WO2021020942A1

WO2021020942A1 - Organic light-emitting element

Info

Publication number: WO2021020942A1
Application number: PCT/KR2020/010164
Authority: WO
Inventors: 금수정; 허동욱; 홍완표; 이우철; 노지영
Original assignee: 주식회사 엘지화학
Priority date: 2019-07-31
Filing date: 2020-07-31
Publication date: 2021-02-04
Also published as: KR20210015720A; CN113228335A; KR102377686B1

Abstract

The present specification provides an organic light-emitting element including: a compound represented by chemical formula 1 or 2; and a compound represented by chemical formula 3.

Description

Organic light emitting element

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

This application claims the interest of the filing date of the Korean Patent Application No. 10-2019-0093157 filed with the Korean Intellectual Property Office on July 31, 2019, the entire contents of which are incorporated herein.

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, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. 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.

Development of a new material for the organic light emitting device as described above is continuously required.

[Prior Technical Literature] (Patent Literature 1) Chinese Patent Publication No. 108137618

An organic light emitting device is described herein.

An exemplary embodiment of the present specification is a first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a first organic material layer including a compound represented by Formula 1 or 2 and a second organic material layer including a compound represented by Formula 3 below. It provides an organic light-emitting device including an organic material layer.

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,

A1, A2, R1 to R3, Z1 and Z2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

n1 to n3 are each an integer of 0 to 3, and when n1 to n3 are each 2 or more, the substituents in two or more parentheses are the same or different from each other,

p1 is 0 or 1,

[Formula 2]

In Formula 2,

E1 to E3 are the same as or different from each other, and each independently an aromatic hydrocarbon ring,

At least one of R4 to R8 is represented by the following formula 1-A or 1-B, or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, the remainder being the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

n4 and n5 are each an integer of 0 to 4, n6 is an integer of 0 to 3, n7 and n8 are each an integer of 0 to 5,

n4 + n5 + n6 + n7 + n8 is 1 or more,

When n4 to n8 are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other,

[Formula 1-A]

[Formula 1-B]

In the formulas 1-A and 1-B,

T1 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,

L11 is a direct bond; Or a substituted or unsubstituted arylene group,

p2 is 0 or 1,

Means a position bonded to Formula 2,

[Formula 3]

In Chemical Formula 3,

At least one of X1 to X3 is N, and the rest are each independently N or CH,

L is a direct bond; Or a substituted or unsubstituted arylene group,

Ar5 and Ar6 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,

Ar7 is a substituted or unsubstituted m is aryl group; Or substituted or unsubstituted m is a cycloalkyl group,

m is an integer of 2 to 4, and when m is 2 or more, the substituents in two or more parentheses are the same or different from each other.

The organic light emitting device described in the present specification includes the compound represented by Formula 1 or 2 in the first organic material layer and the compound represented by Formula 3 in the second organic material layer, thereby having a low driving voltage, excellent efficiency characteristics, and excellent Have a lifespan. Specifically, low driving voltage, high efficiency, and lifespan may be improved by controlling the degree of electron transport through the adjustment of an appropriate HOMO energy level and LUMO energy level.

1, 2, and 8 show examples of an organic light-emitting device according to an exemplary embodiment of the present specification.

3 to 7 show examples of organic light emitting devices including two or more stacks.

[Explanation of code]

1: substrate/ 2: anode/ 3: hole injection layer/ 4: hole transport layer/ 4a: first hole transport layer/ 4b: second hole transport layer/ 4c: third hole transport layer/ 4d: fourth hole transport layer/ 4e: agent 5 hole transport layer/ 4f: sixth hole transport layer/ 4p: p-doped hole transport layer/ 4R: red hole transport layer/ 4G: green hole transport layer/ 4B: blue hole transport layer/ 5: electron blocking layer/ 6: light emitting layer/ 6a: First emitting layer/6b: second emitting layer 6c: third emitting layer 6BF: blue fluorescent emitting layer 6BFa: first blue fluorescent emitting layer 6BFb: second blue fluorescent emitting layer 6YGP: yellow green phosphorescent emitting layer 6RP: red phosphorescent emitting layer / 6GP: green phosphorescent emission layer/ 7: hole blocking layer/ 8: electron injection and transport layer/ 9: electron transport layer/ 9a: first electron transport layer/ 9b: second electron transport layer/ 9c: third electron transport layer/ 10: electron injection Layer/ 11: Cathode/ 12: N-type charge generation layer/ 12a: First N-type charge generation layer/ 12b: Second N-type charge generation layer/ 13: P-type charge generation layer/ 13a: First P-type charge generation Layer/ 13b: second P-type charge generation layer/ 14: capping layer

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

The present specification provides an organic light-emitting device including a first organic material layer including a compound represented by Formula 1 or 2 and a second organic material layer including a compound represented by Formula 3 at the same time. Since the organic light-emitting device includes the first organic material layer and the second organic material layer at the same time, it has characteristics of low voltage, high efficiency, and long life. The emission layer containing the compound of Formula 1 or 2 has a shallow HOMO level, and the compound of Formula 3 has a deep HOMO and LUMO level, so electrons can be easily transferred to the emission layer, thereby exhibiting high efficiency and lifetime.

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.

In this specification, a dotted line or

Means a site bonded to another substituent or a bonding portion.

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); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl group; Alkenyl group; Alkynyl group; Alkoxy group; Alkylthio group; Aryloxy group; Arylthio group; Cycloalkyl group; Aryl group; Amine group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or it means that no substituents are present.

In the present specification, the connection of two or more substituents means that hydrogen of any one of the substituents is replaced 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, "substituted with A or B" includes a case where only A or B is substituted, as well as a case where A and B are substituted.

In the present specification, "substituted or unsubstituted" is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; Alkynyl group having 2 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; Aryloxy group having 6 to 30 carbon atoms; Arylthio group having 6 to 30 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Aryl group having 6 to 30 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or not having any substituents.

In the present specification, "substituted or unsubstituted" is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; An alkyl group having 1 to 6 carbon atoms; An alkenyl group having 2 to 6 carbon atoms; Alkynyl group having 2 to 6 carbon atoms; An alkoxy group having 1 to 6 carbon atoms; An alkylthio group having 1 to 6 carbon atoms; Aryloxy group having 6 to 20 carbon atoms; Arylthio group having 6 to 20 carbon atoms; A cycloalkyl group having 3 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Amine group; And it is substituted with one or more substituents selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.

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 alkyl group includes a linear or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain. According to an example, propyl The group includes an n-propyl group and an isopropyl group, and the butyl group includes an n-butyl group, an isobutyl group and a tert-butyl group.

In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Cycloalkyl 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, an adamantyl group, and the like, but is not limited thereto.

In the present specification, cycloalkene is a cyclic group that has a double bond in the hydrocarbon ring, but is not aromatic, and the number of carbons is not particularly limited, but 3 to 60, 3 to 30, 3 to 20, or 3 to 10 to be. Cycloalkenes include 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 alkoxy group is an aryl group connected to an oxygen atom, an arylthio group is an alkyl group connected to a sulfur atom, and the above-described description of the alkyl group may be applied to the alkyl group of the alkoxy group and the alkylthio group.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , But is not limited thereto.

In the present specification, carbon atom 9 (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, etc., and two substituents may be bonded to each other to form a spiro structure such as cyclopentane and fluorene.

In the present specification, the substituted aryl group may include a form in which an aliphatic ring is condensed with an aryl group. For example, a tetrahydronaphthalene group having the following structure is included in a substituted aryl group. In the following structure, one of the carbons of the benzene ring may be linked to another position.

In the present specification, an aryloxy group is an aryl group connected to an oxygen atom, an arylthio group is an aryl group connected to a sulfur atom, and the aryl group described above may be applied to the aryl group of the aryloxy group and the arylthio group. The aryl group of the aryloxy group is the same as the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group includes a phenylthioxy group, 2- Methylphenyl thioxy group, 4-tert-butylphenyl thioxy group, and the like, but are not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the silyl group includes a dimethyl boron group, a diethyl boron group, a tert-butylmethyl boron group, a vinyl methyl boron group, a propyl methyl boron group, a methylphenyl boron group, a diphenyl boron group, a phenyl boron group, etc., but is not limited thereto. .

In the present specification, the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto. The amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. Can be.

In the present specification, the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted arylheteroarylamine group. The aryl group in the arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a bis(tert-butylphenyl)amine group, etc. , But is not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted arylheteroarylamine group.

In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group, and descriptions of the aryl group and the heteroaryl group to be described later may be applied.

In the present specification, the heterocyclic group is a cyclic group including one or more of N, O, S, and Si as a hetero atom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include a pyridyl group; Quinoline group; Thiophene group; Dibenzothiophene group; Furan group; Dibenzofuran group; Naphthobenzofuran group; Carbazole; Benzocarbazole group; Naphthobenzothiophene group; Hexahydrocarbazole group; Dihydroacridine group; Dihydrodibenzoazacillin group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group; Spiro (dibenzosilol-dibenzoazacillin) group; Spiro (acridine-fluorene) group, and the like, but are not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally close to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.

In the present specification, "the ring formed by bonding adjacent groups" refers to a hydrocarbon ring; Or a hetero ring.

In the present specification, "a 5-membered or 6-membered ring formed by bonding adjacent groups" means that the ring including the substituent participating in the ring formation is 5 or 6 members. It may include condensation of an additional ring to the ring including the substituent participating in the ring formation.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring is Except for those that are not monovalent, the above description of the cycloalkyl group may apply. Examples of the aromatic and aliphatic condensed ring include a 1,2,3,4-tetrahydronaphthalene group, and a 2,3-dihydro-1H-indene group, but are not limited thereto.

In the present specification, the description of the heterocyclic group may be applied, except that the heterocycle is not monovalent.

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

In the present specification, the aliphatic hydrocarbon ring means all hydrocarbon rings except for an aromatic hydrocarbon ring, and may include a cycloalkyl ring. Except that the cycloalkyl ring is a divalent group, the above description of the cycloalkyl group can be applied. The substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring condensed with an aromatic ring.

In the present specification, the description of the aryl group described above may be applied except that the arylene group is a divalent group.

In the present specification, the description of the cycloalkyl group may be applied except that the cycloalkylene group is a divalent group.

Hereinafter, Formula 1 will be described.

[Formula 1]

In the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkylthio group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or one or more substituents selected 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 by bonding with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms Or, two or more groups selected from the group may be substituted or unsubstituted with a connected substituent, and a monocyclic to bicyclic aliphatic or aromatic hydrocarbon ring may be condensed with the aliphatic hydrocarbon ring.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms; Or an aryl group having 6 to 20 carbon atoms; Alternatively, a 6-membered aliphatic hydrocarbon ring is formed in which a monocyclic to bicyclic hydrocarbon ring unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms is condensed or uncondensed by bonding with an adjacent group.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms; Or an aryl group having 6 to 20 carbon atoms; Alternatively, benzene or cyclohexane substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms is condensed or uncondensed to form a 6-membered aliphatic hydrocarbon ring.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; Or a substituted or unsubstituted phenyl group; Or it combines with an adjacent group to form a substituted or unsubstituted cyclohexane, a substituted or unsubstituted tetrahydronaphthalene, or a substituted or unsubstituted decahydronaphthalene. At this time, adjacent groups may be two selected from Ar1 to Ar4.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium; Or, by bonding with an adjacent group, cyclohexane substituted or unsubstituted with deuterium, tetrahydronaphthalene unsubstituted or substituted with deuterium, butyl group or phenyl group, or decahydronaphthalene substituted or unsubstituted with deuterium is formed. At this time, adjacent groups may be two selected from Ar1 to Ar4.

According to an exemplary embodiment of the present specification, two adjacent ones of Ar1 to Ar4 form a substituted or unsubstituted aliphatic hydrocarbon ring, and the other two are the aforementioned substituents.

In the present specification, Ar1 to Ar4 are combined with each other to form a ring Ar1 and Ar3; Or it means that Ar2 and Ar4 are bonded to each other to form a ring.

According to an exemplary embodiment of the present specification, when two of Ar1 to Ar4 are bonded to each other to form an aliphatic hydrocarbon ring, any one selected from the following rings is formed.

In the ring, Ar101 and Ar102 are the same as or different from each other, and among Ar1 to Ar4 are substituents that do not form an aliphatic hydrocarbon ring,

Y1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

y1 is an integer from 0 to 14, and when y1 is 2 or more, Y1 is the same as or different from each other.

According to an exemplary embodiment of the present specification, Y1 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.

According to another exemplary embodiment, Y1 is 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.

According to another exemplary embodiment, Y1 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium.

According to another exemplary embodiment, Y1 is hydrogen; heavy hydrogen; Methyl group; tert-butyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, Y1 is hydrogen; heavy hydrogen; Or a methyl group.

In the exemplary embodiment of the present specification, y1 is an integer of 0 to 8. In another exemplary embodiment, y1 is 0 to 4. In another exemplary embodiment, y1 is 0 or 1.

In the exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, Ar101 and Ar102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar101 and Ar102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, Ar101 and Ar102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluoro group; Methyl group; Ethyl group; Butyl group; Or a phenyl group.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 101 or 102.

In Formulas 101 and 102,

Definitions of A1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are the same as in Formula 1,

G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

G11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

g11 is an integer of 0 to 8, and when g11 is 2 or more, 2 or more G11 are the same as or different from each other,

p3 is 0 or 1.

In the exemplary embodiment of the present specification, the description of Ar1 to Ar4 described above may be applied to G1 to G4.

In the exemplary embodiment of the present specification, the description of Y1 described above may be applied to G11. In another exemplary embodiment, the description of y1 described above may be applied to g11.

In an exemplary embodiment of the present specification, p3 is 1.

In the exemplary embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, G11 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 it combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.

According to another exemplary embodiment, G11 is 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 it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to another exemplary embodiment, G11 is hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; Or a substituted or unsubstituted phenyl group; Or it combines with an adjacent group to form a substituted or unsubstituted cyclohexane, or a substituted or unsubstituted benzene.

According to another exemplary embodiment, G11 is hydrogen; heavy hydrogen; Methyl group; tert-butyl group; Or a phenyl group; Combines with adjacent groups to form cyclohexane substituted or unsubstituted with a methyl group; Or it is combined with an adjacent group to form benzene substituted or unsubstituted with a butyl group or a phenyl group.

According to an exemplary embodiment of the present specification, G11 is hydrogen; heavy hydrogen; Or a methyl group.

In the exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkylthio group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or by bonding with an adjacent group to form a substituted or unsubstituted C 5 to C 30 ring.

In another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group; Or they combine with each other to form a substituted or unsubstituted 5 or 6 membered ring.

According to another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms; Or combine with each other to form a 5 or 6 membered ring,

The aryl group, heterocyclic group or ring of A1 and A2 is at least one substituent selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a silyl group and an aryl group having 6 to 30 carbon atoms, or 2 selected from the

group A

5 or 6 membered hydrocarbon ring substituted or unsubstituted with the substituent to which the above group is connected, or substituted or unsubstituted with the above substituent is condensed or non-condensed.

According to another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms; Or combine with each other to form a 5 or 6 membered ring,

The aryl group, heterocyclic group or ring of A1 and A2 is at least one substituent selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or 2 selected from the group. A 5 or 6 membered hydrocarbon ring substituted or unsubstituted with the substituent to which the above group is connected, or substituted or unsubstituted with the above substituent is condensed or non-condensed.

In the exemplary embodiment of the present specification, A1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combined with A2 to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, A2 is hydrogen; Or deuterium; Or combined with A1 or R1 to form a substituted or unsubstituted ring.

In another exemplary embodiment, A2 is hydrogen; Or deuterium; Combines with A1 to form a substituted or unsubstituted 5- or 6-membered ring; Or combined with R1 to form a substituted or unsubstituted 5-membered or 6-membered ring.

In the exemplary embodiment of the present specification, A2 may form a ring by combining with adjacent A1 or R2.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 103 to 106 below.

In Formulas 103 to 106,

Definitions of R1 to R3, Z1, Z2, p1, Ar1 to Ar4, and n1 to n3 are the same as in Formula 1,

A3, A4, and G5 to G8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

Z3, Z4, G12 and G13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

g12 is an integer of 0 to 8, g13 is an integer of 0 to 4, and when g12 and g13 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different from each other,

p4 and p5 are 0 or 1, respectively.

In one embodiment of the present specification, the description of A1 described above may be applied to A3. In another embodiment, the description of A2 described above may be applied to A4.

In an exemplary embodiment of the present specification, p4 is the same as p1.

In an exemplary embodiment of the present specification, p5 is 1.

In the exemplary embodiment of the present specification, A3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In another exemplary embodiment, A3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In another exemplary embodiment, A3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.

In another exemplary embodiment, the aryl group or heterocyclic group of A3 is at least one substituent selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms; Or substituted or unsubstituted with a substituent to which two or more groups selected from the group are connected; Or a 5- or 6-membered hydrocarbon ring substituted or unsubstituted with the above substituent is condensed or non-condensed.

In another exemplary embodiment, the aryl group or heterocyclic group of A3 is at least one substituent selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms; Or substituted or unsubstituted with a substituent to which two or more groups selected from the group are connected; Or a 5- or 6-membered hydrocarbon ring substituted or unsubstituted with the above substituent is condensed or non-condensed.

In another exemplary embodiment, A3 is at least one substituent selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or a substituent connected with two or more groups selected from the group. An aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with and condensed or uncondensed with a 5- or 6-membered aliphatic hydrocarbon ring; Or one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or 2 to 2 carbon atoms unsubstituted or substituted with a substituent connected to two or more groups selected from the group It is a heterocyclic group of 20.

