TWI716434B - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present application relates to a compound and an organic electronic device comprising the same.

Description

Compounds and organic electronic components containing them

This application is about a compound and organic electronic components containing it. This application claims the priority and rights of Korean patent application No. 10-2015-0117897 filed in the Korean Intellectual Property Office on August 21, 2015. The entire content of the Korean patent application is incorporated into this case for reference .

Representative examples of organic electronic elements include organic light-emitting elements. Generally speaking, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic light emitting element using an organic light emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer sandwiched between the two. Here, the organic material layer may have a multilayered structure composed of different materials to improve the efficiency and stability of the organic light-emitting device in many cases, and for example, may be a hole injection layer, a hole The transport layer, the light emitting layer, the electron transport layer, the electron injection layer, etc. are constituted. In the structure of the organic light-emitting element, if a voltage is applied between two electrodes, holes are injected into the organic material layer from the positive electrode and electrons are injected into the organic material layer from the negative electrode, and when the injected holes are When electrons meet each other, excitons are formed, and they emit light when they fall to the ground state again.

There is a continuing need to develop a new material for the above-mentioned organic light emitting device.

[Citation List] [Patent Document] International Publication No. 2003-012890

[Technical Problem] This application provides a compound and an organic electronic component containing it.

在化學式1中， z為C、Si或Ge， X₁ 至X₃ 彼此相同或不同，且X₁ 至X₃ 中的至少一者為N，且其他為CR， L為直接鍵；經取代或未經取代的伸芳基；經取代或未經取代的二價雜環基；或-NR'-， R與R'彼此相同或不同，且分別獨立地為氫；氘；經取代或未經取代的環烷基；經取代或未經取代的芳基；或者經取代或未經取代的雜環基， Ar₁ 與Ar₂ 彼此相同或不同，且分別獨立地為未經取代或經選自由氘、鹵素基、氰基、硝基、經取代或未經取代的矽烷基、C₁ 至C₄₀ 烷基、C₆ 至C₄₀ 環烷基、C₆ 至C₄₀ 芳基、及C₂ 至C₄₀ 雜環基組成的群組的至少一者取代的環烷基；未經取代或經選自由氘、鹵素基、氰基、硝基、經取代或未經取代的矽烷基、C₆ 至C₄₀ 環烷基、C₆ 至C₄₀ 芳基、及C₂ 至C₄₀ 雜環基組成的群組的至少一者取代的芳基；或者未經取代或經選自由氘、鹵素基、氰基、硝基、經取代或未經取代的矽烷基、C₁ 至C₄₀ 烷基、C₆ 至C₄₀ 環烷基、C₆ 至C₄₀ 芳基、及C₂ 至C₄₀ 雜環基組成的群組的至少一者取代的雜環基， R₁ 至R₄ 彼此相同或不同，且分別獨立地為氫；氘；C₁ 至C₁₀ 烷基；或C₆ 至C₁₂ 芳基， n為0至4的整數，且當n為2或大於2的整數時，多個L彼此相同或不同， p為0至4的整數，且當p為2或大於2的整數時，多個R₁ 彼此相同或不同，且 q、r及s分別為0至5的整數，且當q、r及s分別為2或大於2的整數時，多個R₂ 至R₄ 分別彼此相同或不同。[Technical Solution] This application provides a compound represented by the following Chemical Formula 1. [Chemical formula 1]

In Chemical Formula 1, z is C, Si or Ge, X ₁ to X ₃ are the same or different from each other, and at least one of X ₁ to X ₃ is N, and the others are CR, and L is a direct bond; substituted or Unsubstituted arylene group; substituted or unsubstituted divalent heterocyclic group; or -NR'-, R and R'are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted Substituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group, Ar ₁ and Ar ₂ are the same or different from each other, and are each independently unsubstituted or selected from Deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to Cycloalkyl substituted with at least one of the group consisting of C ₄₀ heterocyclic group; unsubstituted or selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to C ₄₀ heterocyclic group consisting of at least one substituted aryl group; or unsubstituted or selected from deuterium, halogen, cyano Group, nitro group, substituted or unsubstituted silyl group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₄₀ cycloalkyl group, C ₆ to C ₄₀ aryl group, and C ₂ to C ₄₀ heterocyclic group The heterocyclic group substituted by at least one of the group, R ₁ to R ₄ are the same or different from each other, and are each independently hydrogen; deuterium; C ₁ to C ₁₀ alkyl; or C ₆ to C ₁₂ aryl, n Is an integer of 0 to 4, and when n is an integer of 2 or greater, a plurality of Ls are the same or different from each other, p is an integer of 0 to 4, and when p is an integer of 2 or more, a plurality of Rs _{1 is the} same or different from each other, and q, r, and s are each an integer from 0 to 5, and when q, r, and s are each 2 or an integer greater than 2, a plurality of R ₂ to R ₄ are the same or different from each other.

In addition, the present application provides an organic electronic element, the organic electronic element comprising: a first electrode; a second electrode arranged to face the first electrode; and one or more organic material layers arranged on the first electrode; Between an electrode and the second electrode, wherein one or more of the organic material layers include the above-mentioned compound.

