the present specification, the electron transport layer has a multilayer structure of two or more layers, and the electron transport layer adjacent to the cathode includes an n-type dopant.

The electron injection layer may play a role of smoothly injecting electrons. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for 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, , A compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

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

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted as being limited to the Examples and Comparative Examples described below. Examples and comparative examples in the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

합성예 1. 화합물1의 합성Synthesis Example 1. Synthesis of Compound 1

1) Synthesis of Intermediate 1

1-bromo-3-chloro-5-methylbenzene 40g, bis(4-(tert-butyl)phenyl)amine 54.8g, sodium-tert-butoxide 56.1g, bis(tri-tert-butylphos) under nitrogen atmosphere After adding 1.0 g of pin) palladium (0) to 600 ml of toluene, the mixture was stirred under reflux for 2 hours. After extraction was completed after the reaction was completed, 65 g of Intermediate 1 was obtained through recrystallization. (Yield 82%). MS[M+H]+ = 407

2) Synthesis of Intermediate 2

30 g of intermediate 1 under nitrogen atmosphere, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7, 30.5 g of 8-tetrahydronaphthalen-2-amine, 14.2 g of sodium-tert-butoxide, and 0.4 g of bis (tri-tert-butylphosphine) palladium (0) were added to 450 ml of toluene, followed by reflux stirring for 2 hours. After the reaction was completed, extraction was performed, and 45 g of intermediate 2 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 782

3) Synthesis of compound 1

In a nitrogen atmosphere, 25 g of intermediate 2 and 21.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and then 8 g of compound 1 was obtained through recrystallization (yield 32%). MS[M+H]+ = 789

합성예 2. 화합물2의 합성Synthesis Example 2. Synthesis of Compound 2

1) Synthesis of Intermediate 3

Instead of 1-bromo-3-chloro-5-methylbenzene, 40 g of 1-bromo-3-(tert-butyl)-5-chlorobenzene was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 1 to obtain Intermediate 3 60 g was obtained. (Yield 83%). MS[M+H]+ = 449

2) Synthesis of Intermediate 4

Intermediate 3 30g, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetra 43g of intermediate 4 was obtained through recrystallization of 27.5 g of hydronaphthalen-2-amine using the same material and equivalent as in the synthesis method of intermediate 2. (Yield 78%). MS[M+H]+ = 824

3) Synthesis of compound 2

In a nitrogen atmosphere, 25 g of intermediate 4 and 20.2 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction was completed after the reaction was completed, 8.4 g of compound 2 was obtained through recrystallization (yield 33%). MS[M+H]+ = 832

합성예 3. 화합물3의 합성Synthesis Example 3. Synthesis of Compound 3

1) Synthesis of Intermediate 5

Intermediate 1 30g, N-(4-(tert-butyl)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)phenyl)-5, 38.6 g of 5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 46 g of Intermediate 5. (Yield 70%). MS[M+H]+ = 892

2) Synthesis of compound 3

In a nitrogen atmosphere, 25 g of intermediate 5 and 20.2 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed and extracted, 8.1 g of compound 3 was obtained through recrystallization (yield 31%). MS[M+H]+ = 900

합성예 4. 화합물4의 합성Synthesis Example 4. Synthesis of Compound 4

1) Synthesis of Intermediate 6

Intermediate 1 30g, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 28.8g recrystallized using the same material and equivalent as the intermediate 2 synthesis method Through this, 42g of intermediate 6 was obtained. (Yield 75%). MS[M+H]+ = 760

2) Synthesis of compound 4

In a nitrogen atmosphere, 25 g of intermediate 6 and 21.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.9g of compound 4 was obtained through recrystallization (yield 31%). MS[M+H]+ = 767

합성예 5. 화합물5의 합성Synthesis Example 5. Synthesis of Compound 5

1) Synthesis of Intermediate 7

1-bromo-3-chloro-5-methylbenzene 40g, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 75.8g Intermediate 1 72 g of Intermediate 7 was obtained through recrystallization using the same material and equivalent as in the synthesis method. (Yield 72%). MS[M+H]+ = 515

2) Synthesis of Intermediate 8

Intermediate 7 30g, 5-(tert-butyl)-N-(3-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine 30.5g 20.9g the same material as the intermediate 2 synthesis method And 39g of intermediate 8 was obtained through recrystallization using the equivalent. (Yield 80%). MS[M+H]+ = 836

3) Synthesis of compound 5

In a nitrogen atmosphere, 25 g of intermediate 8 and 19.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 8.1 g of compound 5 was obtained through recrystallization (yield 32%). MS[M+H]+ = 844

합성예 6. 화합물6의 합성Synthesis Example 6. Synthesis of Compound 6

1) Synthesis of Intermediate 9

40 g of 1,3-dibromo-5-methylbenzene, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl- 2 hours after adding 98.8 g of 5,6,7,8-tetrahydronaphthalen-2-amine, 92 g of sodium-tert-butoxide, and 0.6 g of bis (tri-tert-butylphosphine) palladium (0) in 1000 ml of toluene Stir at reflux during. After the reaction was completed, extraction was performed, and 80 g of intermediate 9 was obtained through recrystallization. (73% yield). MS[M+H]+ = 912

2) Synthesis of compound 6

In a nitrogen atmosphere, 25 g of intermediate 9 and 18.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.8g of compound 6 was obtained through recrystallization (yield 31%). MS[M+H]+ = 920

합성예 8. 화합물8의 합성Synthesis Example 8. Synthesis of Compound 8

1) Synthesis of Intermediate 11

1-bromo-3-chloro-5-methylbenzene 40g, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetra 77 g of Intermediate 11 was obtained through recrystallization of 80.1 g of methyl-5,6,7,8-tetrahydronaphthalen-2-amine using the same material and equivalent as in the synthesis method of Intermediate 1. (Yield 74%). MS[M+H]+ = 537

2) Synthesis of Intermediate 12

30 g of Intermediate 11 and 22.7 g of bis(4-(2-phenylpropane-2-yl)phenyl)amine were recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 33 g of Intermediate 12. (Yield 65%). MS[M+H]+ = 906

3) Synthesis of compound 8

In a nitrogen atmosphere, 25 g of intermediate 12 and 18.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5g of compound 8 was obtained through recrystallization (yield 30%). MS[M+H]+ = 914

합성예 9. 화합물9의 합성Synthesis Example 9. Synthesis of Compound 9

1) Synthesis of Intermediate 13

Intermediate 7 30g, bis(4-(2-phenylpropane-2-yl)phenyl)amine 23.7g was recrystallized using the same material and equivalent as the intermediate 2 synthesis method to obtain 36g of Intermediate 13. (Yield 70%). MS[M+H]+ = 884

2) Synthesis of compound 9

In a nitrogen atmosphere, 25 g of intermediate 13 and 18.8 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6g of compound 9 was obtained through recrystallization (yield 30%). MS[M+H]+ = 892

합성예 10. 화합물10의 합성Synthesis Example 10. Synthesis of Compound 10

1) Synthesis of Intermediate 14

Intermediate 7 30g, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetra 39 g of intermediate 14 was obtained by recrystallization of 24.7 g of hydronaphthalen-2-amine using the same material and equivalent as in the synthesis method of Intermediate 2. (Yield 75%). MS[M+H]+ = 890

2) Synthesis of compound 10

In a nitrogen atmosphere, 25 g of intermediate 14 and 18.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 7.2 g of compound 10 was obtained through recrystallization (yield 29%). MS[M+H]+ = 898

합성예 11. 화합물11의 합성Synthesis Example 11. Synthesis of Compound 11

1) Synthesis of Intermediate 15

Intermediate 7 30g, N-(5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-yl)-5,5,8,8-tetramethyl- 28.5 g of 5,6,7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 42 g of Intermediate 15. (Yield 75%). MS[M+H]+ = 966

2) Synthesis of compound 11

In a nitrogen atmosphere, 25 g of intermediate 15 and 17.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6g of compound 11 was obtained through recrystallization (yield 30%). MS[M+H]+ = 974

합성예 12. 화합물12의 합성Synthesis Example 12. Synthesis of Compound 12

1) Synthesis of Intermediate 16

Intermediate 7 30g, N-(4-(tert-butyl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 20.4g intermediate 2 33g of Intermediate 16 was obtained through recrystallization using the same material and equivalent as in the synthesis method. (Yield 68%). MS[M+H]+ = 828

2) Synthesis of compound 12

In a nitrogen atmosphere, 25 g of intermediate 16 and 20.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.7g of compound 12 was obtained through recrystallization (yield 31%). MS[M+H]+ = 836

합성예 13. 화합물13의 합성Synthesis Example 13. Synthesis of Compound 13

1) Synthesis of Intermediate 17

Intermediate 7 30g, N-(4-(tert-butyl)phenyl)-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine 20.4g Intermediate 2 32 g of Intermediate 17 was obtained through recrystallization using the same material and equivalent as in the synthesis method. (Yield 66%). MS[M+H]+ = 828

2) Synthesis of compound 13

In a nitrogen atmosphere, 25 g of intermediate 17 and 20.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.5 g of compound 13 was obtained through recrystallization (yield 30%). MS[M+H]+ = 836

합성예 14. 화합물14의 합성Synthesis Example 14. Synthesis of Compound 14

1) Synthesis of Intermediate 18

1-bromo-3-chloro-5-

methylbenzene

40g, 3,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7,8- Tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 78.6g was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 1 to obtain 78g of Intermediate 18. (Yield 76%). MS[M+H]+ = 529

