KR20240142305A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light-emitting device comprising the same.

Description

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME

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

This application claims the benefit of Korean Patent Application No. 10-2023-0036948 filed with the Korean Intellectual Property Office on March 21, 2023, the entire contents of which are incorporated herein by reference.

In general, the organic luminescence phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic luminescence phenomenon usually have a structure including an anode, a cathode, and an organic layer therebetween. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

There is a continued need for the development of new materials for organic light-emitting devices such as the above.

Korean Patent Publication No. 10-2020-129990

The present specification provides a compound and an organic light-emitting device comprising the same.

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[Chemical Formula 1]

In chemical formula 1,

X is NR, O or S,

Y is O or S,

Ar1, Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic heterocycle, provided that at least one of Ar1, Ar2 and Ar3 comprises a heterocycle; or a substituted or unsubstituted aliphatic hydrocarbon ring, and further, when X is NR, at least one of R, Ar1, Ar2 and Ar3 comprises a ring in which substituted or unsubstituted aliphatic hydrocarbon rings are condensed,

When X is NR, at least one of Ar1 and Ar3 can combine with R to form a ring, and Ar2 and Ar3 can combine with each other to form a ring,

R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

In addition, one embodiment of the present specification provides an organic light-emitting device including an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one layer of the organic layers includes the compound described above.

The compound described in this specification can be used as a material of an organic layer of an organic light-emitting device. The compound according to at least one embodiment of this specification can improve narrow half-width, improved efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.

Figure 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (10) are sequentially laminated.
Figure 2 illustrates an example of an organic light-emitting device in which 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), a first electron transport layer (7), a second electron transport layer (8), an electron injection layer (9), and a cathode (10) are sequentially laminated.

The following describes this specification in more detail.

In this specification, when a part is said to "include" a certain component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

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

In this specification, “*” means a position bonded to a chemical formula or compound.

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

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

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group (-CN); a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; a phosphine oxide group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; an aryl group; or a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are connected, or has no substituents. For example, "a substituent connected with two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent in which two phenyl groups are connected.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; an amino group; an alkoxy group; an aryloxy group; an alkyl group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or has no substituents.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; an alkyl group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

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

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

In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, an n-octyl group, etc.

In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto.

Substituents comprising alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight-chain and branched forms.

In the present specification, the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

In the present specification, the alkynyl group is a substituent including a triple bond between carbon atoms, may be linear or branched, and has a carbon number that is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the alkynyl group has 2 to 10 carbon atoms.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The carbon number of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, a diphenylamine group, a phenylpyridylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a dibenzofuranylphenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, or the like, but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, an anthracenyl group, a phenanthrene group, a pyrenyl group, a perylenyl group, a triphenylene group, a chrysenyl group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto. Here, the aryl group includes not only a structure composed of only an aromatic hydrocarbon ring, but also a structure in which an aromatic hydrocarbon ring is condensed with an aliphatic hydrocarbon ring.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

When the above fluorenyl group is substituted, , , Spirofluorenyl group of the back, (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

In this specification, the aryl group among the aryloxy group and the arylamine group can be applied to the description regarding the aryl group described above.

In this specification, the description regarding the alkyl group described above can be applied to the alkyl group among the alkylthioxy group and the alkylsulfoxy group.

In this specification, the description regarding the aryl group described above can be applied to the aryl group among the arylthioxy group and the arylsulfoxy group.

In the present specification, a heterocyclic group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like. Here, the heterocyclic group includes not only a structure composed solely of heterocyclic rings, but also a structure in which a heterocyclic ring is condensed with an aromatic or aliphatic hydrocarbon ring.

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

In this specification, the description of the aryl group may be applied, except that the arylene group is divalent.

In this specification, the description of the heteroaryl group may be applied, except that the heteroarylene group is divalent.

In the present specification, the hydrocarbon ring includes an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring thereof.

In the present specification, a heterocycle includes an aromatic heterocycle, an aliphatic heterocycle, or a condensed ring thereof. In the case of a ring in which two or more rings are condensed, if at least one ring is a ring that includes a heteroatom other than carbon as a ring member, the entire ring may be referred to as a heterocycle. In this case, the ring that may be condensed with a ring that includes a heteroatom as a ring member may be a heterocycle or a hydrocarbon ring.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring; or a heterocycle.

For example, when adjacent groups are bonded to each other to form a ring, a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocyclic ring; a substituted or unsubstituted aromatic heterocyclic ring; or a condensed ring thereof can be formed. The hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The heterocyclic ring refers to a ring including at least one element selected from the group consisting of N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

In this specification, an aliphatic hydrocarbon ring means a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

In this specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.

In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine, and thiocaine.

In this specification, an aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, dryazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, These include, but are not limited to, imidazopyridines, phenoxazines, indolocarbazoles, and indenocarbazoles.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

Hereinafter, the compound of chemical formula 1 is described in detail.

[Chemical Formula 1]

In the above chemical formula 1, the definition of the substituent is as described above.

According to one embodiment, Ar1, Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle; a condensed ring of a substituted or unsubstituted heterocycle and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle; a condensed ring of a substituted or unsubstituted heterocycle and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

According to one embodiment, Ar1, Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle containing O or S as a heteroatom; a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle containing O or S as a heteroatom; A condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom, an aromatic hydrocarbon ring, and an aliphatic hydrocarbon ring.

According to one embodiment, Ar1, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted benzene, a substituted or unsubstituted tetrahydronaphthalene, a substituted or unsubstituted furan, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted tetrahydronaphthofuran, a substituted or unsubstituted tetrahydrobenzonaphthofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted tetrahydronaphthothiophene, or a substituted or unsubstituted tetrahydrobenzonaphthothiophene, and at least one of Ar1, Ar2 and Ar3 is a substituted or unsubstituted tetrahydronaphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted furan, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted benzothiophene ... Unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydrobenzonaphthofuran, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, or substituted or unsubstituted dibenzothiophene, substituted or unsubstituted tetrahydronaphthothiophene, or substituted or unsubstituted tetrahydrobenzonaphthothiophene.

In one embodiment, at least one of Ar1, Ar2 and Ar3 comprises a substituted or unsubstituted tetrahydronaphthalene, or X is NR and R comprises a substituted or unsubstituted tetrahydronaphthalene.

According to one embodiment, at least one of Ar1 and Ar2 is a substituted or unsubstituted tetrahydronaphthalene, or X is NR and R is a substituted or unsubstituted tetrahydronaphthalene, or at least one of Ar1 and Ar2 is a condensed heterocycle of a substituted or unsubstituted tetrahydronaphthalene.

According to one embodiment, the chemical formula 1 is represented by one of the following chemical formulas 11 to 13:

[Chemical Formula 11]

[Chemical Formula 12]

[Chemical Formula 13]

In chemical formulas 11 to 13,

X and Y are as defined in chemical formula 1,

Z1 is CRxRy, O or S,

Ra to Rc, Rx, Ry, R and R' are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or are connected to adjacent groups to form a substituted or unsubstituted ring, a and c are each an integer from 0 to 4, b is an integer from 0 to 3, a' and c' are each an integer from 0 to 2, and b' is 0 or 1.

