KR102391296B1 - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0093187 filed with the Korea Intellectual Property Office on July 31, 2019, the entire contents of which are incorporated herein by reference.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

Chinese Patent Publication No. 108137618

An organic light emitting device is described herein.

An exemplary embodiment of the present specification includes 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 the following Chemical Formula 1 or 2 and a second containing a compound represented by the following Chemical Formula 3 An organic light emitting device including an organic material layer is provided.

[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 combine 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 combine 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, two or more substituents in parentheses are the same as 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 are each independently an aromatic hydrocarbon ring,

At least one of R4 to R8 is combined with a group represented by the following formula 1-A or 1-B or an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, the rest 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,

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

n4 + n5 + n6 + n7 + n8 is greater than or equal to 1,

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

[Formula 1-A]

[Formula 1-B]

In 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 combine 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 combine 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,

는 화학식 2에 결합되는 위치를 의미하고,p2 is 0 or 1,

means a position bonded to Formula 2,

[Formula 3]

In Formula 3,

HAr is a substituted or unsubstituted N-containing heterocyclic group,

L21 and L22 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent heterocyclic group,

Ar21 is a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent heterocyclic group; or -O-;

a and b are each an integer from 1 to 3,

When a is 2 or more, HAr is the same as or different from each other.

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

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 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 lifespan. The light emitting 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 that electrons can be easily transferred to the light emitting layer, thereby exhibiting high efficiency and lifetime.

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

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

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

is another substituent or means a site bonded to the bonding portion.

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

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; silyl group; boron group; an alkyl group; alkenyl group; alkynyl group; alkoxy group; an alkylthio group; aryloxy group; arylthio group; cycloalkyl group; aryl group; amine group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.

의 치환기가 될 수 있다. In the present specification, that two or more substituents are connected means that hydrogen of any one substituent is replaced with another substituent. For example, an isopropyl group and a phenyl group are linked

It can be a substituent of

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 것과 동일하게 적용된다.In the present specification, three substituents are connected to (substituent 1)-(substituent 2)-(substituent 3) as well as consecutively connected (substituent 1) to (substituent 2) and (substituent 3) It also includes connecting. For example, two phenyl groups and an isopropyl group are linked

It can be a substituent of The same applies to those in which 4 or more substituents are connected.

In the present specification, "substituted with A or B" includes not only the case substituted with A or only B, but also the case substituted with A and B.

In the present specification, "substituted or unsubstituted" means deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; silyl group; boron group; an alkyl group having 1 to 10 carbon atoms; an alkenyl group having 2 to 10 carbon atoms; an 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; an aryloxy group having 6 to 30 carbon atoms; an arylthio group having 6 to 30 carbon atoms; a cycloalkyl group having 3 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; amine group; And it means that 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 does not have any substituents.

In the present specification, "substituted or unsubstituted" means deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; silyl group; boron group; an alkyl group having 1 to 6 carbon atoms; an alkenyl group having 2 to 6 carbon atoms; an 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; an aryloxy group having 6 to 20 carbon atoms; an arylthio group having 6 to 20 carbon atoms; a cycloalkyl group having 3 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; amine group; And it means that 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 straight 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. 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 not only monocyclic groups but also bicyclic groups such as bridgeheads, fused rings, and spiros. 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, the cycloalkene (cycloalkene) has a double bond in the hydrocarbon ring, but as a non-aromatic ring group, the number of carbon atoms is not particularly limited, but 3 to 60, 3 to 30, 3 to 20, or 3 to 10 am. Cycloalkenes include not only monocyclic groups but also bicyclic groups such as bridgeheads, fused rings, and spiro rings. Examples of the cycloalkene include, but are not limited to, cyclopropene, cyclobutene, cyclopentene, and cyclohexene.

In the present specification, an alkoxy group is an aryl group connected to an oxygen atom, an acylthio group is an alkyl group connected to a sulfur atom, and the description regarding the alkyl group described above can 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 is 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, a quaterphenyl group, and the like, 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, the 9th carbon atom (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.

In the present specification, the substituted aryl group may include a form in which an aliphatic ring is condensed to an aryl group. For example, a tetrahydronaphthalene group of the following structure is included in a substituted aryl group. In the following structure, one of the carbons of the benzene ring may be connected 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 description regarding the aryl group described above can 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 example of 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, 9-phenanthryloxy group, and the like, and the arylthioxy group includes phenylthioxy group, 2- and a methylphenylthioxy group, a 4-tert-butylphenylthioxy 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. but 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. The silyl group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a tert-butylmethyl boron group, a vinyl methyl boron group, a propylmethyl boron group, a methylphenyl boron group, a diphenyl boron group, a phenyl boron group, and the like. .

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, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

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, and a bis(tert-butylphenyl)amine group. , 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 refers to an amine group substituted with an aryl group and a heteroaryl group, and the description of the above-described aryl group and the heteroaryl group to be described later may be applied.

In the present specification, the heterocyclic group is a ring group including at least one of N, O, S, and Si as heteroatoms, 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, but are not limited to, a pyridyl group; quinoline group; thiophene group; dibenzothiophene group; furan group; dibenzofuran group; naphthobenzofuran group; a carbazole group; benzocarbazole group; naphthobenzothiophene group; hexahydrocarbazole group; dihydroacridine group; dibenzoazacillin group; phenoxazine; phenothiazine; dihydrodibenzoazacillin group; spiro (dibenzosilol-dibenzoazacillin) groups; There is a spiro (acridine-fluorene) group, and the like, but is not limited thereto.

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

As used herein, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent positioned sterically close to the substituent, or another substituent substituted on the atom in which the substituent is substituted.

In the present specification, "a ring formed by bonding adjacent groups" is a hydrocarbon ring; or a heterocyclic ring.

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

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or a 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 the non-monovalent, the above description of the cycloalkyl group may be applied. Examples of the condensed ring of the aromatic and the aliphatic include a 1,2,3,4-tetrahydronaphthalene group, a 2,3-dihydro-1H-indene group, and the like, 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 that it is a divalent group.

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

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

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

Hereinafter, Formula 1 will be described.

[Formula 1]

In an 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 combine 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 C 1 to C 10 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 C 1 to C 10 alkoxy group; a substituted or unsubstituted C 1 to C 10 alkylthio group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or combine 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 combine 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 C 1 to C 10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or combine 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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; or an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; Or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, wherein the aliphatic hydrocarbon ring is 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 , or two or more groups selected from the group may be unsubstituted or substituted with a connected substituent, and a monocyclic to bicyclic aliphatic or aromatic hydrocarbon ring may be condensed to 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 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 combined with an adjacent group is condensed or non-condensed to form a 6-membered 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, it combines with an adjacent group to form a 6-membered aliphatic hydrocarbon ring in which benzene or cyclohexane 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.

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 combined with adjacent groups to form substituted or unsubstituted cyclohexane, substituted or unsubstituted tetrahydronaphthalene, or substituted or unsubstituted decahydronaphthalene. In this case, the adjacent group 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 combine with an adjacent group to form cyclohexane unsubstituted or substituted with deuterium, tetrahydronaphthalene substituted or unsubstituted with deuterium, a butyl group or a phenyl group, or decahydronaphthalene substituted or unsubstituted with deuterium. In this case, the adjacent group may be two selected from Ar1 to Ar4.

According to an exemplary embodiment of the present specification, adjacent two 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 bonded to each other to form a ring means Ar1 and Ar3; or Ar2 and Ar4 combine with each other to form a ring.

According to an exemplary embodiment of the present specification, when two of Ar1 to Ar4 combine with 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 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 C 1 to C 10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

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 C6-C20 aryl group.

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 an 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 an 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 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 10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In another 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 C6-C20 aryl group.

In another 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.

[Formula 101] [Formula 102]

In Formulas 101 and 102,

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

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 combine with an adjacent group to form a substituted or unsubstituted ring,

g11 is an integer from 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 one embodiment of the present specification, p3 is 1.

In an 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 C6-C20 aryl 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 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 C 1 to C 10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or combine 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 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 is formed by combining with an adjacent group.

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 combine with adjacent groups to form substituted or unsubstituted cyclohexane, or substituted or unsubstituted benzene.

According to another exemplary embodiment, G11 is hydrogen; heavy hydrogen; methyl group; tert-butyl group; or a phenyl group; combine with adjacent groups to form cyclohexane substituted or unsubstituted with a methyl group; Alternatively, it combines with an adjacent group to form benzene unsubstituted or substituted 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 an 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 combine 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 C 1 to C 10 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 C 1 to C 10 alkoxy group; a substituted or unsubstituted C 1 to C 10 alkylthio group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.

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 heterocyclic group having 2 to 60 carbon atoms; 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; an 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-membered or 6-membered ring,

The aryl group, heterocyclic group or ring of A1 and A2 is one or more substituents 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 a substituent to which the above groups are 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; an 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-membered or 6-membered ring,

The aryl group, heterocyclic group or ring of A1 and A2 is 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 selected from the group A 5- or 6-membered hydrocarbon ring substituted or unsubstituted with a substituent to which the above groups are connected, or substituted or unsubstituted with the above substituent is condensed or non-condensed.

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

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

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

In an exemplary embodiment of the present specification, A2 may combine with adjacent A1 or R2 to form a ring.

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

[Formula 103] [Formula 104]

[Formula 105] [Formula 106]

In Formulas 103 to 106,

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

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 combine with an adjacent group to form a substituted or unsubstituted ring,

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

p4 and p5 are 0 or 1, respectively.

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

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

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

In an 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 C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, A3 is a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In another embodiment, the aryl group or heterocyclic group of A3 is one or more substituents 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 two or more groups selected from the group are substituted or unsubstituted with a connected substituent; Or a 5- or 6-membered hydrocarbon ring substituted or unsubstituted with the above substituent is condensed or non-condensed.

In another embodiment, the aryl group or heterocyclic group of A3 is 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 two or more groups selected from the group are substituted or unsubstituted with a connected substituent; 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 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 a substituent to which two or more groups selected from the group are connected. an aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with, and a 5- or 6-membered aliphatic hydrocarbon ring is condensed or non-condensed; 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 a substituent selected from the group consisting of two or more groups selected from the group is substituted or unsubstituted It is a cyclic heterocyclic group having 2 to 20 carbon atoms.

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, a fluoro group, a methyl group, an ethyl group, a propyl group, a butyl group, a 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), Ph-d5, a naphthyl group Or a phenyl group unsubstituted or substituted with a tetramethyltetrahydronaphthalene group; a biphenyl group unsubstituted or substituted with deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, a trimethylsilyl group, and a 2-phenylpropan-2-yl group (2-phenylpropan-2-yl); a terphenyl group unsubstituted or substituted with deuterium or a 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 deuterium or a methyl group; a dibenzofuran group unsubstituted or substituted with deuterium or a butyl group; or a dibenzothiophene group unsubstituted or substituted with deuterium or a 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 it combines with R1 to form a substituted or unsubstituted 5-membered or 6-membered ring.

In another exemplary embodiment, A2 is hydrogen; or deuterium; Or it combines with R1 to form a 5-membered or 6-membered ring unsubstituted or substituted 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 combining A2 and R1 is benzofuran, benzothiophene, or indene.

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

In an 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 C6-C20 aryl 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 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 C 1 to C 10 alkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C90 arylsilyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or combine 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 C6-C60 arylsilyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or 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 is formed by combining with an adjacent group.

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 combine with adjacent groups to form substituted or unsubstituted cyclohexane, or 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 is combined with adjacent G13 to form a substituted or unsubstituted ring.

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

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

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

[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 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 above,

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 combine with an adjacent group to form a substituted or unsubstituted ring.

In the present specification, that adjacent groups of Ar21 to Ar24 combine with each other to form a ring means i) two of Ar21 to Ar24 combine with each other to form an aliphatic hydrocarbon ring, or ii) Ar21 to Ar24 participate in ring formation to form an aromatic ring means to form a hydrocarbon ring.

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

In an 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 combine 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 C 1 to C 10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or combine 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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; or an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; Or combined with an adjacent group, is unsubstituted or substituted 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, monocyclic to bicyclic hydrocarbon rings are condensed or non-condensed It forms a 6-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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; or an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; Or combined with an adjacent group, is unsubstituted or substituted 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, cyclohexane or benzene is condensed or non-condensed 6-membered to form a hydrocarbon ring of

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 combined with adjacent groups to form substituted or unsubstituted cyclohexane, substituted or unsubstituted benzene, or substituted or unsubstituted decahydronaphthalene. In this case, the adjacent group 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, a tert-butyl group, or a trimethylsilyl group; Or naphthalene substituted or unsubstituted with a phenyl group is formed. In this case, the adjacent group may be two selected from Ar21 to Ar24.

According to an exemplary embodiment of the present specification, when two of Ar21 to Ar24 combine with 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 are substituents that do not form an aliphatic hydrocarbon ring among Ar21 to Ar24;

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

In an 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 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 10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In another 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 C6-C20 aryl group.