[Advantageous Effects] The compounds according to the exemplary embodiments of the present application are used for organic electronic elements including organic light-emitting elements, and thus may exhibit effects of low driving voltage, high light-emitting efficiency, and/or long life.

Hereinafter, this specification will be explained in more detail.

This specification provides a compound represented by Chemical Formula 1.

Hereinafter, examples of substituents in this specification will be explained, but they are not limited to these.

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent, and the position to be substituted is not limited as long as the position is the position where the hydrogen atom is substituted (ie, substitution The position where the group may be substituted) is sufficient, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In this specification, the term "substituted or unsubstituted" means selected from deuterium; halogen group; cyano group; nitro group; hydroxyl group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; amine group; Group; and one substituent or two or more substituents of the group consisting of a heterocyclic group, substituted by a substituent connected to two or more substituents in the substituent, or without a substituent . For example, the "substituent to which two or more substituents are attached" may be biphenyl. That is, the biphenyl group may also be an aryl group, and can be interpreted as a substituent to which two phenyl groups are connected. In this specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of its carbon atoms is not particularly limited, but it is preferably from 1 to 50, and more preferably from 1 to 40. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, second butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl 2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl , N-octyl, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl Group, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited to these.

In this specification, the alkenyl group may be linear or branched, and the number of its carbon atoms is not particularly limited, but it is preferably 2-40. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentene Group, 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, stilbene, styryl, etc., but not limited to these.

In this specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1-20. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tertiary butoxy, second butoxy, N-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyl Oxy, benzyloxy, p-methylbenzyloxy, etc., but not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and more preferably has 6 to 40 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclopentyl Hexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tertiarybutylcyclohexyl, cycloheptyl, cyclooctyl, etc., but not limited to these.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6-40, and more preferably 6-25. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, etc., but are not limited to these.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 10-24. Specific examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylene, chrysenyl group, chrysenyl group, etc., but are not limited thereto.

In this specification, the stilbene group may be substituted, and adjacent substituents may be combined with each other to form a ring.

、

、

、

、

、

等，但並非僅限於此。When the tungsten group is substituted, the group may be

,

,

,

,

,

Etc., but not limited to this.

等。In the present specification, the heterocyclic group includes one or more of atoms other than carbon (ie, heteroatoms), and specifically, the heteroatoms may include those selected from the group consisting of O, N, Se, and S. One or more atoms of the group. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2-60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline Alkyl, indolyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, dibenzoxazolyl, benzothienyl, dibenzothienyl , Benzofuranyl, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenanthiazinyl, phenanthrazinyl, dibenzofuranyl, and Its fused structure, etc., but not limited to this. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group, such as

Wait.

、

、

等，但並非僅限於此。In this specification, the condensed structure may be a structure in which an aromatic hydrocarbon ring is condensed with a corresponding substituent. Examples of fused rings of benzimidazole include

,

,

Etc., but not limited to this.

In the present specification, the "adjacent" group may mean a substituent substituted by an atom directly connected to the atom in which the corresponding substituent is substituted, a substituent disposed closest to the corresponding substituent in space, or a corresponding substituent therein. The substituent is another substituent substituted by a substituted atom. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted with the same carbon in the aliphatic ring can be interpreted as groups "adjacent" to each other.

In the present specification, the case where adjacent groups are bonded to each other to form a ring means that adjacent groups are bonded to each other to form a 5- to 8-membered hydrocarbon ring or 5- to 8-membered heterocyclic ring as described above, and the The ring may be a single ring or a polycyclic ring, and may be an aliphatic ring, an aromatic ring, or a condensed form thereof, but is not limited to this.

In the present specification, the hydrocarbon ring or heterocyclic ring may be selected from the above examples of cycloalkyl, aryl or heterocyclic groups other than monovalent, and the hydrocarbon ring or heterocyclic ring may be monocyclic or polycyclic, aliphatic ring Or aromatic ring or its condensed form, but not limited to this.

In this specification, an aryl group means that there are two bonding positions in the aryl group, that is, a divalent group. Except that the aryl group is respectively a divalent group, the above description of the aryl group can be applied.

In the present specification, a divalent heterocyclic group means that there are two bonding positions in the heterocyclic group, that is, a divalent group. The above description of the heterocyclic group can be applied except that the heterocyclic group is each a divalent group.

According to the exemplary embodiment of the present application, X ₁ is N.

According to an exemplary embodiment of the present application, X ₂ is N.

According to the exemplary embodiment of the present application, X ₃ is N.

According to an exemplary embodiment of the present application, X ₁ is CR.

According to an exemplary embodiment of the present application, X ₂ is CR.

According to an exemplary embodiment of the present application, X ₃ is CR.

According to an exemplary embodiment of the present application, X ₁ and X ₂ are N.

According to an exemplary embodiment of the present application, X ₁ and X ₃ are N.

According to an exemplary embodiment of the present application, X ₂ and X ₃ are N.

According to an exemplary embodiment of the present application, X ₁ to X ₃ are N.

According to the exemplary embodiment of the present application, L is a direct bond; or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present application, L is selected from the group consisting of: direct bond; substituted or unsubstituted phenylene; substituted or unsubstituted biphenylene; substituted or unsubstituted phenylene; Substituted naphthylene; substituted or unsubstituted anthracenyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted pyrenyl; And substituted or unsubstituted ethylene groups.