2) Synthesis of Intermediate 19

Intermediate 18 30g, N-(3-(tert-butyl)phenyl)-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine 19.9g of intermediate 2 32g of Intermediate 19 was obtained through recrystallization using the same material and equivalent as in the synthesis method. (Yield 68%). MS[M+H]+ = 828

3) Synthesis of compound 14

In a nitrogen atmosphere, 25 g of intermediate 19 and 20.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.8g of compound 14 was obtained through recrystallization (yield 31%). MS[M+H]+ = 836

합성예 15. 화합물15의 합성Synthesis Example 15. Synthesis of Compound 15

1) Synthesis of Intermediate 20

1,3-dibromo-5-methylbenzene 30g, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) 93.5g of amine synthesis method of intermediate 2 77 g of Intermediate 20 was obtained through recrystallization using the same material and equivalent. (Yield 74%). MS[M+H]+ = 868

2) Synthesis of compound 15

In a nitrogen atmosphere, 25 g of intermediate 20 and 19.2 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.8g of compound 15 was obtained through recrystallization (yield 31%). MS[M+H]+ = 876

합성예 16. 화합물16의 합성Synthesis Example 16. Synthesis of Compound 16

1) Synthesis of Intermediate 21

Intermediate 2 with 30 g of 1,3-dibromo-5-methylbenzene and 100.2 g of bis(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 74 g of Intermediate 21 was obtained through recrystallization using the same material and equivalent as in the synthesis method. (Yield 69%). MS[M+H]+ = 896

2) Synthesis of compound 16

In a nitrogen atmosphere, 25 g of intermediate 21 and 18.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.7 g of compound 16 was obtained through recrystallization (yield 31%). MS[M+H]+ = 904

합성예 17. 화합물17의 합성Synthesis Example 17. Synthesis of Compound 17

1) Synthesis of Intermediate 22

Intermediate 11 40g, 4-(tert-butyl)-2-methylaniline 12.2g, sodium-tert-butoxide 21.5g, bis(tri-tert-butylphosphine)palladium(0) 0.4g into 600ml of toluene After refluxing for 1 hour and checking whether the reaction proceeds, 14.3 g of 1-bromo-3-chlorobenzene was added during the reflux reaction, and the reflux reaction was further performed for 1 hour. After the reaction was completed, extraction was performed, and then 44 g of intermediate 22 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 774

2) Synthesis of Intermediate 23

25 g of intermediate 22 and 21.5 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6 g of intermediate 23 was obtained through recrystallization (yield 30%). MS[M+H]+ = 876

3) Synthesis of compound 17

In a nitrogen atmosphere, 7 g of intermediate 23, 1.52 g of diphenylamine, 1.7 g of sodium-tert-butoxide, and 0.05 g of bis (tri-tert-butylphosphine) palladium (0) were added to 80 ml of xylene, followed by reflux agitation for 5 hours. I did. After extraction was completed after the reaction was completed, 7 g of compound 17 was obtained through recrystallization. (Yield 85%). MS[M+H]+ = 915

합성예 18. 화합물18의 합성Synthesis Example 18. Synthesis of Compound 18

1) Synthesis of compound 18

In a nitrogen atmosphere, 7 g of intermediate 23, 1.52 g of bis(4-(tert-butyl)phenyl)amine, 2.6 g of sodium-tert-butoxide, and 0.05 g of bis(tri-tert-butylphosphine)palladium(0) were added to xylene. After putting into 80ml, the mixture was stirred under reflux for 5 hours. After extraction after completion of the reaction, 7.7 g of compound 18 was obtained through recrystallization. (Yield 84%). MS[M+H]+ = 1027

합성예 19. 화합물19의 합성Synthesis Example 19. Synthesis of Compound 19

1) Synthesis of compound 19

Under nitrogen atmosphere, intermediate 23 7g, bis(4-(tert-butyl)-2-methylphenyl)amine 2.77g, sodium-tert-butoxide 2.7g, bis(tri-tert-butylphosphine)palladium(0) 0.5g Was added to 80 ml of xylene and stirred under reflux for 5 hours. After extraction after completion of the reaction, 7.8g of compound 19 was obtained through recrystallization. (Yield 83%). MS[M+H]+ = 1055

합성예 20. 화합물20의 합성Synthesis Example 20. Synthesis of Compound 20

1) Synthesis of Intermediate 24

1-bromo-3-(tert-butyl)-5-chlorobenzene 40g, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8 ,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 66.5g was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 1 to obtain 75g of Intermediate 24. (Yield 80%). MS[M+H]+ = 579

2) Synthesis of Intermediate 25

After adding 40 g of intermediate 24, 11.3 g of 4-(tert-butyl)-2-methylaniline, 19.9 g of sodium-tert-butoxide, and 0.4 g of bis(tri-tert-butylphosphine) palladium (0) in 600 ml of toluene After refluxing for 1 hour and checking whether the reaction proceeds, 13.2 g of 1-bromo-3-chlorobenzene was added during the reflux reaction, and the reflux reaction was further performed for 1 hour. After the reaction was completed, extraction was performed, and then 42 g of intermediate 25 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 816

3) Synthesis of Intermediate 26

In a nitrogen atmosphere, 25 g of the intermediate and 20.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 8.1 g of intermediate 26 was obtained through recrystallization (yield 32%). MS[M+H]+ = 825

4) Synthesis of compound 20

7 g of intermediate 26, 1.5 g of diphenylamine, 1.7 g of sodium-tert-butoxide, and 0.05 g of bis(tri-tert-butylphosphine)palladium(0) were added to 80 ml of xylene, followed by reflux stirring for 5 hours. After the reaction was completed, extraction was performed, and 6.5 g of compound 20 was obtained through recrystallization. (Yield 80%). MS[M+H]+ = 957

합성예 21. 화합물21의 합성Synthesis Example 21. Synthesis of Compound 21

1) Synthesis of Intermediate 27

1-bromo-3-chloro-5-methylbenzene 40g, N-(4-(tert-butyl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8- 55 g of Intermediate 27 was obtained by recrystallization of 56.5 g of tetrahydronaphthalen-2-amine using the same material and equivalent as in the synthesis method of Intermediate 1. (Yield 72%). MS[M+H]+ = 475

2) Synthesis of Intermediate 28

Intermediate 27 40g, 4-(tert-butyl)-2-methylaniline 13.8g, sodium-tert-butoxide 24.3g, bis(tri-tert-butylphosphine)palladium(0) 0.4g was added to 600ml of toluene. After refluxing for 1 hour and checking whether the reaction proceeds, 16.2 g of 1-bromo-3-chlorobenzene was added during the reflux reaction, and the reflux reaction was further performed for 1 hour. After the reaction was completed, extraction was performed, and then 44 g of intermediate 28 was obtained through recrystallization. (73% yield). MS[M+H]+ = 712

3) Synthesis of Intermediate 29

In a nitrogen atmosphere, 25 g of intermediate 28 and 23.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 8.2 g of intermediate 29 was obtained through recrystallization (yield 32%). MS[M+H]+ = 720

4) Synthesis of compound 21

7 g of intermediate 29, 1.7 g of diphenylamine, 1.8 g of sodium-tert-butoxide, and 0.05 g of bis(tri-tert-butylphosphine)palladium(0) were added to 80 ml of xylene, followed by reflux stirring for 5 hours. After extraction after completion of the reaction, 6.6g of compound 21 was obtained through recrystallization. (Yield 70%). MS[M+H]+ = 965

합성예 22. 화합물22의 합성Synthesis Example 22. Synthesis of Compound 22

1) Synthesis of Intermediate 30

Intermediate 7 40g, 5-(tert-butyl)-[1,1'-biphenyl]-2-amine 17.6g, sodium-tert-butoxide 22.4g, bis(tri-tert-butylphosphine)palladium (0 ) After adding 0.4 g to 600 ml of toluene, reflux for 1 hour, and after checking whether the reaction proceeds, 14.9 g of 1-bromo-3-chlorobenzene is added during the reflux reaction, and the reflux reaction is further performed for 1 hour. After the reaction was completed, extraction was performed, and then 45 g of intermediate 30 was obtained through recrystallization. (Yield 71%). MS[M+H]+ = 814

2) Synthesis of Intermediate 31

In a nitrogen atmosphere, 25 g of intermediate 30 and 20.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 8.3 g of intermediate 31 was obtained through recrystallization (yield 33%). MS[M+H]+ = 822

3) Synthesis of compound 22

Intermediate 31 7g, bis(4-(tert-butyl)phenyl)amine 2.4g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and then 6.5 g of compound 22 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1067

합성예 23. 화합물23의 합성Synthesis Example 23. Synthesis of Compound 23

3) Synthesis of compound 23

Intermediate 31 7g, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 3.4g, sodium-tert-butoxide 1.7g, bis(tri- After adding 0.05 g of tert-butylphosphine) palladium (0) to 80 ml of xylene, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 7.4 g of compound 23 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 1175

합성예 25. 화합물25의 합성Synthesis Example 25. Synthesis of Compound 25

1) Synthesis of Intermediate 32

1-bromo-3-chloro-5-

methylbenzene

40g, 1,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7,8- Tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 78.6g was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 1 to obtain 72g of Intermediate 32. (Yield 70%). MS[M+H]+ = 529

2) Synthesis of Intermediate 33

Intermediate 32 40g, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine 16.5g, sodium-tert-butoxide 14.5g, bis(tri-tert- After adding 0.4 g of butylphosphine) palladium (0) to 600 ml of toluene, refluxed for 1 hour, and after confirming the progress of the reaction, 14.5 g of 1-bromo-3-chlorobenzene was added during the reflux reaction, followed by refluxing for 1 hour. The reaction proceeds. After the reaction was completed, extraction was performed, and then 46 g of intermediate 33 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 820