According to one embodiment, the chemical formula 1 is represented by one of the following chemical formulas 21 to 23:

[Chemical Formula 21]

[Chemical Formula 22]

[Chemical Formula 23]

In chemical formulas 21 to 23,

X, Y, Z1, Ra to Rc, a, b, c, a', b' and c' are as described above,

Rd are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or are connected to adjacent groups to form a substituted or unsubstituted ring, and d is an integer from 0 to 4.

According to one embodiment, the chemical formula 1 is represented by one of the following chemical formulas 31 to 34:

[Chemical Formula 31]

[Chemical formula 32]

[Chemical formula 33]

[Chemical Formula 34]

In chemical formulas 31 to 34,

X, Y, Z1, Ra to Rd, a, b, c, d, a', b' and c' are as described above,

Z2 and Z3 are the same or different and are each independently CRxRy, O or S, and Rx and Ry are as described above.

According to one embodiment of the present invention, the chemical formula 1 is represented by one of the following chemical formulas 41 to 43.

[Chemical Formula 41]

[Chemical formula 42]

[Chemical Formula 43]

In chemical formulas 41 to 43,

X and Y are as defined in chemical formula 1,

Z1 and Z2 are each independently CRxRy, O or S,

Ra to Rc, Rx, Ry, R, R', R'' and R''' are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or are connected to adjacent groups to form a substituted or unsubstituted ring, and a and c are each an integer from 0 to 4, and b is an integer from 0 to 3.

According to one embodiment, R and R' of the chemical formulae 41 to 43 combine with each other to form substituted or unsubstituted benzene, or substituted or unsubstituted tetrahydronaphthalene.

According to one embodiment, R and R' of the chemical formulae 41 to 43 combine with each other to form benzene substituted or unsubstituted with an alkyl group, or tetrahydronaphthalene substituted or unsubstituted with an alkyl group.

According to one embodiment, Rb of the chemical formulae 41 to 43 is hydrogen or deuterium, or forms a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle.

According to one embodiment, Rb of the chemical formulae 41 to 43 is hydrogen or deuterium, or forms an aliphatic ring substituted or unsubstituted with deuterium or an alkyl group, an aromatic ring substituted or unsubstituted with deuterium or an alkyl group, or a heterocycle substituted or unsubstituted with deuterium or an alkyl group.

According to one embodiment, Rc of the chemical formulae 41 to 43 is hydrogen or deuterium, or forms a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle.

According to one embodiment, Rc of the chemical formulae 41 to 43 is hydrogen or deuterium, or forms a substituted or unsubstituted hexane, a substituted or unsubstituted benzene, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.

According to one embodiment, Rc of the chemical formulae 41 to 43 is hydrogen or deuterium, or forms hexane substituted or unsubstituted with deuterium or an alkyl group, benzene substituted or unsubstituted with deuterium or an alkyl group, indene substituted or unsubstituted with deuterium or an alkyl group, benzofuran substituted or unsubstituted with deuterium or an alkyl group, or benzothiophene substituted or unsubstituted with deuterium or an alkyl group.

According to one embodiment, the chemical formula 1 includes a C1 to C6 straight-chain or branched-chain alkyl group or cycloalkyl group.

According to one embodiment, the chemical formula 1 includes an arylamine group substituted or unsubstituted with an alkyl group; or a heteroarylamine group substituted or unsubstituted with an alkyl group.

According to one embodiment, Rb is hydrogen, deuterium, a straight or branched alkyl group having C1 to C6, a cycloalkyl group, an arylamine group substituted or unsubstituted with an alkyl group; or a heteroarylamine group substituted or unsubstituted with an alkyl group.

According to one embodiment, Rc is hydrogen, deuterium, a straight or branched alkyl group having C1 to C6, a cycloalkyl group, an arylamine group substituted or unsubstituted with an alkyl group; or a heteroarylamine group substituted or unsubstituted with an alkyl group.

According to one embodiment, Rc is an arylamine group substituted or unsubstituted with hydrogen, deuterium, or an alkyl group.

In one embodiment, X is NR, and R comprises a C1 to C6 straight-chain or branched-chain alkyl group or cycloalkyl group.

In one embodiment, X is NR, and R is phenyl substituted with a C1 to C6 straight chain or branched chain alkyl group or cycloalkyl group, biphenyl substituted with a C1 to C6 straight chain or branched chain alkyl group or cycloalkyl group, tetrahydronaphthalene group substituted with an alkyl group, dibenzofuran, or dibenzothiophene.

According to one implementation, X is NR and Y is O.

According to one implementation, X is NR and Y is S.

According to one implementation, X is O and Y is O.

According to one implementation, X is S and Y is O.

According to one implementation, X is O and Y is S.

According to one implementation, X is S and Y is S.

According to one embodiment, the compound of the chemical formula 1 can be represented by the following compounds:

The substituent of the compound represented by chemical formula 1 according to one embodiment of the present specification can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

In this specification, by introducing various substituents into the core structure of the compound represented by the chemical formula 1, compounds having various energy band gaps can be synthesized. In addition, in this specification, by introducing various substituents into the core structure of the above structure, a narrow half-width can be achieved, and the HOMO and LUMO energy levels of the compound can also be controlled.

In addition, the present specification provides an organic light-emitting device comprising the compound described above.

An organic light-emitting device according to the present specification is an organic light-emitting device comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, characterized in that at least one of the organic layers comprises a compound represented by the chemical formula 1 described above.

The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including at least one layer of a hole transport layer, a hole injection layer, an electron suppression layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole suppression layer, and an electron transport and injection layer as the organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.

In the organic light-emitting device of the present specification, the organic light-emitting device includes a light-emitting layer, and the light-emitting layer may include the compound.

For example, the compound of the above chemical formula 1 may be included as a dopant in the light-emitting layer. At this time, X of the compound may be NR.

In one embodiment of the present invention, the light-emitting layer includes a dopant and a host.

In one embodiment of the present invention, the light-emitting layer contains a dopant and a host in a mass ratio of 1:99 to 5:95.

In one embodiment of the present invention, the light-emitting layer contains the compound of chemical formula 1 as a dopant.

In one embodiment of the present invention, the light-emitting layer contains the compound of chemical formula 1 as a blue dopant.

In one embodiment of the present invention, the light-emitting layer includes a host.

An organic light-emitting device according to one embodiment of the present specification includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 and a compound represented by the following chemical formula H.

[chemical formula H]

In the above chemical formula H,

L21 to L23 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

R21 to R27 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same or different from each other, and each independently represents deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

k is 0 or 1.