According to an exemplary embodiment of the present application, L is selected from the group consisting of: direct bond; phenylene; biphenylene; naphthylene; anthrylene; phenanthrenyl; phenanthrenyl; pyrenyl ; And Shen Jiji.

According to the exemplary embodiment of the present application, L is a direct bond; or a substituted or unsubstituted phenylene group.

According to an exemplary embodiment of the present application, L is a direct bond; or a phenylene group.

或

。在結構式中，虛線為鍵結至化學式1的包含N的雜環及苯環的位置。According to the exemplary embodiment of this application, L is a direct key;

or

. In the structural formula, the dotted line is the position of the N-containing heterocyclic ring and the benzene ring bonded to the chemical formula 1.

According to an exemplary embodiment of the present application, n is 1 or 2.

According to an exemplary embodiment of the present application, n is 3, and three Ls are the same or different from each other.

According to an exemplary embodiment of the present application, n is 4, and the four Ls are the same or different from each other.

According to an exemplary embodiment of the present application, Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently a substituted or unsubstituted C ₆ to C ₂₀ aryl group; or a substituted or unsubstituted C ₂ To C ₂₀ heterocyclic group.

According to an exemplary embodiment of the present application, Ar ₁ and Ar ₂ are the same or different from each other, and are each independently unsubstituted or selected from deuterium, halogen, cyano, nitro, trimethylsilyl, C A C ₆ to C ₂₀ aryl group substituted with at least one of the group consisting of ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to C ₄₀ heterocyclic group; or unsubstituted or selected Free deuterium, halogen, cyano, nitro, trimethylsilyl, C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to C ₄₀ heterocycle A C ₂ to C ₂₀ heterocyclic group substituted by at least one of the group consisting of a group.

According to an exemplary embodiment of the present application, Ar ₁ and Ar ₂ are the same or different from each other, and are each independently unsubstituted or selected from deuterium, halogen, cyano, nitro, trimethylsilyl, C ₆ to at least one unsubstituted C C ₂₀ aryl group and C ₂ to C ₂₀ heterocyclic group composed of ₆ to C ₂₀ aryl group; or an unsubstituted or selected from the group consisting of deuterium, halo, cyano, nitro A C ₂ to C ₂₀ heterocyclic group substituted with at least one of the group consisting of a trimethylsilyl group, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₂₀ aryl group, and a C ₂ to C ₂₀ heterocyclic group .

According to an exemplary embodiment of the present application, Ar ₁ and Ar ₂ are the same or different from each other, and are each independently unsubstituted or selected from deuterium, halogen, cyano, nitro, trimethylsilyl, benzene C ₆ to C ₂₀ aryl group substituted by at least one of the group consisting of phenyl group and biphenyl group; or unsubstituted or selected from deuterium, halogen, cyano, nitro, trimethylsilyl, methyl A C ₂ to C ₂₀ heterocyclic group substituted with at least one of the group consisting of propyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, phenyl, and biphenyl.

According to an exemplary embodiment of the present application, the C ₆ to C ₂₀ aryl group is a phenyl group; a biphenyl group; a naphthyl group; an anthryl group; a phenanthryl group; a phenyl group; a pyrenyl group;

According to an exemplary embodiment of the present application, the C ₂ to C ₂₀ heterocyclic group is pyridyl; pyrimidyl; triazinyl; thienyl; furyl; benzofuranyl; benzothienyl; dibenzofuranyl ；Dibenzothienyl; Zyzolyl; Benzozolyl; Or dibenzozolyl.

According to an exemplary embodiment of the present application, R ₁ to R ₄ are the same or different from each other, and are each independently hydrogen; deuterium; methyl or phenyl.

According to an exemplary embodiment of the present application, R ₁ to R ₄ are hydrogen.

According to an exemplary embodiment of the present application, Z is C, and the compound shown in Chemical Formula 1 is symmetric.

According to an exemplary embodiment of the present application, the compound represented by Chemical Formula 1 is asymmetric.

According to an exemplary embodiment of the present application, Z is C, and the compound shown in Chemical Formula 1 is asymmetric.

According to an exemplary embodiment of the present application, Z is Si, and the compound of Chemical Formula 1 is asymmetric. Specifically, the asymmetric compound in which Z is Si has the effects of low driving voltage, high luminous efficiency and long life.

According to an exemplary embodiment of the present application, the case where the compound represented by Chemical Formula 1 is asymmetric means that Ar ₁ and Ar ₂ are different from each other, or when L is a phenylene group, the bonding position is a meta position or an ortho position .

According to an exemplary embodiment of the present application, the compound represented by Chemical Formula 1 may be any one selected from the following structural formulas.

In addition, this specification provides an organic electronic device containing the above-mentioned compound.

An exemplary embodiment of the present application provides an organic electronic element, the organic electronic element comprising: a first electrode; a second electrode arranged to face the first electrode; and one or more organic material layers arranged in Between the first electrode and the second electrode, wherein one or more of the organic material layers include the compound.

When a member is placed "on" another member in this specification, this includes not only the case where the one member is in contact with the other member, but also the case where there is another member between the two members. The case of a component.

When a part "includes" a component in this specification, unless specifically stated otherwise, this does not mean that another component is excluded, but it means that another component may be further included.