3) Synthesis of Intermediate 34

In a nitrogen atmosphere, 25 g of intermediate 33 and 20.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 7.7 g of intermediate 34 was obtained through recrystallization (yield 31%). MS[M+H]+ = 828

4) Synthesis of compound 25

Intermediate 34 7g, bis(4-(tert-butyl)phenyl)amine 2.4g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction after completion of the reaction, 6.8g of compound 25 was obtained through recrystallization. (Yield 75%). MS[M+H]+ = 1073

합성예 26. 화합물26의 합성Synthesis Example 26. Synthesis of Compound 26

1) Synthesis of Intermediate 35

40 g of 3-bromo-5-chlorophenol, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5, 79.4 g of 6,7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 1 to obtain 70 g of Intermediate 35. (Yield 57%). MS[M+H]+ = 539

2) Synthesis of Intermediate 36

Intermediate 35 40g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride 20ml, potassium carbonate 30g in tetrahydrofuran 400ml, water 200ml 3 After the reaction was completed for a period of time, extraction was performed, and the solution was removed to obtain 58 g of intermediate 36. (Yield 97%). MS[M+H]+ = 805

3) Synthesis of Intermediate 37

In a nitrogen atmosphere, 40 g of intermediate 36, 14 g of bis(4-(tert-butyl)phenyl)amine, 0.85 g of Pd(dba) ₂ , 1.42 g of Xphos, and 48.6 g of cesium carbonate were added to 500 ml of xylene and stirred under reflux for 24 hours. . After extraction after completion of the reaction, 31g of intermediate 37 was obtained through recrystallization (yield 78%). MS[M+H]+ = 802

4) Synthesis of Intermediate 38

25 g of intermediate 37 and 20.8 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.9 g of intermediate 38 was obtained through recrystallization (yield 31%). MS[M+H]+ = 810

5) Synthesis of compound 26

7 g of intermediate 38, 1.46 g of diphenylamine, 2.5 g of sodium-tert-butoxide, and 0.05 g of bis (tri-tert-butylphosphine) palladium (0) were added to 80 ml of xylene, followed by reflux stirring for 5 hours. After extraction was completed after the reaction was completed, 6.2 g of compound 26 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 943

합성예 27. 화합물27의 합성Synthesis Example 27. Synthesis of Compound 27

1) Synthesis of compound 27

Intermediate 38 7g, bis(4-(tert-butyl)phenyl)amine 2.43g, sodium-tert-butoxide 2.5g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.7 g of compound 27 was obtained through recrystallization. (73% yield). MS[M+H]+ = 1055

합성예 29. 화합물29의 합성Synthesis Example 29. Synthesis of Compound 29

1) Synthesis of Intermediate 41

40 g of 1,3-dibromo-5-chlorobenzene under nitrogen atmosphere, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8- Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 121.8 g, sodium-tert-butoxide 56.9 g, bis (tri-tert-butylphosphine) palladium (0) 0.8 g to 1200 ml of toluene After the addition, the mixture was refluxed for 1 hour, extracted after completion of the reaction, and recrystallized to obtain 99 g of intermediate 41. (Yield 72%). MS[M+H]+ = 932

2) Synthesis of Intermediate 42

In a nitrogen atmosphere, 25 g of intermediate 41 and 17.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.7 g of intermediate 42 was obtained through recrystallization (yield 31%). MS[M+H]+ = 940

3) Synthesis of compound 29

Intermediate 42 7g, bis(4-(tert-butyl)phenyl)amine 2.1g, sodium-tert-butoxide 1.5g, bis(tri-tert-butylphosphine)palladium(0) 0.04g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.4 g of compound 29 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1185

합성예 30. 화합물30의 합성Synthesis Example 30. Synthesis of Compound 30

1) Synthesis of Intermediate 43

40 g of intermediate 36 under nitrogen atmosphere, N-(4-(tert-butyl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 17.4 35g of Intermediate 43 was obtained through recrystallization of g using the same material and equivalent weight as the synthesis method of Intermediate 37. (Yield 81%). MS[M+H]+ = 870

2) Synthesis of Intermediate 44

In a nitrogen atmosphere, 25 g of intermediate 43 and 19.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.8 intermediate 44 was obtained through recrystallization (yield 31%). MS[M+H]+ = 878

3) Synthesis of compound 30

Intermediate 44 7g, bis(4-(tert-butyl)phenyl)amine 2.2g, sodium-tert-butoxide 1.5g, bis(tri-tert-butylphosphine)palladium(0) 0.04g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction after completion of the reaction, 6.6g of compound 30 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 1123

합성예 31. 화합물31의 합성Synthesis Example 31. Synthesis of Compound 31

1) Synthesis of Intermediate 45

40 g of 3-bromo-5-chlorophenol and 75.2 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine were added to the intermediate 35 synthesis method and Using the same material and equivalent, 70g of Intermediate 45 was obtained through recrystallization. (Yield 70%). MS[M+H]+ = 517

2) Synthesis of Intermediate 46

40 g of Intermediate 45 was obtained by using the same material and equivalent weight as the synthesis method of Intermediate 36 to obtain 56 g of Intermediate 46. (Yield 92%). MS[M+H]+ = 783

3) Synthesis of Intermediate 47

In a nitrogen atmosphere, 40 g of Intermediate 46 and 16.4 g of di([1,1'-biphenyl]-4-yl)amine were recrystallized using the same material and equivalent as the synthesis method of Intermediate 37 to obtain 34 g of Intermediate 47 ( Yield 81%). MS[M+H]+ = 820

4) Synthesis of Intermediate 48

25 g of Intermediate 47 and 7.5 g of Intermediate 48 were obtained through recrystallization using the same materials and equivalents as in the synthesis method of Intermediate 38 (yield 30%). MS[M+H]+ = 828

5) Synthesis of compound 31

Intermediate 48 7g, bis(4-(tert-butyl)phenyl)amine 1.46g, sodium-tert-butoxide 1.5g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction after completion of the reaction, 6.7 g of compound 31 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 1073

합성예 32. 화합물32의 합성Synthesis Example 32. Synthesis of Compound 32

1) Synthesis of Intermediate 49

In a nitrogen atmosphere, 40 g of Intermediate 46 and 14 g of bis(4-(tert-butyl)phenyl)amine were recrystallized using the same materials and equivalents as those of the synthesis method of Intermediate 37 to obtain 32 g of Intermediate 49. (Yield 83%). MS[M+H]+ = 780

2) Synthesis of Intermediate 50

In a nitrogen atmosphere, 25 g of intermediate 49 and 21.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5 g of intermediate 50 was obtained through recrystallization (yield 30%). MS[M+H]+ = 788

3) Synthesis of compound 32

Intermediate 50 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and then 6.5 g of compound 32 was obtained through recrystallization. (Yield 71%). MS[M+H]+ = 1033

합성예 33. 화합물33의 합성Synthesis Example 33. Synthesis of Compound 33

1) Synthesis of Intermediate 51

In a nitrogen atmosphere, 40 g of Intermediate 46 and 14 g of bis(3-(tert-butyl)phenyl)amine were recrystallized using the same materials and equivalents as in the synthesis method of Intermediate 37 to obtain 30 g of Intermediate 51. (Yield 81%). MS[M+H]+ = 780

2) Synthesis of Intermediate 52

In a nitrogen atmosphere, 25 g of intermediate 51 and 21.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 7.4 g of intermediate 52 was obtained through recrystallization (yield 30%). MS[M+H]+ = 788

3) Synthesis of compound 33

Intermediate 52 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.6 g of compound 33 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1033

합성예 34. 화합물34의 합성Synthesis Example 34. Synthesis of Compound 34

1) Synthesis of Intermediate 53

40 g of intermediate 35 under nitrogen atmosphere, 17.4 g of N-(4-(tert-butyl)phenyl)-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine Intermediate 53 was obtained by recrystallization using the same material and equivalent weight as in the synthesis method of Intermediate 37. (79% yield). MS[M+H]+ = 870

2) Synthesis of Intermediate 54

In a nitrogen atmosphere, 25 g of intermediate 53 and 19.2 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed and extracted, 7.1 g of intermediate 54 was obtained through recrystallization (yield 28%). MS[M+H]+ = 878

3) Synthesis of compound 34

Intermediate 54 7g, bis(4-(tert-butyl)phenyl)amine 2.3g, sodium-tert-butoxide 1.5g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.6 g of compound 34 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 1123

합성예 35. 화합물35의 합성Synthesis Example 35. Synthesis of Compound 35

1) Synthesis of Intermediate 55

In a nitrogen atmosphere, 40 g of intermediate 35 and 19.4 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine were the same material and equivalent as the synthesis method of intermediate 37. 35g of the intermediate 55 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 910

2) Synthesis of Intermediate 56

In a nitrogen atmosphere, 25 g of the intermediate 55 and 18.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.4 g of intermediate 56 was obtained through recrystallization (29% yield). MS[M+H]+ = 918

3) Synthesis of compound 35

Intermediate 56 7g, bis(4-(tert-butyl)phenyl)amine 2.1g, sodium-tert-butoxide 1.5g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and then 6.5 g of compound 35 was obtained through recrystallization. (73% yield). MS[M+H]+ = 1163

합성예 36. 화합물36의 합성Synthesis Example 36. Synthesis of Compound 36

1) Synthesis of Intermediate 57

40 g of 1,3-dibromo-5-chlorobenzene, and 115.3 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine under nitrogen atmosphere as an intermediate 99g of intermediate 57 was obtained through recrystallization using the same material and equivalent as in the synthesis method of 41. (Yield 75%). MS[M+H]+ = 888