In another exemplary embodiment, A3 is 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 tetrahydronaphthalene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In another exemplary embodiment, A3 is deuterium, fluoro group, methyl group, ethyl group, propyl group, butyl group, 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), Ph-d5, naphthyl group Or a phenyl group unsubstituted or substituted with a tetramethyltetrahydronaphthalene group; Biphenyl group unsubstituted or substituted with deuterium, methyl group, ethyl group, propyl group, butyl group, trimethylsilyl group, or 2-phenylpropan-2-yl group; Terphenyl group unsubstituted or substituted with deuterium or butyl group; A naphthyl group unsubstituted or substituted with deuterium; A tetrahydronaphthalene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; A fluorenyl group unsubstituted or substituted with a deuterium or methyl group; Dibenzofuran group unsubstituted or substituted with deuterium or butyl group; Or a dibenzothiophene group unsubstituted or substituted with deuterium or butyl group.

In an exemplary embodiment of the present specification, A4 is hydrogen; Or deuterium; Or it combines with R1 to form a substituted or unsubstituted ring.

In another exemplary embodiment, A2 is hydrogen; Or deuterium; Or combined with R1 to form a substituted or unsubstituted 5-membered or 6-membered ring.

In another exemplary embodiment, A2 is hydrogen; Or deuterium; Or combined with R1 to form a 5- or 6-membered ring substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In another exemplary embodiment, the 5-membered or 6-membered ring formed by bonding of A2 and R1 is benzofuran, benzothiophene, or indene.

In the exemplary embodiment of the present specification, the description of G1 to G4 described above may be applied to G5 to G8. In another exemplary embodiment, the description of G11 described above may be applied to G12 and G13.

In the exemplary embodiment of the present specification, G5 to G8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, G5 to G8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, G5 to G8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, G12 and G13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.

According to another exemplary embodiment, G12 and G13 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; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to another exemplary embodiment, G12 and G13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted trimethylsilyl group; Or a substituted or unsubstituted phenyl group; Or it combines with an adjacent group to form a substituted or unsubstituted cyclohexane, or a substituted or unsubstituted benzene.

According to another exemplary embodiment, G12 is combined with adjacent G12 to form a substituted or unsubstituted ring.

According to another exemplary embodiment, G13 forms a substituted or unsubstituted ring by bonding with adjacent G13.

According to another exemplary embodiment, G12 is hydrogen; heavy hydrogen; Or a methyl group; Or they combine with adjacent G12 to form cyclohexane.

In another exemplary embodiment, G13 is hydrogen; heavy hydrogen; Methyl group; Trimethylsilyl group; Or a phenyl group; Or it combines with adjacent G13 to form benzene substituted or unsubstituted with a phenyl group.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-4 below.

In Formulas 1-1 to 1-4,

The definitions of R1 to R3, n1 to n3, and Ar1 to Ar4 are the same as in Formula 1,

A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

Z1 to Z4 and Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In the present specification, the fact that adjacent groups among Ar21 to Ar24 are bonded to each other to form a ring means i) two of Ar21 to Ar24 are bonded to each other to form an aliphatic hydrocarbon ring, or ii) all of Ar21 to Ar24 participate in ring formation to form a ring. It is meant to form a hydrocarbon ring.

In the exemplary embodiment of the present specification, descriptions of the aforementioned substituents of G5 to G8, the aliphatic hydrocarbon ring to which G11 is connected, and the aromatic hydrocarbon ring to which G12 is connected may be applied to Ar21 to Ar24.

In the exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group; Or it combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or combined with an adjacent group and substituted or unsubstituted with deuterium, an alkyl group having 1 to 6 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms, and a monocyclic to bicyclic hydrocarbon ring condensed or uncondensed It forms a six-membered hydrocarbon ring.

In another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or a six-membered group in which deuterium, an alkyl group having 1 to 6 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms is substituted or unsubstituted by bonding with an adjacent group, and cyclohexane or benzene is condensed or uncondensed To form a hydrocarbon ring.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group; Or it combines with an adjacent group to form a substituted or unsubstituted cyclohexane, a substituted or unsubstituted benzene, or a substituted or unsubstituted decahydronaphthalene. At this time, the adjacent groups may be two selected from Ar21 to Ar24.

According to another exemplary embodiment, Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Methyl group; Ethyl group; Or a phenyl group; Or cyclohexane in combination with an adjacent group; Decahydronaphthalene; Benzene unsubstituted or substituted with a methyl group, tert-butyl group, or trimethylsilyl group; Or a phenyl group substituted or unsubstituted naphthalene is formed. At this time, the adjacent groups may be two selected from Ar21 to Ar24.

According to an exemplary embodiment of the present specification, when two of Ar21 to Ar24 are bonded to each other to form a hydrocarbon ring, any one selected from the following rings is formed.

In the ring, Ar103 and Ar104 are the same as or different from each other, and among Ar21 to Ar24 are substituents that do not form an aliphatic hydrocarbon ring,

Y2 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

y2 is an integer from 0 to 14, and when y2 is 2 or more, Y2 is the same as or different from each other.

In the exemplary embodiment of the present specification, y2 is an integer of 0 to 8. In another exemplary embodiment, y2 is 0 to 4. In another exemplary embodiment, y2 is 0 or 1.

In the exemplary embodiment of the present specification, Ar103 and Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, Ar103 and Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar103 and Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C 1 to C 6 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, Ar103 and Ar104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluoro group; Methyl group; Ethyl group; Butyl group; Or a phenyl group.

[0366] According to an exemplary embodiment of the present specification, Y2 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Y2 is hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, Y2 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium.

According to another exemplary embodiment, Y2 is hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted trimethylsilyl group; Or a substituted or unsubstituted phenyl group.

[0366] According to an exemplary embodiment of the present specification, Y2 is hydrogen; heavy hydrogen; Or a methyl group.

According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkylthio group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or it is combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2-C90 heteroarylamine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Combined with an adjacent group to form a substituted or unsubstituted C2 to C30 ring.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; 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 arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group; Combined with an adjacent group to form a substituted or unsubstituted C2 to C20 ring.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; NY11Y12; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group; Combined with an adjacent group to form a substituted or unsubstituted C2 to C20 ring.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Arylsilyl group having 6 to 90 carbon atoms substituted or unsubstituted with deuterium; An alkylarylsilyl group having 7 to 60 carbon atoms unsubstituted or substituted with deuterium; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; An arylalkyl group having 7 to 60 carbon atoms unsubstituted or substituted with deuterium; One or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected 6 to 30 aryl groups; NY11Y12; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, alkyl group having 1 to 10 carbon atoms, silyl group and aryl group having 6 to 30 carbon atoms, or a substituent connected with two or more groups selected from the group It is a C2-C30 heterocyclic group; Combined with an adjacent group to form a C2 to C30 ring 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 two or more groups selected from the group.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; An arylsilyl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An alkylarylsilyl group having 7 to 40 carbon atoms substituted or unsubstituted with deuterium; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An arylalkyl group having 7 to 40 carbon atoms unsubstituted or substituted with deuterium; One or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or the number of carbon atoms unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected 6 to 20 aryl groups; NY11Y12; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, alkyl group having 1 to 6 carbon atoms, silyl group and aryl group having 6 to 20 carbon atoms, or a substituent connected with two or more groups selected from the group It is a C2-C20 heterocyclic group; Combined with an adjacent group, one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms, or two or more groups selected from the group, are substituted or unsubstituted with a connected substituent to form a ring having 2 to 20 carbon atoms.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; NY11Y12; A substituted or unsubstituted N-containing heterocyclic group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group; Or it combines with an adjacent group to form a substituted or unsubstituted benzofuran or a substituted or unsubstituted ring.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenylnaphthylamine group; A substituted or unsubstituted phenylbiphenylamine group; A substituted or unsubstituted bisbiphenylamine group; A substituted or unsubstituted phenyldibenzofuranamine group; A substituted or unsubstituted phenyldibenzothiophenamine group; A substituted or unsubstituted N-containing heterocyclic group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclo Forms hexene.

In another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenylnaphthylamine group; A substituted or unsubstituted phenylbiphenylamine group; A substituted or unsubstituted bisbiphenylamine group; A substituted or unsubstituted phenyldibenzofuranamine group; A substituted or unsubstituted phenyldibenzothiophenamine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted hexahydrocarbazole group; A substituted or unsubstituted dihydroacridine group; Substituted or unsubstituted phenoxazine; Substituted or unsubstituted phenothiazine group; A substituted or unsubstituted dihydrodibenzoazacillin group; Substituted or unsubstituted spiro (dibenzosilol-dibenzoazacillin group); Substituted or unsubstituted spiro (acridine-fluorene); A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclo Forms hexene.

According to another exemplary embodiment, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluoro group; A methyl group unsubstituted or substituted with deuterium; An isopropyl group unsubstituted or substituted with deuterium; Tert-butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a trifluoromethyl group, a trimethylsilyl group, or a naphthyl group; A naphthyl group unsubstituted or substituted with deuterium; Substituted with deuterium, fluoro group, cyano group, methyl group, CD ₃ , tert-butyl group, 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), trimethylsilyl group, triphenylsilyl group or phenyl group, or A diphenylamine group unsubstituted and condensed or non-condensed with hexene; Phenylnaphthylamine group unsubstituted or substituted with deuterium or tert-butyl group; Phenylbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; Bisbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; A phenyldibenzofuranamine group substituted or unsubstituted with deuterium, a methyl group, or a tertbutyl group and condensed or non-condensed with hexene; A phenyldibenzothiophenamine group substituted or unsubstituted with deuterium, a methyl group, or a tertbutyl group and condensed or non-condensed with hexene; Carbazole group unsubstituted or substituted with deuterium or tert-butyl group; A hexahydrocarbazole group substituted or unsubstituted with deuterium, a fluoro group, a cyano group, a methyl group, a phenyl group, or a Ph-d5, and condensed or non-condensed with hexane, hexene or benzene; A dihydroacridine group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group unsubstituted or substituted with a phenyl group; A spiro (acridine-fluorene) group unsubstituted or substituted with a methyl group; Spiro (dibenzosilol-dibenzoazacillin) group; Dibenzofuran group; Or a dibenzothiophene group.

According to another exemplary embodiment, R1 to R3 are benzofuran unsubstituted or substituted with a tert-butyl group or a phenyl group by bonding with an adjacent group; Naphthobenzofuran; thiophene unsubstituted or substituted with a tert-butyl group; Indole unsubstituted or substituted with a phenyl group; Indene unsubstituted or substituted with a methyl group or a tert-butyl group; spiro (fluorene-indene) unsubstituted or substituted with a tert-butyl group; Cyclopentene unsubstituted or substituted with a methyl group; Or to form a substituted or unsubstituted cyclohexene with a methyl group.

According to another exemplary embodiment, two adjacent R1; R1 and A2; R1 and A4; Or benzofuran unsubstituted or substituted with a tert-butyl group or a phenyl group by bonding adjacent two R 2; Naphthobenzofuran; thiophene unsubstituted or substituted with a tert-butyl group; Indole unsubstituted or substituted with a phenyl group; Indene unsubstituted or substituted with a methyl group or a tert-butyl group; spiro (fluorene-indene) unsubstituted or substituted with a tert-butyl group; Cyclopentene unsubstituted or substituted with a methyl group; Or to form a substituted or unsubstituted cyclohexene with a methyl group.

In another exemplary embodiment, the N-containing heterocyclic group of R1 to R3 may be represented by any one of the following Formulas HAr1 to HAr3, or Formula 1-B.

In the formulas HAr1 to HAr3,

Q1 is CY4Y5 or SiY4Y5, Q2 is C or Si,

Y3 to Y5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocycle,

y3 is an integer of 0 to 8, and when y3 is 2 or more, 2 or more Y3s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Y3 to Y5 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.

According to another exemplary embodiment, Y3 to Y5 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.

According to another exemplary embodiment, Y3 to Y5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium.

According to another exemplary embodiment, Y3 to Y5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; Or a phenyl group.

According to another exemplary embodiment, Y3 is a methyl group.

According to another exemplary embodiment, Y4 and Y5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; Or is a phenyl group

In the exemplary embodiment of the present specification, Y11 and Y12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted aromatic hydrocarbon ring and a condensed cyclic group of an aliphatic hydrocarbon ring.

In another exemplary embodiment, Y11 and Y12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted aromatic hydrocarbon ring and a condensed cyclic group having 9 to 30 carbon atoms of an aliphatic hydrocarbon ring.

In another exemplary embodiment, Y11 and Y12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 heterocyclic group; Or a substituted or unsubstituted aromatic hydrocarbon ring and a condensed cyclic group having 9 to 20 carbon atoms of an aliphatic hydrocarbon ring.

In another exemplary embodiment, Y11 and Y12 are the same as or different from each other, and each independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms. An aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents or a substituent to which two or more groups selected from the group are connected; 2 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, alkyl group having 1 to 10 carbon atoms, silyl group and aryl group having 6 to 30 carbon atoms or a substituent connected with two or more groups selected from the group A heterocyclic group of to 30; Or an aromatic unsubstituted or substituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group and an aryl group having 6 to 30 carbon atoms, or a substituent connected with two or more groups selected from the group. It is a condensed cyclic group having 9 to 30 carbon atoms of a hydrocarbon ring and an aliphatic hydrocarbon ring.

In another embodiment, Y11 and Y12 are the same as or different from each other, and each independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms. An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with one or more substituents or a substituent to which two or more groups selected from the group are connected; 2 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 6 carbon atoms, silyl groups and aryl groups having 6 to 20 carbon atoms, or a substituent connected with two or more groups selected from the group A heterocyclic group of to 20; Or an aromatic unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group and an aryl group having 6 to 20 carbon atoms, or a substituent connected with two or more groups selected from the group. It is a condensed cyclic group having 9 to 20 carbon atoms of a hydrocarbon ring and an aliphatic hydrocarbon ring.

In another embodiment, Y11 and Y12 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 7 to 60 carbon atoms, an alkyl having 1 to 30 carbon atoms A silyl group or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an arylsilyl group having 6 to 90 carbon atoms; A heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms; Or a condensed cyclic group having 9 to 30 carbon atoms of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms.

In another embodiment, Y11 and Y12 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkyl having 1 to 18 carbon atoms A silyl group or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an arylsilyl group having 6 to 60 carbon atoms; A C 2 to C 20 heterocyclic group unsubstituted or substituted with a deuterium or a C 1 to C 6 alkyl group; Or a condensed cyclic group having 9 to 20 carbon atoms of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In another exemplary embodiment, Y11 and Y12 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 naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted tetrahydronaphthalene group.

In another embodiment, Y11 and Y12 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkyl having 1 to 18 carbon atoms A phenyl group unsubstituted or substituted with a silyl group or an arylsilyl group having 6 to 60 carbon atoms; A biphenyl group unsubstituted or substituted with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms; A naphthyl group unsubstituted or substituted with a deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkylsilyl group having 1 to 18 carbon atoms, or an arylsilyl group having 6 to 60 carbon atoms; A dibenzofuran group unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; A dibenzothiophene group unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; Or a tetrahydronaphthalene group unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In another exemplary embodiment, Y11 and Y12 are the same as or different from each other, and each independently deuterium, fluoro group, cyano group, methyl group, CD ₃ , butyl group, trimethylsilyl group, triphenylsilyl group, or 2- Phenyl group unsubstituted or substituted with phenylpropan-2-yl group (2-phenylpropan-2-yl); Biphenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; Dibenzofuran group unsubstituted or substituted with deuterium or butyl group; Dibenzothiophene group unsubstituted or substituted with deuterium or butyl group; Or a tetrahydronaphthalene group unsubstituted or substituted with a deuterium or methyl group.

In the exemplary embodiment of the present specification, R1 to R3 are combined with an adjacent group to form a ring represented by Cy11 or Cy12 below. Specifically, two adjacent R1s; R1 and A2; R1 and A4; Or two adjacent R2s are bonded to each other to form a ring represented by the following formula Cy11 or Cy12.

In the formulas Cy11 and Cy12,

The dotted double line is the condensed position,

Q3 is O; S; NY9; CY10Y11; Or SiY10Y11,

Y7 to Y10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocycle; Combine with adjacent groups to form a substituted or unsubstituted ring,

p10 is 1 or 2,

r31 is an integer of 0 to 4, r32 is an integer of 0 to 8, and when r31 and r32 are each 2 or more, the substituents in two or more parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, Y7 to Y10 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, by bonding with an adjacent group, a ring having 3 to 30 carbon atoms is formed.

According to another exemplary embodiment, Y7 to Y10 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; Alternatively, it is combined with an adjacent group to form a ring having 3 to 20 carbon atoms.

According to another exemplary embodiment, Y7 to Y10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium; Or, by bonding with an adjacent group, hexane substituted or unsubstituted with deuterium, hexene substituted or unsubstituted with deuterium, or benzene substituted or unsubstituted with deuterium is formed.

According to another exemplary embodiment, Y7 to Y10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; tert-butyl group; Or a phenyl group.

According to another exemplary embodiment, Y7 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or a butyl group unsubstituted or substituted with deuterium; Combined with adjacent Y7 to form deuterium-substituted or unsubstituted benzene, or deuterium-substituted or unsubstituted hexene.

According to another exemplary embodiment, Y8 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or a butyl group unsubstituted or substituted with deuterium; It combines with adjacent Y8 to form deuterium substituted or unsubstituted benzene, or deuterium substituted or unsubstituted hexane.

According to another exemplary embodiment, Y9 is a phenyl group unsubstituted or substituted with deuterium.

In another exemplary embodiment, Y10 and Y11 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium or butyl group; Y10 and Y11 are phenyl groups unsubstituted or substituted with deuterium or butyl groups, respectively, and are bonded to each other to form fluorene unsubstituted or substituted with deuterium or butyl groups.

In another exemplary embodiment, Y10 and Y11 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium or butyl group; Y10 and Y11 are phenyl groups unsubstituted or substituted with deuterium or butyl groups, respectively, and are bonded to each other to form dibenzosilole, which is unsubstituted or substituted with deuterium or butyl groups.

In an exemplary embodiment of the present specification, y6 is 0 or 1.

In an exemplary embodiment of the present specification, y8 is 2 or more. In another exemplary embodiment, y8 is 4.

