KR102895427B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

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

Description

Compound and organic light-emitting device comprising the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can 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 continuing need for the development of new materials for organic light-emitting devices such as the above.

Korean Patent Publication No. 10-2013-0049276

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 the above chemical formula 1,

X1 and X2 are the same or different, and are each independently O; or S,

L1 and L2 are the same or different, and each independently represents a monocyclic arylene group; or an arylene group of three or more rings,

m and n are integers from 0 to 3, respectively,

If m and n are each 2 or more, then 2 or more L1 and L2 are each equal to or different from each other,

m+n is greater than or equal to 1.

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 of the organic layers includes a compound represented by the chemical formula 1.

The compounds described herein can be used as materials for an organic layer of an organic light-emitting device. The compounds according to at least one embodiment of the present disclosure can improve efficiency, lower operating voltage, and/or improve lifespan characteristics in organic light-emitting devices. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection materials. In addition, compared to existing organic light-emitting devices, they have the effects of lower operating voltage, higher efficiency, and/or longer lifespan.

Figure 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (5), and a cathode (9) are sequentially stacked.
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), a light-emitting layer (5), an electron transport layer (6), an electron injection layer (7), and a cathode (9) are sequentially laminated.
Figure 3 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a first hole transport layer (4-1), a second hole transport layer (4-2), a light-emitting layer (5), an electron transport and injection layer (8), and a cathode (9) 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 it excludes other components, but rather that it may include other components, 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 the member is in contact with the other member, but also cases where another member exists between the two members.

In this specification, " " or dotted lines indicate positions where the chemical formula or compound is bonded.

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 substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., 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 cyano 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 having no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may 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; halogen; cyano; nitro; hydroxy; amine; silyl; boron; alkoxy; aryloxy; alkyl; cycloalkyl; aryl; and heterocyclic groups, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

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

The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; alkyl groups; and aryl groups, 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, a silyl group may be represented by the chemical formula -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group may be represented by the chemical formula -BY _d Y _e , wherein Y _d and Y _e may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

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 this specification, the description of the alkyl group described above may be applied to the arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

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, etc., 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 number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. 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, and styrenyl groups.

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In 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 is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the aryl group has 6 to 30 carbon atoms. In one embodiment, the aryl group has 6 to 20 carbon atoms.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group (an aryl group having two or more rings). The monocyclic aryl group may refer to a phenyl group; or a group in which two or more phenyl groups are connected. The monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. The polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group, a phenanthrenyl group, etc. The polycyclic aryl group may include, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc.

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 etc. (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 groups may be applied to the description of the aryl group described above.

In this specification, the description regarding the alkyl group described above may be applied to the alkyl group among the alkylthioxy group and 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 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 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. 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.

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 above heterocyclic group may be applied to the divalent heterocyclic group except that the divalent heterocyclic 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, in a substituted or unsubstituted ring formed by bonding with adjacent groups, “ring” means a hydrocarbon ring; or a heterocycle.

The above hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the above cycloalkyl group or aryl group.

In the present specification, forming a ring by bonding with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle 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 the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

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, Examples include, but are not limited to, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

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

The compound represented by Chemical Formula 1 according to the present invention has the advantage of increasing the polarity (dipole moment) of the molecule by including a benzoxazole and/or benzthiazole ring, which is an electron-depleting structure, and easily controlling the balance of electron mobility by connecting the structure via a naphthalene linker. Therefore, when manufacturing an organic light-emitting device including the compound, electron mobility can be smoothly controlled, thereby improving the efficiency and lifespan of the organic light-emitting device and lowering the driving voltage.

Therefore, when the compound represented by the above-described chemical formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and/or long life characteristics can be obtained.

Hereinafter, chemical formula 1 is described in detail.

[Chemical Formula 1]

In the above chemical formula 1,

X1 and X2 are the same or different, and are each independently O; or S,

L1 and L2 are the same or different, and each independently represents a monocyclic arylene group; or an arylene group of three or more rings,

m and n are integers from 0 to 3, respectively,

If m and n are each 2 or more, then 2 or more L1 and L2 are each equal to or different from each other,

m+n is greater than or equal to 1.

In one embodiment of the present invention, X1 and X2 are O.

In one embodiment of the present invention, X1 and X2 are S.

In one embodiment of the present invention, X1 is O and X2 is S.