2) Synthesis of Intermediate 58

In a nitrogen atmosphere, 25 g of intermediate 57 and 18.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction was completed after the reaction was completed, 7.7 g of intermediate 58 was obtained through recrystallization (yield 31%). MS[M+H]+ = 896

3) Synthesis of compound 36

7 g of intermediate 58, 1.4 g of diphenylamine, 1.5 g of sodium-tert-butoxide, and 0.05 g of bis (tri-tert-butylphosphine) palladium (0) were added to 80 ml of xylene, followed by reflux stirring for 5 hours. After the reaction was completed, extraction was performed, and 6.3 g of compound 36 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 1029

합성예 37. 화합물37의 합성Synthesis Example 37. Synthesis of Compound 37

1) Synthesis of compound 37

Intermediate 58 7g, bis(4-(tert-butyl)phenyl)amine 2.2g, sodium-tert-butoxide 1.5g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and then 6.5 g of compound 37 was obtained through recrystallization. (73% yield). MS[M+H]+ = 1141

합성예 38. 화합물38의 합성Synthesis Example 38. Synthesis of Compound 38

1) Synthesis of Intermediate 59

Intermediate 7 40g, dibenzo[b,d]furan-1-amine 14.3g, sodium-tert-butoxide 22.4g, bis(tri-tert-butylphosphine)palladium(0) 0.4g in 600ml of toluene After refluxing for 1 hour and checking whether the reaction proceeds, 20.8 g of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene was added during the reflux reaction, and for 1 hour Further reflux reaction proceeds. After the reaction was completed, extraction was performed, and then 54 g of intermediate 59 was obtained through recrystallization. (Yield 82%). MS[M+H]+ = 848

2) Synthesis of compound 38

In a nitrogen atmosphere, 25 g of intermediate 59 and 19.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5g of compound 38 was obtained through recrystallization (yield 30%). MS[M+H]+ = 856

합성예 39. 화합물39의 합성Synthesis Example 39. Synthesis of Compound 39

1) Synthesis of Intermediate 60

40 g of Intermediate 7 and 15.5 g of dibenzo[b,d]thiophen-1-amine were recrystallized using the same substances and equivalents as in the synthesis method of Intermediate 59 to obtain 52 g of Intermediate 60. (Yield 77%). MS[M+H]+ = 864

2) Synthesis of compound 39

In a nitrogen atmosphere, 25 g of intermediate 60 and 19.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.7 g of compound 39 was obtained through recrystallization (yield 31%). MS[M+H]+ = 872

합성예 40. 화합물40의 합성Synthesis Example 40. Synthesis of Compound 40

1) Synthesis of Intermediate 61

40 g of Intermediate 7 and 16.3 g of 9,9-dimethyl-9H-floren-4-amine were recrystallized using the same substances and equivalents as the synthesis method of Intermediate 59 to obtain 54 g of Intermediate 61. (79% yield). MS[M+H]+ = 874

2) Synthesis of compound 40

In a nitrogen atmosphere, 25 g of intermediate 61 and 19.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5g of compound 40 was obtained through recrystallization (yield 30%). MS[M+H]+ = 882

합성예 41. 화합물41의 합성Synthesis Example 41. Synthesis of Compound 41

1) Synthesis of Intermediate 62

40 g of Intermediate 7 and 14.3 g of dibenzo[b,d]furan-4-amine were recrystallized using the same substances and equivalents as the synthesis method of Intermediate 59 to obtain 53 g of Intermediate 62. (Yield 77%). MS[M+H]+ = 848

2) Synthesis of Compound 41

In a nitrogen atmosphere, 25 g of intermediate 62 and 19.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed and extracted, 7.7 g of compound 41 was obtained through recrystallization (yield 31%). MS[M+H]+ = 856

합성예 42. 화합물42의 합성Synthesis Example 42. Synthesis of Compound 42

1) Synthesis of Intermediate 63

Intermediate 7 40g and dibenzo[b,d]thiophen-4-amine 15.5g were recrystallized using the same substances and equivalents as the synthesis method of Intermediate 59 to obtain 54g of Intermediate 63. (Yield 78%). MS[M+H]+ = 864

2) Synthesis of compound 42

In a nitrogen atmosphere, 25 g of the intermediate 63 and 19.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6 g of compound 42 was obtained through recrystallization (yield 31%). MS[M+H]+ = 872

합성예 43. 화합물43의 합성Synthesis Example 43. Synthesis of Compound 43

1) Synthesis of Intermediate 64

40 g of Intermediate 7 and 16.3 g of 9,9-dimethyl-9H-floren-1-amine were recrystallized using the same substances and equivalents as in the synthesis method of Intermediate 59 to obtain 51 g of Intermediate 64. (Yield 77%). MS[M+H]+ = 874

2) Synthesis of compound 43

In a nitrogen atmosphere, 25 g of intermediate 64 and 19.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 7.2 g of compound 43 was obtained through recrystallization (yield 28%). MS[M+H]+ = 882

합성예 44. 화합물44의 합성Synthesis Example 44. Synthesis of Compound 44

1) Synthesis of Intermediate 65

Intermediate 7 40g, dibenzo[b,d]furan-4-amine 14.3g, 1-bromo-3-(tert-butyl)benzene 16.6g through recrystallization using the same material and equivalent as the synthesis method of Intermediate 59 47 g of intermediate 65 was obtained. (Yield 76%). MS[M+H]+ = 794

2) Synthesis of compound 44

In a nitrogen atmosphere, 25 g of intermediate 65 and 21 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.8g of compound 44 was obtained through recrystallization (yield 31%). MS[M+H]+ = 801

합성예 45. 화합물45의 합성Synthesis Example 45. Synthesis of Compound 45

1) Synthesis of Intermediate 66

Intermediate 7 40g, dibenzo[b,d]furan-1-amine 14.3g, sodium-tert-butoxide 22.4g, bis(tri-tert-butylphosphine)palladium(0) 0.4g in 600ml of toluene After refluxing for 1 hour and checking whether the reaction proceeds, 14.9 g of 1-bromo-3-chlorobenzene was added during the reflux reaction, and the reflux reaction was further performed for 1 hour. After the reaction was completed, extraction was performed, and then 46 g of intermediate 66 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 771

2) Synthesis of Intermediate 67

In a nitrogen atmosphere, 25 g of intermediate 66 and 21.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.8 g of intermediate 67 was obtained through recrystallization (31% yield). MS[M+H]+ = 780

3) Synthesis of compound 45

Intermediate 67 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed and extracted, 6.6g of compound 45 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1025

합성예 46. 화합물46의 합성Synthesis Example 46. Synthesis of Compound 46

1) Synthesis of Intermediate 68

N-(3-chloro-5-methylphenyl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)dibenzo[b,d]furan -1-

amine

40g, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine 16.6g, sodium-tert-butoxide 23.3g, bis(tri- After adding 0.4 g of tert-butylphosphine) palladium (0) to 600 ml of toluene, refluxed for 1 hour, and after confirming the progress of the reaction, 15.5 g of 1-bromo-3-chlorobenzene was added during the reflux reaction and for 1 hour. Further reflux reaction proceeds. After the reaction was completed, extraction was performed, and then 47 g of intermediate 68 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 786

2) Synthesis of Intermediate 69

In a nitrogen atmosphere, 25 g of intermediate 68 and 21.2 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.7 g of intermediate 69 was obtained through recrystallization (yield 30%). MS[M+H]+ = 794

3) Synthesis of compound 46

Intermediate 69 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction after completion of the reaction, 6.8g of compound 46 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 1039

합성예 47. 화합물47의 합성Synthesis Example 47. Synthesis of Compound 47

1) Synthesis of Intermediate 70

Intermediate 46 40g, N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)dibenzo[b,d]furan-1-amine 18.9g, intermediate After the reaction was completed and extracted using the same material and equivalent as in the synthesis method of 47, 34 g of intermediate 70 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 868

2) Synthesis of Intermediate 71

In a nitrogen atmosphere, 25 g of intermediate 70 and 19.2 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5 g of intermediate 71 was obtained through recrystallization (yield 30%). MS[M+H]+ = 876

3) Synthesis of compound 47

7 g of intermediate 71, 2.5 g of bis(4-(tert-butyl)phenyl)amine, 1.7 g of sodium-tert-butoxide, and 0.05 g of bis(tri-tert-butylphosphine)palladium(0) were added to 80 ml of xylene. Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.9 g of compound 47 was obtained through recrystallization. (Yield 70%). MS[M+H]+ = 1120

합성예 48. 화합물48의 합성Synthesis Example 48. Synthesis of Compound 48

1) Synthesis of Intermediate 72

N-(3-chloro-5-(methyl-d3)phenyl)-5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8- Tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 30g, N-(4-(tert-butyl)phenyl)-3,5,5,8,8-penta 20.4 g of methyl-5,6,7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 33 g of Intermediate 72. (Yield 69%). MS[M+H]+ = 831

2) Synthesis of compound 48

In a nitrogen atmosphere, 25 g of intermediate 72 and 20.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.4 g of compound 48 was obtained through recrystallization (yield 29%). MS[M+H]+ = 839

합성예 49. 화합물49의 합성Synthesis Example 49. Synthesis of Compound 49

1) Synthesis of Intermediate 73

30 g of 1,3-dibromo-5-(tert-butyl)benzene, 3,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7, 83 g of 8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 20 to obtain 66 g of Intermediate 73. (Yield 69%). MS[M+H]+ = 938

2) Synthesis of Compound 49

In a nitrogen atmosphere, 25 g of intermediate 73 and 17.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6g of compound 49 was obtained through recrystallization (yield 30%). MS[M+H]+ = 946