The organic material layer of the organic electronic device of the present application may also be composed of a single-layer structure, but may be composed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic electronic device of the present invention, the organic light-emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic electronic element is not limited to this, but may include a smaller number of organic layers.

According to an exemplary embodiment of the present application, the organic electronic element may be selected from the group consisting of organic light emitting element, organic phosphorescent element, organic solar cell, organic photoconductor (OPC) and organic transistor.

Hereinafter, an organic light emitting element will be exemplified.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In the exemplary embodiment of the present application, the organic light emitting element further includes one layer or two or more layers selected from the group consisting of: hole injection layer, hole transport layer, electron transport layer, electron injection Layer, electron blocking layer and hole blocking layer.

In an exemplary embodiment of the present application, an organic light-emitting device includes: a first electrode; a second electrode disposed to face the first electrode; a light-emitting layer disposed on the first electrode and the second electrode And two or more organic material layers are provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein the two or more organic material layers At least one of the material layers includes the compound. In the exemplary embodiment of the present application, as the two or more organic material layers, two or more can be selected from the group consisting of: electron transport layer, electron injection layer, simultaneous transport and injection of electrons The layer and the hole blocking layer.

In an exemplary embodiment of the present application, 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. Specifically, in the exemplary embodiment of the present specification, the compound may also be included in one of the two or more electron transport layers, and may be included in the two or more electron transport layers. In each of the layers.

In addition, in the exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, other materials other than the compound may be the same or different from each other.

In an exemplary embodiment of the present application, in addition to the organic material layer containing the compound, the organic material layer further includes a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer Contains compounds containing an arylamine group, a oxazole group, or a benzoazolazole group.

在化學式A-1中， m為1或大於1的整數， Ar3為經取代或未經取代的單價或更高價的苯並茀基；經取代或未經取代的單價或更高價的螢蒽基；經取代或未經取代的單價或更高價的芘基；或者經取代或未經取代的單價或更高價的䓛基， L1為直接鍵；經取代或未經取代的伸芳基；或者經取代或未經取代的伸雜芳基， Ar4與Ar5彼此相同或不同，且分別獨立地為經取代或未經取代的芳基；經取代或未經取代的矽烷基；經取代或未經取代的烷基；經取代或未經取代的芳基烷基；或者經取代或未經取代的雜環基，抑或可彼此結合而形成經取代或未經取代的環，且 當m為2或大於2時，括弧中的二或更多個結構彼此相同或不同。In an exemplary embodiment of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following chemical formula A-1. [Chemical formula A-1]

In the chemical formula A-1, m is 1 or an integer greater than 1, and Ar3 is a substituted or unsubstituted monovalent or higher valence benzol; substituted or unsubstituted monovalent or higher fluoranthene group ; A substituted or unsubstituted monovalent or higher valence pyrene group; or a substituted or unsubstituted monovalent or higher valence group, L1 is a direct bond; a substituted or unsubstituted arylene group; or For substituted or unsubstituted heteroaryl groups, Ar4 and Ar5 are the same or different from each other, and are each independently substituted or unsubstituted aryl groups; substituted or unsubstituted silyl groups; substituted or unsubstituted Alkyl; substituted or unsubstituted arylalkyl; or substituted or unsubstituted heterocyclic group, or may be combined with each other to form a substituted or unsubstituted ring, and when m is 2 or greater When 2, two or more structures in parentheses are the same or different from each other.

According to an exemplary embodiment in this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by Chemical Formula A-1 as a dopant of the light-emitting layer.

According to the exemplary embodiment of this specification, L1 is a direct key.

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

In the exemplary embodiment of the present specification, Ar3 is a divalent pyrene group that is unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl or tertiary butyl; or is unsubstituted or substituted with deuterium, methyl , Ethyl or tertiary butyl substituted divalent group.

In the exemplary embodiment of the present specification, Ar3 is a divalent pyrene group that is unsubstituted or substituted with an alkyl group; or a divalent pyrene group that is unsubstituted or substituted with an alkyl group.

In the exemplary embodiment of the present specification, Ar3 is a divalent pyrene group that is unsubstituted or substituted with an alkyl group.

In the exemplary embodiment of the present specification, Ar3 is a divalent pyrene group.

According to the exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and are each independently an aryl group that is unsubstituted or substituted with an alkyl group, a nitrile group, or a silyl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same or different from each other, and are each independently unsubstituted or substituted with methyl, ethyl, isopropyl, tertiary butyl, nitrile or alkyl. Silyl substituted aryl.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and are each independently an aryl group substituted with an unsubstituted or silyl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same or different from each other, and are each independently an aryl group that is unsubstituted or substituted with a trimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted The terphenyl.

According to exemplary embodiments of the present specification, Ar4 and Ar5 are the same or different from each other, and are independently unsubstituted or methyl, ethyl, isopropyl, tert-butyl, nitrile, or trimethylsilyl. Substituted phenyl.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same or different from each other, and are each independently a phenyl group that is unsubstituted or substituted with a trimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to the exemplary embodiment of the present specification, Ar4 and Ar5 are the same or different from each other, and are each independently unsubstituted or substituted with methyl, ethyl, tertiary butyl, nitrile, alkyl substituted silyl or benzene. Group substituted heteroaryl.