In an exemplary embodiment of the present specification, y8 is 2 or more, and two of Y8 are substituted or unsubstituted alkyl groups. In another exemplary embodiment, y8 is 2 or more, and two of Y8 are methyl groups unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, two adjacent R1; R1 and A2; R1 and A4; Or two adjacent R2s are bonded to each other to form a ring represented by Chemical Formula Cy11.

In another exemplary embodiment, two adjacent R1s; Or two adjacent R2s are bonded to each other to form a ring represented by the above formula Cy12.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluoro group; A methyl group unsubstituted or substituted with deuterium; An isopropyl group unsubstituted or substituted with deuterium; Tert-butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a trifluoromethyl group, a trimethylsilyl group, or a naphthyl group; A naphthyl group unsubstituted or substituted with deuterium; Substituted with deuterium, fluoro group, cyano group, methyl group, CD ₃ , tert-butyl group, 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), trimethylsilyl group, triphenylsilyl group or phenyl group, or A diphenylamine group unsubstituted and condensed or non-condensed with hexene; Phenylnaphthylamine group unsubstituted or substituted with deuterium or tert-butyl group; Phenylbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; Bisbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; A phenyldibenzofuranamine group substituted or unsubstituted with deuterium, a methyl group, or a tertbutyl group and condensed or non-condensed with hexene; A phenyldibenzothiophenamine group substituted or unsubstituted with deuterium, a methyl group, or a tertbutyl group and condensed or non-condensed with hexene; Deuterium, fluoro group, cyano group, methyl group, phenyl group or Ph-d5 substituted or unsubstituted, hexane, hexene or benzene condensed or uncondensed, or a hexahydrocarbazole group; Benzofuran unsubstituted or substituted with a tert-butyl group or a phenyl group by bonding with an adjacent group; Naphthobenzofuran; thiophene unsubstituted or substituted with a tert-butyl group; Indole unsubstituted or substituted with a phenyl group; Indene unsubstituted or substituted with a methyl group or a tert-butyl group; spiro (fluorene-indene) unsubstituted or substituted with a tert-butyl group; Cyclopentene unsubstituted or substituted with a methyl group; Or to form a substituted or unsubstituted cyclohexene with a methyl group.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Fluoro group; A methyl group unsubstituted or substituted with deuterium; An isopropyl group unsubstituted or substituted with deuterium; Tert-butyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a trifluoromethyl group, a trimethylsilyl group, or a naphthyl group; A naphthyl group unsubstituted or substituted with deuterium; Substituted with deuterium, fluoro group, cyano group, methyl group, CD ₃ , tert-butyl group, 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), trimethylsilyl group, triphenylsilyl group or phenyl group, or A diphenylamine group unsubstituted and condensed or non-condensed with hexene; Phenylnaphthylamine group unsubstituted or substituted with deuterium or tert-butyl group; Phenylbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; Bisbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; Carbazole group unsubstituted or substituted with deuterium or tert-butyl group; A hexahydrocarbazole group substituted or unsubstituted with deuterium, a fluoro group, a cyano group, a methyl group, a phenyl group, or a Ph-d5, and condensed or non-condensed with hexane, hexene or benzene; A dihydroacridine group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group unsubstituted or substituted with a phenyl group; A spiro (acridine-fluorene) group unsubstituted or substituted with a methyl group; Spiro (dibenzosilol-dibenzoazacillin) group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, n1 and n2 are integers of 0 to 2.

According to another exemplary embodiment, n1 and n2 are 0 or 1.

According to an exemplary embodiment of the present specification, n3 is 0 or 1.

According to an exemplary embodiment of the present specification, p1 is 0 or 1.

In the exemplary embodiment of the present specification, Z1 to Z4 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 another exemplary embodiment, Z1 to Z4 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 another exemplary embodiment, Z1 to Z4 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.

In another exemplary embodiment, Z1 to Z4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by any one of the following compounds.

Hereinafter, Formula 2 will be described.

[Formula 2]

According to an exemplary embodiment of the present specification, E1 to E3 are the same as or different from each other, and each independently an aromatic hydrocarbon ring.

According to another exemplary embodiment, E1 to E3 are the same as or different from each other, and each independently benzene or naphthalene.

According to another exemplary embodiment, E1 and E2 are the same as or different from each other, and each independently benzene or naphthalene.

According to another exemplary embodiment, E3 is benzene.

According to another exemplary embodiment, E1 to E3 are benzene.

In an exemplary embodiment of the present specification, at least one of R4 to R8 is represented by the following formula 1-A or 1-B, or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the remainder are the same as or different from each other. And each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

[Formula 1-A]

[Formula 1-B]

In the formulas 1-A and 1-B,

L11 is a direct bond; Or a substituted or unsubstituted arylene group,

p2 is 0 or 1,

Means a position bonded to Formula 2.

In the present specification, the heterocyclic group includes the formula 1-B.

According to another exemplary embodiment, at least one of R4 to R8 is represented by Formula 1-A or 1-B, or is bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, and the remainder is The same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkylthio group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or by bonding with an adjacent group to form a substituted or unsubstituted C 5 to C 30 ring.

According to another exemplary embodiment, at least one of R4 to R8 is represented by the above formula 1-A or 1-B or is bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the remainder are the same or different from each other. , Each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or hetero ring.

According to another exemplary embodiment, at least one of R4 to R8 is represented by the above formula 1-A or 1-B or is bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the remainder are the same or different from each other. , Each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted dimethylamine group; Or a substituted or unsubstituted diphenylamine group; Or a substituted or unsubstituted dihydroacridine group.

In the exemplary embodiment of the present specification, i) at least one of R4 to R8 is represented by Formula 1-A or 1-B, or ii) two adjacent R4s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring. Or iii) two adjacent R5s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, iv) two adjacent R6s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or v) adjacent Two R7s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or vi) two adjacent R8s are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In another exemplary embodiment, i) at least one of R4 to R8 is represented by Formula 1-A or 1-B, or ii) a 5-membered or unsubstituted or substituted with an alkyl group by bonding of two adjacent R4s To form a 6-membered aliphatic hydrocarbon ring, or iii) two adjacent R5s are bonded to each other to form a 5-membered or 6-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, or iv) two adjacent R6s are bonded to each other Forming a 5- or 6-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, v) two adjacent R 7 bonded to each other to form a 5- or 6-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, vi) Two adjacent R8s are bonded to each other to form a 5- or 6-membered aliphatic hydrocarbon ring unsubstituted or substituted with an alkyl group. At this time, the aliphatic hydrocarbon rings of ii) to vi) contain one or more alkyl groups as a substituent, and may also contain substituents other than the alkyl group.

In another exemplary embodiment, i) at least one of R4 to R8 is represented by Formula 1-A or 1-B, or ii) pentene substituted or unsubstituted with a methyl group by bonding of adjacent two R4s, or To form hexene substituted or unsubstituted with a methyl group, or iii) two adjacent R5s are bonded to each other to form pentene substituted or unsubstituted with a methyl group, or hexene substituted or unsubstituted with a methyl group, or iv) two adjacent R6 These are bonded to each other to form pentene substituted or unsubstituted with a methyl group, or hexene substituted or unsubstituted with a methyl group, or v) two adjacent R7s are bonded to each other to form pentene substituted or unsubstituted with a methyl group or substituted with a methyl group or To form unsubstituted hexene, or vi) two adjacent R8s are bonded to each other to form pentene substituted or unsubstituted with a methyl group, or hexene substituted or unsubstituted with a methyl group. At this time, the methyl group may be substituted with deuterium.

The compound of Formula 2 may correspond not only to one of i) to vi), but also to two or more of i) to vi). That is, the compound of compound 2 may correspond to i) and ii).

In an exemplary embodiment of the present specification, at least one of R4 to R8 is represented by Formula 1-A or 1-B, or the remaining substituents that do not form a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with an adjacent group (hereinafter, ' The remaining substituents of R4 to R8 are referred to as'.) are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, the description of R1 to R3 of Formula 1 may be applied to the remaining substituents among R4 to R8.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkylthio group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or it is combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C1 to C30 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 90 carbon atoms; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2-C90 heteroarylamine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Combined with an adjacent group to form a substituted or unsubstituted C2 to C30 ring.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; 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 C 1 to C 18 alkylamine group; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted C2 to C60 heteroarylamine group; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group; Combined with an adjacent group to form a substituted or unsubstituted C2 to C20 ring.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted C 1 to C 18 alkylsilyl group; A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms; 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 C 1 to C 18 alkylamine group; NY11Y12; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group; Combined with an adjacent group to form a substituted or unsubstituted C2 to C20 ring.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Arylsilyl group having 6 to 90 carbon atoms substituted or unsubstituted with deuterium; An alkylarylsilyl group having 7 to 60 carbon atoms unsubstituted or substituted with deuterium; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; An arylalkyl group having 7 to 60 carbon atoms unsubstituted or substituted with deuterium; One or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected 6 to 30 aryl groups; An alkylamine group having 1 to 30 carbon atoms unsubstituted or substituted with deuterium; NY11Y12; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, alkyl group having 1 to 10 carbon atoms, silyl group and aryl group having 6 to 30 carbon atoms, or a substituent connected with two or more groups selected from the group It is a C2-C30 heterocyclic group; Combined with an adjacent group to form a C2 to C30 ring 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 two or more groups selected from the group.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; An arylsilyl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An alkylarylsilyl group having 7 to 40 carbon atoms substituted or unsubstituted with deuterium; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An arylalkyl group having 7 to 40 carbon atoms unsubstituted or substituted with deuterium; One or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or the number of carbon atoms unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected 6 to 20 aryl groups; A substituted or unsubstituted C 1 to C 18 alkylamine group; NY11Y12; Or substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, alkyl group having 1 to 6 carbon atoms, silyl group and aryl group having 6 to 20 carbon atoms, or a substituent connected with two or more groups selected from the group It is a C2-C20 heterocyclic group; Combined with an adjacent group, one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms, or two or more groups selected from the group, are substituted or unsubstituted with a connected substituent to form a ring having 2 to 20 carbon atoms.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trimethylsilyl group; 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 dimethylamine group; NY11Y12; A substituted or unsubstituted N-containing heterocyclic group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group; Or it combines with an adjacent group to form a substituted or unsubstituted benzofuran or a substituted or unsubstituted ring.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trimethylsilyl group; 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 fluorenyl group; A substituted or unsubstituted dimethylamine group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenylnaphthylamine group; A substituted or unsubstituted phenylbiphenylamine group; A substituted or unsubstituted bisbiphenylamine group; A substituted or unsubstituted phenyldibenzofuranamine group; A substituted or unsubstituted phenyldibenzothiophenamine group; A substituted or unsubstituted N-containing heterocyclic group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclo Forms hexene.

In another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted trimethylsilyl group; 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 fluorenyl group; A substituted or unsubstituted dimethylamine group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenylnaphthylamine group; A substituted or unsubstituted phenylbiphenylamine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dihydroacridine group; Substituted or unsubstituted phenoxazine; Substituted or unsubstituted phenothiazine group; A substituted or unsubstituted dihydrodibenzoazacillin group; Substituted or unsubstituted spiro (dibenzosilol-dibenzoazacillin group); Substituted or unsubstituted spiro (acridine-fluorene); A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted benzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted cyclopentene, or a substituted or unsubstituted cyclo Forms hexene.

According to another exemplary embodiment, the remaining substituents of R4 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluoro group; A methyl group unsubstituted or substituted with deuterium; An isopropyl group unsubstituted or substituted with deuterium; Tert-butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, a trifluoromethyl group, a trimethylsilyl group, a butyldimethylsilyl group or a naphthyl group; Biphenyl group unsubstituted or substituted with deuterium, fluoro group, or tert-butyl group; Terphenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A fluorenyl group unsubstituted or substituted with deuterium or a methyl group; A dimethylamine group unsubstituted or substituted with deuterium; Substituted with deuterium, fluoro group, cyano group, methyl group, CD ₃ , tert-butyl group, 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), trimethylsilyl group, triphenylsilyl group or phenyl group, or A diphenylamine group unsubstituted and condensed or non-condensed with hexene; Phenylnaphthylamine group unsubstituted or substituted with deuterium or tert-butyl group; Phenylbiphenylamine group unsubstituted or substituted with deuterium or tert-butyl group; Carbazole group unsubstituted or substituted with deuterium or tert-butyl group; A dihydroacridine group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; Phenoxazine; Phenothiazine; Dihydrodibenzoazacillin group unsubstituted or substituted with a phenyl group; A spiro (acridine-fluorene) group unsubstituted or substituted with a methyl group; Spiro (dibenzosilol-dibenzoazacillin) group; Dibenzofuran group; Or a dibenzothiophene group.

According to another exemplary embodiment, the remaining substituents of R4 to R8 are bonded to adjacent groups to be substituted or unsubstituted with tert-butyl group or phenyl group; Naphthobenzofuran; thiophene unsubstituted or substituted with a tert-butyl group; Indole unsubstituted or substituted with a phenyl group; Indene unsubstituted or substituted with a methyl group or a tert-butyl group; spiro (fluorene-indene) unsubstituted or substituted with a tert-butyl group; Cyclopentene unsubstituted or substituted with a methyl group; Or to form a substituted or unsubstituted cyclohexene with a methyl group.

According to another exemplary embodiment, two adjacent R4; Two adjacent R5s; Two adjacent R6; Two adjacent R7s; Or benzofuran unsubstituted or substituted with a tert-butyl group or a phenyl group by bonding of two adjacent R8s to each other; Naphthobenzofuran; thiophene unsubstituted or substituted with a tert-butyl group; Indole unsubstituted or substituted with a phenyl group; Indene unsubstituted or substituted with a methyl group or a tert-butyl group; spiro (fluorene-indene) unsubstituted or substituted with a tert-butyl group; Cyclopentene unsubstituted or substituted with a methyl group; Or to form a substituted or unsubstituted cyclohexene with a methyl group.

In another exemplary embodiment, the N-containing heterocyclic group of R4 to R8 may be represented by any one of Formulas HAr1 to HAr3, or Formula 1-B.

In the exemplary embodiment of the present specification, the remaining substituents of R4 to R8 are combined with an adjacent group to form a ring represented by Cy11 or Cy12. Specifically, two adjacent R4; Two adjacent R5s; Two adjacent R6; Two adjacent R7s; Or two adjacent R8s are bonded to each other to form a ring represented by the following formula Cy11 or Cy12.

In an exemplary embodiment of the present specification, two adjacent R7; Or two adjacent R8s combine with each other to form a ring represented by the following formula Cy11.

In another embodiment, two adjacent R4; Two adjacent R5s; Two adjacent R6; Two adjacent R7s; Or two adjacent R8s are bonded to each other to form a ring represented by the following formula Cy12.

In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of Chemical Formulas 201 to 203 below.

In Formulas 201 to 203,

The definitions of E1 to E3 and n4 to n8 are the same as in Formula 2,

R4 to R8, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

p6 and p7 are each 1 or 2,

n5" is an integer of 0 to 2, n8" is an integer of 0 to 3, n11 and n12 are each an integer of 0 to 8,

When n5", n8", n11 and n12 are each 2 or more, the substituents in the two or more parentheses are the same or different from each other.

In the exemplary embodiment of the present specification, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C1-C10 alkylthio group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or it is combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.

In another exemplary embodiment, R11 and R12 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 it combines with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic hydrocarbon ring.

In another exemplary embodiment, R11 and R12 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 it combines with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

In another exemplary embodiment, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or, by bonding with an adjacent group, an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring having 3 to 20 carbon atoms substituted or unsubstituted with deuterium is formed.

In another exemplary embodiment, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium; Combines with adjacent groups to form a benzene ring unsubstituted or substituted with deuterium or butyl groups; Combines with adjacent groups to form an indene ring substituted or unsubstituted with deuterium, methyl or butyl groups; Combined with adjacent groups to form spiro (fluorene-indene) substituted or unsubstituted with deuterium, methyl or butyl groups.

In another exemplary embodiment, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, n4 to n6 are 0 or 1, respectively.

In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of Chemical Formulas 211 to 219 below.

In Formulas 211 to 219,

The definition of n4 to n8 is the same as in Formula 2,

R4 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

p6 to p9 are each 1 or 2,

n4" and n5" are each an integer of 0 to 2, n7" and n8" are an integer of 0 to 3, n11 to n14 are each an integer of 0 to 8,

When n4", n5", n7", n8" and n11 to n14 are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, R4 to R8 in Formulas 211 to 219 are hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, the description of R11 described above may be applied to R13. In another embodiment, the description of R12 described above may be applied to R14.

In another exemplary embodiment, R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or, by bonding with an adjacent group, an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aliphatic hydrocarbon ring having 3 to 20 carbon atoms substituted or unsubstituted with deuterium is formed.

In another exemplary embodiment, R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium; Combines with adjacent groups to form a benzene ring unsubstituted or substituted with deuterium or butyl groups; Combines with adjacent groups to form an indene ring substituted or unsubstituted with deuterium, methyl or butyl groups; Combined with adjacent groups to form spiro (fluorene-indene) substituted or unsubstituted with deuterium, methyl or butyl groups.

In an exemplary embodiment of the present specification, at least one of R4 to R8 is bonded to an adjacent group to form an aliphatic hydrocarbon ring,

At least one of the aliphatic hydrocarbon rings is represented by any one of the following formulas Cy1 to Cy3.

In the formulas Cy1 to Cy3,

R31 to R40 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,

R41 to R43 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

n41 is an integer of 0 to 2, n42 and n43 are each an integer of 0 to 4,

When n41 to n43 are each 2 or more, the substituents in the two or more parentheses are the same or different.

In the present specification, the aliphatic hydrocarbon ring included in Formula 2 is 1) an aliphatic hydrocarbon ring formed by bonding of two R 4 to each other, 2) an aliphatic hydrocarbon ring formed by bonding of two R 5 to each other, 3) two R 6 It means at least one of an aliphatic hydrocarbon ring formed by bonding to each other, 4) an aliphatic hydrocarbon ring formed by bonding of two R7s, and 5) an aliphatic hydrocarbon ring formed by bonding of two R8s to each other.