In one embodiment of the present invention, X1 is S and X2 is O.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently represents an arylene group consisting of a monocyclic ring having 6 to 60 carbon atoms; or an arylene group consisting of three or more rings having 12 to 60 carbon atoms.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently represents an arylene group consisting of a monocyclic ring having 6 to 30 carbon atoms; or an arylene group consisting of three or more rings having 12 to 30 carbon atoms.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently represents an arylene group consisting of a monocyclic ring having 6 to 30 carbon atoms; or an arylene group consisting of three or more rings having 13 to 30 carbon atoms.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently is an arylene group composed of a monocyclic ring having 6 to 30 carbon atoms.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a phenylene group; a biphenylene group; a terphenylene group; or a quarterphenylene group.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a phenylene group; or a biphenylene group.

In one embodiment of the present invention, L1 and L2 are the same or different from each other, and each independently is a phenylene group.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a biphenylene group.

In one embodiment of the present invention, L1 is a phenylene group and L2 is a biphenylene group.

In one embodiment of the present invention, L2 is a phenylene group and L1 is a biphenylene group.

In one embodiment of the present invention, L1 and L2 are the same or different from each other, and are each independently represented by one of the following structural formulas.

In the above structural formula, the dotted line indicates the bonding position.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently represented by one of the following structures.

In the above structures, the dotted line indicates the bonding position.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently represented by one of the following structures.

In the above structures, the dotted line indicates the bonding position.

In one embodiment of the present invention, when m is 0, -(L1)m- represents a direct bond.

In one embodiment of the present invention, when n is 0, -(L2)n- represents a direct bond.

In one embodiment of the present invention, -(L1)m- and -(L2)n- are the same as or different from each other, and each independently represents a direct bond; or an arylene group composed of a monocyclic ring having 6 to 30 carbon atoms, and at least one of -(L1)m- and -(L2)n- is an arylene group composed of a monocyclic ring having 6 to 30 carbon atoms.

In one embodiment of the present invention, -(L1)m- is a direct bond; a phenylene group; or a biphenylene group.

In one embodiment of the present invention, -(L2)n- is a direct bond; a phenylene group; or a biphenylene group.

In one embodiment of the present invention, -(L1)m- is a direct bond, and -(L2)n- is a phenylene group; or a biphenylene group.

In one embodiment of the present invention, -(L2)n- is a direct bond, and -(L1)m- is a phenylene group; or a biphenylene group.

In one embodiment of the present invention, m and n are each integers from 0 to 3.

In one embodiment of the present invention, m and n are each integers from 0 to 2.

In one embodiment of the present invention, m is an integer from 0 to 2.

In one embodiment of the present invention, n is an integer from 0 to 2.

In one embodiment of the present invention, m+n is 1 or more.

In one embodiment of the present invention, m+n is 1 to 4.

In one embodiment of the present invention, m is 0 and n is an integer from 1 to 3.

In one embodiment of the present invention, n is 0 and m is an integer from 1 to 3.

In one embodiment of the present invention, m and n are integers of 1 to 3.

In one embodiment of the present invention, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-10.

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

[Chemical Formula 1-3] [Chemical Formula 1-4]

[Chemical Formula 1-5] [Chemical Formula 1-6]

[Chemical Formula 1-7] [Chemical Formula 1-8]

[Chemical Formula 1-9] [Chemical Formula 1-10]

In the above chemical formulas 1-1 to 1-10, the definitions of X1, X2, L1, L2, m and n are the same as those in the above chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3.

[Chemical Formula 2-1]

[Chemical Formula 2-2]

[Chemical Formula 2-3]

In the above chemical formulas 2-1 to 2-3, the definitions of L1, L2, m and n are the same as those in the above chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 3-1 or 3-2.

[Chemical Formula 3-1]

[Chemical Formula 3-2]

In the above chemical formulas 3-1 and 3-2, the definitions of X1, X2, L1 and L2 are the same as those in the above chemical formula 1,

a1 and a2 are each integers from 1 to 3, and when a1 and a2 are each 2 or greater, L1 and L2 are each equal to or different from each other.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 4.

[Chemical Formula 4]

In the above chemical formula 4, the definitions of X1, X2, L1 and L2 are the same as those in the above chemical formula 1,

a1' is an integer from 0 to 3, and when a1' is 2 or greater, L1 are equal to or different from each other,

a2' is an integer from 0 to 2, and when a2' is 2, L2 are equal to or different from each other.