According to exemplary embodiments of the present specification, Ar4 and Ar5 are the same or different from each other, and are each independently unsubstituted or substituted with methyl, ethyl, tertiary butyl, nitrile, trimethylsilyl, or phenyl. The dibenzofuranyl.

According to an exemplary embodiment of the present specification, the chemical formula A-1 is selected from the following compounds.

在化學式A-2中， Ar6與Ar7彼此相同或不同，且分別獨立地為經取代或未經取代的單環芳基；或者經取代或未經取代的多環芳基，且 G1至G8彼此相同或不同，且分別獨立地為氫；經取代或未經取代的單環芳基；或者經取代或未經取代的多環芳基。According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following chemical formula A-2. [Chemical formula A-2]

In the chemical formula A-2, Ar6 and Ar7 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group, and G1 to G8 are each other The same or different, and each independently is hydrogen; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by Chemical Formula A-2 as a host of the light-emitting layer.

According to the exemplary embodiment of the present specification, Ar6 and Ar7 are the same as or different from each other, and are each independently a substituted or unsubstituted polycyclic aryl group.

According to the exemplary embodiment of the present specification, Ar6 and Ar7 are the same as or different from each other, and are each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

According to the exemplary embodiment of the present specification, Ar6 and Ar7 are the same as or different from each other, and are each independently a substituted or unsubstituted naphthyl group.

According to the exemplary embodiment of the present specification, Ar6 and Ar7 are the same as or different from each other, and are each independently substituted or unsubstituted 1-naphthyl.

According to the exemplary embodiment of the present specification, Ar6 and Ar7 are 1-naphthyl.

According to the exemplary embodiment of the present specification, G1 to G8 are hydrogen.

According to an exemplary embodiment of the present specification, the chemical formula A-2 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-1 as a dopant of the light emitting layer, and includes a compound represented by Chemical Formula A-2 As the main body of the light-emitting layer.

In another exemplary embodiment, the organic light emitting element may be an organic light emitting element having a structure (normal type) in which a positive electrode, one or more organic material layers, and a negative electrode are sequentially stacked on a substrate.

In still another exemplary embodiment, the organic light emitting element may be an organic light emitting element having an inverted structure (inverted type) in which a negative electrode, one or more organic material layers, and a positive electrode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting element according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

FIG. 1 illustrates the structure of an organic electronic device in which a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4 are sequentially stacked. In the structure, the compound may be included in the light-emitting layer 3.

FIG. 2 illustrates the structure of an organic electronic element in which the substrate 1, the positive electrode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, the electron transport layer 7, and the negative electrode 4 are sequentially stacked. In the structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

In the structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

Except that one or more layers of the organic material layer include the compound of the present application (ie, the compound), the organic light-emitting device of the present application can be manufactured by materials and methods known in the art.

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

Except that one or more of the organic material layers includes the compound (ie, the compound represented by Chemical Formula 1), the organic light-emitting device of the present application can be manufactured by materials and methods known in the art.

For example, the organic light-emitting device of the present application can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting element can be manufactured by the following method: by using physical vapor deposition (physical vapor deposition, PVD) methods such as sputtering or electron beam evaporation to deposit conductive metal on the substrate Or a metal oxide or an alloy thereof to form a positive electrode, on which an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer is formed, and then a material that can be used as a negative electrode is deposited on it. In addition to the above methods, an organic light-emitting device can be fabricated by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

In addition, when manufacturing an organic light-emitting element, the compound represented by Chemical Formula 1 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, and spray printing. method), roll coating, etc., but not limited to this.

In addition to the above methods, organic light-emitting devices can also be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (International Publication No. 2003/012890). However, the manufacturing method is not limited to this.

In an exemplary embodiment of the present application, the first electrode is a positive electrode, and the second electrode is a negative electrode.

In another exemplary embodiment, the first electrode is a negative electrode, and the second electrode is a positive electrode.

As the positive electrode material, a material having a large work function is generally preferable in order to smoothly inject holes into the organic material layer. Specific examples of positive electrode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide ( IZO); a combination of metals and oxides, such as ZnO: Al or SnO ₂ : Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-di Oxygen)thiophene] (PEDOT), polypyrrole and polyaniline, but not limited to this.

As the negative electrode material, a material having a small work function is generally preferable in order to smoothly inject electrons into the organic material layer. Specific examples of negative electrode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gamma, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials, such as LiF/Al Or LiO ₂ /Al, etc., but not limited to this.

The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, and therefore has the effect of injecting holes at the positive electrode and is aimed at the light-emitting layer or the light-emitting layer. The material has an excellent effect of injecting holes, preventing excitons generated from the light-emitting layer from moving to the electron injection layer or the electron injection material, and is also excellent in film formation ability. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin (porphyrin), oligothiophene (oligothiophene), arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quine Quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but not limited to these.

The hole transport layer is a layer that receives holes from the hole injection layer and transmits the holes to the light emitting layer, and the hole transport material is suitably capable of receiving holes from the positive electrode or the hole injection layer to transfer the holes To the material of the light-emitting layer, and has a large hole mobility (mobility). Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers, etc. (the conjugated portion and the non-conjugated portion are present in the block copolymer together), but are not limited thereto.