In another 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.

According to an exemplary embodiment of the present specification, Y2 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C90 arylsilyl group; or a substituted or unsubstituted C6-C30 aryl group.

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 C6-C60 arylsilyl group; or a substituted or unsubstituted C6-C20 aryl group.

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; a 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.

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 combine 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 C 1 to C 10 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 C 1 to C 10 alkoxy group; a substituted or unsubstituted C 1 to C 10 alkylthio group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted C 3 to C 30 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 alkyl group; a substituted or unsubstituted aryl 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.

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-C30 alkylsilyl group; a substituted or unsubstituted C6-C90 arylsilyl group; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C60 arylamine group; A substituted or unsubstituted C2-C90 heteroarylamine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; It combines with an adjacent group to form a substituted or unsubstituted ring having 2 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 C 1 to C 18 alkylsilyl group; a substituted or unsubstituted C6-C60 arylsilyl group; a substituted or unsubstituted C 1 to C 6 alkyl group; a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C6-C60 arylamine group; a substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms; Or a substituted or unsubstituted C2-20 heterocyclic group; It combines with an adjacent group to form a substituted or unsubstituted 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 C 1 to C 18 alkylsilyl group; a substituted or unsubstituted C6-C60 arylsilyl group; a substituted or unsubstituted C 1 to C 6 alkyl group; a substituted or unsubstituted C6-C20 aryl group; NY11Y12; Or a substituted or unsubstituted C2-20 heterocyclic group; It combines with an adjacent group to form a substituted or unsubstituted 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; an alkylsilyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 90 carbon atoms that is unsubstituted or substituted with deuterium; an alkylarylsilyl group having 7 to 60 carbon atoms that is unsubstituted or substituted with deuterium; an alkyl group having 1 to 10 carbon atoms that is unsubstituted or substituted with deuterium; an arylalkyl group having 7 to 60 carbon atoms that is unsubstituted or substituted with deuterium; 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 selected from the group consisting of two or more groups selected from the group consisting of substituted or unsubstituted carbon atoms an aryl group of 6 to 30; NY11Y12; Or 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 two or more groups selected from the group substituted or unsubstituted with a connected substituent or a heterocyclic group having 2 to 30 carbon atoms; It combines with an adjacent group to form a ring having 2 to 30 carbon atoms, substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or a substituent to which two or more groups selected from the group are connected.

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 that is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium; an alkylarylsilyl group having 7 to 40 carbon atoms that is unsubstituted or substituted with deuterium; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; an arylalkyl group having 7 to 40 carbon atoms that is 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 a substituent selected from the group consisting of two or more groups connected to or unsubstituted carbon number 6 to 20 aryl groups; NY11Y12; Or 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 two or more groups selected from the group substituted or unsubstituted with a connected substituent or a heterocyclic group having 2 to 20 carbon atoms; It combines with an adjacent group to form a ring having 2 to 20 carbon atoms that is 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 selected from the group are connected.

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 combine with an adjacent group to form a substituted or unsubstituted benzofuran, 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 hexene is formed.

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; A substituted or unsubstituted phenoxazine group (phenoxazine); A substituted or unsubstituted phenothiazine group (phenothiazine); A substituted or unsubstituted dihydrodibenzoazacillin group; substituted or unsubstituted spiro (dibenzosilol-dibenzoazacilline 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 hexene is formed.

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; a 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, a fluoro group, a cyano group, a methyl group, CD ₃ , a tert-butyl group, a 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), a trimethylsilyl group, a triphenylsilyl group or a phenyl group; unsubstituted, hexene condensed or non-condensed, diphenylamine group; a substituted or unsubstituted phenylnaphthylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a bisbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a phenyldibenzofuranamine group unsubstituted or substituted with deuterium, a methyl group or a tertbutyl group, and hexene is condensed or uncondensed; a phenyldibenzothiophenamine group unsubstituted or substituted with deuterium, a methyl group or a tertbutyl group, and hexene is condensed or uncondensed; a carbazole group unsubstituted or substituted with deuterium or a tert-butyl group; a hexahydrocarbazole group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, a phenyl group, or Ph-d5, hexane, hexene or benzene is condensed or non-condensed; a dihydroacridine group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; phenoxazine; phenothiazine; a dihydrodibenzoazacilline group unsubstituted or substituted with a phenyl group; a spiro (acridine-fluorene) group unsubstituted or substituted with a methyl group; spiro (dibenzosilol-dibenzoazacillin) groups; 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 in combination 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 cyclohexene unsubstituted or substituted with a methyl group.

According to another embodiment, two adjacent R1; R1 and A2; R1 and A4; Or two adjacent R2 is combined with an adjacent group, tert- butyl group or phenyl group unsubstituted or substituted benzofuran; 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 cyclohexene unsubstituted or substituted 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 Chemical Formulas HAr1 to HAr3, or by Chemical Formula 1-B.

[Formula HAr1] [Formula HAr2] [Formula HAr3]

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 heterocyclic ring,

y3 is an integer of 0 to 8, and when y3 is 2 or more, Y3 of 2 or more 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 C 1 to C 10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

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 C6-C20 aryl group.

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 a phenyl group

In an 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 condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and 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 C6-C30 aryl group; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a condensed ring group having 9 to 30 carbon atoms in a substituted or unsubstituted aromatic hydrocarbon ring and 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 C6-C20 aryl group; a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms; or a condensed ring group having 9 to 20 carbon atoms in a substituted or unsubstituted aromatic 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 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 that is unsubstituted or substituted with one or more substituents or a substituent to which two or more groups selected from the group are connected; 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted C2 to 30 heterocyclic groups; Or 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted aromatic group It is a C9-C30 condensed ring group 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 that is unsubstituted or substituted with one or more substituents or a substituent to which two or more groups selected from the group are connected; At least one substituent 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted C2 to 20 heterocyclic groups; Or 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 group selected from the group consisting of two or more groups selected from the group linked to, substituted or unsubstituted aromatic It is a C9-C20 condensed ring group of a hydrocarbon ring and an aliphatic hydrocarbon ring.

In another exemplary embodiment, Y11 and Y12 are the same as or different from each other, and each independently a 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 group having 1 to 30 carbon atoms. a silyl group or an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an arylsilyl group having 6 to 90 carbon atoms; a heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms; or a condensed ring group having 9 to 30 carbon atoms in 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 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 alkyl having 1 to 18 carbon atoms. a silyl group or an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with an arylsilyl group having 6 to 60 carbon atoms; a heterocyclic group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms; or a condensed ring group having 9 to 20 carbon atoms in 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 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 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 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 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 embodiment, Y11 and Y12 are the same as or different from each other, and each independently deuterium, a fluoro group, a cyano group, a methyl group, CD ₃ , a butyl group, a trimethylsilyl group, a triphenylsilyl group, or 2- a phenyl group unsubstituted or substituted with a phenylpropan-2-yl group; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a dibenzofuran group unsubstituted or substituted with deuterium or a butyl group; a dibenzothiophene group unsubstituted or substituted with deuterium or a butyl group; Or a tetrahydronaphthalene group unsubstituted or substituted with deuterium or a methyl group.

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

[Formula Cy11] [Formula Cy12]

In the above formulas Cy11 and Cy12,

The dotted double line is the condensed position,

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

Y7 to Y11 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 heterocyclic ring; Combined with an adjacent group to form a substituted or unsubstituted ring,

p10 is 1 or 2,

y6 is an integer from 0 to 4, y8 is an integer from 0 to 8, and when y6 and y8 are each 2 or more, two or more substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, Y7 to Y11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 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 ring having 3 to 30 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 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 ring having 3 to 20 carbon atoms.

According to another exemplary embodiment, Y7 to Y11 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 combined with adjacent groups to form hexane unsubstituted or substituted with deuterium, hexene substituted or unsubstituted with deuterium, or benzene unsubstituted or substituted with deuterium.

According to another exemplary embodiment, Y7 to Y11 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; It combines with adjacent Y7 to form benzene unsubstituted or substituted with deuterium, or hexene substituted or unsubstituted with deuterium.

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 Y7 to form benzene substituted or unsubstituted with deuterium, or hexane substituted or unsubstituted with deuterium.

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

In another exemplary embodiment, in Formulas Cy11 and Cy12, 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 a butyl group; Y10 and Y11 are phenyl groups unsubstituted or substituted with deuterium or a butyl group, respectively, and combine with each other to form fluorene substituted or unsubstituted with deuterium or a butyl group.

In another exemplary embodiment, in Formulas Cy11 and Cy12, 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 a butyl group; Y10 and Y11 are phenyl groups unsubstituted or substituted with deuterium or a butyl group, respectively, and combine with each other to form dibenzosilole substituted or unsubstituted with a deuterium or butyl group.

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

In one embodiment of the present specification, two adjacent R1; R1 and A2; R1 and A4; Alternatively, two adjacent R2s combine with each other to form a ring represented by Formula Cy11.

In another embodiment, two adjacent R1; Alternatively, two adjacent R2s combine with each other to form a ring represented by the above formula Cy12.

In an 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; a 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, a fluoro group, a cyano group, a methyl group, CD ₃ , a tert-butyl group, a 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), a trimethylsilyl group, a triphenylsilyl group or a phenyl group; unsubstituted, hexene condensed or non-condensed, diphenylamine group; a substituted or unsubstituted phenylnaphthylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a bisbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a phenyldibenzofuranamine group unsubstituted or substituted with deuterium, a methyl group or a tertbutyl group, and hexene is condensed or uncondensed; a phenyldibenzothiophenamine group unsubstituted or substituted with deuterium, a methyl group or a tertbutyl group, and hexene is condensed or uncondensed; a hexahydrocarbazole group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, a phenyl group, or Ph-d5, condensed or uncondensed with hexane, hexene, or benzene; benzofuran unsubstituted or substituted with a tert-butyl group or a phenyl group in combination 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 cyclohexene unsubstituted or substituted 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, a fluoro group, a cyano group, a methyl group, CD ₃ , a tert-butyl group, a 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), a trimethylsilyl group, a triphenylsilyl group or a phenyl group; unsubstituted, hexene condensed or non-condensed, diphenylamine group; a substituted or unsubstituted phenylnaphthylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a bisbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a carbazole group unsubstituted or substituted with deuterium or a tert-butyl group; a hexahydrocarbazole group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, a phenyl group, or Ph-d5, hexane, hexene or benzene is condensed or non-condensed; a dihydroacridine group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; phenoxazine; phenothiazine; a dihydrodibenzoazacilline group unsubstituted or substituted with a phenyl group; a spiro (acridine-fluorene) group unsubstituted or substituted with a methyl group; spiro (dibenzosilol-dibenzoazacillin) groups; 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 an 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 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 10 alkyl group; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another 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 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 are each independently an aromatic hydrocarbon ring.

According to another exemplary embodiment, E1 to E3 are the same as or different from each other, and are 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 represents 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 combined with a group represented by the following formula 1-A or 1-B or an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the rest 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.

[Formula 1-A]

[Formula 1-B]

In 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 combine 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 combine 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,

는 화학식 2에 결합되는 위치를 의미한다.p2 is 0 or 1,

denotes a position bonded to Formula 2;

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

According to another exemplary embodiment, at least one of R4 to R8 is combined with a group represented by Formula 1-A or 1-B or an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, and the rest 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 C 1 to C 10 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 C 1 to C 10 alkoxy group; a substituted or unsubstituted C 1 to C 10 alkylthio group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.

According to another exemplary embodiment, at least one of R4 to R8 is combined with a group represented by Formula 1-A or 1-B or an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the rest are the same as 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 combine 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 combined with a group represented by Formula 1-A or 1-B or an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, and the rest are the same as 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 an 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 R4 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring or iii) two adjacent R5s combine with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, iv) two adjacent R6s combine with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or v) adjacent Two R7s combine with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, or vi) two adjacent R8s combine with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In another embodiment, i) at least one of R4 to R8 is represented by Formula 1-A or 1-B, or ii) two adjacent R4 are bonded to each other to form a 5-membered group unsubstituted or substituted with an alkyl group; or to form a 6-membered aliphatic hydrocarbon ring, or iii) two adjacent R5s combine with each other to form a 5-membered or 6-membered aliphatic hydrocarbon ring unsubstituted or substituted with an alkyl group, or iv) two adjacent R6s combine with each other to form a 6-membered aliphatic hydrocarbon ring Forms a 5-membered or 6-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group, or v) two adjacent R7 are bonded to each other to form a 5- or 6-membered aliphatic hydrocarbon ring unsubstituted or substituted with an alkyl group, vi) Two adjacent R8s combine with each other to form a 5-membered or 6-membered aliphatic hydrocarbon ring unsubstituted or substituted with an alkyl group. In this case, the aliphatic hydrocarbon ring of ii) to vi) includes at least one alkyl group as a substituent, and may also include a substituent 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) two adjacent R4 are bonded to each other and substituted or unsubstituted with a methyl group pentene, or hexene substituted or unsubstituted with a methyl group is formed, or iii) two adjacent R5s combine with each other to form a pentene substituted or unsubstituted with a methyl group, or a hexene substituted or unsubstituted with a methyl group, or iv) two adjacent R6 are combined with 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 an unsubstituted hexene, or vi) two adjacent R8s combine with each other to form a pentene substituted or unsubstituted with a methyl group, or a hexene substituted or unsubstituted with a methyl group. In this case, 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 may also correspond to ii).