In one embodiment of the present specification, when k is 0, the position of -L23-Ar23 is connected to hydrogen or deuterium.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently represent a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently represent a direct bond; a C6-C30 arylene group; or a C2-C30 heteroarylene group containing N, O, or S, wherein the arylene group or the heteroarylene group is unsubstituted or substituted with a C1-C10 alkyl group, a C6-C30 aryl group, or a C2-C30 heteroaryl group.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently represent deuterium; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently a deuterium; a C6-C30 aryl group substituted or unsubstituted with deuterium; or a C2-C30 heteroaryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently represent deuterium; a substituted or unsubstituted monocyclic to tetracyclic aryl group; or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently represent a deuterium; a monocyclic to tetracyclic aryl group substituted or unsubstituted with deuterium; or a monocyclic to tetracyclic heteroaryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted naphthobenzothiophene group.

In one embodiment of the present specification, Ar21 and Ar22 are different from each other.

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

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

In one embodiment of the present specification, Ar21 is an aryl group substituted or unsubstituted with deuterium, and Ar22 is an aryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar21 is an aryl group substituted or unsubstituted with deuterium, and Ar22 is a heteroaryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R21 to R27 are the same as or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present specification, R21 to R27 are hydrogen.

In one embodiment of the present specification, R21 to R27 are deuterium.

In one embodiment of the present specification, the chemical formula H is represented by the following chemical formula H01.

[Chemical formula H01]

In the above chemical formula H01,

The definitions of L21, L22, Ar21 and Ar22 are as defined in chemical formula H, D represents deuterium, and k1 is 0 to 8.

In one embodiment of the present specification, the compound represented by the chemical formula H is one selected from the following compounds.

The organic light-emitting device of the present specification may further include at least one organic layer among a hole transport layer, a hole injection layer, an electron suppression layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole suppression layer, and a hole injection and transport layer.

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

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

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

Figure 1 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (10) are sequentially laminated. In this structure, the compound may be included in the light-emitting layer (6).

FIG. 2 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), an emitting layer (6), a first electron transport layer (7), a second electron transport layer (8), an electron injection layer (9), and a cathode (10) are sequentially laminated. In this structure, the compound may be included in any one of the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the emitting layer (6), the first electron transport layer (7), and the second electron transport layer (8), for example, the emitting layer (6).

The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound, i.e., the compound represented by the chemical formula 1.

When the above organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

For example, the organic light-emitting device according to the present specification can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

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

The above cathode is an electrode that injects electrons, and it is preferable that the cathode material be a material having a low work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF/Al or LiO ₂ /Al.

The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine series organic compounds, hexanitrilehexaazatriphenylene series organic compounds, quinacridone series organic compounds, perylene series organic compounds, anthraquinone, and conductive polymers of polyaniline and polythiophene series.

According to one embodiment of the present specification, the hole injection layer may include, but is not limited to, a compound represented by the following chemical formula HI-1.

[chemical formula HI-1]

In the above chemical formula HI-1,

X11 is either NR301; O; or S,

R301 is hydrogen; deuterium; or a substituted or unsubstituted aryl group,

R101 and R102 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

R201 and R202 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group,

n101 and n102 are each an integer from 1 to 4, and when n101 and n102 are each 2 or greater, R101 and R102 are each equal to or different from each other,

n201 and n202 are each an integer from 1 to 8, and when n201 and n202 are each 2 or greater, R201 and R202 are each equal to or different from each other.

In one embodiment of the present specification, X11 is NR301.

In one embodiment of the present specification, R301 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, R301 is hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a carbazole group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R201 and R202 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkylamine group; a substituted or unsubstituted C6 to C20 arylamine group; or a substituted or unsubstituted C6 to C20 aryl group.

In one embodiment of the present specification, R201 and R202 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a C6 to C12 arylamine group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, the hole injection layer may include a compound represented by the chemical formula HI-1 and an organic material of the hexanitrilehexaazatriphenylene series.

In one embodiment of the present specification, the hexanitrilehexaazatriphenylene series organic material included in the hole injection layer may be hexanitrilehexaazatriphenylene (HAT-CN) substituted with a nitrile group.

The above-mentioned hole transport layer can play a role in facilitating the transport of holes. As a hole transport material, a material that can transport holes from the anode or the hole injection layer and transfer them to the light-emitting layer is suitable, and a material with high mobility for holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

In one embodiment of the present specification, the hole transport layer may include, but is not limited to, a compound represented by the following chemical formula HT-1.

[chemical formula HT-1]

In the above chemical formula HT-1,

R311 to R313 are the same as or different from each other, and each independently represents one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

r311 is an integer from 1 to 4, and when r311 is 2 or more, two or more R311 are the same as or different from each other,

r312 is an integer from 1 to 4, and when r316 is 2 or more, two or more R312 are the same as or different from each other.

In one embodiment of the present specification, R311 may be hydrogen; deuterium; or a substituted or unsubstituted amine group.

In one embodiment of the present specification, R311 may be an amine group unsubstituted or substituted with one or more selected from the group consisting of hydrogen, deuterium, a phenyl group, a naphthyl group, a carbazole group, and combinations thereof.

In one embodiment of the present specification, R312 may be hydrogen; deuterium; or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R312 may be hydrogen; deuterium; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, R312 may be a carbazole group.

In one embodiment of the present specification, R313 may be hydrogen; deuterium; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R313 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R313 may be a phenyl group.

An electron blocking layer may be provided between the above-described hole transport layer and the above-described light-emitting layer. The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer. It can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes, and known materials can be used without limitation.

In one embodiment of the present specification, the hole blocking material may include a compound represented by the following chemical formula HT-2, but is not limited thereto.

[chemical formula HT-2]

In the above chemical formula HT-2,

R315 to R317 are the same as or different from each other, and each independently is one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

r315 is an integer from 1 to 5, and when r315 is 2 or more, two or more R315 are equal to or different from each other,

r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

In one embodiment of the present specification, R317 may be any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

In one embodiment of the present specification, R317 may be any one selected from the group consisting of a substituted or unsubstituted carbazole group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted triphenylene group; and combinations thereof.

In one embodiment of the present specification, R317 may be a biphenyl group unsubstituted or substituted with one or more selected from the group consisting of hydrogen, deuterium, a phenyl group, and a carbazole group.

In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R315 and R316 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted alkylamine group; or a substituted or unsubstituted arylamine group.

In one embodiment of the present specification, R315 may be a phenyl group.

In one embodiment of the present specification, R316 may be a diphenylamine group.

The above-described light-emitting layer can emit red, green or blue, and can be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer respectively and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. The compound of the above-described chemical formula 1 can be used as the light-emitting layer material, and other specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex ( _Alq 3 ); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole and benzimidazole series compounds; poly(p-phenylenevinylene)(PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

The host material of the above-mentioned light-emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compound includes, but is not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

When the above-mentioned light-emitting layer emits red light, the light-emitting dopant may include, but is not limited to, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum). When the light-emitting layer emits green light, the light-emitting dopant may include, but is not limited to, a phosphorescent material such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymers, or PPV polymers can be used as the emitting dopant, but is not limited thereto.