The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, and combine the holes and electrons to emit light in the visible light region, and is preferably a material that is resistant to fluorescence or phosphorescence. Materials with excellent quantum efficiency. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); oxazole-based compound; dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzene Oxazole, benzothiazole and benzimidazole-based compounds; poly(p-styrene) (PPV)-based polymers; spirocyclic compounds; polypyridine, fluorene, etc., but not limited to these.

The light-emitting layer may include a host material and a dopant material. Examples of host materials include condensed aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specific examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, fused pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and specific examples of the heterocyclic ring-containing compounds Including dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but the examples are not limited to these.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is a material that can well inject electrons from the negative electrode and transfer the electrons to the light emitting layer, and suitably has Materials with high electron mobility. Specific examples thereof include: 8-hydroxyquinoline Al complex; Alq3 containing complex; organic radical compound; hydroxyflavone-metal complex (hydroxyflavone-metal complex), but not limited to this. The electron transport layer can be used with any desired cathode material, as used according to the prior art. Specifically, a suitable example of a cathode material is a typical material with a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound having the ability to transport electrons, has the effect of injecting electrons from the negative electrode and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, and prevents the self-luminous layer The generated excitons move to the hole injection layer and are also excellent in film formation ability. Specific examples thereof include quinone, anthraquinone dimethane, diphenquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane ), anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

Examples of the metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) Hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo(h)quinoline) beryllium, bis(10- Hydroxybenzo(h)quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline) (o-cresol) gallium, bis(2-methyl) But not limited to, but not limited to, but not limited to, hydroxy-8-quinoline) (1-naphthol) aluminum, bis(2-methyl-8-quinoline) (2-naphthol) gallium, etc.

The hole blocking layer is a layer that blocks holes from reaching the positive electrode and can generally be formed under the same conditions as the hole injection layer. Specific examples thereof include oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, bathocuproine (BCP), aluminum complexes, etc., but are not limited to these.

The organic light-emitting element according to the present specification may be a top emission type, a bottom emission type, or a dual emission type depending on the material used.

In an exemplary embodiment of the present application, in addition to the organic light-emitting element, the compound may be included in an organic solar cell or an organic transistor.

The compound according to the present application can function by a principle similar to that applied to the organic light-emitting device, even in organic electronic devices including organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors, etc. The same is true in China.

（1）化合物1A的製備The preparation of the compound represented by Chemical Formula 1 and the organic light-emitting element containing it will be specifically illustrated in the following examples. However, the following examples are provided to illustrate this specification, and the scope of this specification is not limited thereto. <Preparation example><Synthesis example 1>-Preparation of compound represented by compound 1

(1) Preparation of compound 1A

Mix reagent 1 (100.0 g, 250.45 millimoles) with reagent 2 (70.0 g, 275.46 millimoles) and potassium acetate (73.7 g, 751.26 millimoles) under a nitrogen atmosphere, and add the resulting mixture to 1,000 ml Dioxane was heated while stirring. Under reflux, bis(dibenzylideneacetone)palladium (4.3 g, 7.51 mmol) and tricyclohexyl phosphine (4.2 g, 15.03 mmol) were put into the mixture, and the resulting mixture was heated And stirred for 24 hours. After the reaction was completed, the temperature of the mixture was lowered to normal temperature, and then the mixture was filtered. Water was poured into the filtrate, extraction was performed with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization was performed with ethanol to prepare compound 1A (51 g, 61%). (2) Preparation of compound 1

（1）化合物2的製備Compound 1A (14.3 g, 31.09 mmol) and Intermediate 1 (10.0 g, 29.09 mmol) were put into 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium carbonate (12.1 g, 87.26 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (1.0 g, 0.87 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 1 (14.1 g, 77%) was prepared by recrystallization. MS: [M+H]+ = 629 <Synthesis Example 2>-Preparation of compound represented by compound 2

(1) Preparation of compound 2

（1）化合物3的製備Compound 1A (11.7 g, 26.20 mmol) and Intermediate 2 (10.0 g, 23.81 mmol) were put into 250 mL of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium carbonate (9.9 g, 71.44 millimoles) was dissolved in 600 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (0.8 g, 0.71 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 2 (11.1 g, 66%) was prepared by recrystallization. MS: [M+H]+ = 704 <Synthesis Example 3>-Preparation of the compound represented by compound 3

(1) Preparation of compound 3

（1）化合物4的製備Compound 1A (11.7 g, 26.20 millimoles) and Intermediate 3 (10.0 g, 23.81 millimoles) were placed in 250 ml of dioxane under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium phosphate (9.9 g, 71.44 millimoles) was dissolved in 600 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then bis(diphenylmethylene acetone) was introduced into it. ) Palladium (0.8 g, 0.71 millimoles) and tricyclohexylphosphine (0.8 g, 0.71 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 3 (9.9 g, 59%) was prepared by recrystallization. MS: [M+H]+ = 704 <Synthesis Example 4>-Preparation of the compound represented by compound 4

(1) Preparation of compound 4

Compound 1A (18.3 g, 41.09 mmol) and Intermediate 4 (10.0 g, 37.35 mmol) were put into 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium carbonate (15.5 g, 112.06 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (1.3 g, 1.12 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 4 (14.6 g, 71%) was prepared by recrystallization. MS: [M+H]+ = 552 <Synthesis Example 5>-Preparation of compound represented by compound 5 (1) Preparation of compound 5

