KR20220134124A - Organic light emitting device - Google Patents

Abstract

The present specification relates to an organic light emitting device including a compound represented by chemical formula 1. According to the present invention, an organic light emitting device includes: an anode; a cathode; and one or more organic material layers provided between the anode and the cathode. The organic light emitting device may have a low driving voltage, high efficiency, and/or long lifespan.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

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

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

Korean Patent Publication 10-2013-0049276

The present specification provides an organic light emitting device.

One embodiment of the present specification is an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers includes a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

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

R1 to R4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted naphthalene ring,

Ar, L1 and L2 are the same as or different from each other, and each independently represents an arylene group of monocyclic to tricyclic or five or more rings,

m and n are each an integer from 0 to 3,

When m and n are 2 or more, respectively, L1 and L2 of 2 or more are the same as or different from each other,

m+n is greater than or equal to 1.

The organic light emitting device described herein includes the compound represented by Formula 1 in the organic material layer, thereby exhibiting the effects of low driving voltage, high efficiency and/or long life.

1 shows 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.
2 shows 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 in sequence An example of an organic light-emitting device stacked with
3 shows 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. An example of an organic light emitting device in which (8) and a cathode (9) are sequentially stacked is shown.

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

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

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

" 또는 점선은 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "

" or the dotted line means the position bonded to the formula or compound.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; an alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; Or it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; cyano group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.

As used herein, the term "substituted or unsubstituted" refers to deuterium; cyano group; an alkyl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of an aryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

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

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

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is 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, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

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

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, 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.

The substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized 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 an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include 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, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkynyl group is a substituent including a triple bond between a carbon atom and a carbon atom, and may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkynyl group is 2 to 20. According to another exemplary embodiment, the carbon number 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, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

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

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 an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.

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). A monocyclic aryl group is a phenyl group; Or it may mean a group in which two or more phenyl groups are connected. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, but is not limited thereto. The polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group or a phenanthrenyl group. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is not limited thereto.

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.

,

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

spirofluorenyl groups such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the aryloxy group.

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group in the alkyl thiooxy group and the alkyl sulfoxy group.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the arylthioxy group and the arylsulfoxy group.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include 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, and a carba group. There are a sol group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.

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

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

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

In the present 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 an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.

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

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof. The hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. The heterocycle means a ring including at least one selected from elements such as 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 the present specification, the aliphatic hydrocarbon ring refers to a ring made of only carbon and hydrogen atoms as a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, However, the present invention is not limited thereto.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, paraazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazaindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but is not limited thereto.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment 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.

The compound represented by Formula 1 according to the present invention includes an oxazole and/or thiazole ring substituted with an aryl group or a naphthalene ring condensed, thereby increasing the thermal stability of the oxazole and thiazole ring, and improving electron injection and transfer Therefore, when the compound represented by Formula 1 is applied to an organic light emitting device, it is possible to obtain an organic light emitting device having high efficiency, low voltage and/or long life.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

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

R1 to R4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted naphthalene ring,

Ar, L1 and L2 are the same as or different from each other, and each independently represents an arylene group of monocyclic to tricyclic or five or more rings,

m and n are each an integer from 0 to 3,

When m and n are 2 or more, respectively, L1 and L2 of 2 or more are the same as 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 an exemplary embodiment of the present invention, X1 is O, and X2 is S.

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

In one embodiment of the present invention, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted naphthalene ring by combining with an adjacent group. do.

In an exemplary embodiment of the present invention, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted naphthalene ring by combining with an adjacent group. do.

In an exemplary embodiment of the present invention, R1 to R4 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a naphthalene ring.

In an exemplary embodiment of the present invention, R1 to R4 are a phenyl group, or a naphthalene ring by combining adjacent groups with each other.

In one embodiment of the present invention, R1 and R2 are bonded to each other to form a naphthalene ring.

In one embodiment of the present invention, R3 and R4 are combined with each other to form a naphthalene ring.

또는

는 서로 같거나 상이하고, 각각 독립적으로 하기 구조식 중 어느 하나로 표시된다.In an exemplary embodiment of the present invention, when R1 to R4 combine with an adjacent group to form a naphthalene ring,

or

are the same as or different from each other, and are each independently represented by any one of the following structural formulas.

는 L1 또는 L2에 결합하는 위치를 의미한다.In the structural formula,

denotes a position binding to L1 or L2.