A hole-suppressing 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 above electron transport layer or electron injection and transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer is suitable, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, the above-mentioned compound or an Al complex of 8-hydroxyquinoline; a complex containing Alq ₃ ; an organic radical compound; a hydroxyflavone-metal complex, etc.

In one embodiment of the present specification, the electron transport material may include a compound represented by the following chemical formula ET-1 or chemical formula ET-2, but is not limited thereto.

[chemical formula ET-1]

In the above chemical formula ET-1,

R601 to R607 are the same or different from each other, and each independently represents hydrogen; or deuterium,

L601 to L603 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

Ar601 to Ar603 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

k603 is 0 or 1,

[chemical formula ET-2]

In the above chemical formula ET-2,

Z11 to Z13 are the same or different from each other, and are each independently N or CH,

L701 to L703 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

Ar701 to Ar703 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

n701 to n703 are each an integer from 0 to 2, and when n701 to n703 are each 2, L701 to L703 are equal to or different from each other.

In one embodiment of the present specification, all of R601 to R607 are hydrogen or all of deuterium.

In one embodiment of the present specification, L601 to L603 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar603 is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar603 is a benzimidazole group unsubstituted or substituted with one or more atoms selected from the group consisting of hydrogen, deuterium, and phenyl groups.

In one embodiment of the present specification, all of Z11 to Z13 are N.

In one embodiment of the present specification, L701 to L703 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, Ar701 to Ar703 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and at least one of the first electron transport layer and the second electron transport layer may include a compound represented by the chemical formula ET-1 or chemical formula ET-2.

In one embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the first electron transport layer may include a compound represented by the chemical formula ET-1.

In one embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the second electron transport layer may include a compound represented by the chemical formula ET-1.

In one embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the second electron transport layer may include a compound represented by the chemical formula ET-1 and may further include lithium quinolate (Liq).

In one embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the second electron transport layer may include a compound represented by the chemical formula ET-1 and lithium quinolate (Liq), and may include the compound represented by the chemical formula ET-1 and lithium quinolate (Liq) in a weight ratio of 1:1.

In one embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and in this case, the first electron transport layer may be provided between the light-emitting layer and the second electron transport layer.

The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an excellent electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or the light-emitting material, preventing movement of excitons generated in the light-emitting layer to the hole injection layer, and excellent thin film forming ability is preferable. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

As the above metal complex compounds, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

In one embodiment of the present specification, the electron-injecting material may include lithium quinolate (Liq), but is not limited thereto.

The above hole suppression layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

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

Hereinafter, in order to specifically explain this specification, examples will be given and described in detail. However, the examples according to this specification may be modified in various different forms, and the scope of this application is not construed as being limited to the examples described below. The examples of this application are provided to more completely explain this specification to a person having average knowledge in the art.

Preparation example of compound 1 (F-1)

Synthesis of I-1

Under a nitrogen atmosphere, 30 g of 1-bromo-3-chlorobenzene, 61 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 1.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 30 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 57 g. (Yield 73%, Mass [M+] = 501)

Synthesis of I-2

I-1 25 g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 12.5 g, K ₂ CO ₃ 21 g, [bis(tri-tert-butylphosphine)palladium(0)] 0.5 g, tetrahydrofuran 500 mL and water 250 mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with MgSO ₄ (anhydrous) and filtered. The filtered solution was recrystallized to obtain 26 g. (Yield 72%, Mass [M+] = 669)

Synthesis of F-1

Under a nitrogen atmosphere, 20 g of I-2, 20 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.5 g. (Yield 37%, Mass [M+] = 677)

Preparation example of compound 2 (F-2)

Synthesis of I-3

Under a nitrogen atmosphere, 30 g of 1-bromo-3-chlorobenzene, 70 g of 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine, 1.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 30 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 62 g. (Yield 71%, Mass [M+] = 557)

Synthesis of I-4

I-3 25 g, (2-hydroxy-9,9-dimethyl-9H-fluoren-3-yl)boronic acid 11.4 g, K ₂ CO ₃ 19 g, [bis(tri-tert-butylphosphine)palladium(0)] 0.5 g, tetrahydrofuran 500 mL, and water 250 mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23 g. (Yield 70%, Mass [M+] = 731)

Synthesis of F-2

Under a nitrogen atmosphere, 20 g of I-4, 18.2 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.2 g. (Yield 36%, Mass [M+] = 739)

Preparation example of compound 3 (F-3)

Synthesis of I-5

I-3 25 g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 11.2 g, K ₂ CO ₃ 19 g, [bis(tri-tert-butylphosphine)palladium(0)] 0.5 g, tetrahydrofuran 500 mL and water 250 mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25 g. (Yield 77%, Mass [M+] = 725)

Synthesis of F-3

Under a nitrogen atmosphere, 20 g of I-5, 18.4 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 733)

Preparation example of compound 4 (F-4)

Synthesis of I-6

Under a nitrogen atmosphere, 30 g of 1-bromo-3-chloro-5-methylbenzene, 65 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 1.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 28 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 55 g. (Yield 73%, Mass [M+] = 515)

Synthesis of I-7

I-6 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 20.3g, _K2CO3 21g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.5g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 30g. (Yield 72%, Mass [M+]=852)

Synthesis of F-4

Under a nitrogen atmosphere, 20 g of I-7, 15.6 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 860)

Preparation example of compound 5 (F-5)

Synthesis of I-8

Under a nitrogen atmosphere, 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 40 g of N-(4-(adamantan-1-yl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g. (Yield 74%, Mass [M+] = 673)

Synthesis of I-9

I-8 25g, (2-hydroxyphenyl)boronic acid 5.2g, _K2CO3 16g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 21g. (Yield 77%, Mass [M+]=731)

Synthesis of F-5

Under a nitrogen atmosphere, 20 g of I-9, 18.3 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.5 g. (Yield 37%, Mass [M+] = 739)

Preparation example of compound 6 (F-6)

Synthesis of I-10a

Under a nitrogen atmosphere, 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 37.2 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g. (Yield 72%, Mass [M+] = 649)

Synthesis of I-10

I-10a 25g, (3-mercapto-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 9.9g, _{K2CO3 16g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 74%, Mass [M+]=833)

Synthesis of F-6

Under a nitrogen atmosphere, 20 g of I-10, 16 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 841)

Preparation example of compound 7 (F-7)

Synthesis of I-11

Under a nitrogen atmosphere, 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 41.1 g of 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-2-amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 45 g. (Yield 71%, Mass [M+] = 691)

Synthesis of I-12

I-11 25g, (2-hydroxydibenzo[b,d]furan-3-yl)boronic acid 8.3g, _{K2CO3 15g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 76%, Mass [M+]=833)

Synthesis of F-7

Under a nitrogen atmosphere, 20 g of I-12, 16 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 847)

Preparation example of compound 8 (F-8)

Synthesis of I-13

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 41.5 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g. (Yield 73%, Mass [M+] = 591)