In one embodiment of the present specification, the chemical formula 4 is represented by any one of the following chemical formulas 4-1 to 4-3.

[Chemical Formula 4-1]

[Chemical Formula 4-2]

[Chemical Formula 4-3]

In the above chemical formulas 4-1 to 4-3, the definitions of X1, X2, L1, L2, a1' and a2' are the same as those in the above chemical formula 4.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.

The compound represented by Chemical Formula 1 according to one embodiment of the present specification can have a core structure manufactured by a method similar to the following General Formula 1. The substituents can be bonded by a method known in the art, and the type, position, or number of the substituents can be changed according to a technique known in the art.

[General Formula 1]

In the above general formula 1, Z1 and Z2 are the same as or different from each other, and are each independently halogen or -SO ₃ C ₄ F ₉ , preferably chloro, bromo, or -SO ₃ C ₄ F ₉ .

At this time, compounds corresponding to the range of the chemical formula 1 can be synthesized by a synthetic method known in the art using starting materials, intermediate materials, etc. known in the art.

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

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

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

When a part in this specification is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

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, wherein at least one of the organic layers comprises a compound represented by the above-described chemical formula 1.

The organic light-emitting device of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the compound of the above-described chemical formula 1.

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

The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multi-layer 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 blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as the organic layer. 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 one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, electron transport layer, electron transport and injection layer, or hole blocking layer may include a compound represented by the above-described chemical formula 1.

In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, and an electron transport and injection layer, and the electron injection layer, the electron transport layer, and the electron transport and injection layer may include a compound represented by the above-described chemical formula 1.

In one embodiment of the present specification, the organic layer includes an electron control layer, and the electron control layer may include a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by the chemical formula 1.

In the organic light-emitting device of the present specification, the organic layer is an electron transport and injection layer, and the electron transport and injection layer includes a compound represented by the above-described chemical formula 1.

In one embodiment of the present specification, the thickness of the organic layer including the compound of the chemical formula 1 is 50 Å to 600 Å, preferably 100 Å to 500 Å, and more preferably 200 Å to 400 Å.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the above-described chemical formula 1 as a host.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the above-described chemical formula 1 as a dopant.

In another embodiment, the organic layer may further include another organic compound, metal, or metal compound in addition to the compound represented by the above-described chemical formula 1.

In an organic light-emitting device according to one embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer is included in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host.

As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a host, and may further include an additional host.

In one embodiment of the present specification, the dopant includes an arylamine compound, a heterocyclic compound containing boron and nitrogen, or an Ir complex.

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 blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

In one embodiment of the present specification, the organic light-emitting device includes an anode; a cathode; and two or more organic layers provided between the anode and the cathode, and at least one of the two or more organic layers includes a compound represented by the chemical formula 1.

In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.

In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except for the compound represented by the chemical formula 1 may be the same or different from each other.

When the organic layer containing the compound represented by the above chemical formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer may further contain an n-type dopant or an organometallic compound. The n-type dopant or organometallic compound may be one known in the art, and may be, for example, a metal or a metal complex.

For example, the n-type dopant or organometallic compound may be, but is not limited to, LiQ. The electron transport layer, electron injection layer, or electron transport and injection layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate).

In one example, the compound represented by the above chemical formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. In one example, the compound represented by the above chemical formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.

In one embodiment of the present specification, the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one layer of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound represented by the chemical formula 1 is included in each of the two or more hole transport layers, other materials except the compound represented by the chemical formula 1 may be the same or different from each other.

In one embodiment of the present specification, the organic layer may further include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound represented by the chemical formula 1.

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 layers, and a cathode are sequentially stacked on a substrate.

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

In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, and a material known in the art may be used for the electron blocking layer.

The above organic light-emitting device may have a laminated structure, for example, as follows, but is not limited thereto.

(1) Anode/hole transport layer/light emitting layer/cathode

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

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light-emitting layer/cathode

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(18) Anode/hole injection layer/first hole transport layer/second hole transport layer/emission layer/electron transport and injection layer/cathode

(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/emission layer/hole blocking layer/electron transport and injection layer/cathode

(20) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport and injection layer/cathode

The structure of the organic light-emitting device of this specification may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.