In an exemplary embodiment of the present invention, Ar, L1, and L2 are the same as or different from each other, and each independently represents an arylene group of monocyclic, tricyclic, or five or more rings.

In an exemplary embodiment of the present invention, Ar, L1 and L2 are the same as or different from each other, and each independently represents an arylene group having 6 to 60 carbon atoms, a monocyclic to 3 ring, or 5 or more rings.

In an exemplary embodiment of the present invention, Ar, L1 and L2 are the same as or different from each other, and each independently represents an arylene group having 6 to 30 carbon atoms, a monocyclic to 3 ring, or 5 or more rings.

In an exemplary embodiment of the present invention, Ar, L1, and L2 are the same as or different from each other, and each independently represents a monocyclic to tricyclic or 6cyclic arylene group.

In an exemplary embodiment of the present invention, Ar is a monocyclic, tricyclic, or 6-ring arylene group.

In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently represents a monocyclic to tricyclic arylene group.

In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently an arylene group consisting of a monocyclic ring; or a bicyclic arylene group.

In an exemplary embodiment of the present invention, Ar, L1 and L2 are the same as or different from each other, and each independently a phenylene group; biphenylene group; terphenyl group; naphthylene group; phenanthrenylene group; or a spirobifluorenylene group.

In an exemplary embodiment of the present invention, Ar is a phenylene group; biphenylene group; terphenylene group; naphthylene group; phenanthrenylene group; or a spirobifluorenylene group.

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

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

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

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

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

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

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

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

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

In an exemplary 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 a direct bond; or a monocyclic to tricyclic or 6cyclic arylene group having 6 to 30 carbon atoms, and at least one of -(L1)m- and -(L2)n- is a monocyclic to tricyclic or 6cyclic arylene group having 6 to 30 carbon atoms.

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

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

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

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

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

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

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

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

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

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

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, definitions of X1, X2, Ar, L1, L2, m, and n are the same as in Formula 1 above.

In an exemplary embodiment of the present invention, Chemical Formula 1 is represented by any one of Chemical Formulas 2-1 to 2-3 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, definitions of R1 to R4, Ar, L1, L2, m, and n are the same as those of Formula 1 above.

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

[Formula 3-1]

[Formula 3-2]

In Formulas 3-1 and 3-2, the definitions of R1 to R4, X1, X2, L1 and L2 are the same as the definitions in Formula 1 above,

a1 and a2 are each an integer of 1 to 3, and when a1 and a2 are each 2 or more, L1 and L2 are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following compounds.

The compound represented by Formula 1 according to an exemplary embodiment of the present specification may have a core structure prepared by the method as in Formula 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

[General formula 1]

In Formula 1, Y1 and Y2 are the same as or different from each other, and each independently represents halogen or -SO ₃ C ₄ F ₉ , preferably chloro, bromo, or -SO ₃ C ₄ F ₉ .

In this case, compounds corresponding to the range of Formula 1 may be synthesized by a synthesis method known in the art using starting materials, intermediates, 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 Formula 1 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the structure as described above.

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

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

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

An organic light emitting device according to the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 above.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the compound of Formula 1 above.

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

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention comprises at least one 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 an organic material layer. It may have a structure containing However, the structure of the organic light emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic material layers.

In an exemplary embodiment of the present specification, the organic material 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 is a compound represented by Formula 1 may include

In the exemplary embodiment of the present specification, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by Formula 1 above.

In one embodiment of the present specification, the organic material 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, the electron transport layer, the electron transport and injection layer or the hole blocking layer is It may include a compound represented by Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron transport and injection layer, and the electron injection layer, the electron transport layer, or the electron transport and injection layer is represented by the above-described formula (1) It may contain a compound that is

In an exemplary embodiment of the present specification, the organic material layer may include an electron control layer, and the electron control layer may include the compound represented by Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 1 above.

In the organic light emitting device of the present specification, the organic material layer is an electron transport and injection layer, and the electron transport and injection layer includes the compound represented by Chemical Formula 1 described above.

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

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a host.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant.

In another exemplary embodiment, the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 above.

In the organic light emitting device according to the exemplary 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 emission layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

As another example, the organic material layer may include an emission layer, the emission layer may include the compound represented by Formula 1 as a host, and may further include an additional host.