In the exemplary embodiment of the present specification, R31 to R40 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 another exemplary embodiment, R31 to R40 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In another exemplary embodiment, R31 to R40 are substituted or unsubstituted methyl groups.

In another exemplary embodiment, R41 to 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; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, R41 to R43 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 by bonding with an adjacent group to form a substituted or unsubstituted C3 to C20 ring.

In another exemplary embodiment, R41 and R42 are the same as or different from each other, and each independently hydrogen; Or deuterium.

In another exemplary embodiment, R43 is hydrogen; Or deuterium; Four adjacent R43s are bonded to each other to form a substituted or unsubstituted benzene ring.

In another exemplary embodiment, R43 is hydrogen; Or deuterium; Or, four adjacent R43s are bonded to each other to form a benzene ring unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms or a substituent to which two or more groups are connected.

In another exemplary embodiment, R43 is hydrogen; Or deuterium; Or, four adjacent R43s are bonded to each other to form a benzene ring.

In another exemplary embodiment, all aliphatic hydrocarbon rings included in Formula 2 are selected from the above structure,

In another exemplary embodiment, at least one of the aliphatic hydrocarbon rings contained in Formula 2 is selected from the following structures.

In another exemplary embodiment, 1 to 4 of the aliphatic hydrocarbon rings included in Chemical Formula 2 are selected from the above structure.

In another exemplary embodiment, 1) an aliphatic hydrocarbon ring formed by bonding of two R4s to each other, 2) an aliphatic hydrocarbon ring formed by bonding of two R5s, and 3) an aliphatic formed by bonding of two R6 to each other At least one of a hydrocarbon ring, 4) an aliphatic hydrocarbon ring formed by bonding of two R7s to each other, and 5) an aliphatic hydrocarbon ring formed by bonding of two R8s to each other, is selected from the above structure.

In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by Chemical Formula 204 below.

[Formula 204]

In Formula 204,

At least one of R21 to R25 is represented by Formula 1-A or 1-B, the remainder are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combine with an adjacent group to form a substituted or unsubstituted ring,

E1 to E3, n4 to n8, and the definitions of Formulas 1-A and 1-B are the same as in Formula 2.

In the exemplary embodiment of the present specification, T1 to T11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

According to another exemplary embodiment, T1 to T11 are the same as or different from each other, and each independently hydrogen; Or deuterium; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.

According to another exemplary embodiment, T1 to T11 are the same as or different from each other, and each independently hydrogen; Or deuterium; Or it combines with an adjacent group to form a substituted or unsubstituted bridging or conjugated aliphatic hydrocarbon ring.

According to another exemplary embodiment, T1 to T11 are the same as or different from each other, and each independently hydrogen; Or deuterium; T1, T4 and T8 are bonded to each other to form a substituted or unsubstituted bridging or fused aliphatic hydrocarbon ring; Or T2, T6, and T10 are bonded to each other to form a substituted or unsubstituted bridging or fused aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, L11 is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.

In another exemplary embodiment, L11 is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.

In another exemplary embodiment, L11 is a direct bond; Or an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In another exemplary embodiment, L11 is a direct bond; Or a substituted or unsubstituted phenylene group.

In another exemplary embodiment, L11 is a direct bond; Or a phenylene group unsubstituted or substituted with a deuterium or tert-butyl group.

In an exemplary embodiment of the present specification, Formula 1-A is represented by the following Formula 1-A-1 or 1-A-2.

In an exemplary embodiment of the present specification, Formula 1-B is represented by the following Formula 1-B-1 or 1-B-2.

In another exemplary embodiment, the formula 1-A is represented by the following formula 1-A-1 or 1-A-2, and the formula B-1 is the following formula 1-B-1 or 1-B-2 It is represented by

[Formula 1-A-1]

[Formula 1-A-2]

[Formula 1-B-1]

[Formula 1-B-2]

In Formulas 1-A-1 and 1-A-2, the definition of L11 is the same as in Formula 1-A,

In Formulas 1-B-1 and 1-B-2, the definitions of T12 to T17 and p2 are the same as in Formula 1-B,

T18 to T21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

T22 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or by bonding with adjacent groups to form a substituted or unsubstituted ring,

t22 is an integer of 0 to 8, and when t22 is 2 or more, 2 or more T22s are the same as or different from each other.

In the exemplary embodiment of the present specification, the cyclohexyl group and the adamantynyl group of Formulas 1-A-1 and 1-A-2 may be substituted or unsubstituted.

In the exemplary embodiment of the present specification, the cyclohexyl group and adamantynyl group of Formulas 1-A-1 and 1-A-2 may be substituted or unsubstituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, T12 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, T12 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Or it is combined with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.

In another exemplary embodiment, T12 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group; Or by bonding with an adjacent group to form a substituted or unsubstituted C3 to C20 ring.

In another exemplary embodiment, T12 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkylsilyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Arylsilyl group having 6 to 90 carbon atoms substituted or unsubstituted with deuterium; An alkylarylsilyl group having 7 to 60 carbon atoms unsubstituted or substituted with deuterium; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; An arylalkyl group having 7 to 60 carbon atoms unsubstituted or substituted with deuterium; One or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a silyl group, and an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected 6 to 30 aryl groups; Or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium; Combined with an adjacent group to form a C2 to C30 ring 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 two or more groups selected from the group.

In another exemplary embodiment, T12 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; An alkylsilyl group having 1 to 18 carbon atoms substituted or unsubstituted with deuterium; An arylsilyl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; An alkylarylsilyl group having 7 to 40 carbon atoms substituted or unsubstituted with deuterium; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An arylalkyl group having 7 to 40 carbon atoms unsubstituted or substituted with deuterium; One or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a silyl group, and an aryl group having 6 to 20 carbon atoms, or the number of carbon atoms unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected 6 to 20 aryl groups; Or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Combined with an adjacent group, one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms, or two or more groups selected from the group, are substituted or unsubstituted with a connected substituent to form a ring having 2 to 20 carbon atoms.

In another exemplary embodiment, T12 to T15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted methylsilyl group; A substituted or unsubstituted butylsilyl group; A substituted or unsubstituted phenylsilyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted pyridine group; Or it combines with an adjacent group to form a substituted or unsubstituted hexene, or a substituted or unsubstituted benzene.

In another exemplary embodiment, T12 to T15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; Butyldimethylsilyl group unsubstituted or substituted with deuterium; A dimethylphenylsilyl group unsubstituted or substituted with deuterium; A methyldiphenylsilyl group unsubstituted or substituted with deuterium; Triphenylsilyl group unsubstituted or substituted with deuterium; Phenyl group unsubstituted or substituted with deuterium, cyano group, methyl group or butyl group; Biphenyl group unsubstituted or substituted with deuterium, cyano group, methyl group or butyl group; A naphthyl group unsubstituted or substituted with deuterium; Or a pyridine group unsubstituted or substituted with deuterium; Or, it combines with an adjacent group to form hexene unsubstituted or substituted with deuterium or methyl group, or benzene unsubstituted or substituted with deuterium or methyl group.

In another exemplary embodiment, T16 and T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted methyl group.

In the exemplary embodiment of the present specification, Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 2 to C 30 heterocyclic group; Alternatively, two adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

In another exemplary embodiment, Ar11 to Ar14 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; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group; Alternatively, two adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

In another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; Alternatively, two adjacent groups are bonded to each other to form an aliphatic hydrocarbon ring having 3 to 20 carbon atoms, which is substituted or unsubstituted with deuterium, and an aromatic hydrocarbon ring having 6 to 20 carbon atoms is condensed or uncondensed.

In another exemplary embodiment, Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium; Or a pyridine group; Two adjacent groups combine with each other to form cyclohexane or tetrahydronaphthalene.

In the exemplary embodiment of the present specification, two of Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the remaining two are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

In another exemplary embodiment, two of Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium; Or a pyridine group, and the other two are bonded to each other to form cyclohexane or tetrahydronaphthalene.

In the exemplary embodiment of the present specification, the description of Ar11 to Ar14 described above is applied to T18 to T21.

In another exemplary embodiment, T18 to T21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; Or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

In another exemplary embodiment, T18 to T21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium; Or a pyridine group.

In the exemplary embodiment of the present specification, the description of Ar11 to Ar14 described above is applied to T22.

In another exemplary embodiment, T22 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium; Alternatively, two adjacent groups are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

In another exemplary embodiment, T22 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; Alternatively, two adjacent groups are bonded to each other to form benzene substituted or unsubstituted with deuterium.

In the exemplary embodiment of the present specification, t22 is an integer of 0 to 4. In another exemplary embodiment, t22 is an integer of 0 to 2.

In an exemplary embodiment of the present specification, at least one of R4 to R8 is represented by Formula 1-A. In another exemplary embodiment, two or more of R4 to R8 are represented by Formula 1-A.

In an exemplary embodiment of the present specification, R4 is represented by Formula 1-A.

In an exemplary embodiment of the present specification, R5 is represented by Formula 1-A.

In an exemplary embodiment of the present specification, R6 is represented by Formula 1-A.

In an exemplary embodiment of the present specification, R7 is represented by Formula 1-A.

In an exemplary embodiment of the present specification, R8 is represented by Formula 1-A.

In an exemplary embodiment of the present specification, at least one of R4 to R8 is represented by Formula 1-B. In another exemplary embodiment, at least two of R4 to R8 are represented by Formula 1-B.

In an exemplary embodiment of the present specification, R4 is represented by Formula 1-B.

In an exemplary embodiment of the present specification, R5 is represented by Formula 1-B.

In an exemplary embodiment of the present specification, R6 is represented by Formula 1-B.

In an exemplary embodiment of the present specification, R7 is represented by Formula 1-B.

In an exemplary embodiment of the present specification, R8 is represented by Formula 1-B.

In an exemplary embodiment of the present specification, n4 and n5 are each an integer of 0 to 4. In another exemplary embodiment, n4 and n5 are each an integer of 0 to 2.

In the exemplary embodiment of the present specification, n6 is an integer of 0 to 3. In another exemplary embodiment, n6 is 0 or 1.

In the exemplary embodiment of the present specification, n7 and n8 are integers of 0 to 5, respectively. In another exemplary embodiment, n7 and n8 are each an integer of 0 to 3. n7 and n8 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is represented by any one of the following compounds.

Hereinafter, Formula 3 will be described.

[Formula 3]

According to an exemplary embodiment of the present specification, m is 2.

In an exemplary embodiment of the present specification, Chemical Formula 3 is represented by Chemical Formula 3-1 below.

[Formula 3-1]

In Formula 3-1,

X1 to X3, L, Ar5 and Ar6 are the same as in Chemical Formula 3,

L'is a direct bond; Or a substituted or unsubstituted arylene group,

At least one of X1' to X3' is N, and the rest are each independently N or CH,

Ar5' and Ar6' 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,

Ar7' is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted cycloalkylene group.

According to an exemplary embodiment of the present specification, L'is the same as the definition of L.

According to an exemplary embodiment of the present specification, X1' to X3' are the same as the definitions of X1 to X3.

According to an exemplary embodiment of the present specification, Ar5' and Ar6' are the same as the definitions of Ar5 and Ar6.

According to an exemplary embodiment of the present specification, at least one of X1 to X3 is N, and the others are each independently N or CH.

In another exemplary embodiment, 2 or 3 of X1 to X3 is N, and the rest are CH.

In an exemplary embodiment of the present specification, X1 and X2 are N, and X3 is CH.

In another exemplary embodiment, X1 and X3 are N, and X2 is CH.

In another exemplary embodiment, X2 and X3 are N, and X1 is CH.

In another exemplary embodiment, X1 to X3 are N.

In an exemplary embodiment of the present specification, X1' and X2' are N, and X3' is CH.

In another exemplary embodiment, X1' and X3' are N, and X2' is CH.

In another exemplary embodiment, X2' and X3' are N, and X1' is CH.

In another exemplary embodiment, X1' to X3' are N.

According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.

In another embodiment, L is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.

In another embodiment, L is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.

In another embodiment, L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to another exemplary embodiment, L is a direct bond; Or a phenylene group.

According to an exemplary embodiment of the present specification, L'is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.

In another exemplary embodiment, L'is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.

In another exemplary embodiment, L'is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.

In another exemplary embodiment, L'is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to another exemplary embodiment, L'is a direct bond; Or a phenylene group.

In the exemplary embodiment of the present specification, L and L'are the same as or different from each other.

In the exemplary embodiment of the present specification, L and L'are the same as or different from each other, and each independently a direct bond; Or any one selected from the following structures.

In the exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

In another exemplary embodiment, Ar5 and Ar6 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 another exemplary embodiment, Ar5 and Ar6 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms, and the aryl group or heterocyclic group is one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms, or 2 selected from the group. It is unsubstituted or substituted with a substituent to which the above groups are linked.

In another exemplary embodiment, Ar5 and Ar6 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms, and the aryl group or heterocyclic group is one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms, or 2 It is unsubstituted or substituted with a substituent to which the above groups are linked.

In another embodiment, Ar5 and Ar6 are the same as or different from each other, and each independently substituted or provided with a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a haloalkyl group having 1 to 10 carbon atoms A cyclic aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar5 and Ar6 are the same as or different from each other, and each independently substituted or provided with a halogen group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms A cyclic aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, the heterocyclic group of Ar5 and Ar6 includes N, O, or S as a hetero element. It preferably contains N.

In another exemplary embodiment, Ar5 and Ar6 are the same as or different from each other, and each independently a halogen group, a methyl group, a methoxy group, or a phenyl group unsubstituted or substituted with a trifluoromethyl group; Biphenyl group; Naphthyl group; Thiophene group; Or a pyridine group.

In another exemplary embodiment, Ar5 and Ar6 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group; Naphthyl group; Or a pyridine group.

In the exemplary embodiment of the present specification, Ar5' and Ar6' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

In another exemplary embodiment, Ar5' and Ar6' 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 another exemplary embodiment, Ar5' and Ar6' are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms, and the aryl group or heterocyclic group is one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms, or 2 selected from the group. It is unsubstituted or substituted with a substituent to which the above groups are linked.

In another exemplary embodiment, Ar5' and Ar6' are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms, and the aryl group or heterocyclic group is one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms, or 2 It is unsubstituted or substituted with a substituent to which the above groups are linked.

In another embodiment, Ar5' and Ar6' are the same as or different from each other, and each independently substituted with a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a haloalkyl group having 1 to 10 carbon atoms. Or an unsubstituted C6-C30 aryl group; Or a heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, Ar5' and Ar6' are the same as or different from each other, and each independently substituted with a halogen group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. Or an unsubstituted C6-C20 aryl group; Or a heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, the heterocyclic group of Ar5' and Ar6' includes N, O, or S as a hetero element. It preferably contains N.

In another exemplary embodiment, Ar5' and Ar6' are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a halogen group, a methyl group, a methoxy group, or a trifluoromethyl group; Biphenyl group; Naphthyl group; Thiophene group; Or a pyridine group.

In another exemplary embodiment, Ar5' and Ar6' are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group; Naphthyl group; Or a pyridine group.

According to an exemplary embodiment of the present specification, Ar7 is a substituted or unsubstituted C 6 to C 60 m aryl group; Or substituted or m having 3 to 60 carbon atoms is a cycloalkyl group.

In another exemplary embodiment, Ar7 is a substituted or unsubstituted C 6 to C 30 m aryl group; Or a substituted or C 3 to C 30 m is a cycloalkyl group.

In another exemplary embodiment, Ar7 is a substituted or unsubstituted polycyclic m having 6 to 30 carbon atoms is an aryl group; Or substituted or monocyclic m having 3 to 30 carbon atoms is a cycloalkyl group.

According to another exemplary embodiment, Ar7 is a substituted or unsubstituted m is a naphthyl group; A substituted or unsubstituted m is a phenanthrenyl group; Or substituted or unsubstituted m is a cyclohexyl group.

According to an exemplary embodiment of the present specification, Ar7' is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or C 3 to C 60 cycloalkylene group.

In another exemplary embodiment, Ar7' is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or C 3 to C 30 cycloalkylene group.

In another exemplary embodiment, Ar7' is a substituted or unsubstituted polycyclic arylene group having 6 to 30 carbon atoms; Or a substituted or monocyclic cycloalkylene group having 3 to 30 carbon atoms.

According to another exemplary embodiment, Ar7' is a substituted or unsubstituted naphthylene group; A substituted or unsubstituted phenanthrenylene group; Or a substituted or unsubstituted cyclohexylene group.

According to an exemplary embodiment of the present specification, m is 2, and Ar7 is any one selected from the following structures. According to another exemplary embodiment, Ar7' is any one selected from the following structures.

According to an exemplary embodiment of the present specification, of Formula 3-1

Wow

Are the same as each other.

Wow

Are the same as each other.

According to an exemplary embodiment of the present specification, the compound represented by Formula 3 is represented by any one of the following compounds.

According to an exemplary embodiment of the present invention, the compounds of

Formulas

1 and 2 may be prepared as shown in Scheme 1 below, and the compound of Formula 3 may be prepared as in Scheme 2 below.

Reaction Schemes

1 and 2 below describe the synthesis process of some compounds corresponding to Formulas 1 to 3 of the present application, but various compounds corresponding to Formulas 1 to 3 of the present application can be synthesized using a synthesis procedure such as

Schemes

1 and 2 below. In addition, the substituents may be bonded by methods known in the art, and the type, position and number of the substituents may be changed according to techniques known in the art.

[Scheme 1]

[Scheme 2]

In Reaction Scheme 1, A ₁ to A ₃ denotes an aromatic hydrocarbon ring, and R denotes a substituent connected to the core, and may be R1 to R8, A1 or A2 of the present invention. In Scheme 2, the definition of the substituent is as described above.