합성예 50. 화합물50의 합성Synthesis Example 50. Synthesis of Compound 50

1) Synthesis of Intermediate 74

N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N-(3-chloro-5-(methyl-d3)phenyl)-5,5,8,8 -Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 40g, 4-(tert-butyl)-2-methylaniline 12.1g, sodium-tert-butoxide 21.4g, bis(tri-tert -After adding 0.4 g of butylphosphine)palladium (0) to 600 ml of toluene, refluxed for 1 hour, and after confirming the progress of the reaction, 14.2 g of 1-bromo-3-chlorobenzene was added during the reflux reaction, and further for 1 hour. The reflux reaction proceeds. After the reaction was completed, extraction was performed, and then 42 g of intermediate 74 was obtained through recrystallization. (73% yield). MS[M+H]+ = 777

2) Synthesis of Intermediate 75

In a nitrogen atmosphere, 25 g of intermediate 74 and 21.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 7.5 g of intermediate 75 was obtained through recrystallization (yield 30%). MS[M+H]+ = 785

3) Synthesis of compound 50

Intermediate 75 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 7.1 g of compound 50 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 1030

합성예 51. 화합물51의 합성Synthesis Example 51. Synthesis of Compound 51

1) Synthesis of Intermediate 76

N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N-(3-chloro-5-methylphenyl)-1,1,3,3-tetramethyl-2 ,3-dihydro-1H-inden-5-amine 40g, 4-(tert-butyl)-2-methylaniline 12.1g, sodium-tert-butoxide 22.1g, bis(tri-tert-butylphosphine)palladium (0) 0.4g was added to 600ml of toluene, refluxed for 1 hour, and after checking whether the reaction proceeded, 14.6g of 1-bromo-3-chlorobenzene was added during the reflux reaction, and the reflux reaction was further performed for 1 hour. After the reaction was completed, extraction was performed, and then 43 g of intermediate 76 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 760

2) Synthesis of Intermediate 77

In a nitrogen atmosphere, 25 g of intermediate 76 and 21.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.1 g of intermediate 77 was obtained through recrystallization (yield 28%). MS[M+H]+ = 768

3) Synthesis of compound 51

Intermediate 77 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction was completed after the reaction was completed, 6.5 g of compound 51 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1013

합성예 52. 화합물52의 합성Synthesis Example 52. Synthesis of Compound 52

1) Synthesis of Intermediate 78

N-(3-chloro-5-(methyl-d3)phenyl)-1,1,3,3-tetramethyl-N-(1,1,3,3-tetramethyl-2,3-dihydro-1H -Inden-5-yl)-2,3-dihydro-1H-inden-5-amine 30g, N-(4-(tert-butyl)phenyl)-1,1,3,3,6-pentamethyl- 27.4 g of 2,3-dihydro-1H-inden-5-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 33 g of Intermediate 78. (Yield 78%). MS[M+H]+ = 789

2) Synthesis of compound 52

In a nitrogen atmosphere, 25 g of intermediate 78 and 21.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction was completed after the reaction was completed, 7.5 g of compound 52 was obtained through recrystallization (yield 30%). MS[M+H]+ = 797

합성예 53. 화합물53의 합성Synthesis Example 53. Synthesis of Compound 53

1) Synthesis of Intermediate 79

1,3-dibromo-5-

methylbenzene

30g, 1,1,3,3,6-pentamethyl-N-(1,1,3,3-tetramethyl-2,3-dihydro-1H-indene 66 g of Intermediate 79 was obtained by recrystallization of 90.1 g of -5-yl)-2,3-dihydro-1H-inden-5-amine using the same material and equivalent as in the synthesis method of Intermediate 20. (Yield 66%). MS[M+H]+ = 840

2) Synthesis of compound 53

In a nitrogen atmosphere, 25 g of the intermediate 79 and 19.8 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.3g of compound 53 was obtained through recrystallization (yield 29%). MS[M+H]+ = 848

합성예 54. 화합물54의 합성Synthesis Example 54. Synthesis of Compound 54

1) Synthesis of Intermediate 80

N-(3-chloro-5-(methyl-d3)phenyl)-5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8- Tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 40g, dibenzo[b,d]furan-1-amine 14.2g, sodium-tert-butoxide 22.3g, After adding 0.4 g of bis(tri-tert-butylphosphine)palladium(0) to 600 ml of toluene, refluxed for 1 hour, and after confirming the progress of the reaction, 14.1 g of 1-bromo-3-chlorobenzene was added during the reflux reaction. And further reflux reaction for 1 hour. After the reaction was completed, extraction was performed, and 41 g of intermediate 80 was obtained through recrystallization. (Yield 68%). MS[M+H]+ = 775

2) Synthesis of Intermediate 81

In a nitrogen atmosphere, 25 g of the intermediate 80 and 21.5 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5 g of intermediate 81 was obtained through recrystallization (yield 30%). MS[M+H]+ = 783

3) Synthesis of compound 54

Intermediate 81 7g, bis(4-(tert-butyl)phenyl)amine 2.5g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.6g of compound 54 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1028

합성예 55. 화합물55의 합성Synthesis Example 55. Synthesis of Compound 55

1) Synthesis of Intermediate 82

Intermediate 46 40g, N-(4-(dibenzo[b,d]furan-1-yl)phenyl)-3-methyl-[1,1'-biphenyl]-4-amine 31g Synthesis of Intermediate 37 55 g of Intermediate 82 was obtained through recrystallization using the same material and equivalent weight as. (Yield 78%). MS[M+H]+ = 924

2) Synthesis of Intermediate 83

In a nitrogen atmosphere, 25 g of intermediate 82 and 18 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.2 g of intermediate 83 was obtained through recrystallization (29% yield). MS[M+H]+ = 932

3) Synthesis of compound 55

Intermediate 83 7g, bis(4-(tert-butyl)phenyl)amine 2.1g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.4 g of compound 55 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1177

합성예 56. 화합물56의 합성Synthesis Example 56. Synthesis of Compound 56

1) Synthesis of Intermediate 84

Intermediate 46 40g, N-(4-(dibenzo[b,d]thiophene-2-yl)phenyl)-3-methyl-[1,1'-biphenyl]-4-amine 34g Synthesis of Intermediate 37 54 g of intermediate 84 was obtained through recrystallization using the same material and equivalent as in the method. (Yield 74%). MS[M+H]+ = 940

2) Synthesis of Intermediate 85

In a nitrogen atmosphere, 25 g of intermediate 84 and 17.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.5 g of intermediate 85 was obtained through recrystallization (yield 30%). MS[M+H]+ = 948

3) Synthesis of compound 56

Intermediate 85 7g, bis(4-(tert-butyl)phenyl)amine 2.1g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction was completed after the reaction was completed, 6.6 g of compound 56 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1235

합성예 57. 화합물57의 합성Synthesis Example 57. Synthesis of Compound 57

1) Synthesis of Intermediate 86

Intermediate 46 40g, N-(4-(9,9-dimethyl-9H-floren-1-yl)phenyl)-3-methyl-[1,1'-biphenyl]-4-amine 35g, intermediate 37 53 g of intermediate 86 was obtained through recrystallization using the same material and equivalent as the synthesis method of. (Yield 72%). MS[M+H]+ = 950

2) Synthesis of Intermediate 87

In a nitrogen atmosphere, 25 g of intermediate 86 and 17.5 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.7 g of intermediate 87 was obtained through recrystallization (yield 31%). MS[M+H]+ = 958

3) Synthesis of compound 57

Intermediate 87 7g, bis(4-(tert-butyl)phenyl)amine 2.1g, sodium-tert-butoxide 1.7g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction after completion of the reaction, 6.8g of compound 57 was obtained through recrystallization. (Yield 75%). MS[M+H]+ = 1245

합성예 58. 화합물58의 합성Synthesis Example 58. Synthesis of Compound 58

1) Synthesis of Intermediate 88

Intermediate 46 40g, 4-(tert-butyl)-N-(3-chlorophenyl)-2-methylaniline 15g was recrystallized using the same material and equivalent as the synthesis method of Intermediate 37 to obtain 31g of Intermediate 88. (79% yield). MS[M+H]+ = 772

2) Synthesis of Intermediate 89

In a nitrogen atmosphere, 25 g of the intermediate 88 and 21.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6 g of intermediate 89 was obtained through recrystallization (yield 30%). MS[M+H]+ = 780

3) Synthesis of compound 58

Intermediate 89 7g, bis(4-(tert-butyl)phenyl)amine 4.3g, sodium-tert-butoxide 2.1g, bis(tri-tert-butylphosphine)palladium(0) 0.05g in 80ml xylene Then, the mixture was stirred under reflux for 5 hours. After extraction was completed after the reaction was completed, 7.2 g of compound 58 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 1270

합성예 59. 화합물59의 합성Synthesis Example 59. Synthesis of Compound 59

1) Synthesis of compound 59

Intermediate 58 7g, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 3g, sodium-tert-butoxide 1.5g, bis(tri-tert -Butylphosphine)Palladium (0) 0.04g was added to 80ml of xylene and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 7.1 g of compound 59 was obtained through recrystallization. (73% yield). MS[M+H]+ = 1249

합성예 60. 화합물60의 합성Synthesis Example 60. Synthesis of Compound 60

1) Synthesis of Intermediate 90

1-bromo-3-chloro-5-methylbenzene 40g under nitrogen atmosphere, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-9,9,10, After adding 89.5 g of 10-tetramethyl-9,10-dihydroanthracene-2-amine, 56.1 g of sodium-tert-butoxide, and 1.0 g of bis (tri-tert-butylphosphine) palladium (0) in 600 ml of toluene Stir at reflux for 2 hours. After extraction was completed after the reaction was completed, 88 g of intermediate 90 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 585