In the exemplary embodiment of the present specification, the dopant includes an arylamine-based compound, a heterocyclic compound including boron and nitrogen, or an Ir complex.

The organic light emitting device of the present specification may further include an organic material layer of at least one 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. can

In an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, two or more organic material 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 an exemplary embodiment of the present specification, two or more organic material 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 the exemplary embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1 above. Specifically, in an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one 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 the exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other.

When the organic material layer including the compound represented by 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 is an n-type dopant or an organometallic compound may further include. As the n-type dopant or organometallic compound, those known in the art may be used, for example, a metal or a metal complex may be used.

For example, the n-type dopant or the organometallic compound may be LiQ, but is not limited thereto. The electron transport layer, the electron injection layer, or the electron transport and injection layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).

According to an example, the compound represented by Formula 1 and the n-type dopant or the organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to an example, the compound represented by Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.

In an exemplary embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Formula 1 above. Specifically, in an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more hole transporting layers, and may be included in each of the two or more hole transporting layers.

In addition, in an exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. have.

In an exemplary embodiment of the present specification, the organic material layer includes 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 material layer including the compound represented by Formula 1 may include

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

In the exemplary 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 stacked on a substrate.

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

The organic light emitting diode may have, for example, a stacked structure 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 / light emitting layer / electron transport and injection layer / cathode

(19) anode / hole injection layer / first hole transport layer / second hole transport layer / light emitting 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 the present specification may have a structure as shown in FIGS. 1 to 3 , but is not limited thereto.

1 shows 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. In such a structure, the compound may be included in the light emitting layer 5 .

2 shows 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 in sequence An example of an organic light-emitting device stacked with In such a 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 .

3 shows 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. An example of an organic light emitting device in which (8) and a cathode (9) are sequentially stacked is shown. In this structure, the compound is 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) can be included in

In one embodiment of the present specification, the electron transport and injection layer and the light emitting layer may be provided adjacent to each other.

In one embodiment of the present specification, the electron transport layer and the light emitting layer may be provided adjacent to each other.

In one embodiment of the present specification, the electron transport and injection layer and the light emitting layer may be provided adjacent to each other.

In one embodiment of the present specification, the hole blocking layer and the light emitting layer may be provided adjacent to each other.

In one embodiment of the present specification, the hole blocking layer and the electron transport layer may be provided adjacent to each other.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1 above.

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

For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and an organic material 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 is formed thereon, and then a material that can be used as a cathode is deposited thereon. can be In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

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

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage. The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

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

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

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

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

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

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light-emitting layer emits blue light, the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

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

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include the above-mentioned compound or Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport characteristics can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

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

The organic light emitting diode according to the present specification may be included in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, and the like, but is not limited thereto.

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those of ordinary skill in the art.

<Preparation Example 1: Synthesis of Compound 1>

Bromo-2-chloronaphthalene (7.25 g, 30 mmol) and the compound 1-1 (14.76 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), tetrakis (triphenylphosphine) palladium (0) (0.3 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized twice with toluene to prepare Compound 1-2.

Compound 1-2 (95.1 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-diox) Saborolane) (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). After adding potassium acetate (58.0 g) and Pd(dppf)Cl ₂ ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g), the mixture was stirred and refluxed for 12 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 1-3.

Compound 1-3 (17.21 g, 30 mmol) and 2-chloronaphtho [2,1-d] oxazole (6.72 g, 33 mmol) were mixed with tetrahydro Furan (300 mL) was added. 2M K ₂ CO ₃ (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, and for 5 hours Stirred and refluxed. After cooling to room temperature, the solid produced by filtration was recrystallized twice with toluene to prepare Compound 1.

(3.9 g, yield 21%, MS:[M+H] ⁺ = 615).