In an exemplary embodiment of the present specification, at least one of R4 to R8 is a remaining substituent that does not form a substituted or unsubstituted aliphatic hydrocarbon ring by combining with a group represented by Formula 1-A or 1-B or an adjacent group (hereinafter, ' The remaining substituents among R4 to R8 are referred to as '.) are the same as or different from each other and are 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.

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

In another exemplary embodiment, the remaining substituents among 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 C 1 to C 10 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 C 1 to C 10 alkoxy group; a substituted or unsubstituted C 1 to C 10 alkylthio group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted C 3 to C 30 ring.

In another exemplary embodiment, the remaining substituents among 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 combine with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, the remaining substituents among 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-C30 alkylsilyl group; a substituted or unsubstituted C6-C90 arylsilyl group; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; A substituted or unsubstituted C1-C30 alkylamine group; a substituted or unsubstituted C6-C60 arylamine group; A substituted or unsubstituted C2-C90 heteroarylamine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; It combines with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In another exemplary embodiment, the remaining substituents among 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 C6-C60 arylsilyl group; a substituted or unsubstituted C 1 to C 6 alkyl group; a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C 1 to C 18 alkylamine group; a substituted or unsubstituted C6-C60 arylamine group; a substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms; Or a substituted or unsubstituted C2-20 heterocyclic group; It combines with an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

In another exemplary embodiment, the remaining substituents among 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 C6-C60 arylsilyl group; a substituted or unsubstituted C 1 to C 6 alkyl group; a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C 1 to C 18 alkylamine group; NY11Y12; Or a substituted or unsubstituted C2-20 heterocyclic group; It combines with an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

In another exemplary embodiment, the remaining substituents among 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 that is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 90 carbon atoms that is unsubstituted or substituted with deuterium; an alkylarylsilyl group having 7 to 60 carbon atoms that is unsubstituted or substituted with deuterium; an alkyl group having 1 to 10 carbon atoms that is unsubstituted or substituted with deuterium; an arylalkyl group having 7 to 60 carbon atoms that is unsubstituted or substituted with deuterium; 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted carbon number an aryl group of 6 to 30; an alkylamine group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; NY11Y12; Or 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 two or more groups selected from the group substituted or unsubstituted with a connected substituent or a heterocyclic group having 2 to 30 carbon atoms; It combines with an adjacent group to form a ring having 2 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or a substituent to which two or more groups selected from the group are connected.

In another exemplary embodiment, the remaining substituents among 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 that is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium; an alkylarylsilyl group having 7 to 40 carbon atoms that is unsubstituted or substituted with deuterium; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; an arylalkyl group having 7 to 40 carbon atoms that is unsubstituted or substituted with deuterium; At least one substituent 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted carbon number 6 to 20 aryl groups; a substituted or unsubstituted C 1 to C 18 alkylamine group; NY11Y12; Or 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 two or more groups selected from the group are linked with a substituent substituted or unsubstituted or a heterocyclic group having 2 to 20 carbon atoms; It combines with an adjacent group to form a ring having 2 to 20 carbon atoms, substituted or unsubstituted 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 selected from the group are connected.

In another exemplary embodiment, the remaining substituents among 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 combine with an adjacent group to form a substituted or unsubstituted benzofuran, substituted or unsubstituted ring.

In another exemplary embodiment, the remaining substituents among 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 hexene is formed.

In another exemplary embodiment, the remaining substituents among 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; A substituted or unsubstituted phenoxazine group (phenoxazine); A substituted or unsubstituted phenothiazine group (phenothiazine); A substituted or unsubstituted dihydrodibenzoazacillin group; substituted or unsubstituted spiro (dibenzosilol-dibenzoazacilline 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 hexene is formed.

According to another exemplary embodiment, the remaining substituents among 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; a 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; a biphenyl group unsubstituted or substituted with deuterium, a fluoro group, or a tert-butyl group; a terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; Deuterium, a fluorenyl group unsubstituted or substituted with a methyl group; a dimethylamine group unsubstituted or substituted with deuterium; Substituted with deuterium, a fluoro group, a cyano group, a methyl group, CD ₃ , a tert-butyl group, a 2-phenylpropan-2-yl group (2-phenylpropan-2-yl), a trimethylsilyl group, a triphenylsilyl group or a phenyl group; unsubstituted, hexene condensed or non-condensed, diphenylamine group; a substituted or unsubstituted phenylnaphthylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a substituted or unsubstituted phenylbiphenylamine group unsubstituted or substituted with deuterium or a tert-butyl group; a carbazole group unsubstituted or substituted with deuterium or a tert-butyl group; a dihydroacridine group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; phenoxazine; phenothiazine; a dihydrodibenzoazacilline group unsubstituted or substituted with a phenyl group; a spiro (acridine-fluorene) group unsubstituted or substituted with a methyl group; spiro (dibenzosilol-dibenzoazacillin) groups; dibenzofuran group; or a dibenzothiophene group.

According to another exemplary embodiment, the remaining substituents among R4 to R8 are benzofuran unsubstituted or substituted with a tert-butyl group or a phenyl group in combination 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 cyclohexene unsubstituted or substituted with a methyl group.

According to another embodiment, two adjacent R4; two adjacent R5s; two adjacent R6; two adjacent R7; or two adjacent R8s are bonded to each other and are benzofuran unsubstituted or substituted with a tert-butyl group or a 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 cyclohexene unsubstituted or substituted 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 among R4 to R8 combine with an adjacent group to form a ring represented by Cy11 or Cy12. Specifically, adjacent two R4; two adjacent R5s; two adjacent R6; two adjacent R7; Alternatively, two adjacent R8s combine with each other to form a ring represented by the following formula Cy11 or Cy12.

In one embodiment of the present specification, two adjacent R7; Alternatively, 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 R7; Alternatively, two adjacent R8s combine with 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.

[Formula 201] [Formula 202]

[Formula 203]

In Formulas 201 to 203,

The definitions of E1 to E3, 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 combine with an adjacent group to form a substituted or unsubstituted ring,

p6 and p7 are each 1 or 2,

n5" is an integer from 0 to 2, n8" is an integer from 0 to 3, n11 and n12 are each an integer from 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 as or different from each other.

In an 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 C 1 to C 10 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 C 1 to C 10 alkoxy group; a substituted or unsubstituted C 1 to C 10 alkylthio group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C6-C30 aryloxy group; a substituted or unsubstituted C6-C30 arylthio group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted C 3 to C 30 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 alkyl group; or a substituted or unsubstituted aryl group; Or combine 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 C 1 to C 10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, 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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; or an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; Alternatively, it combines with an adjacent group to form 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.

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; combine with an adjacent group to form a benzene ring unsubstituted or substituted with deuterium or a butyl group; combine with an adjacent group to form an indene ring substituted or unsubstituted with deuterium, a methyl group, or a butyl group; Combines 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 one embodiment of the present specification, n4 to n6 are 0 or 1, respectively.

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

[Formula 211] [Formula 212]

[Formula 213] [Formula 214]

[Formula 215] [Formula 216]

[Formula 217] [Formula 218]

[Formula 219]

In Formulas 211 to 219,

The definitions of n4 to n8 are 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 combine 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 from 0 to 2, n7" and n8" are integers from 0 to 3, n11 to n14 are each an integer from 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 one 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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; or an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; Alternatively, it combines with an adjacent group to form 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.

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; combine with an adjacent group to form a benzene ring unsubstituted or substituted with deuterium or a butyl group; combine with an adjacent group to form an indene ring substituted or unsubstituted with deuterium, a methyl group, or a butyl group; Combines 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 combined with 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.

[Formula Cy1] [Formula Cy2] [Formula Cy3]

In the formula Cy1 to Cy3,

R31 to R40 are the same as or different from each other, and each independently represents 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 combine with an adjacent group to form a substituted or unsubstituted ring,

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

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

In the present specification, the aliphatic hydrocarbon ring included in Formula 2 is 1) an aliphatic hydrocarbon ring formed by bonding two R4 to each other, 2) an aliphatic hydrocarbon ring formed by bonding two R5 to each other, 3) two R6 refers to at least one of an aliphatic hydrocarbon ring formed by bonding to each other, 4) an aliphatic hydrocarbon ring formed by bonding two R7s to each other, and 5) an aliphatic hydrocarbon ring formed by bonding two R8 to each other.

In an exemplary embodiment of the present specification, R31 to R40 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C10 alkyl group.

In another exemplary embodiment, R31 to R40 are the same as or different from each other, and each independently represent a substituted or unsubstituted C 1 to C 6 alkyl group.

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 combine 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 it combines with an adjacent group to form a substituted or unsubstituted ring having 3 to 20 carbon atoms.

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

In another embodiment, R43 is hydrogen; or deuterium; Four adjacent R43s combine with each other to form a substituted or unsubstituted benzene ring.

In another embodiment, R43 is hydrogen; or deuterium; Alternatively, four adjacent R43s combine with 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 embodiment, R43 is hydrogen; or deuterium; Alternatively, four adjacent R43s combine with each other to form a benzene ring.

In another 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 included in Formula 2 is selected from the following structure.

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

In another exemplary embodiment, 1) an aliphatic hydrocarbon ring formed by bonding two R4 to each other, 2) an aliphatic hydrocarbon ring formed by bonding two R5 to each other, 3) an aliphatic ring formed by bonding two R6 to each other At least one ring among a hydrocarbon ring, 4) an aliphatic hydrocarbon ring formed by bonding two R7 to each other, and 5) an aliphatic hydrocarbon ring formed by bonding two R8 to each other is selected from the above structure.

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

[Formula 204]

In Formula 204,

At least one of R21 to R25 is represented by Formula 1-A or 1-B, the rest 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,

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

In an 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 combine 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 combine 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 combine with an adjacent group to form an aliphatic hydrocarbon ring of a substituted or unsubstituted bridge tree or a fused 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 combine with each other to form an aliphatic hydrocarbon ring of a substituted or unsubstituted bridge tree or a fused ring; Or T2, T6 and T10 combine with each other to form an aliphatic hydrocarbon ring of a substituted or unsubstituted bridge tree or a fused ring.

In one embodiment of the present specification, L11 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

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

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

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

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

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

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

In another exemplary embodiment, Formula 1-A is represented by Formula 1-A-1 or 1-A-2, and Formula B-1 is Formula 1-B-1 or 1-B-2 is displayed as

[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 combine with an adjacent group to form a substituted or unsubstituted ring,

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

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.

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 unsubstituted or substituted with deuterium or an alkyl group having 1 to 6 carbon atoms.

In an 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 combine with an adjacent group to form a substituted or unsubstituted ring.

In another 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 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or it combines with an adjacent group to form a substituted or unsubstituted C 3 to C 30 ring.

In another 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 C6-C20 aryl group; Or a substituted or unsubstituted C2-20 heterocyclic group; Or it combines with an adjacent group to form a substituted or unsubstituted ring having 3 to 20 carbon atoms.

In another 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 that is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 90 carbon atoms that is unsubstituted or substituted with deuterium; an alkylarylsilyl group having 7 to 60 carbon atoms that is unsubstituted or substituted with deuterium; an alkyl group having 1 to 10 carbon atoms that is unsubstituted or substituted with deuterium; an arylalkyl group having 7 to 60 carbon atoms that is unsubstituted or substituted with deuterium; 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted carbon number an aryl group of 6 to 30; Or a heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium; It combines with an adjacent group to form a ring having 2 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and an alkyl group having 1 to 10 carbon atoms, or a substituent to which two or more groups selected from the group are connected.

In another 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 that is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium; an alkylarylsilyl group having 7 to 40 carbon atoms that is unsubstituted or substituted with deuterium; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; an arylalkyl group having 7 to 40 carbon atoms that is unsubstituted or substituted with deuterium; At least one substituent 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 selected from the group consisting of two or more groups selected from the group consisting of a substituted or unsubstituted carbon number 6 to 20 aryl groups; Or a heterocyclic group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium; It combines with an adjacent group to form a ring having 2 to 20 carbon atoms, substituted or unsubstituted 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 selected from the group are connected.