2) Synthesis of Intermediate 91

In a nitrogen atmosphere, 30 g of intermediate 90, 14.5 g of bis(4-(tert-butyl)phenyl)amine, 9.9 g of sodium-tert-butoxide, 0.3 g of bis(tri-tert-butylphosphine)palladium(0), 450 ml of toluene After putting in, the mixture was stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and 34 g of intermediate 91 was obtained through recrystallization. (Yield 80%). MS[M+H]+ = 830

3) Synthesis of compound 60

In a nitrogen atmosphere, 25 g of intermediate 91 and 20.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.5 g of compound 60 was obtained through recrystallization (yield 30%). MS[M+H]+ = 838

합성예 61. 화합물61의 합성Synthesis Example 61. Synthesis of Compound 61

1) Synthesis of Intermediate 92

Intermediate 90 30g, 9,9,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-yl) under nitrogen atmosphere 23.2 g of -9,10-dihydroanthracene-2-amine, 9.9 g of sodium-tert-butoxide, 0.3 g of bis (tri-tert-butylphosphine) palladium (0) were added to 450 ml of toluene and refluxed for 2 hours. Stirred. After the reaction was completed, extraction was performed, and 38 g of intermediate 92 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 1000

2) Synthesis of Compound 61

In a nitrogen atmosphere, 25 g of intermediate 92 and 20.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.6g of compound 61 was obtained through recrystallization (yield 30%). MS[M+H]+ = 1008

합성예 62. 화합물62의 합성Synthesis Example 62. Synthesis of Compound 62

1) Synthesis of Intermediate 93

Intermediate 90 30g, 3,5,5,8,8-pentammethyl-5,6,7,8-tetrahydronaphthalen-2-amine 14.9g, sodium-tert-butoxide 19.8g, bis(tri After adding 0.4 g of -tert-butylphosphine) palladium (0) to 600 ml of toluene, refluxed for 1 hour, and after confirming the progress of the reaction, 13.1 g of 1-bromo-3-chlorobenzene was added during the reflux reaction for 1 hour. During further reflux reaction proceeds. After the reaction was completed, extraction was performed, and then 44 g of intermediate 93 was obtained through recrystallization. (73% yield). MS[M+H]+ = 876

(Yield 77%). MS[M+H]+ = 585

2) Synthesis of Intermediate 94

In a nitrogen atmosphere, 25 g of intermediate 93 and 19 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After completion of the reaction, extraction was performed, and 8.0 g of intermediate 94 was obtained through recrystallization (yield 32%). MS[M+H]+ = 884

3) Synthesis of compound 62

In a nitrogen atmosphere, 7 g of intermediate 94, 14.5 g of bis(4-(tert-butyl)phenyl)amine, 9.9 g of sodium-tert-butoxide, 0.3 g of bis(tri-tert-butylphosphine)palladium(0), 150 ml of toluene After putting in, the mixture was stirred under reflux for 2 hours. After extraction after completion of the reaction, 6.9g of compound 62 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 1129

합성예 63. 화합물63의 합성Synthesis Example 63. Synthesis of Compound 63

1) Synthesis of Intermediate 95

1,3-dibromo-5-

methylbenzene

30g, 9,9,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8 under nitrogen atmosphere -Tetrahydronaphthalene-2-yl)-9,10-dihydroanthracene-2-amine 108 g, sodium-tert-butoxide 70 g, bis (tri-tert-butylphosphine) palladium (0) 1.2 g toluene 600 ml After putting in, the mixture was stirred under reflux for 2 hours. After extraction was completed after the reaction was completed, 88 g of intermediate 95 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1012

2) Synthesis of Intermediate 96

In a nitrogen atmosphere, 25 g of the intermediate 95 and 16.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.9 g of intermediate 96 was obtained through recrystallization (yield 31%). MS[M+H]+ = 1020

3) Synthesis of compound 63

In a nitrogen atmosphere, 7 g of intermediate 96, 1.93 g of bis(4-(tert-butyl)phenyl)amine, 1.32 g of sodium-tert-butoxide, and 0.03 g of bis(tri-tert-butylphosphine)palladium(0) were added to xylene. The mixture was added to 80ml and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.9g of compound 63 was obtained through recrystallization. (79% yield). MS[M+H]+ = 1265

합성예 64. 화합물64의 합성Synthesis Example 64. Synthesis of Compound 64

1) Synthesis of compound 64

Intermediate 58 7g, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 1.93g, sodium-tert-butoxide 1.52g, bis(tri-tert) under nitrogen atmosphere -Butylphosphine)Palladium (0) 0.04 g was added to 80 ml of xylene and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.5 g of compound 64 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 1061

합성예 65. 화합물65의 합성Synthesis Example 65. Synthesis of Compound 65

1) Synthesis of compound 65

Intermediate 58 7g, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.05g, sodium-tert-butoxide under nitrogen atmosphere 1.52 g, bis (tri-tert-butylphosphine) palladium (0) 0.04 g was added to 80 ml of xylene and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.7 g of compound 65 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 1117

합성예 66. 화합물66의 합성Synthesis Example 66. Synthesis of Compound 66

1) Synthesis of compound 66

7 g of intermediate 71, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.06 g, sodium-tert-butoxide under nitrogen atmosphere 1.55 g, bis (tri-tert-butylphosphine) palladium (0) 0.04 g was added to 80 ml of xylene and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 6.9 g of compound 66 was obtained through recrystallization. (79% yield). MS[M+H]+ = 1097

합성예 67. 화합물67의 합성Synthesis Example 67. Synthesis of Compound 67

1) Synthesis of Intermediate 97

1,3-dibromo-5-chlorobenzene 30g, N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)dibenzo[b] under a nitrogen atmosphere ,d] 82 g of furan-4-amine, 64 g of sodium-tert-butoxide, and 0.6 g of bis (tri-tert-butylphosphine) palladium (0) were added to 600 ml of toluene, followed by reflux stirring for 2 hours. After extraction after completion of the reaction, 69g of intermediate 97 was obtained through recrystallization. (73% yield). MS[M+H]+ = 848

2) Synthesis of Intermediate 98

In a nitrogen atmosphere, 25 g of the intermediate 97 and 19.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.2 g of intermediate 98 was obtained through recrystallization (29% yield). MS[M+H]+ = 856

3) Synthesis of compound 67

7 g of intermediate 98 under nitrogen atmosphere, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.1 g, sodium-tert-butoxide 1.6 g, bis (tri-tert-butylphosphine) palladium (0) 0.04 g was added to 80 ml of xylene and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 7.0 g of compound 67 was obtained through recrystallization. (79% yield). MS[M+H]+ = 1077

합성예 68. 화합물68의 합성Synthesis Example 68. Synthesis of Compound 68

1) Synthesis of compound 68

Intermediate 67 7g, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.31g, sodium-tert-butoxide under nitrogen atmosphere 1.8 g, bis (tri-tert-butylphosphine) palladium (0) 0.05 g was added to 80 ml of xylene and stirred under reflux for 5 hours. After the reaction was completed, extraction was performed, and 7.1 g of compound 68 was obtained through recrystallization. (79% yield). MS[M+H]+ = 1001

합성예 71. 화합물71의 합성Synthesis Example 71. Synthesis of Compound 71

1) Synthesis of Intermediate 99

N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N-(3-chloro-5-methylphenyl)-1,1,3,3-tetra under nitrogen atmosphere Methyl-2,3-dihydro-1H-inden-5-amine 30g, bis(4-(tert-butyl)phenyl)amine 16.5g, sodium-tert-butoxide 11.1g, bis(tri-tert-butylphos) Pin) Palladium (0) 0.3g was added to 450ml of toluene and stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and 34 g of intermediate 99 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 768

2) Synthesis of Compound 71

In a nitrogen atmosphere, 25 g of intermediate 99 and 21.7 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After extraction after completion of the reaction, 7.3g of compound 71 was obtained through recrystallization (29% yield). MS[M+H]+ = 776

합성예 72. 화합물72의 합성Synthesis Example 72. Synthesis of Compound 72

1) Synthesis of Intermediate 100

Intermediate 1 30g, 3-(tert-butyl)-N-(4-(tert-butyl)phenyl)aniline 15.7g, sodium-tert-butoxide 10.8g, bis(tri-tert-butylphosphine) under nitrogen atmosphere After adding 0.3 g of palladium (0) to 450 ml of toluene, the mixture was stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and 33 g of the intermediate 100 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 782

2) Synthesis of compound 72

In a nitrogen atmosphere, 25 g of the intermediate 100 and 21.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.5 g of compound 72 was obtained through recrystallization (yield 30%). MS[M+H]+ = 790

By introducing various substituents using the same method as in the above synthesis example, in addition to the above compound, a compound represented by Chemical Formula 100 may be synthesized.

<실험예 1> 소자예<Experimental Example 1> Device Example

실시예 1-1Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,400Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

First and second hole injection layers were formed by thermal vacuum deposition of the following HI-A and HAT-CN to a thickness of 650 Å and 50 Å, respectively, on the ITO transparent electrode prepared as described above. On the hole injection layer, the following HT-A was vacuum deposited to a thickness of 600 Å to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. Subsequently, a light emitting layer was formed by vacuum depositing 4 parts by weight of Compound 1 of the present invention as a blue light emitting dopant on the electron blocking layer to a thickness of 200 Å as a host and 4 parts by weight of the compound 1 based on 100 parts by weight of the emission layer. Then, 50 Å of the following compound ET-A was vacuum-deposited on the light-emitting layer as a first electron transport layer, and subsequently ET-B and LiQ were vacuum-deposited at a 1:1 weight ratio to form a second electron transport layer having a thickness of 360 Å. LiQ was vacuum deposited on the second electron transport layer to form an electron injection layer by vacuum deposition to a thickness of 5 Å. A cathode was formed by depositing aluminum and silver at a thickness of 220 Å on the electron injection layer at a weight ratio of 10:1, and depositing aluminum to a thickness of 1000 Å thereon.