<Preparation Example 2: Synthesis of Compound 2>

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

MS: [M+H] ⁺ = 539

<Preparation Example 3: Synthesis of Compound 3>

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

MS: [M+H] ⁺ = 539

<Preparation Example 4: Synthesis of Compound 4>

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

MS: [M+H] ⁺ = 539

<Preparation Example 5: Synthesis of Compound 5>

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

MS: [M+H] ⁺ = 539

<Preparation Example 6: Synthesis of Compound 6>

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

MS: [M+H] ⁺ = 643

<Preparation Example 7: Synthesis of Compound 7>

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

MS: [M+H] ⁺ = 643

<Preparation Example 8: Synthesis of Compound 8>

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

MS: [M+H] ⁺ = 831

<Preparation Example 9: Synthesis of compound 9>

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

MS: [M+H] ⁺ = 795

<Preparation Example 10: Synthesis of Compound 10>

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

MS: [M+H] ⁺ = 631

<Preparation Example 11: Synthesis of Compound 11>

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

MS: [M+H] ⁺ = 743

<Preparation Example 12: Synthesis of Compound 12>

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

MS: [M+H] ⁺ = 539

<Preparation Example 13: Synthesis of Compound 13>

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

MS: [M+H] ⁺ = 591

<Preparation Example 14: Synthesis of Compound 14>

4'-bromo-5'-chloro-1,1':2',1''-terphenyl (4'-bromo-5'-chloro-1,1':2',1''-terphenyl) (10.31 g, 30 mmol) and the compound 14-1 (13.97 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), tetrakis (triphenylphosphine) palladium (0) (0.3 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with toluene to prepare Compound 14-2.

The compound 14-2 (16.80 g, 30 mmol) and the compound 14-3 (12.25 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, and then for 5 hours Stirred and refluxed. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with toluene to prepare Compound 14.

(6.92 g, yield 30%, MS:[M+H] ⁺ = 769).

<Preparation Example 15: Synthesis of Compound 15>

Compound 15 was prepared in the same manner as in Preparation Example 14, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 717

<Preparation Example 16: Synthesis of Compound 16>

9-bromo-10-chlorophenanthrene (9-bromo-10-chlorophenanthrene) (8.75 g, 30 mmol) and the compound 16-1 (24.5 g, 66 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, and then for 5 hours Stirred and refluxed. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with toluene to prepare compound 16.

(14.76 g, yield 74%, MS:[M+H] ⁺ = 665).

<Preparation Example 17: Synthesis of Compound 17>

Compound 17 was prepared in the same manner as in Preparation Example 16, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 565

<Preparation Example 18: Synthesis of Compound 18>

Compound 18 was prepared in the same manner as in Preparation Example 16, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 717

<Preparation Example 19: Synthesis of Compound 19>

Compound 19 was prepared in the same manner as in Preparation Example 16, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 665

<Preparation Example 20: Synthesis of Compound 20>

Compound 20 was prepared in the same manner as in Preparation Example 16, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 521

<Preparation Example 21: Synthesis of Compound 21>

Compound 21 was prepared in the same manner as in Preparation Example 16, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 597

<Preparation Example 22: Synthesis of Compound 22>

Compound 22 was prepared in the same manner as in Preparation Example 16, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 565

[Example]

<Example 1-1>

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

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

Then, the following compound BH and compound BD were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 Å on the second hole transport layer to form a light emitting layer.

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

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

<Examples 1-2 to Examples 1-22>

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that Compounds 2 to 22 shown in Table 1 were used instead of Compound 1 of Example 1-1.

<Comparative Examples 1-1 to 1-12>

An organic light emitting diode 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 of Example 1-1. The structures of compounds ET-1 to ET-12 of Table 1 are as follows.

[Experimental example]