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 combine with adjacent groups 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; a trimethylsilyl group unsubstituted or substituted with deuterium; a butyldimethylsilyl group unsubstituted or substituted with deuterium; a dimethylphenylsilyl group unsubstituted or substituted with deuterium; a methyldiphenylsilyl group unsubstituted or substituted with deuterium; a triphenylsilyl group unsubstituted or substituted with deuterium; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a methyl group, or a butyl group; a biphenyl group unsubstituted or substituted with deuterium, a cyano group, a methyl group, or a butyl group; a naphthyl group unsubstituted or substituted with deuterium; or a pyridine group unsubstituted or substituted with deuterium; Or combine with adjacent groups to form hexene substituted or unsubstituted with deuterium or methyl group, or benzene unsubstituted or substituted with deuterium or methyl group.

In another 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 an 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 combine 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 C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or two adjacent groups combine with each other to form a substituted or unsubstituted C 3 to C 30 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 C 1 to C 6 alkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-20 heterocyclic group; Or 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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; Or a heterocyclic group having 2 to 20 carbon atoms that is unsubstituted or substituted 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 unsubstituted or substituted with deuterium, and in which 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 join together to form cyclohexane, or tetrahydronaphthalene.

In an 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 C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the other two are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

In another 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 combined with each other to form cyclohexane or tetrahydronaphthalene.

In the exemplary embodiment of the present specification, the descriptions of Ar11 to Ar14 described above are 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; a C 1 to C 6 alkyl group unsubstituted or substituted with deuterium; an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a heterocyclic group having 2 to 20 carbon atoms that is unsubstituted or substituted 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 embodiment, T22 is hydrogen; heavy hydrogen; or an alkyl group having 1 to 6 carbon atoms that is unsubstituted or substituted with deuterium; Alternatively, two adjacent groups combine with each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

In another embodiment, T22 is hydrogen; heavy hydrogen; or a methyl group unsubstituted or substituted with deuterium; Or two adjacent groups combine with each other to form benzene unsubstituted or substituted 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, at least two 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 one 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 one embodiment of the present specification, n6 is an integer of 0 to 3. In another exemplary embodiment, n6 is 0 or 1.

In one embodiment of the present specification, n7 and n8 are each an integer of 0 to 5. 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]

In an exemplary embodiment of the present specification, HAr is a substituted or unsubstituted N-containing monocyclic to tricyclic heterocyclic group.

In an exemplary embodiment of the present specification, HAr is a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted quinazoline group; Or a substituted or unsubstituted benzimidazole group.

In an exemplary embodiment of the present specification, HAr is represented by any one of the following Chemical Formulas A1 to A5.

[Formula A1]

[Formula A2]

[Formula A3]

[Formula A4]

[Formula A5]

In the formulas A1 to A5,

X1 to X3 are the same as or different from each other, each independently N, CH, or CD,

At least one of X1 to X3 is N,

Ar22 and Ar23 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, or a substituted or unsubstituted ring by combining with an adjacent group,

R21 to R26 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,

n21 is an integer from 0 to 7, n22 is an integer from 0 to 5, n24 and n26 are integers from 0 to 4, and when n21, n22, n24, and n26 are each 2 or more, the substituents in two or more parentheses are the same or different,

The dotted line is a region connected to L21.

In an exemplary embodiment of the present specification, Formula A1 is any one selected from the following Formula.

In the above formula, dotted lines, Ar22 and Ar23 are as defined in formula A1.

In an exemplary embodiment of the present specification, Formula A2 is any one selected from the following Formula.

In the above formula, dotted lines, R21 and n21 are as defined in formula A2.

In an exemplary embodiment of the present specification, Formula A3 is any one selected from the following Formula.

In the above formula, dotted lines, R22 and n22 are as defined in formula A3.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted divalent to tetravalent phenyl group; a substituted or unsubstituted divalent to tetravalent biphenyl group; a substituted or unsubstituted divalent to tetravalent terphenyl group; a substituted or unsubstituted divalent to tetravalent tetraphenyl group; and a substituted or unsubstituted divalent to tetravalent naphthyl group, or a divalent group to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted divalent to tetravalent phenyl group; a substituted or unsubstituted divalent to tetravalent biphenyl group; a substituted or unsubstituted divalent to tetravalent terphenyl group; a substituted or unsubstituted divalent to tetravalent tetraphenyl group; and a substituted or unsubstituted divalent to tetravalent naphthyl group, or a divalent group in which two groups selected from the group are connected.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted divalent to tetravalent phenyl group; a substituted or unsubstituted divalent to tetravalent biphenyl group; a substituted or unsubstituted divalent to tetravalent terphenyl group; a substituted or unsubstituted divalent to tetravalent tetraphenyl group; or a substituted or unsubstituted divalent to tetravalent naphthyl group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; Or one or more substituents selected from the group consisting of deuterium, a cyano group, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or a substituent selected from the group consisting of two or more groups selected from the group consisting of 6 to 30 carbon atoms unsubstituted or substituted It is a monocyclic or polycyclic divalent to tetravalent aryl group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; Or one or more substituents selected from the group consisting of deuterium, a cyano group, an aryl group having 6 to 20 carbon atoms and a heterocyclic group having 2 to 20 carbon atoms, or a substituent selected from the group consisting of two or more groups selected from the group consisting of 6 to 20 carbon atoms unsubstituted or substituted It is a monocyclic or polycyclic divalent to tetravalent aryl group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a divalent to tetravalent phenyl group unsubstituted or substituted with deuterium, a cyano group, a phenyl group, a phenanthrene, a dibenzofuran group, a dibenzothiophene group, or a pyridine group; a divalent to tetravalent biphenyl group unsubstituted or substituted with deuterium, a cyano group, or a pyridine group; a divalent to tetravalent terphenyl group unsubstituted or substituted with deuterium or a cyano group; a divalent to tetravalent tetraphenyl group unsubstituted or substituted with deuterium or a cyano group; or a divalent to tetravalent naphthyl group unsubstituted or substituted with deuterium or a cyano group.

In one embodiment of the present specification, a is 1 or 2.

In one embodiment of the present specification, b is 1 or 2.

In an exemplary embodiment of the present specification, Chemical Formula 3 is represented by the following Chemical Formula 3-1 or 2-2.

[Formula 3-1]

[Formula 3-2]

In Formulas 3-1 and 2-2,

L22 and b are as defined in Formula 3 above,

HAr1 to HAr3 are the same as the definition of HAr above,

L24 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L25 is a substituted or unsubstituted trivalent aryl group; Or a substituted or unsubstituted trivalent heterocyclic group.

In the exemplary embodiment of the present specification, the description of L21 described above is applied to L24 and L25.

In an exemplary embodiment of the present specification, -L22-(CN) _b of Formula 3 is selected from the following structure.

In the structure,

L23 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R51 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n51 is an integer from 0 to 4, n51' is an integer from 0 to 3,

The dotted line is a position connected to the Ar21.

In one embodiment of the present specification, L23 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L23 is a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

In one embodiment of the present specification, L23 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L23 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 6 alkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; At least one substituent selected from the group consisting of a cyano group, an aryl group having 2 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms, or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted by a substituent to which two or more groups selected from the group are connected .

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; It is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of a cyano group, an aryl group having 2 to 20 carbon atoms, and a heterocyclic group having 2 to 25 carbon atoms, or a substituent to which two or more groups selected from the group are connected. .

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; An aryl group having 6 to 20 carbon atoms is unsubstituted or substituted with a cyano group, an aryl group having 2 to 25 carbon atoms, or a heterocyclic group having 2 to 25 carbon atoms.

In an exemplary embodiment of the present specification, R51 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with a cyano group or a pyridine group; a fluorenyl group unsubstituted or substituted with a phenyl group; phenanthrenyl group; dibenzofuran group; dibenzothiophene group; spiro [fluorene-xanthene] group; or a spiro [fluorene-thioxanthene] group.

In an exemplary embodiment of the present specification, Ar21 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 25 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic divalent heterocyclic group having 2 to 25 carbon atoms; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 20 carbon atoms; a substituted or unsubstituted polycyclic arylene group having 10 to 25 carbon atoms; a substituted or unsubstituted polycyclic divalent heterocyclic group having 12 to 25 carbon atoms; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted binaphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted spirobifluorenylene group; A substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; a substituted or unsubstituted divalent spiro [fluorene-xanthene] group; a substituted or unsubstituted divalent spiro [fluorene-thioxanthene] group; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a direct bond; At least one substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms, or a substituent selected from the group consisting of two or more groups selected from the group consisting of 6 to 30 carbon atoms substituted or unsubstituted a monocyclic or polycyclic arylene group; a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a direct bond; a monocyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with an aryl group having 6 to 25 carbon atoms or a heterocyclic group having 2 to 25 carbon atoms; a polycyclic arylene group having 10 to 25 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; a polycyclic divalent heterocyclic group having 12 to 25 carbon atoms; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a phenylene group unsubstituted or substituted with a diphenylfluorenyl group, a spiro[fluorene-xanthene] group, or a spiro[fluorene-thioxanthene] group; a biphenylene group unsubstituted or substituted with a diphenylfluorenyl group, a spiro[fluorene-xanthene] group, or a spiro[fluorene-thioxanthene] group; a terphenylene group unsubstituted or substituted with a diphenylfluorenyl group, a spiro[fluorene-xanthene] group, or a spiro[fluorene-thioxanthene] group; naphthylene group; binaphthylene group; a fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group; spirobifluorenylene group; a divalent dibenzofuran group; a divalent dibenzothiophene group; a divalent spiro [fluorene-xanthene] group; a divalent spiro[fluorene-thioxanthene] group; or -O-.

In an exemplary embodiment of the present specification, Ar21 is a direct bond; phenylene group; biphenylene group; naphthylene group; dimethyl fluorenylene group; diphenylfluorenylene group; It is a spirobifluorenylene group.

In an exemplary embodiment of the present specification, Ar21 is -O-; or selected from the following structures.

In the structure,

X4 and X5 are the same as or different from each other, and each independently represent CR52R53; O; or S;

R27 to R30, R52 and R53 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n27, n28, n28', n29 and n30 are each an integer from 0 to 4,

n29' and n30' are each an integer of 0 to 3,

n29" and n30" are each an integer from 0 to 2;

n28 + n28' is 6 or less,

When n27, n28 to n30 and n28' to n30' are each 2 or more, the substituents in the two or more parentheses are the same as or different from each other,

When n29" and n30" are each 2, the substituents in parentheses are the same as or different from each other,

A dotted line indicates a position connected to the L21 or L22.

In one embodiment of the present specification, X4 is O or S.

In one embodiment of the present specification, X5 is CR52R53.

In an exemplary embodiment of the present specification, X5 is O; or S.

In an exemplary embodiment of the present specification, R52 and R53 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R52 and R53 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R52 and R53 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.

In an exemplary embodiment of the present specification, R27 to R30 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R27 to R30 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R27 to R30 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 C6-C25 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In an exemplary embodiment of the present specification, R27 to R30 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted spiro [fluorene-xanthene] group; a substituted or unsubstituted spiro[fluorene-thioxanthene] group.

In an exemplary embodiment of the present specification, R27 is hydrogen; heavy hydrogen; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted spiro [fluorene-xanthene] group; a substituted or unsubstituted spiro[fluorene-thioxanthene] group.

In an exemplary embodiment of the present specification, R28 to R30 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, the phenylene group (divalent phenyl group) of L21, L22, L24 or Ar21 is one selected from the following structure.

The structure is deuterium; cyano group; a substituted or unsubstituted aryl group; Or substituted or unsubstituted with a substituted or unsubstituted heterocyclic group. Specifically, it is unsubstituted or substituted with a substituent connected to L21, L22, L24 or Ar24 described above.

In an exemplary embodiment of the present specification, the biphenylene group (divalent biphenyl group) of L21, L22, L24 or Ar21 is one selected from the following structure.

The structure is deuterium; cyano group; a substituted or unsubstituted aryl group; Or substituted or unsubstituted with a substituted or unsubstituted heterocyclic group. Specifically, it is unsubstituted or substituted with a substituent connected to L21, L22, L24 or Ar24 described above.

In the exemplary embodiment of the present specification, the terphenylene group (divalent terphenyl group) of L21, L22, L24 or Ar21 is one selected from the following structure.

The structure is deuterium; cyano group; a substituted or unsubstituted aryl group; Or substituted or unsubstituted with a substituted or unsubstituted heterocyclic group. Specifically, it is unsubstituted or substituted with a substituent connected to L21, L22, L24 or Ar24 described above.

In the exemplary embodiment of the present specification, the naphthylene group (divalent naphthyl group) of L21, L22, L24 or Ar21 is one selected from the following structure.

The structure is deuterium; cyano group; a substituted or unsubstituted aryl group; Or substituted or unsubstituted with a substituted or unsubstituted heterocyclic group. Specifically, it is unsubstituted or substituted with a substituent connected to L21, L22, L24 or Ar24 described above.