（1）化合物6的製備Compound 1A (12.6 g, 28.33 mmol) and Intermediate 5 (10.0 g, 25.76 mmol) were placed in 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium carbonate (15.5 g, 112.06 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (0.9 g, 0.77 millimolar). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 5 (9.9 g, 61%) was prepared by recrystallization. MS: [M+H]+ = 629 <Synthesis Example 6>-Preparation of compound represented by compound 6

(1) Preparation of compound 6

（1）化合物7A的製備Compound 1A (14.3 g, 31.99 mmol) and Intermediate 6 (10.0 g, 29.09 mmol) were put into 250 ml of dioxane under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium phosphate (12.1 g, 87.26 millimoles) was dissolved in 600 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then bis(diphenylmethylene acetone) was introduced into it. ) Palladium (0.8 g, 0.71 millimoles) and tricyclohexylphosphine (0.8 g, 0.71 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 6 (14.6 g, 71%) was prepared by recrystallization. MS: [M+H]+ = 629 <Synthesis Example 7>-Preparation of compound represented by compound 7

(1) Preparation of compound 7A

Reagent 7-1 (16.2 g, 84.62 mmol) was put into 170 ml of anhydrous tetrahydrofuran, and the resulting mixture was cooled to -78°C. After that, while stirring the mixture, n-butyllithium (40.6 mL, 101.54 mmol) was slowly added dropwise thereto over 30 minutes, and then the resulting mixture was allowed to react for 1 hour. After that, the reagent 7-2 in a solid state was introduced therein, and the resultant mixture was allowed to react for 1 hour, and then slowly heated to a normal temperature to perform the reaction for 2 hours. After the reaction, water was poured therein to end the reaction, the water layer was separated from the organic layer, and then the organic layer was distilled under reduced pressure to obtain a solid, and the solid was dried to Prepare compound 7A (21.0 g, 92%). N-butyllithium, reagent 7-1 and reagent 7-2 were purchased from Aldrich Chemical Co. and TCI America Inc., respectively. (2) Preparation of compound 7B

Compound 7A (21.0 g, 56.61 mmol) was mixed with reagent 2 (15.8 g, 62.27 mmol) and potassium acetate (16.7 g, 169.83 mmol) under a nitrogen atmosphere, and the resulting mixture was added to 300 mL Dioxane was heated while stirring. Under reflux, bis(dibenzylideneacetone)palladium (1.0 g, 1.70 mmol) and tricyclohexylphosphine (1.0 g, 3.40 mmol) were put into the mixture, and the resulting mixture was heated and Stirred for 24 hours. After the reaction was completed, the temperature of the mixture was reduced to normal temperature, and then the mixture was filtered. Water was poured into the filtrate, extraction was performed with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization was performed with ethanol to prepare compound 7B (23 g, 88%). (3) Preparation of compound 7

（1）化合物8的製備Compound 7B (14.8 g, 31.99 mmol) and Intermediate 1 (10.0 g, 29.09 mmol) were put into 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium carbonate (12.1 g, 87.26 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (1.0 g, 0.87 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 7 (11.4 g, 61%) was prepared by recrystallization. MS: [M+H]+ = 645 <Synthesis Example 8>-Preparation of compound represented by compound 8

(1) Preparation of compound 8

（1）化合物9的製備Compound 7B (12.1 g, 26.20 mmol) and Intermediate 2 (10.0 g, 23.81 mmol) were put into 300 ml of dioxane under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium phosphate (15.2 g, 71.44 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then bis(benzylideneacetone) was introduced into it. ) Palladium (0.4 g, 0.71 millimoles) and tricyclohexylphosphine (0.4 g, 1.43 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 8 (13.5 g, 79%) was prepared by recrystallization. MS: [M+H] ⁺ = 721 <Synthesis Example 9>-Preparation of compound represented by compound 9

(1) Preparation of compound 9

（1）化合物10的製備Compound 7B (12.1 g, 26.20 mmol) and Intermediate 3 (10.0 g, 23.81 mmol) were put into 300 mL of dioxane under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium phosphate (15.2 g, 71.44 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then bis(benzylideneacetone) was introduced into it. ) Palladium (0.4 g, 0.71 millimoles) and tricyclohexylphosphine (0.4 g, 1.43 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 9 (10.3 g, 60%) was prepared by recrystallization. MS: [M+H]+ = 721 <Synthesis Example 10>-Preparation of the compound represented by compound 10

(1) Preparation of compound 10

（1）化合物11的製備Compound 7B (14.8 g, 31.99 mmol) and Intermediate 4 (10.0 g, 37.35 mmol) were put into 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium carbonate (12.1 g, 87.26 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (1.3 g, 1.12 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 10 (14.0 g, 66%) was prepared by recrystallization. MS: [M+H]+ = 568 <Synthesis Example 11>-Preparation of the compound represented by compound 11