Synthesis of I-14

I-13 25g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 10.5g, _{K2CO3 18g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24g. (Yield 75%, Mass [M+]=759)

Synthesis of F-8

Under a nitrogen atmosphere, 20 g of I-14, 18 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 767)

Preparation example of compound 9 (F-9)

Synthesis of I-15

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 43 g of 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, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g. (Yield 71%, Mass [M+] = 605)

Synthesis of I-16

I-15 25g, (2-mercapto-9,9-dimethyl-9H-fluoren-3-yl)boronic acid 11.2g, _{K2CO3 18g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25g. (Yield 76%, Mass [M+]=795)

Synthesis of F-9

Under a nitrogen atmosphere, 20 g of I-16, 17 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 803)

Preparation example of compound 10 (F-10)

Synthesis of I-17

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 52 g of N-(5-(adamantan-1-yl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 52 g. (Yield 71%, Mass [M+] = 691)

Synthesis of I-18

I-17 25g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 9g, _{K2CO3 15g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24g. (Yield 77%, Mass [M+]=860)

Synthesis of F-10

Under a nitrogen atmosphere, 20 g of I-18, 15.5 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 867)

Preparation example of compound 11 (F-11)

Synthesis of I-19

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 31.4 g of 7,7,10,10-tetramethyl-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-ol, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 38 g. (Yield 72%, Mass [M+] = 496)

Composite of I-20

I-19 25g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 12.5g, _{K2CO3 21g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25g. (Yield 75%, Mass [M+]=664)

Synthesis of F-11

Under a nitrogen atmosphere, 20 g of I-20, 20 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 672)

Preparation example of compound 12 (F-12)

Synthesis of I-21a

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 43.9 g of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After completion of the reaction, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 50 g. (Yield 77%, Mass [M+] = 613)

Synthesis of I-21

I-21a 25g, (3-hydroxydibenzo[b,d]furan-2-yl)boronic acid 9.4g, _{K2CO3 17g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 74%, Mass [M+]=761)

F-12 composite

Under a nitrogen atmosphere, 20 g of I-21, 17.5 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 769)

Preparation example of compound 13 (F-13)

Synthesis of I-22

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 40 g of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-3-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g. (Yield 71%, Mass [M+] = 571)

Synthesis of I-23

I-22 25g, (3-mercapto-9,9-dimethyl-9H-fluoren-2-yl)boronic acid 11.8g, _{K2CO3 19g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24g. (Yield 72%, Mass [M+]=761)

F-13 composite

Under a nitrogen atmosphere, 20 g of I-23, 18 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 769)

Preparation example of compound 14 (F-14)

Synthesis of I-24

I-13 25g, (3-hydroxydibenzo[b,d]thiophen-2-yl)boronic acid 10g, _{K2CO3 17g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 75%, Mass [M+]=755)

F-14 composite

Under a nitrogen atmosphere, 20 g of I-24, 18 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 763)

Preparation example of compound 15 (F-15)

Synthesis of I-25

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 29.5 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 36 g. (Yield 71%, Mass [M+] = 478)

Synthesis of I-26

I-25 25g, (2-hydroxy-9,9-dimethyl-9H-fluoren-3-yl)boronic acid 13.3g, _{K2CO3 22g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 26g. (Yield 76%, Mass [M+]=652)

F-15 composite

Under a nitrogen atmosphere, 20 g of I-26, 21 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.5 g. (Yield 37%, Mass [M+] = 660)

Preparation example of compound 16 (F-16)

Synthesis of I-27

I-13 25g, (2-hydroxy-9,9-dimethyl-9H-fluoren-3-yl)boronic acid 10.8g, _{K2CO3 18g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 22g. (Yield 68%, Mass [M+]=765)

F-16 composite

Under a nitrogen atmosphere, 20 g of I-27, 18 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.7 g. (Yield 38%, Mass [M+] = 773)

Preparation example of compound 17 (F-17)

Synthesis of I-28

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 47.5 g of 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 51 g. (Yield 74%, Mass [M+] = 647)

Composite of I-29

I-28 25g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 9.6g, _{K2CO3 16g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 73%, Mass [M+]=815)

F-17 composite

Under a nitrogen atmosphere, 20 g of I-29, 17 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.2 g. (Yield 36%, Mass [M+] = 823)

Preparation example of compound 18 (F-18)

Synthesis of I-30

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 43.9 g of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 50 g. (Yield 77%, Mass [M+] = 613)

Synthesis of I-31

I-30 25g, (2-hydroxydibenzo[b,d]furan-3-yl)boronic acid 9.3g, _{K2CO3 17g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24g. (Yield 77%, Mass [M+]=761)

F-18 composite

Under a nitrogen atmosphere, 20 g of I-31, 18 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 769)

Preparation example of compound 19 (F-19)

Synthesis of I-32

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 53 g of 7,7,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 52 g. (Yield 70%, Mass [M+] = 695)

Synthesis of I-33

I-32 25g, (2-hydroxydibenzo[b,d]thiophen-3-yl)boronic acid 8.8g, _{K2CO3 15g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 74%, Mass [M+]=859)

F-19 composite

Under a nitrogen atmosphere, 20 g of I-33, 16 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 867)

Preparation example of compound 20 (F-20)

Synthesis of I-34

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 43 g of 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, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g. (Yield 71%, Mass [M+] = 605)

Synthesis of I-35

I-34 25g, (3-hydroxy-9,9-dimethyl-9H-fluoren-2-yl)boronic acid 11g, _{K2CO3 18g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25g. (Yield 75%, Mass [M+]=779)

Synthesis of F-20

Under a nitrogen atmosphere, 20 g of I-35, 17 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 787)

Preparation example of compound 21 (F-21)

Synthesis of I-36

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 45 g of N-(4-(adamantan-1-yl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After completion of the reaction, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 49 g. (Yield 73%, Mass [M+] = 629)

Synthesis of I-37

I-36 25g, (3-Mercaptodibenzo[b,d]thiophen-2-yl)boronic acid 10.4g, _{K2CO3 17g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 72%, Mass [M+]=809)

F-21 composite

Under a nitrogen atmosphere, 20 g of I-37, 17 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 817)

Preparation example of compound 22 (F-22)

Synthesis of I-38

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 33.1 g of 7,7,10,10-tetramethyl-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 42 g. (Yield 77%, Mass [M+] = 512)

Synthesis of I-39

I-38 25g, (2-hydroxy-9,9-dimethyl-9H-fluoren-3-yl)boronic acid 12.4g, _{K2CO3 20.3g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25g. (Yield 78%, Mass [M+]=686)

F-22 composite

Under a nitrogen atmosphere, 20 g of I-37, 19.5 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.2 g. (Yield 36%, Mass [M+] = 694)

Preparation example of compound 23 (F-23)

Composite of I-40

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]thiophene, 43.1 g of N-(4-(adamantan-1-yl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g. (Yield 71%, Mass [M+] = 645)

Synthesis of I-41

I-40 25g, (3-mercapto-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 10.3g, _{K2CO3 16.1g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24g. (Yield 75%, Mass [M+]=829)