In an exemplary embodiment of the present specification, the binaphthylene group (divalent binaphthyl group) of L21, L22, L24 or Ar21 is one selected from the following structure.

The structure is deuterium; cyano group; a substituted or unsubstituted aryl group; Or substituted or unsubstituted with a substituted or unsubstituted heterocyclic group. Specifically, it is unsubstituted or substituted with a substituent connected to L21, L22, L24 or Ar24 described above.

In one embodiment of the present specification, at least two or more of X1 to X3 is N.

In one embodiment of the present specification, X1 to X3 are each N.

In an exemplary embodiment of the present specification, Ar22 and Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar22 and Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 25 carbon atoms.

In an exemplary embodiment of the present specification, Ar22 and Ar23 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 spirobifluorenyl group; a substituted or unsubstituted spiro [fluorene-xanthene] group; or a substituted or unsubstituted spiro [fluorene-thioxanthene] group.

In an exemplary embodiment of the present specification, Ar22 and Ar23 are the same as or different from each other, and each independently a phenyl group; biphenyl group; spiro [fluorene-xanthene] group; or a spiro [fluorene-thioxanthene] group.

In an exemplary embodiment of the present specification, R21 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R21 to R26 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 C6-C20 aryl group.

In an exemplary embodiment of the present specification, R21 to R26 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 ethyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, R21 to R26 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; tert-butyl group unsubstituted or substituted with deuterium; a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, R21 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; ethyl group; tert-butyl group; phenyl group; biphenyl group; or a naphthyl group.

In an exemplary embodiment of the present specification, R22 is hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, R23 is hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted tert-butyl group; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, R25 is hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In an exemplary embodiment of the present specification, R21, R24 and R26 are the same as or different from each other, and each independently represents hydrogen or deuterium.

In an exemplary embodiment of the present specification, R21, R24 and R26 are each hydrogen.

In an exemplary embodiment of the present specification, the compound represented by Formula 3 is any one selected from 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 shown in Scheme 2 below. Although the following Schemes 1 and 2 describe the synthesis process of some compounds corresponding to Formulas 1 to 3 of the present application, various compounds corresponding to Formulas 1 to 3 of the present application can be synthesized using the synthesis procedures such as Schemes 1 and 2 below. And, the substituents may be combined by methods known in the art, and the type, position, and number of the substituents may be changed according to the techniques known in the art.

[Scheme 1]

[Scheme 2]

In Scheme 1, A ₁ to A ₃ denote 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 Chemical Formula 1 or 2, and the second organic material layer is formed using the compound represented by Chemical Formula 3, it is generally It can be manufactured by the manufacturing method and material of the organic light emitting device.

The first organic layer including the compound represented by Formula 1 or 2 and the second organic layer including the compound represented by Formula 3 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., 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, or may have a structure further including an additional organic material layer. The additional organic material layer may be one or more 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. 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 a light emitting 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 light emitting layer.

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

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a light emitting layer, and the compound represented by Formula 1 or 2 is included as a dopant of the light emitting layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a light emitting layer, and the compound represented by Formula 1 or 2 is used as a dopant of the light emitting 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 based on 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 one 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 two or more emission layers includes the compound represented by Formula 1 or 2.

In one 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 is blue, 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 an 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 light emitting layer including the compound represented by Formula 1 or 2 emits blue light.

The organic material layer of the organic light emitting device according to an exemplary embodiment of the present specification includes two or more light emitting layers, the maximum emission peak of one light emitting layer (light emitting layer 1) is 400 nm to 500 nm, and the other light emitting layer (light emitting layer 2) ) has a maximum emission peak between 510 nm and 580 nm; Alternatively, it may exhibit a maximum emission peak of 610 nm and 680 nm. In this case, the light emitting 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 diode 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 an organic light emitting diode according to another exemplary embodiment, the second organic material layer is an electron injection and transport layer.

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

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

In an exemplary embodiment of the present specification, the second organic material layer further includes one 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 the n-type dopant, it is possible to secure the stability of the hole from the light emitting layer, thereby improving the lifespan of the organic light emitting device. In addition, by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to the electron mobility of the electron transport layer, it is possible to maximize the balance between holes and electrons in the light emitting 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 2 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the compound of Formula 2 and the n-type dopant may be included in an amount 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 the exemplary 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 an exemplary 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.

1 shows 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 this sequentially stacked organic light emitting device is exemplified. 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 . there is.

2 shows 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 this sequentially stacked organic light emitting device is exemplified. In such a structure, the compound represented by Formula 1 or 2 may be included in the emission 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, The structure of the organic light emitting device 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 may include a first electron transport layer 9a, a second electron transport layer ( 9b) and the electron injection layer 10 may be included in one or more layers.

According to an 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 an exemplary embodiment, the tandem structure may have a form in which each organic light emitting device is bonded to a charge generating layer. Since a device having a tandem structure can be driven at a lower current than a unit device based on the same brightness, there is an advantage in that the lifespan characteristics of the device are greatly improved.

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

According to an exemplary embodiment of the present specification, the organic material layer may include: a first stack including one or more light emitting layers; a second stack comprising at least one light emitting layer; and a third stack including one or more light emitting layers, between the first stack and the second stack; and one or more charge generating layers, respectively, between the second stack and the third stack.

In the present specification, the charge generating layer (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. As used herein, 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 in the anode direction through the LUMO level of the N-type charge generating layer, and holes are transported in the cathode direction through the HOMO level of the P-type organic material layer.

The first stack, the second stack, and the third stack each include one or more light emitting layers, and further include 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 It may further include one or more layers of a layer for simultaneous injection (a hole injection and transport layer), and a layer for simultaneously performing an electron transport and electron injection (electron injection and transport layer).

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

3 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting 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 light emitting 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 exemplified. In such a structure, the compound represented by Formula 1 or 2 may be included in the first light emitting layer 6a or the second light emitting 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 .

The organic light emitting diodes including the first to third stacks are illustrated in FIGS. 4 to 7 .

4 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, The first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the second hole transport layer 4b, the second light-emitting layer 6b, the second electron transport layer 9b, the 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 light emitting layer 6c, the third electron transport layer 9c and the cathode 11 are sequentially stacked The structure of the light emitting device is illustrated. In such a structure, the compound represented by Formula 1 or 2 may be included in the first light-emitting layer 6a, the second light-emitting layer 6b, and the third light-emitting layer 6c, and the compound represented by Formula 3 is the first It may be included in one or more layers 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, 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 phosphorescence 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 , the second blue fluorescent light emitting layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked, the structure of the organic light emitting device is exemplified. In such a structure, the compound represented by Chemical Formula 1 or 2 may be included in the first blue fluorescent light-emitting layer 6BFa or the second blue fluorescent light-emitting layer 6BFb, and the compound represented by Chemical 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, a first electron transport layer ( 9a), the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the red phosphorescent emission layer 6RP, the green phosphorescence emission layer 6GP, the second electrons 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 ), the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked, the structure of the organic light emitting device is exemplified. In such a structure, the compound represented by Chemical Formula 1 or 2 may be included in the first blue fluorescent light-emitting layer 6BFa or the second blue fluorescent light-emitting layer 6BFb, and the compound represented by Chemical 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).

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, The first electron transport layer 9a, the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the fourth hole transport layer 4d, the 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 , the third blue fluorescent light emitting layer 6BFc, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked, the structure of the organic light emitting device is exemplified. 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 blue fluorescent light-emitting layer 6BFb. and the compound represented by Formula 2 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-pe Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivatives and the like, but is not limited thereto. In an exemplary embodiment, the N-type charge generation layer may include a benzimidazophenanthrine-based derivative and a metal of Li at the same time.

The P-type charge generation layer may include an arylamine-based derivative and a compound including a cyano group at the same time.

The organic light emitting device of the present specification may be manufactured using 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 above-described first organic material layer and the second organic material layer thereon, It can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer 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 layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode material is preferably 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; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects 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 capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) 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 the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. In one embodiment of the present specification, the hole injection layer has a two-layer structure, and each layer includes the same or different materials from each other.

The hole transport layer may serve to facilitate hole transport, and has a single-layer or multi-layered structure of two or more layers. As the hole transport material, a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. In one embodiment of the present specification, the hole transport layer has a two-layer structure, and each layer includes the same or different materials from each other.

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 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 light emitting layer. For the electron blocking layer, a material known in the art may be used.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray 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 for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

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

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. 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, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphor such as (4,6-F ₂ ppy) ₂ Irpic, or spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA). ), a PFO-based polymer, a fluorescent material such as 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 a material 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 electron mobility 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 electron injection. 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 for a light emitting layer or a light emitting material, and an excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. 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 to be construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer is formed using the heterocyclic compound.

Synthesis Example 1. Synthesis of compound 1

1) Synthesis of Intermediate 1

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

2) Synthesis of Intermediate 2

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

3) Synthesis of compound 1

25 g of Intermediate 2 and 21.3 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 8 g of compound 1 was obtained through recrystallization (yield 32%). MS[M+H]+ = 789

Synthesis Example 2. Synthesis of compound 2

1) Synthesis of Intermediate 3

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

2) Synthesis of compound 2

25 g of Intermediate 3 and 20.2 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 8.1 g of compound 2 was obtained through recrystallization (yield 31%). MS[M+H]+ = 900

Synthesis Example 3. Synthesis of compound 3

1) Synthesis of Intermediate 4

40 g of 1-bromo-3-chloro-5-methylbenzene and 75.8 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine 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 substance as in the synthesis method of Intermediate 2 And 39g of intermediate 5 was obtained through recrystallization using the equivalent. (yield 80%). MS[M+H]+ = 840

3) Synthesis of compound 3

25 g of Intermediate 5 and 19.9 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere and stirred at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 8.1 g of compound 3 was obtained through recrystallization (yield 32%). MS[M+H]+ = 849

Synthesis Example 4. Synthesis of compound 4

1) Synthesis of Intermediate 5

36 g of Intermediate 5 was obtained through recrystallization of 30 g of Intermediate 4 and 23.7 g of bis(4-(2-phenylpropan-2-yl)phenyl)amine using the same materials and equivalents as in the synthesis method of Intermediate 2. (yield 70%). MS[M+H]+ = 884

2) Synthesis of compound 4

25 g of Intermediate 5 and 18.8 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere and stirred at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.6 g of compound 4 was obtained through recrystallization (yield 30%). MS[M+H]+ = 892

Synthesis Example 5. Synthesis of compound 5

1) Synthesis of Intermediate 6

Intermediate 4 30 g, 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 through recrystallization of 24.7 g of hydronaphthalen-2-amine using the same materials and equivalents as those of intermediate 2 synthesis. (yield 75%). MS[M+H]+ = 890

2) Synthesis of compound 5

25 g of Intermediate 6 and 18.7 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° 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

Synthesis Example 6. Synthesis of compound 6

1) Synthesis of Intermediate 7

Intermediate 4 30 g, N-(5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-yl)-5,5,8,8-tetramethyl- 42 g of Intermediate 7 was obtained through recrystallization of 28.5 g of 5,6,7,8-tetrahydronaphthalen-2-amine using the same material and equivalent as the method for synthesizing Intermediate 2. (yield 75%). MS[M+H]+ = 966

2) Synthesis of compound 6

25 g of Intermediate 7 and 17.3 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After extraction after completion of the reaction, 7.6 g of compound 6 was obtained through recrystallization (yield 30%). MS[M+H]+ = 974

Synthesis Example 7. Synthesis of compound 7

1) Synthesis of Intermediate 8

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

25 g of Intermediate 8 and 20.1 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.7 g of compound 7 was obtained through recrystallization (yield 31%). MS[M+H]+ = 836

Synthesis Example 8. Synthesis of compound 8

1) Synthesis of Intermediate 9

1,3-dibromo-5-tert-butylbenzene 20 g, 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 was added to 400 ml of toluene, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 41.7 g of Intermediate 9 was obtained through recrystallization. (Yield 68%). MS[M+H]+ = 938

2) Synthesis of compound 8

25 g of Intermediate 9 and 20.1 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, and then stirred at 150° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.8 g of compound 8 was obtained through recrystallization (yield 31%). MS[M+H]+ = 946

Synthesis Example 9. Synthesis of compound 9

1) Synthesis of Intermediate 10

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

2) Synthesis of compound 9

15 g of Intermediate 10 and 11 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, and then stirred at 150° C. for 4 hours. After completion of the reaction, extraction was performed, and 5 g of compound 9 was obtained through recrystallization (yield 33%). MS[M+H]+ = 808