Figure 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (5), and a cathode (9) are sequentially laminated. In such a structure, the compound may be included in the light-emitting layer (5).

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), a light-emitting layer (5), an electron transport layer (6), an electron injection layer (7), and a cathode (9) are sequentially laminated. In this structure, the compound may be included in the hole injection layer (3), the hole transport layer (4), the light-emitting layer (5), the electron transport layer (6), or the electron injection layer (7).

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

In one embodiment of the present specification, the electron transport and injection layer and the light-emitting layer may be provided adjacently.

In one embodiment of the present specification, the electron transport layer and the light-emitting layer may be provided adjacently.

In one embodiment of the present specification, the electron transport and injection layer and the light-emitting layer may be provided adjacently.

In one embodiment of the present specification, the hole blocking layer and the light emitting layer may be provided adjacently.

In one embodiment of the present specification, the hole blocking layer and the electron transport layer may be provided adjacently.

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 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 blocking 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 above organic layer may further include at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers by using various polymer materials and a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

The anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred 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; and 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 the cathode material is preferably a material with a low work function to facilitate electron injection 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, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine series organic materials, hexanitrilehexaazatriphenylene series organic materials, quinacridone series organic materials, perylene series organic materials, anthraquinone, and polyaniline and polythiophene series conductive polymers. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

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

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

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be formed using the above-described compound or a material known in the art.

The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. 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.

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

When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-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 polymer, or PPV polymer can be used as the light-emitting dopant, but is not limited thereto.

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

The above electron 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, 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; and a hydroxyflavone-metal complex. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from being increased to improve electron movement due to the electron transport layer being too thick.

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 electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an 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.

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

The above hole blocking 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, back-emitting, or double-sided emitting type depending on the material used.

The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

Hereinafter, examples will be provided to specifically explain the present specification. However, the embodiments described herein may be modified in various ways, and the scope of the present application is not limited to the embodiments described below. The embodiments of the present application are provided to more fully explain the present specification to those of ordinary skill in the art.

<Manufacturing Example 1-1: Synthesis of Compound 1>

Bromo-2-chloronaphthalene (7.25 g, 30 mmol) and the compound 1-1 (13.11 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL) and tetrakis(triphenylphosphine)palladium(0) (0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice with toluene to prepare the compound 1-2.

Compound 1-2 (12.96 g, 30 mmol) and compound 1-3 (13.11 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 1. (4.2 g, yield 21%, MS: [M+H] ⁺ = 667).

<Manufacturing Example 1-2: Synthesis of Compound 2>

Compound 2 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 667

<Manufacturing Example 1-3: Synthesis of Compound 3>

Compound 3 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 667

<Manufacturing Example 1-4: Synthesis of Compound 4>

Compound 4 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 607

<Manufacturing Example 1-5: Synthesis of Compound 5>

Compound 5 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 607

<Manufacturing Example 1-6: Synthesis of Compound 6>

Compound 6 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-7: Synthesis of Compound 7>

Compound 7 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 623

<Manufacturing Example 1-8: Synthesis of Compound 8>

Compound 8 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 667

<Manufacturing Example 1-9: Synthesis of Compound 9>

Compound 9 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 607

<Manufacturing Example 1-10: Synthesis of Compound 10>

Compound 10 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-11: Synthesis of Compound 11>

Compound 11 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-12: Synthesis of Compound 12>

Compound 12 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 623

<Manufacturing Example 1-13: Synthesis of Compound 13>

Compound 13 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-14: Synthesis of Compound 14>

Compound 14 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 515

<Manufacturing Example 1-15: Synthesis of Compound 15>

Compound 15 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-16: Synthesis of Compound 16>

Compound 16 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 623

<Manufacturing Example 1-17: Synthesis of Compound 17>

Compound 17 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-18: Synthesis of Compound 18>

Compound 18 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-19: Synthesis of Compound 19>

Compound 19 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-20: Synthesis of Compound 20>

Compound 20 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 607

<Manufacturing Example 1-21: Synthesis of Compound 21>

Compound 21 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 591

<Manufacturing Example 1-22: Synthesis of Compound 22>

The above compounds 2-bromo-6-chloronaphthalene (47.65 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) were added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl ₂ ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, stirred and refluxed for 12 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice with ethyl acetate to prepare the compound 22-1.