F-23 composite

Under a nitrogen atmosphere, 20 g of I-41, 16.1 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 837)

Preparation example of compound 24 (F-24)

Synthesis of I-42

I-40 25g, (3-hydroxydibenzo[b,d]furan-2-yl)boronic acid 8.9g, _{K2CO3 16.1g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 75%, Mass [M+]=793)

F-24 composite

Under a nitrogen atmosphere, 20 g of I-42, 16.8 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 801)

Preparation example of compound 25 (F-25)

Synthesis of I-43

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]thiophene, 26.3 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-ol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 35 g. (Yield 73%, Mass [M+] = 478)

Synthesis of I-44

I-43 25g, (3-hydroxydibenzo[b,d]furan- ₂ -yl)boronic acid 12g, _K2CO3 22g, [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24g. (Yield 73%, Mass [M+]=626)

F-25 composite

Under a nitrogen atmosphere, 20 g of I-44, 21.3 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 634)

Preparation example of compound 26 (F-26)

Composite of I-45

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]thiophene, 49.8 g of 7,7,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 55 g. (Yield 77%, Mass [M+] = 711)

Synthesis of I-46

I-45 25g, (3-Mercaptodibenzo[b,d]furan-2-yl)boronic acid 8.6g, _{K2CO3 15g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 75%, Mass [M+]=875)

F-26 composite

Under a nitrogen atmosphere, 20 g of I-46, 15.2 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 883)

Preparation example of compound 27 (F-27)

Synthesis of I-47

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 29.5 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 37 g. (Yield 73%, Mass [M+] = 478)

Synthesis of I-48

I-47 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-mercaptophenyl)boronic acid 22.7g, _K2CO3 21.7g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.5g, 500mL of tetrahydrofuran and 250mL of water were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 31g. (Yield 71%, Mass [M+]=831)

F-27 composite

Under a nitrogen atmosphere, 20 g of I-48, 16 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.5 g. (Yield 37%, Mass [M+] = 839)

Preparation example of compound 28 (F-28)

Composite of I-49

I-28 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 16.8g, _K2CO3 16g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.4g, tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 29g. (Yield 76%, Mass [M+]=984)

F-28 composite

Under a nitrogen atmosphere, 20 g of I-49, 13.5 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 992)

Preparation example of compound 29 (F-29)

Composite of I-50

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 23.5 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 33 g. (Yield 74%, Mass [M+] = 422)

Synthesis of I-51

I-50 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 25.7g, _K2CO3 24.6g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.6g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 33g. (Yield 73%, Mass [M+]=759)

F-29 composite

Under a nitrogen atmosphere, 20 g of I-51, 17.6 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.2 g. (Yield 36%, Mass [M+] = 767)

Preparation example of compound 30 (F-30)

Synthesis of I-52

I-19 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 21.9g, _K2CO3 20.9g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.5g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 32g. (Yield 76%, Mass [M+]=833)

F-30 composite

Under a nitrogen atmosphere, 20 g of I-52, 16 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.2 g. (Yield 36%, Mass [M+] = 841)

Preparation example of compound 31 (F-31)

Synthesis of I-53

I-13 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 18.4g, _K2CO3 17.6g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 29g. (Yield 74%, Mass [M+]=928)

F-31 composite

Under a nitrogen atmosphere, 20 g of I-53, 14.4 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 936)

Preparation example of compound 32 (F-32)

Composite of I-54

I-13 25g, (5-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 17.7g, _K2CO3 17.6g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.4g, 500mL of tetrahydrofuran and 250mL of water were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 28g. (Yield 71%, Mass [M+]=928)

F-32 composite

Under a nitrogen atmosphere, 20 g of I-54, 14.4 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 936)

Preparation example of compound 33 (F-33)

Composite of I-55

Under a nitrogen atmosphere, 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 41.5 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 44 g. (Yield 70%, Mass [M+] = 591)

Synthesis of I-56

I-55 25g, (5-(bis(4-(tert-butyl)phenyl)amino)-2-mercaptophenyl)boronic acid 18.4g, _K2CO3 27.6g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 29g. (Yield 73%, Mass [M+]=944)

F-33 composite

Under a nitrogen atmosphere, 20 g of I-56, 14.1 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 952)

Preparation example of compound 34 (F-34)

Synthesis of I-57

Under a nitrogen atmosphere, 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 27.8 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-ol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 37 g. (Yield 75%, Mass [M+] = 462)

Synthesis of I-58

I-57 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boronic acid 22.6g, _K2CO3 22.5g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.6g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 32g. (Yield 74%, Mass [M+]=799)

F-34 composite

Under a nitrogen atmosphere, 20 g of I-58, 16.7 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.4 g. (Yield 37%, Mass [M+] = 807)

Preparation example of compound 35 (F-35)

Composite of I-59

Under a nitrogen atmosphere, 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 35.9 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 17.7 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 41 g. (Yield 70%, Mass [M+] = 635)

Composite of I-60

I-59 25g, (4-(bis(4-(tert-butyl)phenyl)amino)-2-mercaptophenyl)boronic acid 17.1g, _K2CO3 16.3g, [bis(tri-tert- _{butylphosphine} )palladium(0)] 0.4g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 29g. (Yield 75%, Mass [M+]=989)

F-35 composite

Under a nitrogen atmosphere, 20 g of I-50, 13.5 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.5 g. (Yield 37%, Mass [M+] = 996)

Preparation example of compound 36 (F-36)

Synthesis of I-61

Under a nitrogen atmosphere, 40 g of 3-bromo-5-chlorophenol, 75.1 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 2 g of [bis(tri-tert-butylphosphine)palladium(0)], 37.1 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 72 g. (Yield 72%, Mass [M+] = 517)

Synthesis of I-62

I-61 40g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride 35.1g, _{K2CO3 32.1g} , tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 3 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous) and filtered. The filtered solution was recrystallized to obtain 52g. (Yield 84%, Mass [M+]=799)

Synthesis of I-63

I-62 40g, (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid 12.4g, _{K2CO3 20.8g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 600mL and water 300mL were added, heated under reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25g. (Yield 71%, Mass [M+]=989)

Synthesis of I-64

Under a nitrogen atmosphere, 20 g of I-63, 19 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.6 g. (Yield 38%, Mass [M+] = 711)

F-36 composite

Under a nitrogen atmosphere, 7 g of I-64, 2.5 g of bis(4-(tert-butyl)phenyl)amine, 0.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 2 g of sodium-tert-butoxide, and 100 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 6.7 g. (Yield 71%, Mass [M+] = 956)

Preparation example of compound 37 (F-37)

Composite of I-65

Under a nitrogen atmosphere, 40 g of 3-bromo-5-chlorophenol, 77.8 g of 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, 2 g of [bis(tri-tert-butylphosphine)palladium(0)], 37.1 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 73 g. (Yield 70%, Mass [M+] = 540)