Synthesis Example 10. Synthesis of compound 10

1) Synthesis of intermediate 11

1-bromo-3-(tert-butyl)-5-chlorobenzene 40 g, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8 66.5 g of ,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine was recrystallized using the same material and equivalent as in the synthesis method of Intermediate 1 to obtain 75 g 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 put in 600ml toluene and refluxed for 1 hour, After checking whether the reaction proceeds, 13.2 g of 1-bromo-3-chlorobenzene is added during the reflux reaction, and the reflux reaction is further performed for 1 hour. After completion of the reaction, 28.8 g of Intermediate 12 was obtained through recrystallization after extraction. (Yield 52%). MS[M+H]+ = 801

3) Synthesis of Intermediate 13

25 g of Intermediate 12 and 20.4 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After extraction after completion of the reaction, 5.5 g 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 and stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 4.6 g of compound 10 was obtained through recrystallization. (yield 80%). MS[M+H]+ = 943

Synthesis Example 11. Synthesis of compound 11

1) Synthesis of Intermediate 14

Intermediate 4 40 g, 5-(tert-butyl)-[1,1'-biphenyl]-2-amine 17.6 g, sodium-tert-butoxide 22.4 g, bis(tri-tert-butylphosphine)palladium (0 ) 0.4 g of toluene is added to 600 ml of toluene, refluxed 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 continued for 1 hour. After completion of the reaction, 45 g of intermediate 14 was obtained through recrystallization after extraction. (Yield 71%). MS[M+H]+ = 814

2) Synthesis of Intermediate 15

25 g of Intermediate 14 and 20.4 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 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 putting 0.05 g of tert-butylphosphine) palladium (0) in 80 ml of xylene, the mixture was stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 7.4 g of compound 11 was obtained through recrystallization. (yield 74%). MS[M+H]+ = 1175

Synthesis 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'- 70 g of biphenyl]-2-yl)(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)-5-chlorophenol 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-tetrahydronaphthalene- 2-yl)amino)-5-chlorophenol 40g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride 20ml, potassium carbonate 30g tetrahydro After putting in 400 ml of furan and 200 ml of water, after reacting for 3 hours, after the reaction was completed, the solution was removed and 58 g of intermediate 16 was obtained. (yield 97%).

2) Synthesis of intermediate 17

Under 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 placed in 500 ml of xylene and stirred under reflux for 24 hours. . After completion of the reaction, extraction was performed, and 31 g 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 placed in 250 ml of 1,2-dichlorobenzene, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 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 completion of the reaction, extraction was performed, and 6.2 g of compound 12 was obtained through recrystallization. (yield 76%). MS[M+H]+ = 948

Synthesis Example 13. Synthesis of compound 13

1) Synthesis of Intermediate 19

After adding 40 g of intermediate 4, 14.3 g of dibenzo[b,d]furan-1-amine, 22.4 g of sodium-tert-butoxide, and 0.4 g of bis(tri-tert-butylphosphine)palladium (0) to 600 ml of toluene, After refluxing for 1 hour, after 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 completion of the reaction, 54 g of intermediate 19 was obtained through recrystallization after extraction. (yield 82%). MS[M+H]+ = 848

2) Synthesis of compound 13

25 g of Intermediate 19 and 19.7 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, and then stirred at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.5 g of compound 13 was obtained through recrystallization (yield 30%). MS[M+H]+ = 856

Synthesis Example 14. Synthesis of compound 14

1) Synthesis of Intermediate 20

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

2) Synthesis of compound 14

25 g of Intermediate 20 and 19.3 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° 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

Synthesis Example 15. Synthesis of compound 15

1) Synthesis of Intermediate 21

40g of Intermediate 4, 18.1g of dibenzo[b,d]furan-4-bromide, 11.6g of 3-(tert-butyl)aniline, 50g of Intermediate 21 through recrystallization using the same material and equivalent as in the synthesis method of Intermediate 19 obtained. (yield 76%). MS[M+H]+ = 850

2) Synthesis of compound 15

25 g of Intermediate 21 and 21 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 8.3 g of compound 15 was obtained through recrystallization (yield 31%). MS[M+H]+ = 858

Synthesis Example 16. Synthesis of compound 16

1) Synthesis of Intermediate 22

After adding 40 g of intermediate 4, 14.3 g of dibenzo[b,d]furan-1-amine, 22.4 g of sodium-tert-butoxide, and 0.4 g of bis(tri-tert-butylphosphine)palladium (0) to 600 ml of toluene, After refluxing for 1 hour, 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 completion of the reaction, 46 g of intermediate 22 was obtained through recrystallization after extraction. (yield 77%). MS[M+H]+ = 771

2) Synthesis of intermediate 23

25 g of Intermediate 22 and 21.6 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.8 g 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) After adding 0.05 g of palladium (0) to 80 ml of xylene, the mixture was stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 6.1 g of compound 16 was obtained through recrystallization. (yield 72%). MS[M+H]+ = 945

Synthesis 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- Tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine 30 g, 3,5,5,8,8-pentamethyl-N-(m-tolyl)-5,6 31.3 g of Intermediate 24 was obtained through recrystallization of 17.9 g of ,7,8-tetrahydronaphthalen-2-amine using the same material and equivalent as in the synthesis method of Intermediate 2. (yield 69%). MS[M+H]+ = 789

2) Synthesis of compound 17

25 g of Intermediate 24 and 20.4 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7 g of compound 17 was obtained through recrystallization (yield: 29%). MS[M+H]+ = 797

Synthesis 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 40 g of 3-dihydro-1H-inden-5-amine, 12.1 g of 4-(tert-butyl)-2-methylaniline, 22.1 g of sodium-tert-butoxide, bis(tri-tert-butylphosphine)palladium (0) 0.4 g of toluene was added to 600 ml of toluene, refluxed for 1 hour, and after checking whether the reaction proceeded, 14.6 g of 1-bromo-3-chlorobenzene was added during the reflux reaction and the reflux reaction was continued for 1 hour. After completion of the reaction, 43 g of intermediate 25 was obtained through recrystallization after extraction. (yield 74%). MS[M+H]+ = 760

2) Synthesis of Intermediate 26

25 g of Intermediate 25 and 21.9 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After extraction after completion of the reaction, 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 into 80ml xylene After that, the mixture was stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 6.5 g of compound 18 was obtained through recrystallization. (yield 72%). MS[M+H]+ = 1013

Synthesis 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 prepared by the synthesis method of Intermediate 35 and 70 g of intermediate 27 was obtained through recrystallization using the same material and equivalent. (yield 70%). MS[M+H]+ = 517

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

2) Synthesis of intermediate 29

Synthesis of intermediate 17 by 40 g of intermediate 28, 34 g of N-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-3-methyl-[1,1'-biphenyl]-4-amine 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

25 g of Intermediate 29 and 17.7 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After extraction after completion of the reaction, 7.5 g of intermediate 30 was obtained through recrystallization (yield 30%). MS[M+H]+ = 948

3) Synthesis of compound 19

7 g of Intermediate 30, 2.1 g of bis(4-(tert-butyl)phenyl)amine, 1.7 g of sodium-tert-butoxide, and 0.05 g of bis(tri-tert-butylphosphine)palladium (0) were added to 80 ml of xylene After that, the mixture was stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 6.6 g of compound 19 was obtained through recrystallization. (yield 72%). MS[M+H]+ = 1235

Synthesis 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 99 g of Intermediate 31 was obtained through recrystallization using the same material and equivalent as in the synthesis method of Intermediate 9. (yield 75%). MS[M+H]+ = 888

2) Synthesis of Intermediate 32

25 g of Intermediate 31 and 18.7 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, and then stirred at 160° 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) 0.04 g was put in 80 ml of xylene, and the mixture was stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 7.1 g of compound 20 was obtained through recrystallization. (yield 73%). MS[M+H]+ = 1249

Synthesis Example 21. Synthesis of compound 21

1) Synthesis of intermediate 33

25 g of Intermediate 33 was obtained by using 25 g of bis(3-isopropylphenyl)amine in the same manner as for synthesizing Intermediate 1 of Synthesis Example 1. (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 in the same manner as for synthesizing Intermediate 2 of Synthesis Example 1 32.2 g of intermediate 34 was obtained by using 27.3 g of -9,10-dihydroanthracen-2-amine. (Yield 71%). MS[M+H]+ = 858

3) Synthesis of compound 21

25 g of Intermediate 34 and 20.1 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.3 g of compound 21 was obtained through recrystallization (yield: 29%). MS[M+H]+ = 866

Synthesis Example 22. Synthesis of compound 22

1) Synthesis of compound 22

Under nitrogen atmosphere, 7 g of intermediate 32, 4a,9a-dimethyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 1.93 g, sodium-tert-butoxide 1.52 g, bis 0.04 g of (tri-tert-butylphosphine) palladium (0) was added to 80 ml of xylene and stirred under reflux for 5 hours. After completion of the reaction, extraction was performed, and 6.9 g of compound 22 was obtained through recrystallization. (yield 78%). MS[M+H]+ = 1137

Synthesis Example 23. Synthesis of compound 23

1) Synthesis of Intermediate 36

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

2) Synthesis of intermediate 37

N-(5,5,8,8-tetramenyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d] in the same manner as for synthesizing Intermediate 17 of Synthesis Example 12 31.8 g of Intermediate 37 was obtained by using 20.4 g of furan-1-amine. (yield 72%). MS[M+H]+ = 799

3) Synthesis of Intermediate 38

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

3) Synthesis of compound 23

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

Synthesis Example 24. Synthesis of compound 24

1) Synthesis of Intermediate 39

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

2) Synthesis of Intermediate 40

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

3) Synthesis of compound 24

In the same manner as in the synthesis of Compound 11 of Synthesis Example 1, 4.2 g of Compound 24 was obtained using 20 g of Intermediate 39. (Yield 21%). MS[M+H]+ = 864

Synthesis Example 25. Synthesis of compound 25

1) Synthesis of intermediate 41

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

2) Synthesis of Intermediate 42

*

Under nitrogen atmosphere, 40 g of intermediate 41, 5-(tert-butyl)-[1,1'-biphenyl]-2-amine 16.9 g, bis(tri-tert-butylphosphine) palladium (0) 0.4 g, sodium- After adding 18 g of tert-butoxide to 600 ml of toluene, the mixture was 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, and the mixture was stirred under reflux 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

25 g of Intermediate 42 and 20.0 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After extraction after completion of the reaction, 7.4 g of intermediate 43 was obtained through recrystallization (yield: 29%). MS[M+H]+ = 843

4) Synthesis of compound 25

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

Synthesis Example 26. Synthesis of compound 26

1) Synthesis of compound 26

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

Synthesis Example 27. Synthesis of compound 27

1) Synthesis of Intermediate 44

40 g of A2 under nitrogen atmosphere, 71.9 g of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-4-amine , 37.4 g of sodium-tert-butoxide, and 1.0 g of bis(tri-tert-butylphosphine)palladium (0) were added to 600 ml of toluene, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, extraction was performed, and 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), and 19 g of sodium-tert-butoxide were dissolved in 600 ml of toluene. After addition, 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, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, and 45 g of intermediate 45 was obtained through recrystallization. (yield 74%). MS[M+H]+ = 752

3) Synthesis of intermediate 46

25 g of Intermediate 45 and 22.1 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.7 g of intermediate 46 was obtained through recrystallization (yield 30%). MS[M+H]+ = 760

4) Synthesis of compound 27

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

Synthesis Example 28. Synthesis of compound 28

1) Synthesis of intermediate 47

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

2) Synthesis of Intermediate 48

Under 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 placed in 600ml of toluene and stirred under reflux for 1 hour. did After confirming the progress of the reaction, 15.5 g of 1-bromo-3-chlorobenzene was added while stirring, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 44 g of intermediate 48 was obtained through recrystallization. (Yield 71%). MS[M+H]+ = 768

3) Synthesis of Intermediate 49

25 g of Intermediate 48 and 21.7 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.4 g of intermediate 49 was obtained through recrystallization (yield: 29%). MS[M+H]+ = 776

4) Synthesis of compound 28

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

Synthesis Example 29. Synthesis of compound 29

1) Synthesis of Intermediate 50

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

2) Synthesis of intermediate 51

25 g of Intermediate 50 and 24.8 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, 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

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

Synthesis Example 30. Synthesis of compound 30

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

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

Synthesis Example 31. Synthesis of Intermediate 53

Starting material B1 (20 g, 1eq.), bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)amine (35.6 g, 2.05eq.), A flask containing Pd(P t Bu ₃ ) ₂ (1.1 g, 0.05eq), NaO t Bu (12.8g, 3eq.) and toluene (250ml) 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 then the solvent was distilled off under reduced pressure. It was purified by recrystallization (toluene/hexane) to obtain an intermediate 53 (30.9 g). (yield 65%). MS[M+H]+ = 1066