In the above process, the deposition rate of organic materials was maintained at 0.4 ~ 0.9 Å/sec, and the deposition rate of aluminum at the cathode was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^-7 ~ 5 Х 10 ^-8 torr. To prepare an organic light emitting device

실시예 1-2 내지 1-6, 1-8 내지 1-23, 1-25 내지 1-27 및 1-29 내지 1-68Examples 1-2 to 1-6, 1-8 to 1-23, 1-25 to 1-27 and 1-29 to 1-68

A device was fabricated in the same manner as in Example 1-1, except that the dopant of the light emitting layer in Example 1-1 was used as the compound shown in Table 1 below.

비교예 1-1 및 1-2Comparative Examples 1-1 and 1-2

The efficiency, lifetime, and color coordinates (based on 1931 CIE color coordinates) at a current density of 10 mA/cm 2 of the organic light emitting devices fabricated in the above Examples and Comparative Examples were measured, and the results are shown in Table 1 below.

	도펀트 물질Dopant material	효율(cd/A)Efficiency (cd/A)	색좌표Color coordinates		수명life span
	도펀트 물질Dopant material	효율(cd/A)Efficiency (cd/A)	CIE (x)CIE (x)	CIE (y)CIE (y)	T95(hr)T95(hr)
실시예 1-1 Example 1-1	화합물 1Compound 1	9.129.12	0.150.15	0.050.05	271271
실시예 1-2 Example 1-2	화합물 2Compound 2	9.129.12	0.150.15	0.050.05	272272
실시예 1-3 Example 1-3	화합물 3Compound 3	9.249.24	0.140.14	0.050.05	283283
실시예 1-4 Example 1-4	화합물 4Compound 4	9.289.28	0.150.15	0.050.05	285285
실시예 1-5 Example 1-5	화합물 5Compound 5	9.299.29	0.150.15	0.050.05	282282
실시예 1-6 Example 1-6	화합물 6Compound 6	9.299.29	0.150.15	0.050.05	284284
실시예 1-8 Example 1-8	화합물 8Compound 8	9.149.14	0.140.14	0.050.05	273273
실시예 1-9 Example 1-9	화합물 9Compound 9	9.269.26	0.140.14	0.050.05	284284
실시예 1-10 Example 1-10	화합물 10Compound 10	9.459.45	0.150.15	0.060.06	291291
실시예 1-11 Example 1-11	화합물 11Compound 11	9.449.44	0.150.15	0.060.06	292292
실시예 1-12 Example 1-12	화합물 12Compound 12	9.459.45	0.150.15	0.060.06	289289
실시예 1-13 Example 1-13	화합물 13Compound 13	9.459.45	0.150.15	0.050.05	291291
실시예 1-14 Example 1-14	화합물 14Compound 14	9.49.4	0.150.15	0.050.05	292292
실시예 1-15 Example 1-15	화합물 15Compound 15	9.779.77	0.140.14	0.050.05	294294
실시예 1-16 Example 1-16	화합물 16Compound 16	9.779.77	0.140.14	0.050.05	292292
실시예 1-17 Example 1-17	화합물 17Compound 17	9.159.15	0.150.15	0.060.06	274274
실시예 1-18 Example 1-18	화합물 18Compound 18	9.159.15	0.150.15	0.060.06	272272
실시예 1-19 Example 1-19	화합물 19Compound 19	9.169.16	0.150.15	0.060.06	273273
실시예 1-20 Example 1-20	화합물 20Compound 20	9.159.15	0.150.15	0.060.06	275275
실시예 1-21 Example 1-21	화합물 21Compound 21	9.159.15	0.150.15	0.060.06	276276
실시예 1-22 Example 1-22	화합물 22Compound 22	9.299.29	0.150.15	0.060.06	283283
실시예 1-23 Example 1-23	화합물 23Compound 23	9.519.51	0.150.15	0.060.06	289289
실시예 1-25 Example 1-25	화합물 25Compound 25	9.489.48	0.150.15	0.060.06	291291
실시예 1-26 Example 1-26	화합물 26Compound 26	9.199.19	0.140.14	0.050.05	277277
실시예 1-27 Example 1-27	화합물 27Compound 27	9.29.2	0.140.14	0.050.05	280280
실시예 1-29 Example 1-29	화합물 29Compound 29	9.349.34	0.140.14	0.050.05	281281
실시예 1-30 Example 1-30	화합물 30Compound 30	9.339.33	0.140.14	0.050.05	283283
실시예 1-31 Example 1-31	화합물 31Compound 31	9.319.31	0.150.15	0.060.06	281281
실시예 1-32 Example 1-32	화합물 32Compound 32	9.339.33	0.140.14	0.050.05	280280
실시예 1-33 Example 1-33	화합물 33Compound 33	9.339.33	0.140.14	0.050.05	281281
실시예 1-34 Example 1-34	화합물 34Compound 34	9.329.32	0.140.14	0.050.05	280280
실시예 1-35 Example 1-35	화합물 35Compound 35	9.489.48	0.150.15	0.050.05	290290
실시예 1-36 Example 1-36	화합물 36Compound 36	9.819.81	0.150.15	0.050.05	290290
실시예 1-37 Example 1-37	화합물 37Compound 37	9.839.83	0.150.15	0.050.05	289289
실시예 1-38 Example 1-38	화합물 38Compound 38	9.59.5	0.150.15	0.060.06	285285
실시예 1-39 Example 1-39	화합물 39Compound 39	9.499.49	0.150.15	0.060.06	287287
실시예 1-40 Example 1-40	화합물 40Compound 40	9.59.5	0.150.15	0.060.06	285285
실시예 1-41 Example 1-41	화합물 41Compound 41	9.59.5	0.150.15	0.060.06	286286
실시예 1-42 Example 1-42	화합물 42Compound 42	9.59.5	0.150.15	0.060.06	282282
실시예 1-43 Example 1-43	화합물 43Compound 43	9.59.5	0.150.15	0.060.06	284284
실시예 1-44 Example 1-44	화합물 44Compound 44	9.319.31	0.150.15	0.060.06	280280
실시예 1-45 Example 1-45	화합물 45Compound 45	9.299.29	0.150.15	0.050.05	281281
실시예 1-46 Example 1-46	화합물 46Compound 46	9.39.3	0.150.15	0.050.05	280280
실시예 1-47 Example 1-47	화합물 47Compound 47	9.469.46	0.150.15	0.050.05	288288
실시예 1-48 Example 1-48	화합물 48Compound 48	9.459.45	0.150.15	0.050.05	286286
실시예 1-49 Example 1-49	화합물 49Compound 49	9.789.78	0.140.14	0.050.05	290290
실시예 1-50 Example 1-50	화합물 50Compound 50	9.169.16	0.150.15	0.060.06	274274
실시예 1-51 Example 1-51	화합물 51Compound 51	9.149.14	0.150.15	0.060.06	275275
실시예 1-52 Example 1-52	화합물 52Compound 52	9.439.43	0.150.15	0.050.05	284284
실시예 1-53 Example 1-53	화합물 53Compound 53	9.759.75	0.140.14	0.050.05	293293
실시예 1-54 Example 1-54	화합물 54Compound 54	9.39.3	0.150.15	0.050.05	283283
실시예 1-55 Example 1-55	화합물 55Compound 55	9.319.31	0.150.15	0.060.06	285285
실시예 1-56 Example 1-56	화합물 56Compound 56	9.39.3	0.150.15	0.060.06	284284
실시예 1-57 Example 1-57	화합물 57Compound 57	9.319.31	0.150.15	0.060.06	284284
실시예 1-58 Example 1-58	화합물 58Compound 58	9.339.33	0.150.15	0.050.05	283283
실시예 1-59 Example 1-59	화합물 59Compound 59	9.899.89	0.150.15	0.050.05	290290
실시예 1-60 Examples 1-60	화합물 60Compound 60	9.159.15	0.150.15	0.050.05	274274
실시예 1-61 Example 1-61	화합물 61Compound 61	9.479.47	0.150.15	0.060.06	290290
실시예 1-62 Example 1-62	화합물 62Compound 62	9.319.31	0.150.15	0.060.06	285285
실시예 1-63 Example 1-63	화합물 63Compound 63	9.869.86	0.150.15	0.050.05	289289
실시예 1-64Example 1-64	화합물 64Compound 64	9.859.85	0.150.15	0.050.05	295295
실시예 1-65Example 1-65	화합물 65Compound 65	9.889.88	0.150.15	0.050.05	294294
실시예 1-66Example 1-66	화합물 66Compound 66	9.489.48	0.150.15	0.050.05	291291
실시예 1-67Example 1-67	화합물 67Compound 67	9.399.39	0.140.14	0.050.05	290290
실시예 1-68Example 1-68	화합물 68Compound 68	9.349.34	0.150.15	0.050.05	288288
비교예 1-1Comparative Example 1-1	화합물 BD1Compound BD1	7.547.54	0.150.15	0.050.05	240240
비교예 1-2Comparative Example 1-2	화합물 BD2Compound BD2	7.837.83	0.150.15	0.050.05	245245

As can be seen in Table 1, when the compound represented by Chemical Formula 100 is used as a dopant for an emission layer of an organic light-emitting device, it can be seen that the efficiency and lifetime of the device are increased.