Synthesis of I-66

I-65 40g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride 33.6g, _{K2CO3 31g} , tetrahydrofuran 500mL and water 250mL were added, heated under reflux and stirred for 3 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, the reaction solution was separated, treated with _MgSO4 (anhydrous) and filtered. The filtered solution was recrystallized to obtain 51g. (Yield 85%, Mass [M+]=814)

Synthesis of I-67

I-66 40g, (2-hydroxy-9,9-dimethyl-9H-fluoren-3-yl)boronic acid 12.5g, _{K2CO3 20.4g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.5g, tetrahydrofuran 600mL, and water 300mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 26g. (Yield 73%, Mass [M+]=723)

Composite of I-68

Under a nitrogen atmosphere, 20 g of I-67, 18.4 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.5 g. (Yield 37%, Mass [M+] = 731)

F-37 composite

Under a nitrogen atmosphere, 7 g of I-68, 2.5 g of bis(4-(tert-butyl)phenyl)amine, 0.05 g of [bis(tri-tert-butylphosphine)palladium(0)], 2 g of sodium-tert-butoxide, and 100 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 6.8 g. (Yield 73%, Mass [M+] = 976)

Preparation example of compound 38 (F-38)

Composite of I-69

Under a nitrogen atmosphere, 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 45.5 g of 7,7,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 17.7 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO ₄ (anhydrous), and filtered. The filtered solution was recrystallized to obtain 51 g. (Yield 75%, Mass [M+] = 740)

Composite of I-70

I-69 25g, (3-hydroxy-9,9-dimethyl-9H-fluoren-2-yl)boronic acid 8.6g, _{K2CO3 14g} , [bis(tri-tert-butylphosphine)palladium(0)] 0.05g, tetrahydrofuran 500mL, and water 250mL were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with _MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 22g. (Yield 71%, Mass [M+]=913)

F-38 composite

Under a nitrogen atmosphere, 20 g of I-70, 14.6 g of boron triiodide, and 200 mL of dichlorobenzene were added, heated under reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO ₄ (anhydrous), and filtered. After removing the filtered solution, it was recrystallized to obtain 7.3 g. (Yield 36%, Mass [M+] = 921)

Example 1

A glass substrate coated with a 1,400Å thick ITO (indium tin oxide) film was placed in distilled water containing a detergent and cleaned using ultrasonic waves. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After the ITO was washed for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After the distilled water washing was complete, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, the substrate was transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum deposition device.

As described above, HI-A and HAT-CN below were vacuum-deposited to a thickness of 650 Å and 50 Å, respectively, on the ITO transparent electrode prepared as described above to form a hole injection layer. HT-A below was vacuum-deposited to a thickness of 600 Å on the hole injection layer to form a hole transport layer. HT-B below was vacuum-deposited to a thickness of 50 Å on the hole transport layer to form an electron blocking layer. Subsequently, 2 parts by weight of compound F-1 according to the chemical formula 1 of the present invention as a light-emitting dopant based on 100 parts by weight of the light-emitting layer and compound BH below as a host were vacuum-deposited to a thickness of 200 Å on the electron blocking layer to form a light-emitting layer. Then, 50Å of the following compound ET-A was vacuum-deposited as a first electron transport layer on the light-emitting layer, and subsequently, ET-B and LiQ were vacuum-deposited at a weight ratio of 1:1 to form a second electron transport layer with a thickness of 360Å. LiQ was vacuum-deposited on the second electron transport layer to a thickness of 5Å to form an electron injection layer. Aluminum and silver were deposited at a weight ratio of 10:1 on the electron injection layer to a thickness of 220Å, and aluminum was deposited thereon to a thickness of 1000Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the aluminum of the cathode was maintained at a deposition rate of 2 Å/sec, and the vacuum during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr, thereby producing an organic light-emitting device.

Examples 2 to 38

Organic light-emitting devices of Examples 2 to 38 were manufactured in the same manner as in Example 1, except that the compound of Table 1 below was used instead of Compound F-1 in Example 1. The voltage, efficiency, and lifespan of the organic light-emitting devices manufactured in Examples 2 to 37 and Comparative Examples 1 to 3 were measured, and the results are shown in Table 1 below.

Comparative examples 1 to 6

Organic light-emitting devices of Comparative Examples 1 to 6 were manufactured in the same manner as in Example 1, except that the compound of Table 1 below was used instead of compound F-1 in Example 1.

The voltage, efficiency, and lifespan of the organic light-emitting devices manufactured in Examples 1 to 38 and Comparative Examples 1 to 6 were measured, and the results are shown in Table 1 below.

Organic light emitting diode Voltage (V) Efficiency (CB) Life T95(hr) Example 1 (Compound 1) 3.52 180 220 Example 2 (Compound 2) 3.53 181 222 Example 3 (Compound 3) 3.51 181 221 Example 4 (Compound 4) 3.40 191 230 Example 5 (Compound 5) 3.52 182 220 Example 6 (Compound 6) 3.45 191 231 Example 7 (Compound 7) 3.46 190 233 Example 8 (Compound 8) 3.41 193 231 Example 9 (Compound 9) 3.47 192 234 Example 10 (Compound 10) 3.45 190 235 Example 11 (Compound 11) 3.54 180 220 Example 12 (Compound 12) 3.51 184 223 Example 13 (Compound 13) 3.55 183 221 Example 14 (Compound 14) 3.45 192 231 Example 15 (Compound 15) 3.52 181 224 Example 16 (Compound 16) 3.43 194 233 Example 17 (Compound 17) 3.44 192 231 Example 18 (Compound 18) 3.55 182 221 Example 19 (Compound 19) 3.45 193 234 Example 20 (Compound 20) 3.44 191 230 Example 21 (Compound 21) 3.45 194 235 Example 22 (Compound 22) 3.52 185 223 Example 23 (Compound 23) 3.43 191 235 Example 24 (Compound 24) 3,45 194 231 Example 25 (Compound 25) 3.51 182 225 Example 26 (Compound 26) 3.45 194 232 Example 27 (Compound 27) 3.46 194 233 Example 28 (Compound 28) 3.41 196 237 Example 29 (Compound 29) 3.47 193 234 Example 30 (Compound 30) 3.46 194 232 Example 31 (Compound 31) 3.42 198 238 Example 32 (Compound 32) 3.43 196 237 Example 33 (Compound 33) 3.41 195 238 Example 34 (Compound 34) 3.46 193 234 Example 35 (Compound 35) 3.41 198 238 Example 36 (Compound 36) 3.41 197 236 Example 37 (Compound 37) 3.42 196 235 Example 38 (Compound 38) 3.45 191 234 Comparative Example 1 (BD1) 4.22 143 145 Comparative Example 2 (BD2) 4.53 141 123 Comparative Example 3 (BD3) 4.12 138 133 Comparative Example 4 (BD4) 4.31 139 136 Comparative Example 5 (BD5) 4.41 141 152 Comparative Example 6 (BD6) 4.05 152 150

According to Table 1 above, it can be confirmed that the organic light-emitting devices of Comparative Examples 1 and 2 using Comparative Example compounds BD1 and BD2, in which at least one of Ar1 to Ar3 of the chemical formula 1 of the present invention is a heterocycle containing nitrogen (N) as a heteroatom, have significantly higher voltages than those of Examples 1 to 38 of the present invention.