Synthesis Example 32. Synthesis of compound 31

To the flask containing Intermediate 53 (25 g) and toluene (150 ml), n-butyllithium pentane solution (18.7 ml, 2.5M in hexane, 2eq.) was added at 0° C. under 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, 1.5eq.) was added, the temperature was raised to room temperature, and the mixture was 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 separation by adding Sat.aq.NaCl and ethyl acetate, the solvent was distilled off under reduced pressure. Purification by recrystallization (Toluene/Hexane) gave compound 31 (6.3 g). (yield 27%). MS[M+H]+ = 996

Synthesis Example 33. Synthesis of compound 2-1

1) Synthesis of intermediate 55

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

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

2) Synthesis of compound 2-1

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

Synthesis Example 34. Synthesis of compound 2-2

1) Synthesis of Intermediate 72

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

2) Synthesis of intermediate 57

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

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

3) Synthesis of compound 2-2

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

Synthesis 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 mixed with toluene. After putting in 600ml, the mixture was stirred under reflux for 1 hour. After confirming the progress of the reaction, 20.1 g of 1-bromo-3-chlorobenzene was added while stirring, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 54 g of intermediate 73 was obtained through recrystallization. (yield 79%). MS[M+H]+ = 656

2) Synthesis of Intermediate 74

25 g of Intermediate 73 and 25.4 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, 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 (6.9 g, yield 74%) was obtained by using the starting material of the above formula in the same manner as for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 886

Synthesis Example 36. Synthesis of compound 2-4

1) Synthesis of Intermediate 58

Intermediate 58 (32 g, yield 76%)) was obtained by using the starting material of the above formula in the same manner as 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 by using the starting material of the above formula in the same manner as for synthesizing Intermediate 48 of Synthesis Example 28. MS[M+H]+ = 701

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

3) Synthesis of compound 2-4

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

Synthesis Example 37. Synthesis of compound 2-5

1) Synthesis of Intermediate 62

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

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

2) Synthesis of compound 2-5

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

Synthesis Example 38. Synthesis of compound 2-6

1) Synthesis of Intermediate 64

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

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

2) Synthesis of compound 2-6

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

Synthesis Example 39. Synthesis of compound 2-7

1) Synthesis of intermediate 68

Under nitrogen atmosphere, 40 g of A2, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 39.2g, bis(tri-tert-butylphosphine)palladium(0)1.0 g, 38 g of sodium-tert-butoxide was placed in 600 ml of toluene and stirred under reflux for 4 hours. After completion of the reaction, 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 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), 29.5 g of sodium-tert-butoxide were mixed with 600 ml of toluene After putting it in, it 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, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 55 g of intermediate 69 was obtained through recrystallization. (yield 77%). MS[M+H]+ = 584

3) Synthesis of compound 2-7

25 g of Intermediate 69 and 28.5 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 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, and 0.05 g of bis(tri-tert-butylphosphine)palladium (0) were dissolved in 100 ml of toluene. After putting in the reflux and stirring for 6 hours. After completion of the reaction, extraction was performed, and 7.4 g of compound 2-7 was obtained through recrystallization. (yield 75%). MS[M+H]+ = 836

Synthesis Example 40. Synthesis of compound 2-8

1) Synthesis of Intermediate 71

In 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), 29.5 g of sodium-tert-butoxide were mixed with 600 ml of toluene After putting it in, it 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, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 54 g of intermediate 71 was obtained through recrystallization. (yield 76%). MS[M+H]+ = 584

2) Synthesis of compound 2-8

25 g of Intermediate 71 and 28.5 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, 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, and 0.05 g of bis(tri-tert-butylphosphine)palladium (0) were dissolved in 100 ml of toluene. After putting in the reflux and stirring for 6 hours. After completion of the reaction, extraction was performed, and 7.6 g of compound 2-8 was obtained through recrystallization. (yield 76%). MS[M+H]+ = 836

Synthesis Example 41. Synthesis of compound 2-9

1) Synthesis of compound 2-9

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

Synthesis 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, and 0.05 g of bis(tri-tert-butylphosphine)palladium (0) were dissolved in 100 ml of toluene. After putting in the reflux and stirring for 6 hours. After completion of the reaction, extraction was performed, and 7.5 g of compound 2-10 was obtained through recrystallization. (yield 78%). MS[M+H]+ = 909

Synthesis Example 43. Synthesis of compound 2-11

1) Synthesis of Intermediate 75

Under nitrogen atmosphere, 40 g of A1, 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 35.7 g, bis(tri-tert-butylphosphine)palladium (0) 0.9 g, 34 g of sodium-tert-butoxide was placed in 600 ml of toluene and stirred under reflux for 4 hours. After extraction after completion of the reaction, 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), 27.8 g of sodium-tert-butoxide were mixed with 600 ml of toluene After putting it in, it 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, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 55 g of intermediate 76 was obtained through recrystallization. (yield 79%). MS[M+H]+ = 604

3) Synthesis of compound 2-11

25 g of Intermediate 76 and 27.6 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.2 g of intermediate 77 was obtained through recrystallization (yield: 28%). MS[M+H]+ = 612

In 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, and 0.05 g of bis(tri-tert-butylphosphine)palladium (0) were dissolved in 100 ml of toluene. After putting in the reflux and stirring for 6 hours. After completion of the reaction, extraction was performed, and 7.9 g of compound 2-11 was obtained through recrystallization. (Yield 63%). MS[M+H]+ = 1102

Synthesis Example 44. Synthesis of compound 2-12

1) Synthesis of Intermediate 78

Under a nitrogen atmosphere, 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, sodium-tert-butoxide 23.9 g was added to 600 ml of toluene, and the mixture was stirred under reflux for 1 hour. After confirming the progress of the reaction, 19.1 g of 1-bromo-3-chlorobenzene was added while stirring, and the mixture was stirred under reflux for 4 hours. After extraction after completion of the reaction, 53 g of intermediate 78 was obtained through recrystallization. (yield 77%). MS[M+H]+ = 694

2) Synthesis of compound 2-12

25 g of Intermediate 78 and 24.0 g of boron triiodide were placed in 250 ml of 1,2-dichlorobenzene under a nitrogen atmosphere, followed by stirring at 160° C. for 4 hours. After completion of the reaction, extraction was performed, and 7.4 g of intermediate 79 was obtained through recrystallization (yield: 29%). MS[M+H]+ = 702

In 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, and 0.05 g of bis(tri-tert-butylphosphine)palladium (0) were mixed with 100 ml of toluene. After putting in the reflux and stirring for 6 hours. After completion of the reaction, extraction was performed, and 8.3 g of compound 2-12 was obtained through recrystallization. (yield 70%). MS[M+H]+ = 1192

Synthesis Example 45. Synthesis of compound 2-13

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

Intermediate 81 (5.9 g, 29%) was obtained by using 20 g of Intermediate 80 in the same manner as for 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 for synthesizing compound 29 of Synthesis Example 29. MS[M+H]+ = 1097

Synthesis Example 46. Synthesis of compound 32

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

5.3 g of compound 32 was obtained by using 16 g of intermediate 82 in the same manner as for preparing compound 3 of Synthesis Example 3. (yield 33%). MS[M+H]+ = 655

Synthesis Example 47. Synthesis of compound 33

1) Synthesis of Intermediate 84

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

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

2) Synthesis of compound 33

8.5 g of compound 33 was obtained by using the material of the above formula in the same manner as for preparing compound 20 of Synthesis Example 20. (yield 70%). MS[M+H]+ = 913

The present specification also provides a method of manufacturing an organic light emitting device formed using the heterocyclic compound.

Synthesis Example 48.

Compound 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine A2-1 20 g, B-1 27 g, potassium carbonate 21 g Tetrahydrofuran 380 After adding mL and 50 mL of water, 1.1 g of tetrakis (triphenylhosphine) palladium (0) [tetrakis (triphenylhosphine) palladium (0)] Pd (PPh ₃ ) ₄ was added, followed by heating and stirring for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, the organic solvent was removed, dissolved in toluene for extraction, and the organic solvent was treated with MgSO ₄ (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/ethylacetate) to obtain 26 g of compound E1. (Yield 82%, Mass [M+]=613)

Synthesis Example 49.

18 g of Intermediate 2-1 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48 except that 16 g of B-2 was used instead of the starting material B-1. (Yield 77%, Mass [M+]=452)

A flask containing 18 g of Intermediate 2-1, 23 g of potassium carbonate, 10.7 mL of perfluorobutanesulfonyl fluoride and 180 mL of dimethylformamide (DMF) was stirred at room temperature for 1 hour. After the reaction was completed, water was added and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in toluene and then aq. NH ₄ Cl was added for extraction, followed by MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/Hexane) to obtain 24 g of Intermediate 2-2. (Yield 82%, Mass [M+]=734)

15 g of E2 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 24 g of Intermediate 2-2 instead of A2-1 and 8.8 g of B-3 were used instead of B-1. (Yield 75%, Mass [M+]=613)

Synthesis Example 50.

17 g of Intermediate 2-4 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 34. except that 16.7 g of B-4 was used instead of B-1. (Yield 74%, Mass [M+]=452)

22 g of Intermediate 2-5 was obtained in the same manner as in Synthesis of Intermediate 2-2 of Synthesis Example 49 except that 17 g of Intermediate 2-4 was used instead of Intermediate 2-1. (Yield 80%, Mass [M+]=734)

14 g of E3 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 22 g of Intermediate 2-5 instead of A2-1 and 6.2 g of B-5 instead of B-1 were used. (Yield 76%, Mass [M+]=613)

Synthesis Example 51.

16 g of Intermediate 2-6 was obtained in the same manner as in Synthesis of Compound E1 of Synthesis Example 34., except that 20 g of A2-2 instead of A2-1 and 19.6 g of B-6 instead of B-1 were used. (Yield 84%, Mass [M+]=271)

25 g of E4 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 16 g of Intermediate 2-6 instead of A2-1 and 15.8 g of B-3 instead of B-1 were used. (Yield 79%, Mass [M+]=536)

Synthesis Example 52.

27 g of E5 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 20 g of A2-3 instead of A2-1 and 17.2 g of B-7 instead of B-1 were used. (Yield 77%, Mass [M+]=526)

Synthesis Example 53.

16 g of Intermediate 2-7 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 10 g of A2-4 instead of A2-1 and 15 g of B-8 instead of B-1 were used. (Yield 81%, Mass [M+]=599)

15 g of E6 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 16 g of Intermediate 2-7 instead of A2-1 and 7.2 g of B-3 instead of B-1 were used. (Yield 76%, Mass [M+]=741)

Synthesis Example 54.

16 g of Intermediate 2-8 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48. except that 10 g of A2-4 instead of A2-1 and 15.6 g of B-9 were used instead of A2-1. (Yield 79%, Mass [M+]=615)

16 g of Intermediate 2-8 instead of A2-1 and 16 g of E7 were obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 7.0 g of B-3 was used instead of A2-1. (Yield 81%, Mass [M+]=757)

Synthesis Example 55.

23 g of Intermediate 2-9 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 20 g of A2-5 instead of A2-1 and 20.5 g of B-9 were used instead of A2-1. (Yield 74%, Mass [M+]=642)

26 g of Intermediate 2-10 was obtained in the same manner as in Synthesis of Intermediate 2-2 of Synthesis Example 49 except that 23 g of Intermediate 2-9 was used instead of Intermediate 2-1. (Yield 79%, Mass [M+]=924)

15 g of E8 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 26 g of Intermediate 2-10 instead of A2-1 and 5.0 g of B-10 instead of B-1 were used. (Yield 73%, Mass [M+]=727)

Synthesis Example 56.

26 g of E9 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48 except that 26 g of B-11 was used instead of B-1. (Yield 84%, Mass [M+]=603)

Synthesis Example 57.

25 g of E10 was obtained in the same manner as in the synthesis of Compound E1 of Synthesis Example 48, except that 20 g of A2-6 instead of A2-1 and 28.9 g of B-12 instead of B-1 were used. (Yield 78%, Mass [M+]=725).

<Element example 1>

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following HI-A compound to a thickness of 600 Å and the HAT compound to a thickness of 50 Å on the prepared ITO transparent electrode. A hole transport layer was formed by vacuum-depositing 600 Å of the following HT-A compound on the hole injection layer.

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

Compound E1 and the following LiQ compound were vacuum deposited on the light emitting layer in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 350 Å. 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 of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1Х10 ^-7 to 5Х10 ^-5 torr, an organic light-emitting device was manufactured.