<실험예 2> MD 계산 (Host-dopant system에서의 분자간의 거리계산)<Experimental Example 2> MD calculation (Calculation of distance between molecules in Host-dopant system)

실시예 2-1Example 2-1

A system containing compound 1 (dopant) and compound BH (host) in a weight ratio of 5:95 was implemented. Specifically, using the OPLS3e force field, set 300 molecules (host 95%, dopant 5% ratio), temperature 300K, simulation time 3ns, and calculate NVT and NPT as Molecular Dynamics. By calculation, the environment of the doped device was calculated and chemically implemented.

실시예 2-2 내지 2-5Examples 2-2 to 2-5

A molecular system was calculated in the same manner as in Example 2-1, except that the dopant shown in Table 2 below was used instead of Compound 1 in Example 2-1.

비교예 2-1 및 2-2Comparative Examples 2-1 and 2-2

A molecular system was calculated in the same manner as in Example 2-1, except that the dopant shown in Table 2 below was used instead of Compound 1 in Example 1.

The implemented molecular model is shown in FIGS. 3 to 9. 3 to 7 show the systems of Examples 2-1 to 2-5, respectively, and FIGS. 8 and 9 show the systems of Comparative Examples 2-1 and 2-2. The values obtained by calculating the total density and the average distance between different molecules at this time are shown in Table 2 below.

	도펀트 Dopant	전체 밀도Density(g/cm³)Overall Density(g/cm ³ )	분자간 평균 거리Radial(Å)Average distance between molecules Radial (Å)
실시예 2-1Example 2-1	화합물 1 Compound 1	1.0931.093	15.2015.20
실시예 2-2Example 2-2	화합물 10 Compound 10	1.0901.090	15.4715.47
실시예 2-3Example 2-3	화합물 59Compound 59	1.071.07	15.7715.77
실시예 2-4Example 2-4	화합물 71Compound 71	1.0861.086	15.2415.24
실시예 2-5Example 2-5	화합물 72Compound 72	1.0921.092	15.3215.32
비교예 2-1Comparative Example 2-1	화합물 BD1Compound BD1	1.121.12	14.714.7
비교예 2-2Comparative Example 2-2	화합물 BD2Compound BD2	1.0941.094	15.115.1

Referring to Table 2 and FIGS. 3 to 9, it can be seen that as the aliphatic hydrocarbon ring is substituted with a methyl group, the distance between the host and the dopant increases, and the overall density decreases. When substances in a space are concentrated, dexter transfer between molecules occurs, reducing efficiency. In the case of including an aliphatic hydrocarbon ring substituted with a methyl group, as in Examples 2-1 to 2-5 of the present invention, the distance between molecules increases and the density decreases, increasing the efficiency of the device, and injection of unnecessary electrons and holes This decreases, thus improving the life of the device.

Claims

Polycyclic compound represented by the following formula 100:

[Chemical Formula 100]

In Formula 100,

R1 and R301 are the same as or different from each other, and each independently deuterium; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

x101 is 1 or 2,

Cy3 and Cy4 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocycle, or a ring in which two or more rings selected from the group are fused,

R302 is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n1 is an integer of 1 to 3, n301 is an integer of 1 to 4, n302 is an integer of 0 to 10,

When n1, n301 and n302 are each 2 or more, the substituents in parentheses are the same as or different from each other,

At least one of Cy3 and Cy4 is one selected from Formulas A-1 to A-3,

In the formulas A-1 to A-3,

The dotted line is the position connected to Formula 100,

Q1 is O; S; Or C(R118)(R119),

R101 to R104, R118 and R119 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

x11 is 1 or 2,

n101 is an integer from 0 to 7, n102 is an integer from 0 to 11, n103 is an integer from 0 to 4, n104 is an integer from 0 to 5,

When n101 to n104 are each 2 or more, the substituents in parentheses are the same as or different from each other,

At least one of the aliphatic rings contained in Formula 100 is selected from the following structures,

In the above structure,

The dotted double line is the condensed position,

R105 to R114 are the same as or different from each other, and each independently, a substituted or unsubstituted alkyl group,

R115 to R117 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n115 is an integer of 0 to 2, n116 and n117 are each an integer of 0 to 4,

When n115 to n117 are each 2 or more, the substituents in parentheses are the same as or different from each other.
The method of claim 1, wherein the formula 100 is a polycyclic compound represented by any one of the following formulas 1 to 3:

[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

R1, Cy3, Cy4 and n1 are as defined in Chemical Formula 100,

R3 and R4 are the same as or different from each other, and each independently, deuterium; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R2, R5, R6, and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n3 and n4 are each an integer of 1 to 4, n2, n5 and n6 are each an integer of 0 to 10, n8 is an integer of 0 to 8,

When n2 to n6 and n8 are each 2 or more, the substituents in parentheses are the same as or different from each other.
The method according to claim 1, Cy3 and Cy4 are the same as or different from each other, each independently, is selected from the following groups A-11 to A-14, At least one of Cy3 and Cy4 is selected from the following groups A-11 to A-13 Polycyclic compound:

[Group A-11]

[Group A-12]

[Group A-13]

[Group A-14]

In the above groups A-11 to A-14,

The dotted line is the position connected to Formula 100,

Q1 is O; S; Or C(R118)(R119),

R41 to R44, R46 to R50, R53 to R55, R118 and R119 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R45, R51 and R52 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

n41, n43 and n44 are each an integer of 0 to 7, n42, n49 and n50 are each an integer of 0 to 5,

When n41 to n44, n49 and n50 are each 2 or more, the substituents in parentheses are the same as or different from each other.
The method according to claim 1,

Formula 100 is a polycyclic compound represented by any one of the following Formulas 101 to 109:

[Formula 101]

[Formula 102]

[Chemical Formula 103]

[Formula 104]

[Chemical Formula 105]

[Chemical Formula 106]

[Chemical Formula 107]

[Formula 108]

[Formula 109]

In Formulas 101 to 109,

Cy3 and Cy4 are as defined in Chemical Formula 100,

R22, R31, G1, G2 and Y1 to Y6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R21 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

At least one of G1 and G2 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

n22 and n31 are each an integer of 0 to 2, y1 and y5 are each an integer of 0 to 4, y2 to y4 and y6 are each an integer of 0 to 6,

When n22, n31 and y1 to y6 are each 2 or more, the substituents in parentheses are the same as or different from each other.
The method according to claim 1,

Formula 100 is a polycyclic compound represented by any one of the following Formulas 201 to 209:

[Formula 201]

[Formula 202]

[Formula 203]

[Formula 204]

[Formula 205]

[Formula 206]

[Formula 207]

[Chemical Formula 208]

[Chemical Formula 209]

In Formulas 201 to 209,

Q1 is as defined in Chemical Formula 100,

Cy5 to Cy7 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocycle, or a ring in which two or more rings selected from the group are fused,

R22, R31 to R38, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

R21 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

At least one of G1 and G2 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

x1 to x3 are each 1 or 2,

n22, n31, n36 and n37 are each an integer of 0 to 2, n32 and n35 are each an integer of 0 to 4, n33 is an integer of 0 to 5, n34 and n38 are each an integer of 0 to 3,

When n22 and n31 to n38 are each 2 or more, the substituents in parentheses are the same as or different from each other,

Cy11 to Cy13 are the same as or different from each other, and each independently, is selected from the following structures,

In the above structure,

The dotted double line is the condensed position,

R121 to R123 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; Or a substituted or unsubstituted heterocyclic group, or bonded to each other with an adjacent substituent to form a substituted or unsubstituted ring,

n121 is an integer of 0 to 2, n122 and n123 are each an integer of 0 to 4, when n121 to n123 are each 2 or more. The substituents in parentheses are the same as or different from each other.
The method according to claim 1,

R1 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Arylheteroarylamine group having 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group; Or a polycyclic compound of the formula Het1:

[Chemical Formula Het1]

In the formula Het1,

The dotted line is the position connected to Chemical Formula 100,

R203 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms or a substituent connected with two or more groups selected from the group,

n205 is an integer from 0 to 12, and when n205 is 2 or more, R205 is the same as or different from each other.
The method of claim 4,

Any one of G1 and G2 is an alkyl group having 1 to 6 carbon atoms unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; A C6-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group, a C6-C20 aryl group, or a C7-C30 alkylaryl group; Or -N(R211)(R121), and the other is hydrogen or deuterium,

At least one of Cy3 and Cy4 is selected from Formulas A-1 to A-3, and the rest are at least one substituent selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 30 carbon atoms or selected from the group. It is an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with a substituent connected to two or more groups,

R21 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Deuterium, an N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group; Or -N(R211)(R121),

R211 and R212 are the same as or different from each other, each independently substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms in which an aliphatic hydrocarbon ring having 5 or 6 carbon atoms is condensed or uncondensed ; Or a polycyclic compound that is a heterocyclic group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms.
The method according to claim 1,

Formula 100 is a polycyclic compound represented by any one of the following compounds:

.
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the polycyclic compound according to any one of claims 1 to 8. device.
The method of claim 9,

The organic material layer includes an emission layer, and the emission layer includes the polycyclic compound.
The method of claim 9,

The organic material layer includes a light emitting layer,

The emission layer includes the polycyclic compound as a dopant of the emission layer, and an organic light-emitting device comprising a compound represented by Formula H as a host of the emission layer:

[Formula H]

In the formula H,

L21 and L22 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 heteroarylene group,

Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R201 and R202 are the same as or different from each other, and each independently 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,

n202 is an integer from 0 to 7, and when n202 is 2 or more, R202 is the same as or different from each other.
The organic material of claim 9, wherein the organic material layer further comprises one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. Light-emitting element.