In the organic light emitting device of the present specification, except that the first organic material layer is formed using the compound represented by

Formula

1 or 2 and the second organic material layer is formed using the compound represented by Formula 3 above, It can be manufactured by the method and material of the organic light emitting device.

The first organic material layer including the compound represented by

Formula

1 or 2 and the second organic material layer including the compound represented by Formula 3 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light-emitting device of the present specification may have a structure including only the first organic material layer and the second organic material layer, but may have a structure in which an additional organic material layer is further included. As the additional organic material layer, at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, and a hole blocking layer may be used. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the first electrode is an anode, the second electrode is a cathode, the first organic material layer is an emission layer, and the second organic material layer is the second electrode and the first It is provided between the organic material layers. That is, the second organic material layer is provided between the cathode and the emission layer.

In the organic light emitting device according to the exemplary embodiment of the present specification, the first organic material layer is an emission layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is an emission layer, and the compound represented by

Formula

1 or 2 is included as a dopant of the emission layer.

In the organic light emitting device according to the exemplary embodiment of the present specification, the first organic material layer is an emission layer, and the compound represented by

Formula

1 or 2 is used as a dopant for the emission layer, and further includes a fluorescent host or a phosphorescent host. In this case, the dopant in the light emitting layer may be included in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host, preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight. When within the above range, energy transfer from the host to the dopant occurs efficiently.

In the exemplary embodiment of the present specification, the host is an anthracene derivative.

In the exemplary embodiment of the present specification, the organic material layer includes two or more emission layers, and one of the emission layers of the two or more layers includes a compound represented by

Formula

1 or 2.

In the exemplary embodiment of the present specification, the maximum emission peaks of the two or more emission layers are different from each other. The light emitting layer including the compound represented by

Formula

1 or 2 has a blue color, and the light emitting layer not including the compound represented by

Formula

1 or 2 may include a blue, red, or green light emitting compound known in the art.

In an exemplary embodiment of the present specification, the emission layer including the compound represented by

Formula

1 or 2 includes a fluorescent dopant, and the emission layer not including the compound represented by

Formula

1 or 2 includes a phosphorescent dopant.

In the exemplary embodiment of the present specification, the maximum emission peak of the emission layer including the compound represented by

Formula

1 or 2 is 400 nm to 500 nm. That is, the emission layer including the compound represented by

Chemical Formula

1 or 2 emits blue light.

The organic material layer of the organic light emitting device according to the exemplary embodiment of the present specification includes two or more emission layers, the maximum emission peak of one emission layer (light emission layer 1) is 400 nm to 500 nm, and the emission layer of the other layer (light emission layer 2 ) The maximum emission peak of 510 nm to 580 nm; Alternatively, a maximum emission peak of 610 nm and 680 nm may be exhibited. In this case, the emission layer 1 includes the compound represented by

Formula

1 or 2.

In the organic light emitting device according to the exemplary embodiment of the present specification, the second organic material layer is an electron transport region. Specifically, the second organic material layer includes at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

In the organic light emitting device according to another exemplary embodiment, the second organic material layer includes one or two layers selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

In the organic light emitting device according to another exemplary embodiment, the second organic material layer is a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer.

In the organic light emitting device according to another exemplary embodiment, the second organic material layer is a hole blocking layer.

In the organic light emitting device according to another exemplary embodiment, the second organic material layer is an electron transport layer.

In the organic light emitting device according to another exemplary embodiment, the second organic material layer is an electron injection and transport layer.

In the organic light emitting device according to another exemplary embodiment, the second organic material layer includes a hole blocking layer and an electron injection and transport layer. In this case, the hole blocking layer is provided adjacent to the light emitting layer, and the electron injection and transport layer is provided adjacent to the cathode.

In the exemplary embodiment of the present specification, the second organic material layer is provided in contact with the first organic material layer.

In the exemplary embodiment of the present specification, the second organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals.

When the organic alkali metal compound or the organic alkaline earth metal compound is used as an n-type dopant, stability against holes from the light emitting layer can be secured, thereby improving the life of the organic light emitting device. In addition, the electron mobility of the electron transport layer may be adjusted by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance between holes and electrons in the emission layer, thereby increasing luminous efficiency.

LiQ is more preferable as the n-type dopant used in the second organic material layer in the present specification.

The second organic material layer may include the compound of Formula 3 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the compound of Formula 3 and the n-type dopant may be included in a ratio of 2:8 to 8:2, more preferably 3:7 to 7:3.

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.

In one embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

The structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1, 2, and 8, but is not limited thereto.

In FIG. 1, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 The structure of the sequentially stacked organic light-emitting devices is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the hole blocking layer 7 or the electron injection and transport layer 8 have.

2, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron injection and transport layer 8, and a cathode 11 The structure of the sequentially stacked organic light emitting devices is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in the light emitting layer 6, and the compound represented by Formula 3 may be included in the electron injection and transport layer 8.

8 shows a substrate 1, an anode 2, a p-doped hole transport layer 4p, a

hole transport layer

4R, 4G, 4B, a light emitting layer 6RP, 6GP, 6BF, a first electron transport layer 9a, A structure of an organic light emitting diode in which the second electron transport layer 9b, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in the light emitting layer (6RP, 6GP, 6BF), and the compound represented by Formula 3 is the first electron transport layer 9a and the second electron transport layer ( It may be included in one or more layers of 9b) and the electron injection layer 10.

According to the exemplary embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may be a form in which each organic light emitting device is bonded to a charge generation layer. Since the tandem device can be driven at a lower current than the unit device based on the same brightness, there is an advantage in that the lifespan of the device is greatly improved.

According to an exemplary embodiment of the present specification, the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And at least one charge generation layer provided between the first stack and the second stack.

According to an exemplary embodiment of the present specification, the organic material layer includes: a first stack including one or more emission layers; A second stack including one or more light emitting layers; And a third stack including one or more emission layers, and between the first stack and the second stack; And one or more charge generation layers, respectively, between the second stack and the third stack.

In the present specification, a charge generating layer means a layer in which holes and electrons are generated when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. In the present specification, the N-type charge generation layer refers to a charge generation layer located closer to the anode than the P-type charge generation layer, and the P-type charge generation layer refers to a charge generation layer located closer to the cathode than the N-type charge generation layer.

The N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed. By the NP junction, holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported toward the anode through the LUMO level of the N-type charge generation layer, and holes are transported toward the cathode through the HOMO level of the P-type organic material layer.

Each of the first stack, the second stack, and the third stack includes one or more light emitting layers, and additionally, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport and a hole One or more layers of a layer for simultaneous injection (hole injection and transport layer), and a layer for simultaneous electron transport and electron injection (electron injection and transport layer) may be further included.

An organic light-emitting device including the first stack and the second stack is illustrated in FIG. 3.

In FIG. 3, a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first emission layer 6a, a first electron transport layer 9a, An N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second emission layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. The structure of the organic light emitting device is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in the first emission layer 6a or the second emission layer 6b, and the compound represented by Formula 3 is the first electron transport layer 9a or It may be included in the electron injection and transport layer 8.

Organic light-emitting devices including the first to third stacks are illustrated in FIGS. 4 to 7.

In FIG. 4, the substrate 1, the anode 2, the hole injection layer 3, the first hole transport layer 4a, the electron blocking layer 5, the first emission layer 6a, the first electron transport layer 9a, First N-type charge generation layer (12a), first P-type charge generation layer (13a), second hole transport layer (4b), second emission layer (6b), second electron transport layer (9b), second N-type charge An organic layer in which the generation layer 12b, the second P-type charge generation layer 13b, the third hole transport layer 4c, the third emission layer 6c, the third electron transport layer 9c, and the cathode 11 are sequentially stacked. The structure of a light emitting device is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in the first emission layer 6a, the second emission layer 6b, and the third emission layer 6c, and the compound represented by Formula 3 is It may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9b, and the third electron transport layer 9c.

5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer. 9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), red phosphorescent emission layer (6RP), yellow green phosphorescence emission layer (6YGP), green phosphorescence Light-emitting layer (6GP), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fourth hole transport layer (4d), fifth hole transport layer (4e) , A structure of an organic light-emitting device in which the second blue fluorescent emission layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11 and the capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in the first blue fluorescent layer 6BFa or the second blue fluorescent layer 6BFb, and the compound represented by Formula 3 is the first electron transport layer (9a), the second electron transport layer (9b), the third electron transport layer (9c), and may be included in one or more of the electron injection layer (10).

6 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, and a first electron transport layer. 9a), a first N-type charge generation layer (12a), a first P-type charge generation layer (13a), a third hole transport layer (4c), a red phosphorescent layer (6RP), a green phosphorescent layer (6GP), a second electron Transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fourth hole transport layer 4d, fifth hole transport layer 4e, second blue fluorescent light emitting layer 6BFb ), a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14 are sequentially stacked. In such a structure, the compound represented by

Formula

7 shows a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, First electron transport layer (9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), fourth hole transport layer (4d), second blue fluorescence Light emitting layer (6BFb), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fifth hole transport layer (4e), sixth hole transport layer (4f) , A structure of an organic light-emitting device in which a third blue fluorescent emission layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11 and a capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by

Formula

1 or 2 may be included in one or more layers of the first blue fluorescent light emitting layer 6BFa, the second blue fluorescent light emitting layer 6BFb, and the third clean fluorescent light emitting layer 6BFb. In addition, the compound represented by Formula 3 may be included in one or more layers of the first electron transport layer 9a, the second electron transport layer 9c, the third electron transport layer 9c, and the electron injection layer 10.

The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-P Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivative And the like, but is not limited thereto. In an exemplary embodiment, the N-type charge generation layer may include a benzoimidazophenanthrinine derivative and a metal of Li at the same time.

The P-type charge generation layer may simultaneously include an arylamine derivative and a compound containing a cyano group.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that the organic material layer includes the compound.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials. The organic light-emitting device according to the present specification forms an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and after forming an organic material layer including the first organic material layer and the second organic material layer described above, It can be manufactured 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 including the first organic material layer and the second organic material layer further includes a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, etc. It may be a multi-layered 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 has a single layer or a multilayer structure of two or more layers. The hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the 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. In an exemplary embodiment of the present specification, the hole injection layer has a two-layer structure, and each of the layers includes the same or different materials.

The hole transport layer may serve to facilitate the transport of holes, and has a single layer or a multilayer structure of two or more layers. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and 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. In the exemplary embodiment of the present specification, the hole transport layer has a two-layer structure, and each of the layers includes the same or different materials.

The hole injection and transport layer is a layer that simultaneously transports and injects holes, and a hole transport layer material and/or a hole injection layer material known in the art may be used.

The electron injection and transport layer is a layer that simultaneously transports electrons and injects electrons, and an electron transport layer material and/or an electron injection layer material known in the art may be used.

An electron blocking layer may be provided between the hole transport layer and the emission layer. Materials known in the art may be used for the electron blocking layer.

The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against 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 Alq ₃ (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-F ₂ ppy) ₂ Irpic, but 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 the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, 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 electron injection layer serves to facilitate injection of electrons. As the electron injection material, a compound having an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect to a light emitting layer or a light emitting material, and excellent in thin film formation 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 organic light emitting device according to the present specification 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, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7, under a nitrogen atmosphere 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

Intermediate 1 30g, N-(4-(tert-butyl)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)phenyl)-5, 46 g of Intermediate 3 was obtained by recrystallization of 38.6 g of 5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine using the same materials and equivalents as in the synthesis method of Intermediate 2. (Yield 70%). MS[M+H]+ = 892

2) Synthesis of compound 2

In a nitrogen atmosphere, 25 g of intermediate 3 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, extraction was performed, and 8.1 g of compound 2 was obtained through recrystallization (yield 31%). MS[M+H]+ = 900

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

1) Synthesis of Intermediate 4

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 4 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 5

Intermediate 4 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 5 was obtained through recrystallization using an equivalent amount. (Yield 80%). MS[M+H]+ = 840

3) Synthesis of compound 3

In a nitrogen atmosphere, 25 g of intermediate 5 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 3 was obtained through recrystallization (yield 32%). MS[M+H]+ = 849

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

1) Synthesis of intermediates

Intermediate 4 30g, bis(4-(2-phenylpropane-2-yl)phenyl)amine 23.7g is recrystallized using the same material and equivalent as in the synthesis method of intermediate 2 to obtain intermediate 5-methyl-N1,N1-bis(4). -(2-phenylpropan-2-yl)phenyl)-N3,N3-bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,3-diamine 36g was obtained. (Yield 70%). MS[M+H]+ = 884

2) Synthesis of compound 4

In a nitrogen atmosphere, the intermediate 5-methyl-N1,N1-bis(4-(2-phenylpropan-2-yl)phenyl)-N3,N3-bis(5,5,8,8-tetramethyl-5,6,7, 25 g of 8-tetrahydronaphthalen-2-yl)benzene-1,3-diamine 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 4 was obtained through recrystallization (yield 30%). MS[M+H]+ = 892

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

1) Synthesis of Intermediate 6

Intermediate 4 30g, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetra 39 g of intermediate 6 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 5

In a nitrogen atmosphere, 25 g of intermediate 6 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 5 was obtained through recrystallization (yield 29%). MS[M+H]+ = 898

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

1) Synthesis of Intermediate 7

Intermediate 4 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 7. (Yield 75%). MS[M+H]+ = 966

2) Synthesis of compound 6

In a nitrogen atmosphere, 25 g of intermediate 7 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 the reaction was completed, extraction was performed, and 7.6 g of compound 6 was obtained through recrystallization (yield 30%). MS[M+H]+ = 974

합성예 7. 화합물7의 합성Synthesis Example 7. Synthesis of Compound 7

1) Synthesis of Intermediate 8

Intermediate 4 30g, N-(4-(tert-butyl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine 20.4g 2 33g of Intermediate 8 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 7

In a nitrogen atmosphere, 25 g of intermediate 8 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, 7.7 g of compound 7 was obtained through recrystallization (yield 31%). MS[M+H]+ = 836

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

1) Synthesis of Intermediate 9

1,3-dibromo-5-tert-

butylbenzene

20g, 3,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen- 2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 55.3 g, sodium-tert-butoxide 16.5 g, bis (tri-tert-butylphosphine) palladium (0) 1.0 g in 400 ml of toluene After adding, the mixture was stirred under reflux for 4 hours. After the reaction was completed, extraction was performed, and 41.7 g of Intermediate 9 was obtained through recrystallization. (Yield 68%). MS[M+H]+ = 938

2) Synthesis of compound 8

In a nitrogen atmosphere, 25 g of intermediate 9 and 20.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 150 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.8 g of compound 8 was obtained through recrystallization (yield 31%). MS[M+H]+ = 946

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

1) Synthesis of Intermediate 10

Intermediate 1 15g, N-(5-(tert-butyl)-2'-fluoro-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7, 15.8 g of 8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 20.3 g of Intermediate 10. (Yield 69%). MS[M+H]+ = 780

2) Synthesis of compound 9

In a nitrogen atmosphere, 15 g of intermediate 10 and 11 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 150 ^O C for 4 hours. After the reaction was completed and extracted, 5 g of compound 9 was obtained through recrystallization (yield 33%). MS[M+H]+ = 808

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

1) Synthesis of Intermediate 11

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 11. (Yield 80%). MS[M+H]+ = 579

2) Synthesis of Intermediate 12

Intermediate 11 40g, 4-tert-butylaniline 11.3g, sodium-tert-butoxide 19.9g, bis (tri-tert-butylphosphine) palladium (0) 0.4g was added to 600ml of toluene and refluxed for 1 hour, After confirming the progress of the reaction, 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 completion of the reaction, extraction was performed, and then 28.8 g of intermediate 12 was obtained through recrystallization. (Yield 52%). MS[M+H]+ = 801

3) Synthesis of Intermediate 13

In a nitrogen atmosphere, 25 g of intermediate 12 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, 5.5g of intermediate 13 was obtained through recrystallization (yield 22%). MS[M+H]+ = 809

4) Synthesis of compound 10

5 g of intermediate 16, 1.5 g of diphenylamine, 1.2 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, 4.6 g of compound 10 was obtained through recrystallization. (Yield 80%). MS[M+H]+ = 943

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

1) Synthesis of Intermediate 14

Intermediate 4 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 14 was obtained through recrystallization. (Yield 71%). MS[M+H]+ = 814

2) Synthesis of Intermediate 15

In a nitrogen atmosphere, 25 g of intermediate 14 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 15 was obtained through recrystallization (yield 33%). MS[M+H]+ = 822

3) Synthesis of compound 11

Intermediate 15 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 extraction was completed after the reaction was completed, 7.4 g of compound 11 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 1175

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

1) Synthesis of Intermediate 16

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

3-((5-(tert-butyl)-[1,1'-biphenyl]-2-yl)(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) amino)-5-

chlorophenol

40g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride 20ml, potassium carbonate 30g tetrahydrofuran 400ml, water 200ml After the reaction was added to the mixture for 3 hours, the reaction was completed, the solution was extracted, and the solution was removed to obtain 58 g of intermediate 16. (Yield 97%).