The compound 22-1 (8.66 g, 30 mmol) and the compound 2-chlorobenzo[d]thiazole (5.60 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M _K2CO3 (200 _mL ) and tetrakis(triphenylphosphine)palladium(0) (0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 22-2.

The above compounds 22-2 (8.87 g, 30 mmol) and 22-3 (13.11 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered, and recrystallized twice with toluene to prepare the above compound 22. (2.9 g, yield 18%, MS: [M+H] ⁺ = 531).

<Manufacturing Example 1-23: Synthesis of Compound 23>

Compound 23 was prepared in the same manner as in Manufacturing Example 1-22, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 515

<Manufacturing Example 1-24: Synthesis of Compound 24>

Compound 24 was prepared in the same manner as in Manufacturing Example 1-22, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 515

<Manufacturing Example 1-25: Synthesis of Compound 25>

Compound 25 was prepared in the same manner as in Manufacturing Example 1-22, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 531

<Manufacturing Example 1-26: Synthesis of Compound 26>

Compound 26 was prepared in the same manner as in Manufacturing Example 1-22, except that each starting material was prepared as in the above reaction formula.

MS: [M+H] ⁺ = 547

[Example]

<Example 1-1>

A glass substrate coated with a 1000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compound HAT at 50 Å and the following compound HT-A at 60 Å were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

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

On the above-mentioned light-emitting layer, the previously prepared compound 1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron transport and injection layer with a thickness of 350 Å. On the above-mentioned electron transport and injection layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 1000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 Å/sec to 0.9 Å/sec, the lithium fluoride of the cathode was maintained at 0.3 Å/sec, and the aluminum was maintained at 2 Å/sec. The vacuum during deposition was maintained at 1 X 10 ^-7 torr to 5 X 10 ^-5 torr, thereby manufacturing an organic light-emitting device.

<Examples 1-2 to 1-26>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds 2 to 26 described in Table 1 below were used instead of compound 1 of Example 1-1.

<Comparative Examples 1-1 to 1-12>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-12 in Table 1 below were used instead of compound 1 in Example 1-1. The structures of compounds ET-1 to ET-12 in Table 1 below are as follows.

[Experimental Example]

For the organic light-emitting devices manufactured in Examples 1-1 to 1-26 and Comparative Examples 1-1 to 1-12, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and the time (T90) for reaching 90% of the initial luminance was measured at a current density of 20 mA/cm ² . The results are shown in Table 1 below.

division compound Voltage (V)
(@10 mA/cm ² ) Efficiency (cd/A)
(@10 mA/cm ² ) Color coordinates
(x, y) Lifespan (hr)
(T90 at 20 mA/cm ² ) Example 1-1 1 4.19 4.99 (0.140, 0.092) 217 Example 1-2 2 4.15 5.06 (0.140, 0.093) 205 Example 1-3 3 4.23 4.91 (0.140, 0.093) 237 Example 1-4 4 4.19 5.02 (0.141, 0.092) 211 Example 1-5 5 4.31 4.74 (0.140, 0.092) 202 Example 1-6 6 4.25 4.81 (0.140, 0.093) 205 Example 1-7 7 4.11 5.10 (0.140, 0.093) 202 Example 1-8 8 4.23 4.95 (0.141, 0.092) 227 Example 1-9 9 4.34 4.78 (0.140, 0.092) 200 Example 1-10 10 4.39 4.75 (0.140, 0.093) 205 Example 1-11 11 4.31 4.82 (0.140, 0.093) 200 Example 1-12 12 4.38 4.70 (0.140, 0.092) 207 Example 1-13 13 4.39 4.71 (0.140, 0.093) 204 Example 1-14 14 4.32 4.63 (0.140, 0.093) 218 Example 1-15 15 4.31 4.78 (0.140, 0.092) 195 Example 1-16 16 4.33 4.67 (0.140, 0.093) 211 Example 1-17 17 4.39 4.71 (0.140, 0.093) 204 Example 1-18 18 4.31 4.78 (0.141, 0.092) 198 Example 1-19 19 4.34 4.74 (0.140, 0.092) 200 Example 1-20 20 4.34 4.74 (0.140, 0.093) 208 Example 1-21 21 4.31 4.78 (0.141, 0.092) 198 Example 1-22 22 4.38 4.82 (0.140, 0.092) 191 Example 1-23 23 4.40 4.85 (0.140, 0.093) 196 Example 1-24 24 4.27 4.84 (0.140, 0.093) 185 Example 1-25 25 4.37 4.60 (0.140, 0.092) 193 Example 1-26 26 4.34 4.83 (0.140, 0.093) 191 Comparative Example 1-1 ET-1 4.28 2.71 (0.140, 0.093) 160 Comparative Example 1-2 ET-2 4.25 4.22 (0.141, 0.092) 30 Comparative Example 1-3 ET-3 4:30 4.06 (0.140, 0.092) 36 Comparative Example 1-4 ET-4 4.31 4.18 (0.140, 0.093) 31 Comparative Example 1-5 ET-5 4:30 4.12 (0.140, 0.093) 42 Comparative Example 1-6 ET-6 4.59 2.44 (0.141, 0.092) 112 Comparative Example 1-7 ET-7 4.65 2.40 (0.140, 0.093) 110 Comparative Example 1-8 ET-8 4.58 2.53 (0.140, 0.093) 128 Comparative Example 1-9 ET-9 4.54 4.13 (0.140, 0.093) 109 Comparative Example 1-10 ET-10 4.59 4.09 (0.141, 0.092) 111 Comparative Example 1-11 ET-11 4.50 4.17 (0.140, 0.093) 108 Comparative Example 1-12 ET-12 4.58 4.03 (0.141, 0.092) 113