When X in the chemical formula 1 of the present invention is NR, it can be confirmed that the organic light-emitting devices of Comparative Examples 3 and 6 using Comparative Examples BD3 and BD6, which do not include a ring in which at least one substituted or unsubstituted aliphatic hydrocarbon ring is fused, have higher voltage, lower efficiency, and worse lifespan characteristics compared to Examples 1 to 38 of the present invention.

It can be confirmed that the organic light-emitting device of Comparative Example 4 using Comparative Example Compound BD4, in which at least one of Ar1, Ar2 and Ar3 of the chemical formula 1 of the present invention does not include a heterocycle; or a substituted or unsubstituted aliphatic hydrocarbon ring, has significantly lower efficiency and device characteristics than Examples 1 to 38 of the present invention.

It can be confirmed that the organic light-emitting device of Comparative Example 5, which uses Comparative Example Compound BD5, which has a different core structure from Chemical Formula 1 of the present invention, and in which Y of Chemical Formula 1 is N, has a significantly higher voltage and lower efficiency and device characteristics than Examples 1 to 38 of the present invention.

In conclusion, it was confirmed that the organic light-emitting devices of Examples 1 to 38 using the compound according to Chemical Formula 1 of the present specification were significantly superior in voltage, efficiency, and lifespan characteristics compared to the organic light-emitting devices of Comparative Examples 1 to 6.

1: Substrate
2: Bipolar
3: Hole injection layer
4: Hole transport layer
5: Electromagnetic barrier layer
6: Emissive layer
7: 1st electron transport layer
8: Second electron transport layer
9: Electron injection layer
10: Negative

Claims (15)

A compound represented by the following chemical formula 1:
[Chemical Formula 1]

In chemical formula 1,
X is NR, O or S,
Y is O or S,
Ar1, Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic heterocycle, provided that at least one of Ar1, Ar2 and Ar3 comprises a heterocycle; or a substituted or unsubstituted aliphatic hydrocarbon ring, and further, when X is NR, at least one of R, Ar1, Ar2 and Ar3 comprises a ring in which substituted or unsubstituted aliphatic hydrocarbon rings are condensed,
When X is NR, at least one of Ar1 and Ar3 can combine with R to form a ring, and Ar2 and Ar3 can combine with each other to form a ring,
R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. A compound according to claim 1, wherein Ar1, Ar2, and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle; a condensed ring of a substituted or unsubstituted heterocycle and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle, an aromatic hydrocarbon ring, and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2, and Ar3 is a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle; a condensed ring of a substituted or unsubstituted heterocycle and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle, an aromatic hydrocarbon ring, and an aliphatic hydrocarbon ring. In claim 1, Ar1, Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle containing O or S as a heteroatom; a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle containing O or S as a heteroatom; A compound which is a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom and an aromatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted heterocycle containing O or S as a heteroatom, an aromatic hydrocarbon ring, and an aliphatic hydrocarbon ring. In claim 1, Ar1, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted benzene, a substituted or unsubstituted tetrahydronaphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted furan, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted tetrahydronaphthofuran, a substituted or unsubstituted tetrahydrobenzonaphthofuran, a substituted or unsubstituted thiophene, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted tetrahydronaphthothiophene, or a substituted or unsubstituted tetrahydronaphthothiophene, and at least one of Ar1, Ar2 and Ar3 is a substituted or unsubstituted tetrahydronaphthalene, a substituted or unsubstituted furan, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted A compound which is unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydrobenzonaphthofuran, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, or substituted or unsubstituted dibenzothiophene, substituted or unsubstituted tetrahydronaphthothiophene, or substituted or unsubstituted tetrahydrobenzonaphthothiophene. A compound according to claim 1, wherein at least one of Ar1, Ar2 and Ar3 comprises a substituted or unsubstituted tetrahydronaphthalene, or wherein X is NR and R comprises a substituted or unsubstituted tetrahydronaphthalene. A compound according to claim 1, wherein at least one of Ar1 and Ar2 is a substituted or unsubstituted tetrahydronaphthalene, or X is NR and R is a substituted or unsubstituted tetrahydronaphthalene, or at least one of Ar1 and Ar2 is a condensed heterocycle of a substituted or unsubstituted tetrahydronaphthalene. In claim 1, the chemical formula 1 is a compound represented by any one of the following chemical formulas 11 to 13:
[Chemical Formula 11]

[Chemical Formula 12]

[Chemical Formula 13]

In chemical formulas 11 to 13,
X and Y are as defined in chemical formula 1,
Z1 is CRxRy, O or S,
Ra to Rc, Rx, Ry, R and R' are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or are connected to adjacent groups to form a substituted or unsubstituted ring, a and c are each an integer from 0 to 4, b is an integer from 0 to 3, a' and c' are each an integer from 0 to 2, and b' is 0 or 1. In claim 1, the chemical formula 1 is a compound represented by any one of the following chemical formulas 21 to 23:
[Chemical Formula 21]

[Chemical Formula 22]

[Chemical Formula 23]

In chemical formulas 21 to 23,
X, Y, Z1, Ra to Rc, a, b, c, a', b' and c' are as described above,
Rd are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or are connected to adjacent groups to form a substituted or unsubstituted ring, and d is an integer from 0 to 4. In claim 1, the chemical formula 1 is a compound represented by any one of the following chemical formulas 31 to 34:
[Chemical Formula 31]

[Chemical formula 32]

[Chemical formula 33]

[Chemical Formula 34]

In chemical formulas 31 to 34,
X, Y, Z1, Ra to Rd, a, b, c, d, a', b' and c' are as described above,
Z2 and Z3 are the same or different and are independently CRxRy, O or S, and the definitions of Rx and Ry are as described above. In claim 1, the chemical formula 1 is a compound represented by any one of the following chemical formulas 41 to 43:
[Chemical Formula 41]

[Chemical formula 42]

[Chemical Formula 43]

In chemical formulas 41 to 43,
X and Y are as defined in chemical formula 1,
Z1 and Z2 are each independently CRxRy, O or S,
Ra to Rc, Rx, Ry, R, R', R'' and R''' are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or are connected to adjacent groups to form a substituted or unsubstituted ring, and a and c are each an integer from 0 to 4, and b is an integer from 0 to 3. In claim 10, a compound wherein R and R' of the chemical formula 43 combine with each other to form a substituted or unsubstituted benzene, or a substituted or unsubstituted tetrahydronaphthalene. In claim 1, the compound represented by the chemical formula 1 is a compound represented by any one of the following compounds:

. An organic light-emitting device comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 12. An organic light-emitting device according to claim 13, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound. An organic light-emitting device according to claim 14, wherein the compound is included as a dopant.