2) Synthesis of Intermediate 17

In a nitrogen atmosphere, 40 g of intermediate 16, 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 17 was obtained through recrystallization (yield 78%). MS[M+H]+ = 802

3) Synthesis of Intermediate 18

25 g of intermediate 17 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 18 was obtained through recrystallization (yield 31%). MS[M+H]+ = 810

4) Synthesis of compound 12

7 g of intermediate 18, 1.5 g of diphenylamine-d5, 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 and stirred under reflux for 5 hours. . After extraction was completed after the reaction was completed, 6.2 g of compound 12 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 948

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

1) Synthesis of Intermediate 19

Intermediate 4 40g, dibenzo[b,d]furan-1-amine 14.3g, sodium-tert-butoxide 22.4g, bis(tri-tert-butylphosphine)palladium(0) 0.4g into 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 19 was obtained through recrystallization. (Yield 82%). MS[M+H]+ = 848

2) Synthesis of compound 13

In a nitrogen atmosphere, 25 g of intermediate 19 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 13 was obtained through recrystallization (yield 30%). MS[M+H]+ = 856

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

1) Synthesis of Intermediate 20

Intermediate 4 40g and dibenzo[b,d]thiophen-4-amine 15.5g were recrystallized using the same material and equivalent as the synthesis method of Intermediate 19 to obtain 54g of Intermediate 20. (Yield 78%). MS[M+H]+ = 864

2) Synthesis of compound 14

In a nitrogen atmosphere, 25 g of intermediate 20 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 14 was obtained through recrystallization (yield 31%). MS[M+H]+ = 872

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

1) Synthesis of Intermediate 21

Intermediate 4 40g, dibenzo[b,d]furan-4-bromide 18.1g, 3-(tert-butyl)aniline 11.6g was recrystallized using the same material and equivalent as the synthesis method of Intermediate 19 to obtain 50g of Intermediate 21 I did. (Yield 76%). MS[M+H]+ = 850

2) Synthesis of compound 15

In a nitrogen atmosphere, 25 g of intermediate 21 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 was completed after the reaction was completed, 8.3 g of compound 15 was obtained through recrystallization (yield 31%). MS[M+H]+ = 858

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

1) Synthesis of Intermediate 22

Intermediate 4 40g, dibenzo[b,d]furan-1-amine 14.3g, sodium-tert-butoxide 22.4g, bis(tri-tert-butylphosphine)palladium(0) 0.4g into 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 22 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 771

2) Synthesis of Intermediate 23

In a nitrogen atmosphere, 25 g of intermediate 22 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, 7.8g of intermediate 23 was obtained through recrystallization (yield 31%). MS[M+H]+ = 780

3) Synthesis of compound 16

Intermediate 23 7g, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 1.8g, sodium-tert-butoxide 1.7g, 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 6.1 g of compound 16 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 945

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

1) Synthesis of Intermediate 24

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, 3,5,5,8,8-pentamethyl-N-(m-tolyl)-5,6, 17.9 g of 7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 2 to obtain 31.3 g of Intermediate 24. (Yield 69%). MS[M+H]+ = 789

2) Synthesis of compound 17

In a nitrogen atmosphere, 25 g of intermediate 24 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, 7 g of compound 17 was obtained through recrystallization (yield 29%). MS[M+H]+ = 797

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

1) Synthesis of Intermediate 25

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 25 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 760

2) Synthesis of Intermediate 26

In a nitrogen atmosphere, 25 g of the intermediate 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 completion of the reaction, extraction was performed, and 7.1 g of intermediate 26 was obtained through recrystallization (yield 28%). MS[M+H]+ = 768

3) Synthesis of compound 18

Intermediate 26 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 18 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1013

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

1) Synthesis of Intermediate 28

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 70 g of Intermediate 27 was obtained through recrystallization using the same material and equivalent. (Yield 70%). MS[M+H]+ = 517

40 g of Intermediate 27 was obtained by using the same material and equivalent weight as the synthesis method of Intermediate 16 to obtain 56 g of Intermediate 28. (Yield 92%). MS[M+H]+ = 783

2) Synthesis of Intermediate 29

Intermediate 28 40g, N-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-3-methyl-[1,1'-biphenyl]-4-amine 34g Synthesis of Intermediate 17 54 g of Intermediate 29 was obtained through recrystallization using the same material and equivalent as in the method. (Yield 74%). MS[M+H]+ = 940

3) Synthesis of Intermediate 30

In a nitrogen atmosphere, 25 g of intermediate 29 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 completion of the reaction, extraction was performed, and 7.5 g of intermediate 30 was obtained through recrystallization (yield 30%). MS[M+H]+ = 948

3) Synthesis of compound 19

Intermediate 30 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, 6.6g of compound 19 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1235

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

1) Synthesis of Intermediate 31

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 31 was obtained through recrystallization using the same material and equivalent as in the synthesis method of 9. (Yield 75%). MS[M+H]+ = 888

2) Synthesis of Intermediate 32

In a nitrogen atmosphere, 25 g of intermediate 31 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 after completion of the reaction, 7.7 g of intermediate 32 was obtained through recrystallization (yield 31%). MS[M+H]+ = 896

3) Synthesis of compound 20

Intermediate 32 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 20 was obtained through recrystallization. (73% yield). MS[M+H]+ = 1249

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

1) Synthesis of Intermediate 33

In the same manner as the method of synthesizing Intermediate 1 of Synthesis Example 1, 25g of Intermediate 33 was obtained using 25g of bis(3-isopropylphenyl)amine. (Yield 67%). MS[M+H]+ = 378

2) Synthesis of Intermediate 34

N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-9,9,10,10-tetramethyl by the same method as the method for synthesizing Intermediate 2 of Synthesis Example 1 Using 27.3 g of -9,10-dihydroanthracene-2-amine, 32.2 g of Intermediate 34 was obtained. (Yield 71%). MS[M+H]+ = 858

3) Synthesis of compound 21

In a nitrogen atmosphere, 25 g of intermediate 34 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, 7.3g of compound 21 was obtained through recrystallization (29% yield). MS[M+H]+ = 866

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

1) Synthesis of compound 22

Intermediate 32 7g, 4a,9a-dimethyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 1.93g, sodium-tert-butoxide 1.52g, bis(tri- 0.04 g of tert-butylphosphine) palladium (0) 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 22 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 1137

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

1) Synthesis of Intermediate 36

In the same manner as the method of synthesizing Intermediate 16 of Synthesis Example 12, 40.5g of Intermediate 36 was obtained using 35g of di([1,1'-biphenyl]-3-yl)amine. (Yield 51%).

2) Synthesis of Intermediate 37

In the same manner as the method of synthesizing Intermediate 17 of Synthesis Example 12, N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-1- Using 20.4 g of amine, 31.8 g of intermediate 37 was obtained. (Yield 72%). MS[M+H]+ = 799

3) Synthesis of Intermediate 38

11.8 g of Intermediate 38 was obtained using 30 g of Intermediate 37 in the same manner as the method of synthesizing Intermediate 18 of Synthesis Example 12. (39% yield). MS[M+H]+ = 808

3) Synthesis of compound 23

Intermediate 38 7ㅎ, 4a,9a-dimethyl-6-(trimethylsilyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.4g in the same manner as the method of synthesizing compound 12 of Synthesis Example 12 Compound 23 was obtained by using 6.2g. (Yield 69%). MS[M+H]+ = 1045

합성예 24. 화합물24의 합성Synthesis Example 24. Synthesis of Compound 24

1) Synthesis of Intermediate 39

3'-bromo-5'-chloro-2,6-dimethyl-1,1'-biphenyl 25g, bis(3-(tert-butyl)phenyl)amine 23.8 in the same manner as the method of synthesizing Intermediate 1 of Synthesis Example 1 Using g, 27.3g of intermediate 39 was obtained. (Yield 65%). MS[M+H]+ = 496

2) Synthesis of Intermediate 40

Intermediate 39 22g and 9,9-dimethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) in the same manner as the method of synthesizing Intermediate 2 of Synthesis Example 1 23.9 g of intermediate 40 was obtained using 17.5 g of -9H-fluoren-4-amine. (Yield 63%). MS[M+H]+ = 856

3) Synthesis of compound 24

In the same manner as the synthesis of compound 11 of Synthesis Example 1, 20 g of intermediate 39 was used to obtain 4.2 g of compound 24. (Yield 21%). MS[M+H]+ = 864

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

1) Synthesis of Intermediate 41

A1 40g, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 69g, sodium-tert-butoxide 34.1g, bis(tri 0.9 g of -tert-butylphosphine) palladium (0) was added to 600 ml of toluene and stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and 70 g of intermediate 41 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 535

2) Synthesis of Intermediate 42

40 g of intermediate 41, 16.9 g of 5-(tert-butyl)-[1,1′-biphenyl]-2-amine, 0.4 g of bis(tri-tert-butylphosphine) palladium(0), sodium- 18 g of tert-butoxide was added to 600 ml of toluene and stirred under reflux for 1 hour. After confirming the progress of the reaction, 14.3 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After completion of the reaction, extraction was performed, and 45 g of intermediate 42 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 835

3) Synthesis of Intermediate 43

In a nitrogen atmosphere, 25 g of intermediate 42 and 20.0 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 43 was obtained through recrystallization (yield 29%). MS[M+H]+ = 843

4) Synthesis of compound 25

Intermediate 43 7g, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 4.3g, sodium-tert-butoxide under nitrogen atmosphere 1.6 g, bis (tri-tert-butylphosphine) palladium (0) 0.05 g was added to 100 ml of toluene, followed by reflux stirring for 6 hours. After extraction after completion of the reaction, 7.7 g of compound 25 was obtained through recrystallization. (Yield 72%). MS[M+H]+ = 1284

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

1) Synthesis of compound 26

Intermediate 4 7g, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole-5,6,7,8-d4 1.6g, sodium-tert- under nitrogen atmosphere 1.6 g of butoxide and 0.04 g of bis (tri-tert-butylphosphine) palladium (0) were added to 100 ml of toluene and stirred under reflux for 6 hours. After extraction was completed after the reaction was completed, 6.5 g of compound 26 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 1065

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

1) Synthesis of Intermediate 44

A2 40g under nitrogen atmosphere, N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)dibenzo[b,d]furan-4-amine 71.9g , Sodium-tert-butoxide 37.4 g, bis (tri-tert-butylphosphine) palladium (0) 1.0 g was added to 600 ml of toluene and stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and then 72 g of intermediate 44 was obtained through recrystallization. (Yield 75%). MS[M+H]+ = 495

2) Synthesis of Intermediate 45

In a nitrogen atmosphere, 40 g of intermediate 44, 14.8 g of dibenzo[b,d]furan-4-amine, 0.4 g of bis(tri-tert-butylphosphine)palladium(0), 19 g of sodium-tert-butoxide were added to 600 ml of toluene. After adding, the mixture was stirred under reflux for 1 hour. After confirming the progress of the reaction, 15.5 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After the reaction was completed, extraction was performed, and 45 g of an intermediate 45 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 752

3) Synthesis of Intermediate 46

In a nitrogen atmosphere, 25 g of intermediate 45 and 22.1 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 and extracted, 7.7 g of intermediate 46 was obtained through recrystallization (yield 30%). MS[M+H]+ = 760

4) Synthesis of compound 27

Intermediate 46 7g, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.4g, sodium-tert-butoxide under nitrogen atmosphere 1.8 g, bis (tri-tert-butylphosphine) palladium (0) 0.05 g was added to 100 ml of toluene and stirred under reflux for 6 hours. After the reaction was completed, extraction was performed, and 6.7 g of compound 27 was obtained through recrystallization. (Yield 74%). MS[M+H]+ = 981

합성예 28. 화합물28의 합성Synthesis Example 28. Synthesis of Compound 28

1) Synthesis of Intermediate 47

A2 40g, N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)dibenzo[b,d]furan-1-amine 71.9g under nitrogen atmosphere , Sodium-tert-butoxide 37.4 g, bis (tri-tert-butylphosphine) palladium (0) 1.0 g was added to 600 ml of toluene and stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and 73 g of Intermediate 47 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 495

2) Synthesis of Intermediate 48

In a nitrogen atmosphere, 40 g of intermediate 47, 16.1 g of dibenzo[b,d]thiophen-4-amine, and 0.4 g of bis(tri-tert-butylphosphine)palladium(0) were added to 600 ml of toluene and stirred under reflux for 1 hour. I did. After confirming the progress of the reaction, 15.5 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After the reaction was completed, extraction was performed, and 44 g of Intermediate 48 was obtained through recrystallization. (Yield 71%). MS[M+H]+ = 768

3) Synthesis of Intermediate 49

In a nitrogen atmosphere, 25 g of intermediate 48 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 was completed after the reaction was completed, 7.4 g of intermediate 49 was obtained through recrystallization (yield 29%). MS[M+H]+ = 776

4) Synthesis of compound 28

Intermediate 49 7g, 4a,5,7,9a-tetramethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.1g, sodium-tert-butoxide 1.8g, bis under nitrogen atmosphere 0.05 g of (tri-tert-butylphosphine) palladium (0) was added to 100 ml of toluene and stirred under reflux for 6 hours. After extraction after completion of the reaction, 6.8g of compound 28 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 969

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

1) Synthesis of Intermediate 50

1,3-dibromo-5-chlorobenzene 20g, bis(4-(tert-butyl)phenyl)amine 41.6g, sodium-tert-butoxide 35.5g, bis(tri-tert-butylphosphine) under nitrogen atmosphere After adding 0.4 g of palladium (0) to 300 ml of toluene, the mixture was stirred under reflux for 2 hours. After the reaction was completed, extraction was performed, and 35 g of intermediate 50 was obtained through recrystallization. (Yield 70%). MS[M+H]+ = 672

2) Synthesis of Intermediate 51

In a nitrogen atmosphere, 25 g of intermediate 50 and 24.8 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.4 g of intermediate 51 was obtained through recrystallization (yield 29%). MS[M+H]+ = 680

3) Synthesis of compound 29

Intermediate 51 7g, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 2.1g, sodium-tert-butoxide 2.0g, bis(tri-tert) under nitrogen atmosphere -Butylphosphine)palladium (0) 0.05g was added to 100ml of toluene and stirred under reflux for 6 hours. After extraction after completion of the reaction, 6.8g of compound 29 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 845

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

26.6g of intermediate 52 was obtained using 15g of bis(4-cyclohexylphenyl)amine in the same method as the method of preparing intermediate 5 of Synthesis Example 3. (73% yield). MS[M+H]+ = 812

In the same manner as in the method of preparing compound 3 of Synthesis Example 3, 9.2 g of compound 30 was obtained using 20 g of intermediate 52. (Yield 46%). MS[M+H]+ = 820

합성예 31. 중간체 53의 합성Synthesis Example 31. Synthesis of Intermediate 53

Starting materials B1 (20g, 1eq.), bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)amine (35.6g, 2.05eq.), Pd( A flask containing P t Bu ₃ ) ₂ (1.1 g, 0.05 eq), NaO t Bu (12.8 g, 3 eq.) and toluene (250 ml) was heated at 110° C. and stirred for 6 hours. The reaction solution was cooled to room temperature, water and toluene were added to separate the mixture, and the solvent was distilled off under reduced pressure. Purified with recrystallization (toluene/hexane) to obtain an intermediate 53 (30.9 g). (Yield 65%). MS[M+H]+ = 1066

합성예 32. 화합물 31의 합성Synthesis Example 32. Synthesis of Compound 31

To a flask containing the intermediate 53 (25 g) and toluene (150 ml), an n-butyllithium pentane solution (18.7 ml, 2.5 M in hexane, 2 eq.) was added at 0° C. under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 50° C. and stirred for 2 hours. After cooling to -40°C, boron tribromide (3.4 ml, 1.5 eq.) was added, and the mixture was heated to room temperature and stirred for 4 hours. After that, it was cooled to 0°C again, N,N-diisopropylethylamine (10 ml) was added, and the reaction solution was further stirred at room temperature for 30 minutes. After separating by adding Sat.aq.NaCl and ethyl acetate, the solvent was distilled off under reduced pressure. It purified by recrystallization (Toluene/Hexane) to obtain compound 31 (6.3 g). (Yield 27%). MS[M+H]+ = 996

합성예 33. 화합물2-1의 합성Synthesis Example 33. Synthesis of Compound 2-1

1) Synthesis of Intermediate 55

Intermediate 54 (41g, yield 63%) was prepared using the starting material of the above formula in the same manner as the method of synthesizing Intermediate 53 of Synthesis Example 31. MS[M+H]+ = 623

Intermediate 55 (7.5 g, 49%) was obtained using 15 g of intermediate 54 in the same manner as in the method of preparing compound 3 of Synthesis Example 3. MS[M+H]+ = 631

2) Synthesis of compound 2-1

Compound 2-1 (8.6g, yield 77%) was obtained by using the starting material of the above formula in the same manner as the method for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 778

합성예 34. 화합물2-2의 합성Synthesis Example 34. Synthesis of Compound 2-2

1) Synthesis of Intermediate 72

A2 40g, 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 50.1g, bis(tri-tert-butyl) under nitrogen atmosphere Phosphine) palladium (0) 1.0 g, sodium-tert-butoxide 38 g was added to 600 ml of toluene and stirred under reflux for 4 hours. After extraction was completed after the reaction was completed, 52g of intermediate 72 was obtained through column purification. (Yield 70%). MS[M+H]+ = 383

2) Synthesis of Intermediate 57

Intermediate 56 (39.5g, 59% yield) was obtained by using the starting material of the above formula in the same manner as the method of synthesizing Intermediate 48 of Synthesis Example 28. MS[M+H]+ = 695

Intermediate 57 (8.5 g, 44%) was obtained using 19 g of intermediate 56 in the same manner as in the method of preparing compound 3 of Synthesis Example 3. MS[M+H]+ = 703

3) Synthesis of compound 2-2

Compound 2-2 (6.9g, yield 71%) was obtained by using the starting material of the above formula in the same manner as the method for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 865

합성예 35. 화합물 2-3의 합성Synthesis Example 35. Synthesis of Compound 2-3

1) Synthesis of Intermediate 73

In a nitrogen atmosphere, 40 g of intermediate 72, 20.9 g of dibenzo[b,d]thiophen-4-amine, 0.6 g of bis(tri-tert-butylphosphine)palladium(0), and 25.2 g of sodium-tert-butoxide were added to toluene. After adding to 600ml, the mixture was stirred under reflux for 1 hour. Then, after checking the progress of the reaction, 20.1 g of 1-bromo-3-chlorobenzene was added during stirring, followed by reflux stirring for 4 hours. After the reaction was completed, extraction was performed, and 54 g of intermediate 73 was obtained through recrystallization. (79% yield). MS[M+H]+ = 656

2) Synthesis of Intermediate 74

In a nitrogen atmosphere, 25 g of intermediate 73 and 25.4 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 intermediate 74 was obtained through recrystallization (yield 29%). MS[M+H]+ = 664