Examples 2 to 19 and Comparative Examples 1 to 7

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

For the organic light-emitting devices of Examples 1 to 19 and Comparative Examples 1 to 7, the driving voltage and luminous efficiency (conversion efficiency) were measured at a current density of 10 mA/cm ² , and initially at a current density of 15 mA/cm ² The time (T95) at which it becomes 95% of the luminance was measured, and the relative value was displayed based on Comparative Example 1. The results are shown in Table 1 below.

entry compound 10mA/cm ² 15mA/ ^cm2 dopant electron injection
and transport layer Voltage conversion efficiency
(cd/A/y) T95
ratio (%) Example 1 compound 1 E1 4.47 56.0 2.03 Example 2 compound 3 E1 4.48 56.40 2.21 Example 3 compound 29 E2 4.51 54.5 2.42 Example 4 compound 31 E2 4.52 60.5 2.66 Example 5 compound 10 E3 4.61 57.2 2.79 Example 6 compound 14 E3 4.60 57.9 2.93 Example 7 compound 32 E4 4.40 50.0 1.30 Example 8 compound 2-10 E4 4.38 56.8 1.94 Example 9 compound 16 E5 4.51 58.0 2.06 Example 10 compound 33 E5 4.52 50.3 1.27 Example 11 compound 2-1 E6 4.40 52.4 2.43 Example 12 compound 2-2 E6 4.42 53.6 1.98 Example 13 compound 20 E7 4.42 66.9 2.07 Example 14 compound 25 E7 4.42 61.5 2.07 Example 15 compound 17 E8 4.51 61.8 2.04 Example 16 compound 2-2 E8 4.5 58.0 1.91 Example 17 compound 21 E9 4.42 56.7 2.00 Example 18 compound 2-5 E9 4.41 52.9 2.04 Example 19 compound 2-11 E10 4.42 61.3 1.99 Comparative Example 1 BD-A ET-A 4.56 45.0 1.00 Comparative Example 2 BD-A ET-B 4.51 45.9 0.90 Comparative Example 3 BD-A ET-D 4.79 46.4 0.75 Comparative Example 4 compound 21 ET-A 4.56 48.4 1.14 Comparative Example 5 compound 29 ET-B 4.51 49.3 1.01 Comparative Example 6 compound 2-2 ET-C 4.70 48.9 0.92 Comparative Example 7 BD-A E10 4.41 47.9 1.66

Referring to Table 1, the organic light emitting device including the compound of Formula 1 or 2 of the present invention as a dopant of the light emitting layer and using the compound of Formula 3 of the present invention as an electron injection and transport layer has excellent high efficiency and/or long life characteristics can be known <Element example 2>

Example 20

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by sequentially thermal vacuum deposition of the following HI-A compound to a thickness of 600 Å and the HAT compound to a thickness of 50 Å on the thus prepared ITO transparent electrode. A hole transport layer was formed by vacuum-depositing 600 Å of the following 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.

Then, the BH-B compound (host) and compound 22 (dopant) were vacuum-deposited at a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer.

Compound E1 was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 50 Å. On the hole blocking layer, the following compound ET-E and the LiQ compound were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed 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.

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 of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1Х10 ^-7 to 5Х10 ^-5 torr, an organic light-emitting device was manufactured.

Examples 21 to 38 and Comparative Examples 8 to 14

An organic light emitting diode was manufactured in the same manner as in Example 20, except that the materials shown in Table 2 below were used for the dopant material and the hole blocking layer material of the emission layer.

For the organic light emitting devices of Examples 20 to 38 and Comparative Examples 8 to 14, the driving voltage and luminous efficiency (conversion efficiency) were measured at a current density of 10 mA/cm ² , and initially at a current density of 15 mA/cm ² A relative value was displayed based on Comparative Example 8 by measuring the time (T95) at which it became 95% of the luminance. The results are shown in Table 2 below.

entry compound 10mA/cm ² 15mA/ ^cm2 dopant hole blocking layer Voltage conversion efficiency
(cd/A/y) T95
ratio (%) Example 20 compound 22 E1 4.25 60.3 2.00 Example 21 compound 2-4 E1 4.24 57.2 2.14 Example 22 compound 2 E2 4.30 56.4 2.38 Example 23 compound 33 E2 4.31 52.9 1.62 Example 24 compound 1 E3 4.38 55.6 2.75 Example 25 compound 30 E3 4.38 55.9 2.56 Example 26 compound 6 E4 4.17 57.4 1.93 Example 27 compound 32 E4 4.16 52.1 1.44 Example 28 compound 12 E5 4.30 56.6 2.28 Example 29 compound 24 E6 4.22 57.0 2.14 Example 30 compound 2-7 E6 4.21 59.7 2.05 Example 31 compound 4 E7 4.21 61.8 1.81 Example 32 compound 26 E7 4.22 61.8 2.21 Example 33 compound 8 E8 4.30 66.7 2.04 Example 34 compound 2-9 E8 4.29 62.9 2.03 Example 35 compound 15 E9 4.21 60.1 2.10 Example 36 compound 28 E9 4.21 59.2 2.04 Example 37 compound 2-12 E10 4.22 62.6 2.07 Example 38 compound 11 E10 4.21 61.9 1.97 Comparative Example 8 BD-A ET-B 4.34 45.5 1.00 Comparative Example 9 BD-A ET-C 4.47 46.9 0.90 Comparative Example 10 compound 1 ET-A 4.34 51.4 1.13 Comparative Example 11 compound 28 ET-C 4.47 50.9 0.98 Comparative Example 12 compound 33 ET-B 4.30 48.0 0.68 Comparative Example 13 compound 2-7 ET-D 4.56 50.5 0.90 Comparative Example 14 BD-A E5 4.31 48.7 1.32

Looking at Table 2, it can be seen that the high efficiency and/or long life characteristics of the organic light emitting device including the compound of Formula 1 or 2 of the present invention as a dopant of the light emitting layer and using the compound of Formula 3 of the present invention as a hole blocking layer are excellent. can

<Element example 3>

Example 39

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. 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 sequentially thermally vacuum deposited to a thickness of 600 Å and the HAT compound to a thickness of 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. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. Then, a BH-C compound (host) and compound 3 (dopant) were vacuum-deposited at a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer.

Compound E1 was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 50 Å. Compound E7 and the following LiQ compound were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed 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.

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 of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1Х10 ^-7 to 5Х10 ^-5 torr, an organic light-emitting device was manufactured.

Examples 40 to 47 and Comparative Examples 15 to 17

An organic light emitting diode was manufactured in the same manner as in Example 39, except that the materials shown in Table 3 below were used for the dopant material of the emission layer, the hole blocking layer material, and the electron injection and transport layer material.

For the organic light emitting devices of Examples 39 to 47 and Comparative Examples 15 to 17, the driving voltage and luminous efficiency (conversion efficiency) were measured at a current density of 10 mA/cm ² , and initially at a current density of 15 mA/cm ² A relative value was displayed based on Comparative Example 15 by measuring the time (T95) at which it became 95% of the luminance. The results are shown in Table 3 below.

entry compound 10mA/cm ² 15mA/ ^cm2 dopant hole blocking layer electron injection
and transport layer Voltage conversion efficiency
(cd/A/y) T95
ratio (%) Example 39 compound 3 E1 E7 4.32 62.2 2.83 Example 40 compound 9 E5 E10 4.37 58.3 2.19 Example 41 compound 18 E7 E3 4.45 62.0 3.07 Example 42 compound 19 E10 E4 4.23 59.7 2.29 Example 43 compound 23 E4 E2 4.32 60.9 2.72 Example 44 compound 27 E8 E5 4.46 61.5 2.57 Example 45 compound 2-3 E2 E9 4.37 59.4 3.18 Example 46 compound 2-8 E6 E8 4.37 65.5 2.57 Example 47 compound 2-13 E3 E1 4.50 59.0 3.21 Comparative Example 15 BD-A ET-A ET-C 4.33 45.1 1.00 Comparative Example 16 BD-A E9 ET-D 4.63 49.0 1.40 Comparative Example 17 BD-A ET-D E6 4.61 49.9 1.43

Referring to Table 3 above, low voltage, high efficiency and low voltage, high efficiency and / or it can be seen that the long life characteristics are excellent.

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: second 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 light-emitting layer/6b: second light-emitting layer/ 6c: third light-emitting layer/ 6BF: blue fluorescent light-emitting layer/ 6BFa: first blue fluorescent light-emitting layer/ 6BFb: second blue fluorescent light-emitting layer/ 6YGP: yellow green phosphorescent light-emitting layer/ 6RP: red phosphorescent light-emitting layer / 6GP: green phosphorescent light emitting 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

Claims (17)

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 the following Chemical Formula 1 or 2 and a second organic material layer including a compound represented by the following Chemical Formula 3:
[Formula 1]

In Formula 1,
Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, or a ring condensed thereof,
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 alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a ring condensed therewith,
R1 and R2 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 aryl group; Or a substituted or unsubstituted silyl group, combined with an adjacent substituent to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a condensed ring thereof,
R3 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted silyl group, combined with an adjacent substituent to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a condensed ring thereof,
Z1 and Z2 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 combine 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 as 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 are each independently an aromatic hydrocarbon ring,
At least one of R4 to R8 is combined with a group represented by the following formula 1-A or 1-B or an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, the rest 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 combine with an adjacent group to form a substituted or unsubstituted ring,
n4 and n5 are each an integer from 0 to 4, n6 is an integer from 0 to 3, n7 and n8 are each an integer from 0 to 5,
n4 + n5 + n6 + n7 + n8 is greater than or equal to 1,
When each of n4 to n8 is 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
[Formula 1-A]

[Formula 1-B]

In 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; or a cyano group; Or combine 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; Deuterium; A substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine 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 Formula 3,
HAr is a substituted or unsubstituted N-containing heterocyclic group,
L21 and L22 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent heterocyclic group,
Ar21 is a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent heterocyclic group; or -O-;
a and b are each an integer from 1 to 3,
When a is 2 or more, HAr is the same as 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:
[Formula 101] [Formula 102]

In Formulas 101 and 102,
The definitions of A1, A2, R1 to R3, Z1, Z2, p1 and n1 to n3 are the same as in Formula 1 above,
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 alkyl group; a substituted or unsubstituted aryl 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 cycloalkyl group; a substituted or unsubstituted aryl 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 aliphatic ring, a substituted or unsubstituted aromatic ring, or a ring condensed thereof,
g11 is an integer from 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 Formulas 103 to 106:
[Formula 103] [Formula 104]

[Formula 105] [Formula 106]

In Formulas 103 to 106,
The definitions of R1 to R3, Z1, Z2, p1, Ar1 to Ar4, and n1 to n3 are the same as in Formula 1 above,
A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group; Or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, or a ring condensed thereof,
G5 to G8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Z3, Z4, G12 and G13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine with an adjacent group to form a substituted or unsubstituted ring,
g12 is an integer from 0 to 8, g13 is an integer from 0 to 4, and when g12 and g13 are each 2 or more, two or more substituents in parentheses are the same as 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 Formulas 1-1 to 1-4:
[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 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 above,
A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl 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; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine 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 Formulas 201 to 203:
[Formula 201] [Formula 202]

[Formula 203]

In Formulas 201 to 203,
The definitions of E1 to E3, 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 alkyl group; a substituted or unsubstituted aryl 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,
p6 and p7 are each 1 or 2,
n5" is an integer from 0 to 2, n8" is an integer from 0 to 3, n11 and n12 are each an integer from 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 as or different from each other. The method according to claim 1,
The organic light emitting device of Formula 2 is 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 rest 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 combine with an adjacent group to form a substituted or unsubstituted ring,
Definitions of E1 to E3, n4 to n8, and Formulas 1-A and 1-B are the same as in Formula 2 above. The method according to claim 1,
Formula 2 is an organic light emitting device represented by any one of Formulas 211 to 219:
[Formula 211] [Formula 212]

[Formula 213] [Formula 214]

[Formula 215] [Formula 216]

[Formula 217] [Formula 218]

[Formula 219]

In Formulas 211 to 219,
The definitions of n4 to n8 are 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 alkyl group; a substituted or unsubstituted aryl 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,
p6 to p9 are each 1 or 2,
n4" and n5" are each an integer from 0 to 2, n7" and n8" are integers from 0 to 3, n11 to n14 are each an integer from 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 Chemical Formulas Cy1 to Cy3:
[Formula Cy1] [Formula Cy2] [Formula Cy3]

In the formula Cy1 to Cy3,
R31 to R40 are the same as or different from each other, and each independently represents 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 combine with an adjacent group to form a substituted or unsubstituted ring,
n41 is an integer from 0 to 2, n42 and n43 are each an integer from 0 to 4;
When n41 to n43 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,
Formula 1-A is represented by Formula 1-A-1 or 1-A-2, and Formula 1-B is an organic light emitting device represented by 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 combine with an adjacent group to form a substituted or unsubstituted ring,
t22 is an integer from 0 to 8, and when t22 is 2 or more, two or more T22s are the same as or different from each other. The organic light emitting diode of claim 1, wherein -L22-(CN) _b of Formula 2 is selected from the following structure:

In the structure,
L23 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
R51 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n51 is an integer from 0 to 4, n51' is an integer from 0 to 3,
The dotted line is a position connected to the Ar21. 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 a light emitting 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 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.

Images