For the organic light emitting devices prepared in Examples 1-1 to 1-22 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 20 mA/cm At a current density of ² , the time (T90) to be 90% of the initial luminance was measured. 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) Lifetime (hr)
(T90 at 20 mA/cm ² ) Example 1-1 One 4.36 4.84 (0.140, 0.093) 243 Example 1-2 2 4.34 4.90 (0.140, 0.093) 230 Examples 1-3 3 4.39 4.76 (0.140, 0.093) 264 Examples 1-4 4 4.37 4.86 (0.141, 0.094) 236 Examples 1-5 5 4.50 4.60 (0.140, 0.093) 227 Examples 1-6 6 4.44 4.66 (0.140, 0.093) 230 Examples 1-7 7 4.29 4.94 (0.140, 0.092) 227 Examples 1-8 8 4.42 4.80 (0.141, 0.092) 253 Examples 1-9 9 4.53 4.64 (0.140, 0.092) 225 Examples 1-10 10 4.58 4.61 (0.140, 0.092) 230 Examples 1-11 11 4.50 4.67 (0.140, 0.093) 225 Examples 1-12 12 4.57 4.56 (0.140, 0.093) 232 Examples 1-13 13 4.58 4.57 (0.140, 0.092) 229 Examples 1-14 14 4.66 4.49 (0.140, 0.092) 244 Examples 1-15 15 4.50 4.64 (0.140, 0.092) 219 Examples 1-16 16 4.62 4.53 (0.140, 0.093) 236 Examples 1-17 17 4.58 4.57 (0.140, 0.093) 229 Examples 1-18 18 4.50 4.64 (0.141, 0.094) 223 Examples 1-19 19 4.53 4.60 (0.140, 0.093) 225 Examples 1-20 20 4.53 4.60 (0.140, 0.093) 233 Example 1-21 21 4.50 4.64 (0.141, 0.094) 223 Example 1-22 22 4.57 4.67 (0.140, 0.093) 215 Comparative Example 1-1 ET-1 4.47 2.67 (0.140, 0.092) 182 Comparative Example 1-2 ET-2 4.44 4.11 (0.141, 0.093) 45 Comparative Example 1-3 ET-3 4.49 3.95 (0.140, 0.093) 51 Comparative Example 1-4 ET-4 4.50 4.07 (0.140, 0.092) 46 Comparative Example 1-5 ET-5 4.49 4.01 (0.140, 0.093) 57 Comparative Example 1-6 ET-6 4.78 2.42 (0.141, 0.093) 131 Comparative Example 1-7 ET-7 4.84 2.38 (0.140, 0.092) 129 Comparative Examples 1-8 ET-8 4.77 2.50 (0.140, 0.092) 148 Comparative Example 1-9 ET-9 4.73 4.02 (0.140, 0.093) 128 Comparative Example 1-10 ET-10 4.78 3.98 (0.141, 0.092) 130 Comparative Example 1-11 ET-11 4.69 4.06 (0.140, 0.093) 127 Comparative Example 1-12 ET-12 4.77 3.92 (0.141, 0.093) 133

As shown in Table 1, in the case of the organic light emitting device using the compound of Formula 1 according to the present invention, it was confirmed that excellent characteristics in driving voltage, efficiency and/or lifespan.

Specifically, the compound of the present invention is characterized by having at least two linkers between two 5-membered ring (oxazole or thiazole) rings substituted with an aryl group or condensed with a naphthalene ring. In the case of the device using the compound of the present invention, it can be seen that the voltage, efficiency and lifespan characteristics are improved compared to the case of using the comparative example compound containing benzoxazole or benzothiazole or having one linker.

In addition, it can be confirmed that the voltage, efficiency and lifespan characteristics are improved compared to the case where the 5-membered ring is unsubstituted or uncondensed, or the linker is not an arylene group, but a comparative example compound is used.

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: light emitting layer
6: electron transport layer
7: electron injection layer
8: electron transport and injection layer
9: cathode

Claims (11)

anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
X1 and X2 are the same as or different from each other, and each independently O; or S;
R1 to R4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted naphthalene ring,
Ar, L1 and L2 are the same as or different from each other, and each independently represents an arylene group of monocyclic to tricyclic or five or more rings,
m and n are each an integer from 0 to 3,
When m and n are 2 or more, respectively, L1 and L2 of 2 or more are the same as or different from each other,
m+n is greater than or equal to 1. The organic light emitting diode of claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, the definitions of X1, X2, Ar, L1, L2, m, and n are the same as in Formula 1 above. The organic light-emitting device of claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 2-1 to 2-3:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, definitions of R1 to R4, Ar, L1, L2, m, and n are the same as in Formula 1 above. The organic light emitting diode of claim 1, wherein Ar, L1, and L2 are the same as or different from each other, and each independently a monocyclic to tricyclic or six-ring arylene group. The organic light emitting diode of claim 1, wherein Ar, L1, and L2 are the same as or different from each other and each independently represented by any one of the following structures:

In the above structures, the dotted line indicates a bonding position. The organic light emitting diode of claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

. The organic light emitting device according to claim 1, wherein the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer includes the compound. . The organic light emitting diode of claim 7, wherein the electron transport layer, the electron injection layer, or the electron transport and injection layer further comprises an n-type dopant. The organic light emitting diode of claim 8 , wherein the compound and the n-type dopant are included in a weight ratio of 2:8 to 8:2. The organic light-emitting device of claim 1 , wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound. The method according to claim 1, wherein the organic material layer is 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 one or more of the electron transport and injection layer more An organic light emitting device comprising a.

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