2) Synthesis of compound 2-3

Compound 2-3 (6.9g, yield 74%) was obtained using the starting material of the above formula in the same manner as the method for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 886

합성예 36. 화합물2-4의 합성Synthesis Example 36. Synthesis of Compound 2-4

1) Synthesis of Intermediate 58

Intermediate 58 (32 g, yield 76%)) was obtained using the starting material of the above formula in the same manner as the method for synthesizing Intermediate 72 of Synthesis Example 34. MS[M+H]+ = 410

2) Synthesis of Intermediate 60

Intermediate 59 (20.7 g, yield 62%) was obtained using the starting material of the above formula in the same manner as the method for synthesizing Intermediate 48 of Synthesis Example 28. MS[M+H]+ = 701

Intermediate 60 (5.8 g, 38%) was obtained using 15 g of intermediate 59 in the same manner as in the method of preparing compound 3 of Synthesis Example 3. MS[M+H]+ = 709.44

3) Synthesis of compound 2-4

Compound 2-4 (4.4g, yield 66%) was obtained using the starting material of the above formula in the same manner as the method for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 949

합성예 37. 화합물2-5의 합성Synthesis Example 37. Synthesis of Compound 2-5

1) Synthesis of Intermediate 62

Intermediate 61 (26g, yield 79%) was obtained using the starting material of the above formula in the same manner as the method of synthesizing Intermediate 72 of Synthesis Example 34. MS[M+H]+ = 396

Intermediate 62 (15.9g, yield 67%) was obtained by using the starting material of the above formula in the same manner as the method of synthesizing Intermediate 34 of Synthesis Example 21. MS[M+H]+ = 691

2) Synthesis of compound 2-5

Compound 2-5 (5g, 35%) was obtained using 14g of intermediate 62 in the same manner as in the method of preparing compound 3 of Synthesis Example 3. MS[M+H]+ = 699

합성예 38. 화합물2-6의 합성Synthesis Example 38. Synthesis of Compound 2-6

1) Synthesis of Intermediate 64

Intermediate 63 (26.3g, yield 76%) was obtained using the starting material of the above formula in the same manner as the method of synthesizing Intermediate 72 of Synthesis Example 34. MS[M+H]+ = 424

Intermediate 64 (29.8g, yield 70%) was obtained using the starting material of the above formula in the same manner as the method of synthesizing Intermediate 34 of Synthesis Example 21. MS[M+H]+ = 754

2) Synthesis of compound 2-6

Compound 2-6 (7.5g, 39%) was obtained using 19g of intermediate 64 in the same manner as in the method of preparing compound 3 of Synthesis Example 3. MS[M+H]+ = 761

합성예 39. 화합물2-7의 합성Synthesis Example 39. Synthesis of Compound 2-7

1) Synthesis of Intermediate 68

A2

40g, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 39.2g, bis(tri-tert-butylphosphine)palladium(0) 1.0 under nitrogen atmosphere g, sodium-tert-butoxide 38g was added to 600ml of toluene and stirred under reflux for 4 hours. After the reaction was completed, extraction was performed, and 49 g of intermediate 68 was obtained through column purification. (Yield 77%). MS[M+H]+ = 326

2) Synthesis of Intermediate 69

Under a nitrogen atmosphere, 40 g of intermediate 68, 22.5 g of dibenzo[b,d]furan-1-amine, 0.6 g of bis(tri-tert-butylphosphine)palladium(0), and 29.5 g of sodium-tert-butoxide 600 ml of toluene After putting in, the mixture was stirred under reflux for 1 hour. After confirming the progress of the reaction, 23.5 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After the reaction was completed, extraction was performed, and 55 g of intermediate 69 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 584

3) Synthesis of compound 2-7

In a nitrogen atmosphere, 25 g of intermediate 69 and 28.5 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, 7.8 g of intermediate 70 was obtained through recrystallization (yield 31%). MS[M+H]+ = 592

In a nitrogen atmosphere, 7 g of intermediate 70, 3.4 g of bis(4-(tert-butyl)phenyl)amine, 2.3 g of sodium-tert-butoxide, 0.05 g of bis(tri-tert-butylphosphine)palladium(0) were added to 100 ml of toluene. After putting in, the mixture was stirred under reflux for 6 hours. After the reaction was completed, extraction was performed, and 7.4 g of compound 2-7 was obtained through recrystallization. (Yield 75%). MS[M+H]+ = 836

합성예 40. 화합물2-8의 합성Synthesis Example 40. Synthesis of Compound 2-8

1) Synthesis of Intermediate 71

Under a nitrogen atmosphere, 40 g of intermediate 68, 22.5 g of dibenzo[b,d]furan-4-amine, 0.6 g of bis(tri-tert-butylphosphine)palladium(0), and 29.5 g of sodium-tert-butoxide 600 ml of toluene After putting in, the mixture was stirred under reflux for 1 hour. After confirming the progress of the reaction, 23.5 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After completion of the reaction, extraction was performed, and 54 g of intermediate 71 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 584

2) Synthesis of compound 2-8

In a nitrogen atmosphere, 25 g of intermediate 71 and 28.5 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene, followed by stirring at 160 ^O C for 4 hours. After the reaction was completed, extraction was performed, and 7.6 g of intermediate 72 was obtained through recrystallization (yield 30%). MS[M+H]+ = 592

In a nitrogen atmosphere, 7 g of intermediate 72, 3.4 g of bis(4-(tert-butyl)phenyl)amine, 2.3 g of sodium-tert-butoxide, 0.05 g of bis(tri-tert-butylphosphine)palladium(0) were added to 100 ml of toluene. After putting in, the mixture was stirred under reflux for 6 hours. After the reaction was completed, extraction was performed, and 7.6 g of compound 2-8 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 836

합성예 41. 화합물2-9의 합성Synthesis Example 41. Synthesis of Compound 2-9

1) Synthesis of compound 2-9

7 g of intermediate 72, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 4.6 g, sodium-tert-butoxide 2.3 g, bis 0.05 g of (tri-tert-butylphosphine) palladium (0) was added to 100 ml of toluene and stirred under reflux for 6 hours. After the reaction was completed, extraction was performed, and 7.5 g of compound 2-9 was obtained through recrystallization. (Yield 76%). MS[M+H]+ = 945

합성예 42. 화합물2-10의 합성Synthesis Example 42. Synthesis of Compound 2-10

1) Synthesis of compound 2-10

In a nitrogen atmosphere, 7 g of intermediate 74, 3.5 g of bis(4-(tert-butyl)phenyl)amine, 2.1 g of sodium-tert-butoxide, 0.05 g of bis(tri-tert-butylphosphine)palladium(0), 100 ml of toluene After putting in, the mixture was stirred under reflux for 6 hours. After the reaction was completed, extraction was performed, and 7.5 g of compound 2-10 was obtained through recrystallization. (Yield 78%). MS[M+H]+ = 909

합성예 43. 화합물2-11의 합성Synthesis Example 43. Synthesis of Compound 2-11

1) Synthesis of Intermediate 75

A1

40g, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 35.7g, bis(tri-tert-butylphosphine)palladium(0) 0.9 under nitrogen atmosphere g, sodium-tert-butoxide 34g was added to 600ml of toluene and stirred under reflux for 4 hours. After the reaction was completed, extraction was performed, and 47 g of intermediate 75 was obtained through column purification. (Yield 77%). MS[M+H]+ = 347

2) Synthesis of Intermediate 76

In a nitrogen atmosphere, 40 g of intermediate 75, 21.2 g of dibenzo[b,d]furan-4-amine, 0.6 g of bis(tri-tert-butylphosphine)palladium(0), and 27.8 g of sodium-tert-butoxide 600 ml of toluene After putting in, the mixture was stirred under reflux for 1 hour. After confirming the progress of the reaction, 22.1 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After the reaction was completed, extraction was performed, and 55 g of intermediate 76 was obtained through recrystallization. (79% yield). MS[M+H]+ = 604

3) Synthesis of compound 2-11

In a nitrogen atmosphere, 25 g of intermediate 76 and 27.6 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 77 was obtained through recrystallization (yield 28%). MS[M+H]+ = 612

Under a nitrogen atmosphere, 7 g of intermediate 77, 6.5 g of bis(4-(tert-butyl)phenyl)amine, 2.1 g of sodium-tert-butoxide, 0.05 g of bis(tri-tert-butylphosphine)palladium(0), 100 ml of toluene After putting in, the mixture was stirred under reflux for 6 hours. After extraction after completion of the reaction, 7.9g of compound 2-11 was obtained through recrystallization. (Yield 63%). MS[M+H]+ = 1102

합성예 44. 화합물2-12의 합성Synthesis Example 44. Synthesis of Compound 2-12

1) Synthesis of Intermediate 78

40 g of intermediate 72, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine 21.6 g, bis(tri-tert-butylphosphine) palladium ( 0) 0.5 g and 23.9 g of sodium-tert-butoxide were added to 600 ml of toluene, followed by reflux stirring for 1 hour. After confirming the progress of the reaction, 19.1 g of 1-bromo-3-chlorobenzene was added while stirring, followed by reflux stirring for 4 hours. After the reaction was completed, extraction was performed, and 53 g of intermediate 78 was obtained through recrystallization. (Yield 77%). MS[M+H]+ = 694

2) Synthesis of compound 2-12

In a nitrogen atmosphere, 25 g of intermediate 78 and 24.0 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 79 was obtained through recrystallization (yield 29%). MS[M+H]+ = 702

Under a nitrogen atmosphere, 7 g of intermediate 79, 5.6 g of bis(4-(tert-butyl)phenyl)amine, 2.0 g of sodium-tert-butoxide, 0.05 g of bis(tri-tert-butylphosphine)palladium(0), 100 ml of toluene After putting in, the mixture was stirred under reflux for 6 hours. After the reaction was completed, extraction was performed, and 8.3 g of compound 2-12 was obtained through recrystallization. (Yield 70%). MS[M+H]+ = 1192

합성예 45. 화합물 2-13의 합성Synthesis Example 45. Synthesis of Compound 2-13

Using

Intermediate

28 and 4a,5,7,9a-tetramethyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole in the same manner as the method of synthesizing Intermediate 17 of Synthesis Example 12 22 g of intermediate 80 was obtained. (Yield 61%). MS[M+H]+ = 804

Intermediate 81 (5.9 g, 29%) was obtained using 20 g of intermediate 80 in the same manner as in the method of preparing compound 3 of Synthesis Example 3. MS[M+H]+ = 811

Compound 2-13 (5.4 g, yield 68%) was obtained by using the starting material of the above formula in the same manner as the method for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 1097

합성예 46. 화합물 32의 합성Synthesis Example 46. Synthesis of Compound 32

16.3g of Intermediate 82 was obtained using the substance of the above formula in the same manner as in the method of preparing Intermediate 5 of Synthesis Example 3. (Yield 77%). MS[M+H]+ = 647

In the same manner as in the method of preparing compound 3 of Synthesis Example 3, 16 g of intermediate 82 was used to obtain 5.3 g of compound 32. (Yield 33%). MS[M+H]+ = 655

합성예 47. 화합물 33의 합성Synthesis Example 47. Synthesis of Compound 33

1) Synthesis of Intermediate 84

In the same manner as the method of preparing Intermediate 31 of Synthesis Example 20, 32 g of Intermediate 83 was obtained using the substance of the above formula. (Yield 71%). MS[M+H]+ = 663

In the same manner as in the method of preparing Intermediate 32 of Synthesis Example 20, 10 g of Intermediate 84 was obtained using the substance of the above formula. (Yield 32%). MS[M+H]+ = 671

2) Synthesis of compound 33

In the same manner as in the method of preparing compound 20 of Synthesis Example 20, 8.5 g of compound 33 was obtained using the substance of the above formula. (Yield 70%). MS[M+H]+ = 913

합성예 48. 화합물 E1의 합성Synthesis Example 48. Synthesis of Compound E1

The compound C-1 (8 g, 27.98 mmol, 1 eq.) and the compound I-1 (26.4 g, 58.75 mmol, 2.1 eq.) were completely dissolved in tetrahydrofuran (80 mL), and then potassium carbonate (9.7 g , 69.94 mmol, 2.5eq) was added by dissolving in 30 mL of water. After tetrakistriphenyl-phosphinopalladium (1.0g, 0.84 mmol) was added, the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed, the white solid was filtered, and washed with water and ethanol. The filtered white solid was washed twice with ethyl acetate and hexane, respectively, to prepare compound E1 (15.3 g, yield 71%). MS [M+H]+ = 771

합성예 49. 화합물 E4의 합성Synthesis Example 49. Synthesis of Compound E4

In the same manner as the method for synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E4 (16.9 g, yield 77%) was prepared using I-2 (20.8g) and C-2 (8g). . MS[M+H] ⁺ =591

합성예 50. 화합물 E10의 합성Synthesis Example 50. Synthesis of Compound E10

In the same method as the method for synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E10 (18.9 g, yield 74%) was prepared using I-3 (24.7g) and C-2 (8g). . MS[M+H] ⁺ =691

합성예 51. 화합물 E2의 합성Synthesis Example 51. Synthesis of Compound E2

In the same manner as the method for synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E2 (16.8 g, yield 81%) was prepared using I-4 (25.6g) and C-3 (8g). . MS[M+H] ⁺ =743

합성예 52. 화합물 E5의 합성Synthesis Example 52. Synthesis of Compound E5

In the same manner as the method for synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E5 (14.7 g, yield 78%) was prepared using I-4 (21.8g) and C-4 (8g). . MS[M+H] ⁺ =793

합성예 53. 화합물 E9의 합성Synthesis Example 53. Synthesis of Compound E9

In the same manner as the method of synthesizing compound E1 of Synthesis Example 48, a compound represented by Formula E9 (16.2 g, yield 74%) was prepared using I-2 (20.8g) and C-5 (8g). . MS[M+H] ⁺ =793

합성예 54. 화합물 E3의 합성Synthesis Example 54. Synthesis of Compound E3

In the same manner as the method for synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E3 (14.1 g, yield 68%) was prepared using I-5 (25.5g) and C-6 (8g). . MS[M+H] ⁺ =741

합성예 55. 중간체 C-8의 합성Synthesis Example 55. Synthesis of Intermediate C-8

Compound C-7 (10g, 44.83mmol, 1eq.), potassium carbonate (8.1 g, 58.28 mmol, 1.3eq) and perfluorobutanesulfonyl fluoride (16.3g, 53.8mmol, 1.2eq.) Was dissolved in 100 mL of acetonitrile and 50 mL of distilled water, followed by stirring at room temperature for 2 hours. After the reaction was completed, acetonitrile was removed by distillation under reduced pressure, and then 100 mL of acetonitrile and aq. Add 50 mL of NaCl and separate the organic layer using a separatory funnel. The separated organic layer is treated with anhydrous MgSO ₄ and then filtered. The filtered solution was distilled off under reduced pressure, and purified by column chromatography (developing solution: ethyl acetate/hexane) to give intermediate C-8 (18.3 g, yield 81%).

합성예 56. 화합물 E8의 합성Synthesis Example 56. Synthesis of Compound E8

In the same manner as the method of synthesizing compound E1 of Synthesis Example 48, a compound represented by Formula E8 (14.1 g, yield 68%) was prepared using I-4 (18.1g) and C-8 (10g). . MS[M+H] ⁺ =743

합성예 57. 중간체 C-10의 합성Synthesis Example 57. Synthesis of Intermediate C-10

In the same manner as the method for synthesizing intermediate C-8 of Synthesis Example 55, a compound represented by Chemical Formula C-10 (23.9 g, yield 77%) was prepared using C-9 (10g).

합성예 58. 화합물 E6의 합성Synthesis Example 58. Synthesis of Compound E6

In the same manner as the method for synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E6 (6.8 g, yield 71%) was prepared using I-5 (8g) and C-10 (10g). MS[M+H] ⁺ =799

합성예 59. 화합물 E7의 합성Synthesis Example 59. Synthesis of Compound E7

In the same manner as the method of synthesizing Compound E1 of Synthesis Example 48, a compound represented by Formula E7 (5.7 g, yield 68%) was prepared using I-7 (6.8g) and C-10 (10g). . MS[M+H] ⁺ =699

<소자예 1><Device Example 1>

실시예 1Example 1

A glass substrate coated with a thin film of 1000 Å of ITO (indium tin oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. 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.

On the thus prepared ITO transparent electrode, the following HI-A compound was thermally vacuum deposited to a thickness of 600 Å and the HAT compound 50 Å to form a hole injection layer. A hole transport layer was formed by vacuum depositing 600 Å of the following HT-A compound on the hole injection layer.

Subsequently, the following BH-A compound (host) and compound 1 (dopant) with a film thickness of 200 Å were vacuum-deposited at a weight ratio of 25:1 on the hole transport layer to form a light emitting layer.

Compound E1 and the following LiQ compound were vacuum-deposited on the emission layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350Å. By sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer A cathode was formed.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree at the time of deposition was 1Х10 ^-7. To 5Х10 ^-5 torr was maintained, an organic light emitting device was manufactured.

실시예 2 내지 22 및 비교예 1 내지 6Examples 2 to 22 and Comparative Examples 1 to 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the materials shown in Table 1 were used as the dopant material and the electron injection transport layer material of the emission layer.

Were measured for the examples 1 to 22 and Comparative Examples 1 to 6, the organic light emitting element driving voltage and luminous efficiency at a current density of 10 mA / cm ² with respect to the (in terms of efficiency), initially at a current density of 15 mA / cm ² A relative value was displayed based on Comparative Example 1 by measuring the time (T95) that became 95% of the luminance. The results are shown in Table 1 below.