As described in Table 1 above, it was confirmed that the organic light-emitting device using the compound of chemical formula 1 according to the present invention exhibited excellent characteristics in terms of driving voltage, efficiency, and/or lifespan.

Specifically, the compound of the present invention is characterized by having one naphthalene linker between two benzoxazoles or benzthiazoles, and an additional monocyclic or tricyclic or more linker. In the case of a device using the compound of the present invention, it can be confirmed that the voltage, efficiency, and life characteristics are improved compared to when a comparative compound containing two or more naphthalene linkers or a linker not containing naphthalene is used.

Additionally, it can be confirmed that the voltage, efficiency and life characteristics are improved compared to when a comparative compound is used that does not include an additional linker other than naphthalene, does not include benzoxazole or benzthiazole, or does not have an arylene group as the linker.

1: Substrate
2: Anode
3: Hole injection layer
4: Hole transport layer
4-1: First hole transport layer
4-2: Second hole transport layer
5: Emissive layer
6: Electron transport layer
7: Electron injection layer
8: Electron transport and injection layer
9: Cathode

Claims (13)

A compound represented by any one of the following chemical formulas 1-1 to 1-9:
[Chemical Formula 1-1] [Chemical Formula 1-2]

[Chemical Formula 1-3] [Chemical Formula 1-4]

[Chemical Formula 1-5] [Chemical Formula 1-6]

[Chemical Formula 1-7] [Chemical Formula 1-8]

[Chemical Formula 1-9]

In the above chemical formulas 1-1 to 1-9,
X1 and X2 are the same or different, and are each independently O; or S,
L1 and L2 are the same or different, and each independently represents a monocyclic arylene group; or an arylene group of three or more rings,
m and n are integers from 0 to 3, respectively,
If m and n are each 2 or more, then 2 or more L1 and L2 are each equal to or different from each other,
m+n is greater than or equal to 1. delete delete delete A compound according to claim 1, wherein L1 and L2 are the same or different from each other and each independently represent an arylene group consisting of a monocyclic ring having 6 to 30 carbon atoms. In claim 1, the compound wherein L1 and L2 are the same or different from each other and are each independently represented by one of the following structures:



In the above structures, the dotted line indicates the bonding position. In claim 1, any one of the chemical formulas 1-1 to 1-9 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 and 5 to 7. An organic light-emitting device according to claim 8, wherein the organic layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, electron injection layer, or electron transport and injection layer includes the compound. An organic light-emitting device according to claim 9, wherein the electron transport layer, electron injection layer, or electron transport and injection layer further includes an n-type dopant. An organic light-emitting device according to claim 10, wherein the compound and the n-type dopant are included in a weight ratio of 2:8 to 8:2. An organic light-emitting device according to claim 8, wherein the organic layer includes a hole-blocking layer, and the hole-blocking layer includes the compound. An organic light-emitting device according to claim 8, wherein the organic layer further includes at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.