	화합물compound		10mA/cm² 10mA / cm ²		15mA/cm² 15mA / cm ²
	도펀트Dopant	전자 주입 및 수송층Electron injection and transport layer	전압(V)Voltage(V)	환산 효율(cd/A/y)Conversion efficiency (cd/A/y)	T95Ratio (%)T95Ratio (%)
실시예 1Example 1	화합물 1Compound 1	E1E1	4.414.41	59.259.2	1.381.38
실시예 2Example 2	화합물 2Compound 2	E2E2	4.194.19	64.164.1	1.081.08
실시예 3Example 3	화합물 4Compound 4	E3E3	4.324.32	62.262.2	1.161.16
실시예 4Example 4	화합물 6Compound 6	E4E4	4.464.46	59.459.4	1.631.63
실시예 5Example 5	화합물 15Compound 15	E5E5	4.234.23	65.965.9	1.281.28
실시예 6Example 6	화합물 17Compound 17	E6E6	4.214.21	66.766.7	1.191.19
실시예 7Example 7	화합물 11Compound 11	E7E7	4.284.28	67.167.1	1.131.13
실시예 8Example 8	화합물 12Compound 12	E8E8	4.324.32	63.863.8	1.581.58
실시예 9Example 9	화합물 20Compound 20	E9E9	4.414.41	66.866.8	1.611.61
실시예 10Example 10	화합물 24Compound 24	E10E10	4.464.46	57.457.4	1.601.60
실시예 11Example 11	화합물 30Compound 30	E1E1	4.424.42	59.459.4	1.291.29
실시예 12Example 12	화합물 22Compound 22	E4E4	4.464.46	61.861.8	1.521.52
실시예 13Example 13	화합물 25Compound 25	E5E5	4.244.24	65.965.9	1.221.22
실시예 14Example 14	화합물 26Compound 26	E7E7	4.284.28	65.465.4	1.221.22
실시예 15Example 15	화합물 28Compound 28	E9E9	4.394.39	61.761.7	1.621.62
실시예 16Example 16	화합물 32Compound 32	E1E1	4.194.19	54.054.0	1.021.02
실시예 17Example 17	화합물 33Compound 33	E10E10	4.334.33	53.853.8	1.011.01
실시예 18Example 18	화합물 2-4Compound 2-4	E2E2	4.184.18	63.863.8	1.171.17
실시예 19Example 19	화합물 2-5Compound 2-5	E8E8	4.314.31	57.057.0	1.401.40
실시예 20Example 20	화합물 2-7Compound 2-7	E6E6	4.194.19	65.465.4	1.191.19
실시예 21Example 21	화합물 2-9Compound 2-9	E3E3	4.314.31	62.762.7	1.321.32
실시예 22Example 22	화합물 2-12Compound 2-12	E10E10	4.454.45	63.663.6	1.551.55
비교예 1Comparative Example 1	BD-ABD-A	ET-AET-A	4.564.56	45.545.5	1.001.00
비교예 2Comparative Example 2	BD-ABD-A	ET-CET-C	4.554.55	46.046.0	0.950.95
비교예 3Comparative Example 3	화합물 1Compound 1	ET-AET-A	4.544.54	50.950.9	1.131.13
비교예 4Comparative Example 4	화합물 28Compound 28	ET-BET-B	4.544.54	52.152.1	1.091.09
비교예 5Comparative Example 5	화합물 2-5Compound 2-5	ET-CET-C	4.534.53	47.147.1	1.141.14
비교예 6Comparative Example 6	BD-ABD-A	E2E2	4.194.19	50.850.8	0.980.98

Referring to Table 1, the low voltage, high efficiency and/or long life characteristics of an organic light-emitting device containing the compound of

Formula

1 or 2 of the present invention as a dopant of the emission layer, and using the compound of Formula 3 of the present invention as an electron injection and transport layer You can see that it is excellent.

<소자예 2><Device Example 2>

실시예 23Example 23

On the prepared ITO transparent electrode, the HI-A compound was sequentially thermally vacuum deposited to a thickness of 600 Å and the HAT compound 50 Å to form a hole injection layer. A hole transport layer was formed by vacuum depositing 600 Å of the HT-A compound on the hole injection 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, on the electron blocking layer, a BH-B compound (host) and compound 1 (dopant) were vacuum-deposited at a weight ratio of 25:1 with a film thickness of 200 Å to form a light emitting layer.

Compound E3 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50Å. On the hole blocking layer, the following compound ET-D and the LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

실시예 24 내지 37 및 비교예 7 내지 11Examples 24 to 37 and Comparative Examples 7 to 11

An organic light-emitting device was manufactured in the same manner as in Example 23, except that the materials shown in Table 2 below were used as the dopant material and the hole blocking layer material of the emission layer.

Example 23 to 37 and Comparative were Examples 7 to 11, the measurement of driving voltage and light emission efficiency (conversion efficiency) at a current density of 10 mA / cm ^2, the organic light emitting device, the initial current density of 15 mA / cm ² A relative value was displayed based on Comparative Example 7 by measuring the time (T95) that became 95% of the luminance. The results are shown in Table 2 below.

	화합물compound		10mA/cm² 10mA / cm ²		15mA/cm² 15mA / cm ²
	도펀트Dopant	정공차단층Hole blocking layer	전압(V)Voltage(V)	환산 효율(cd/A/y)Conversion efficiency (cd/A/y)	T95Ratio (%)T95Ratio (%)
실시예 23Example 23	화합물 1 Compound 1	E3E3	4.134.13	61.661.6	1.241.24
실시예 24Example 24	화합물 3 Compound 3	E4E4	4.264.26	60.060.0	1.691.69
실시예 25Example 25	화합물 8 Compound 8	E5E5	4.054.05	70.470.4	1.231.23
실시예 26Example 26	화합물 31Compound 31	E6E6	4.004.00	71.871.8	1.221.22
실시예 27Example 27	화합물 14 Compound 14	E7E7	4.094.09	68.868.8	1.141.14
실시예 28Example 28	화합물 10 Compound 10	E1E1	4.224.22	63.163.1	1.401.40
실시예 29Example 29	화합물 21Compound 21	E2E2	4.004.00	65.065.0	1.181.18
실시예 30Example 30	화합물 16Compound 16	E9E9	4.224.22	65.165.1	1.631.63
실시예 31Example 31	화합물 29Compound 29	E9E9	4.224.22	60.660.6	1.501.50
실시예 32Example 32	화합물 32Compound 32	E4E4	4.264.26	53.453.4	1.101.10
실시예 33Example 33	화합물 2-1Compound 2-1	E5E5	4.054.05	55.655.6	1.451.45
실시예 34Example 34	화합물 2-2Compound 2-2	E8E8	4.134.13	62.162.1	1.321.32
실시예 35Example 35	화합물 2-6Compound 2-6	E10E10	4.264.26	56.056.0	1.501.50
실시예 36Example 36	화합물 2-10Compound 2-10	E7E7	4.094.09	66.466.4	1.141.14
실시예 37Example 37	화합물 2-11Compound 2-11	E3E3	4.134.13	66.366.3	1.321.32
비교예 7Comparative Example 7	BD-ABD-A	ET-AET-A	4.354.35	46.246.2	1.001.00
비교예 8Comparative Example 8	화합물 21Compound 21	ET-CET-C	4.314.31	51.851.8	1.081.08
비교예 9Comparative Example 9	화합물 29Compound 29	ET-BET-B	4.314.31	51.751.7	1.011.01
비교예 10Comparative Example 10	화합물 2-2Compound 2-2	ET-BET-B	4.314.31	50.850.8	1.021.02
비교예 11Comparative Example 11	BD-ABD-A	E8E8	4.134.13	50.150.1	1.171.17

Referring to Table 2, the organic light-emitting device comprising the compound of

Formula

1 or 2 of the present invention as a dopant of the emission layer and using the compound of Formula 3 of the present invention as a hole blocking layer has excellent low voltage, high efficiency and/or long life characteristics. Can be seen.

<소자예 3><Device Example 3>

실시예 38Example 38

On the thus prepared ITO transparent electrode, the HI-A compound was sequentially thermally vacuum deposited to a thickness of 600 Å and a thickness of the following HAT compound 50 Å to form a hole injection layer. A hole transport layer was formed by vacuum depositing 600 Å of the HT-A compound on the hole injection layer. The HT-B was vacuum-deposited on the hole transport layer to a thickness of 50 Å to form an electron blocking layer. Subsequently, a BH-C compound (host) and a compound 3 (dopant) were deposited on the hole transport layer to a film thickness of 200 Å. A light emitting layer was formed by vacuum deposition at a weight ratio of 25:1.

Compound E8 was vacuum-deposited on the emission layer to form a hole blocking layer with a thickness of 50Å. Compound E9 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

실시예 39 내지 46 및 비교예 12 내지 14Examples 39 to 46 and Comparative Examples 12 to 14

An organic light-emitting device was manufactured in the same manner as in Example 38, except that the dopant material, the hole blocking layer material, and the electron injection and transport layer material of the emission layer were used as shown in Table 3 below.

The Examples 38 to 46 and Comparative were measured the driving voltage and light emission efficiency (conversion efficiency) at a current density of 10 mA / cm ^2, the organic light emitting device of Examples 12 to 14, initially at a current density of 15 mA / cm ² A relative value was displayed based on Comparative Example 12 by measuring the time (T95) that became 95% of the luminance. The results are shown in Table 3 below.

	화합물compound			10mA/cm² 10mA / cm ²		15mA/cm² 15mA / cm ²
	도펀트Dopant	정공차단층Hole blocking layer	전자 주입 및 수송층Electron injection and transport layer	전압(V)Voltage(V)	환산 효율(cd/A/y)Conversion efficiency (cd/A/y)	T95Ratio (%)T95Ratio (%)
실시예 38Example 38	화합물 3 Compound 3	E8E8	E9E9	4.304.30	63.363.3	1.541.54
실시예 39Example 39	화합물 9Compound 9	E1E1	E9E9	4.254.25	60.360.3	1.381.38
실시예 40Example 40	화합물 18Compound 18	E3E3	E4E4	4.164.16	61.261.2	1.431.43
실시예 41Example 41	화합물 19Compound 19	E5E5	E2E2	4.094.09	67.967.9	1.151.15
실시예 42Example 42	화합물 23Compound 23	E4E4	E1E1	4.084.08	61.861.8	1.401.40
실시예 43Example 43	화합물 27Compound 27	E9E9	E9E9	4.034.03	61.261.2	1.521.52
실시예 44Example 44	화합물 2-3Compound 2-3	E5E5	E6E6	4.144.14	69.469.4	1.041.04
실시예 45Example 45	화합물 2-8Compound 2-8	E7E7	E10E10	4.084.08	64.364.3	1.251.25
실시예 46Example 46	화합물 2-13Compound 2-13	E10E10	E5E5	4.204.20	64.664.6	1.251.25
비교예 12Comparative Example 12	BD-ABD-A	ET-AET-A	ET-AET-A	4.334.33	46.846.8	1.001.00
비교예 13Comparative Example 13	BD-ABD-A	E1E1	ET-BET-B	4.374.37	49.449.4	1.081.08
비교예 14Comparative Example 14	BD-ABD-A	ET-CET-C	E10E10	4.454.45	48.948.9	1.201.20

Referring to Table 3, the low voltage, high efficiency and high efficiency of an organic light emitting device containing the compound of

Formula

1 or 2 of the present invention as a dopant of the emission layer, and using the compound of Formula 3 of the present invention as a hole blocking layer and an electron injection and transport layer / Or it can be seen that the long life characteristics are excellent.

Claims

A first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,

The organic material layer is an organic light-emitting device including a first organic material layer including a compound represented by Formula 1 or 2 and a second organic material layer including a compound represented by Formula 3 below:

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,

A1, A2, R1 to R3, Z1 and Z2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

n1 to n3 are each an integer of 0 to 3, and when n1 to n3 are each 2 or more, the substituents in two or more parentheses are the same or different from each other,

p1 is 0 or 1,

[Formula 2]

In Formula 2,

E1 to E3 are the same as or different from each other, and each independently an aromatic hydrocarbon ring,

At least one of R4 to R8 is represented by the following formula 1-A or 1-B, or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, the remainder being the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

n4 and n5 are each an integer of 0 to 4, n6 is an integer of 0 to 3, n7 and n8 are each an integer of 0 to 5,

n4 + n5 + n6 + n7 + n8 is 1 or more,

When n4 to n8 are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other,

[Formula 1-A]

[Formula 1-B]

In the formulas 1-A and 1-B,

T1 to T17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

Ar11 to Ar14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring,

L11 is a direct bond; Or a substituted or unsubstituted arylene group,

p2 is 0 or 1,
Means a position bonded to Formula 2,

[Formula 3]

In Chemical Formula 3,

At least one of X1 to X3 is N, and the rest are each independently N or CH,

L is a direct bond; Or a substituted or unsubstituted arylene group,

Ar5 and Ar6 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,

Ar7 is a substituted or unsubstituted m is aryl group; Or substituted or unsubstituted m is a cycloalkyl group,

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

Formula 1 is an organic light-emitting device represented by Formula 101 or 102 below:

In Formulas 101 and 102,

Definitions of A1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are the same as in Formula 1,

G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

G11 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

g11 is an integer of 0 to 8, and when g11 is 2 or more, 2 or more G11 are the same as or different from each other,

p3 is 0 or 1.
The method according to claim 1,

Formula 1 is an organic light emitting device represented by any one of the following Formulas 103 to 106:

In Formulas 103 to 106,

Definitions of R1 to R3, Z1, Z2, p1, Ar1 to Ar4, and n1 to n3 are the same as in Formula 1,

A3, A4, and G5 to G8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

Z3, Z4, G12 and G13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

g12 is an integer of 0 to 8, g13 is an integer of 0 to 4, and when g12 and g13 are each 2 or more, the substituents in the parentheses of 2 or more are the same or different from each other,

p4 and p5 are 0 or 1, respectively.
The method according to claim 1,

Formula 1 is an organic light emitting device represented by any one of the following Formulas 1-1 to 1-4:

In Formulas 1-1 to 1-4,

The definitions of R1 to R3, n1 to n3, and Ar1 to Ar4 are the same as in Formula 1,

A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

Z1 to Z4 and Ar21 to Ar24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring.
The method according to claim 1,

Formula 2 is an organic light-emitting device represented by any one of the following Formulas 201 to 203:

In Formulas 201 to 203,

The definitions of E1 to E3 and n4 to n8 are the same as in Formula 2,

R4 to R8, R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

p6 and p7 are each 1 or 2,

n5" is an integer of 0 to 2, n8" is an integer of 0 to 3, n11 and n12 are each an integer of 0 to 8,

When n5", n8", n11 and n12 are each 2 or more, the substituents in the two or more parentheses are the same or different from each other.
The method according to claim 1,

Formula 2 is an organic light emitting device represented by the following Formula 204:

[Formula 204]

In Formula 204,

At least one of R21 to R25 is represented by Formula 1-A or 1-B, the remainder are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combine with an adjacent group to form a substituted or unsubstituted ring,

E1 to E3, n4 to n8, and the definitions of Formulas 1-A and 1-B are the same as in Formula 2.
The method according to claim 1,

Formula 2 is an organic light-emitting device represented by any one of the following Formulas 211 to 219:

In Formulas 211 to 219,

The definition of n4 to n8 is the same as in Formula 2,

R4 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

p6 to p9 are each 1 or 2,

n4" and n5" are each an integer of 0 to 2, n7" and n8" are an integer of 0 to 3, n11 to n14 are each an integer of 0 to 8,

When n4", n5", n7", n8" and n11 to n14 are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other.
The method according to claim 1,

At least one of R4 to R8 is combined with an adjacent group to form an aliphatic hydrocarbon ring,

At least one of the aliphatic hydrocarbon rings is an organic light-emitting device represented by any one of the following formulas Cy1 to Cy3:

In the formulas Cy1 to Cy3,

R31 to R40 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,

R41 to R43 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or combined with an adjacent group to form a substituted or unsubstituted ring,

n41 is an integer of 0 to 2, n42 and n43 are each an integer of 0 to 4,

When n41 to n43 are each 2 or more, the substituents in the two or more parentheses are the same or different.
The method according to claim 1,

The formula 1-A is represented by the following formula 1-A-1 or 1-A-2, and the formula B-1 is represented by the following formula 1-B-1 or 1-B-2. :

[Formula 1-A-1]

[Formula 1-A-2]

[Formula 1-B-1]

[Formula 1-B-2]

In Formulas 1-A-1 and 1-A-2, the definition of L11 is the same as in Formula 1-A,

In Formulas 1-B-1 and 1-B-2, the definitions of T12 to T17 and p2 are the same as in Formula 1-B,

T18 to T21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

T22 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group; Or by bonding with adjacent groups to form a substituted or unsubstituted ring,

t22 is an integer of 0 to 8, and when t22 is 2 or more, 2 or more T22s are the same as or different from each other.
The method according to claim 1,

Formula 3 is an organic light-emitting device represented by Formula 3-1:

[Formula 3-1]

In Formula 3-1,

The definitions of X1 to X3, L, Ar5 and Ar6 are the same as in Chemical Formula 3,

L'is a direct bond; Or a substituted or unsubstituted arylene group,

At least one of X1' to X3' is N, and the rest are each independently N or CH,

Ar5' and Ar6' 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,

Ar7' is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted cycloalkylene group.
The method according to claim 1,

The compound represented by Formula 1 is an organic light emitting device represented by any one of the following compounds:

.
The method according to claim 1,

The compound represented by Formula 2 is an organic light emitting device represented by any one of the following compounds:

.
The method according to claim 1,

Formula 3 is an organic light-emitting device represented by any one of the following compounds:

.
The method according to claim 1,

The first electrode is an anode, the second electrode is a cathode, the first organic material layer is an emission layer, and the second organic material layer is provided between the second electrode and the first organic material layer.
The method according to claim 1,

The organic material layer includes two or more light-emitting layers, and one of the two or more light-emitting layers includes a compound represented by Formula 1 or 2 above.
The method according to claim 1,

The second organic material layer is an organic light-emitting device further comprising one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
The method according to claim 1,

The second organic material layer is an organic light emitting device comprising at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.