(1) Preparation of compound 11

（1）化合物12的製備Compound 7B (13.1 g, 31.99 mmol) and Intermediate 5 (10.0 g, 37.35 mmol) were put into 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and brought to reflux. After that, potassium carbonate (10.7 g, 77.27 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then the tetra-triphenyl-phosphine group was introduced into it. Palladium (0.9 g, 0.77 millimolar). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 11 (13.2 g, 71%) was prepared by recrystallization. MS: [M+H]+ = 719 <Synthesis Example 12>-Preparation of the compound represented by compound 12

(1) Preparation of compound 12

Compound 7B (14.8 g, 31.99 mmol) and Intermediate 6 (10.0 g, 29.09 mmol) were placed in 300 ml of dioxane under a nitrogen atmosphere, and the resulting mixture was stirred and allowed to reflux. After that, potassium phosphate (18.5 g, 87.26 millimoles) was dissolved in 100 ml of water, the resulting solution was introduced into the above mixture, the resulting mixture was thoroughly stirred, and then bis(benzylideneacetone) was introduced into it. ) Palladium (0.5 g, 0.87 millimoles) and tricyclohexylphosphine (0.5 g, 1.75 millimoles). After reacting for 12 hours, the temperature was lowered to normal temperature, and the produced solid was filtered. After filtration, the solid was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. After that, the material was extracted by using chloroform and water, and then compound 12 (10.3 g, 60%) was prepared by recrystallization. MS: [M+H]+ = 644 <Example> <Experimental example 1-1>

A glass substrate (Corning 7059 glass) thinly coated with indium oxide (ITO) to have a thickness of 1,000 angstroms was placed in distilled water in which a dispersant was dissolved, and ultrasonic washing was performed. A product manufactured by Fischer Co. is used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. is used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes using distilled water. After the washing with distilled water was completed, ultrasonic washing was performed with isopropanol, acetone, and methanol solvents in this order, and then dried.

On the thus prepared transparent ITO electrode, capronitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 angstroms, thereby forming a hole injection layer. HT1 (400 angstroms) as a material transport hole was vacuum deposited on it, and then a compound of host H1 and dopant D1 was used as a light-emitting layer and vacuum deposited to have a thickness of 300 angstroms. The compound 1 prepared in Synthesis Example 1 and lithium quinolinate (LiO) were vacuum deposited on the light-emitting layer at a weight ratio of 1:1, thereby forming an electron injection and transport layer having a thickness of 350 angstroms. Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron injection and transport layer to have a thickness of 12 Egypt and 2,000 angstroms, thereby forming a negative electrode to manufacture an organic light-emitting device.

＜實驗例1-2＞In the above procedure, the deposition rate of organic materials is maintained at 0.4 angstroms/sec to 0.7 angstroms/sec, the deposition rates of lithium fluoride and aluminum in the negative electrode are maintained at 0.3 angstroms/sec and 2 angstroms/sec, respectively, and the vacuum during the deposition The temperature is maintained at 2 × 10 ^-7 Torr to 5 × 10 ^-6 Torr, thereby manufacturing an organic light-emitting device.

<Experimental example 1-2>

As the electron transport layer, compound 2 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experiment example 1-3>

As the electron transport layer, compound 3 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental example 1-4>

As the electron transport layer, compound 4 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental Example 1-5>

As the electron transport layer, compound 5 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental Example 1-6>

As the electron transport layer, compound 6 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental example 1-7>

As the electron transport layer, Compound 7 was used instead of Compound 1, and an experiment was performed in the same manner as Experimental Example 1-1, except that Compound 7 was used. ＜Experimental example 1-8＞

As the electron transport layer, compound 8 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental example 1-9>

As the electron transport layer, compound 9 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental example 1-10>

As the electron transport layer, compound 10 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental example 1-11>

As the electron transport layer, compound 11 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1 except that. <Experimental example 1-12>

As the electron transport layer, compound 12 was used instead of compound 1, and an experiment was performed in the same manner as in Experimental Example 1-1, except for that. <Comparative example 1>

＜比較例2＞An organic light emitting element was manufactured in the same manner as in Experimental Example 1-1 except that the compound shown in ET1 below was used instead of Compound 1 in Experimental Example 1-1.

＜Comparative example 2＞

An organic light emitting element was manufactured in the same manner as in Experimental Example 1-1 except that the compound shown in ET2 below was used instead of Compound 1 in Experimental Example 1-1.

For the organic light-emitting element manufactured by using each compound as the electron transport layer material in Experimental Example 1-1 to Experimental Example 1-12 and Comparative Example 1 and Comparative Example 2, the current density is 10 mA/cm² The driving voltage and luminous efficiency were measured, and the time to reach 95% of the initial brightness (LT ₉₅ ) was measured at a current density of 20 mA/cm². The results are shown in Table 1 below. [Table 1]

As can be seen in Table 1, it can be seen that when compared with the case of using the materials in Comparative Example 1 and Comparative Example 2, the organic light-emitting element manufactured using the compound of this specification as the electron transport layer material is more efficient and stable Shows excellent characteristics in terms of sex.

Although the preferred exemplary embodiments of the present invention have been described above, the present invention is not limited to this, but various modifications and implementations can be made within the scope of the patent application and detailed description of the present invention, and the various Retouching also belongs to the scope of the present invention.

1‧‧‧Substrate 2‧‧‧Positive 3‧‧‧Light-emitting layer 4‧‧‧Negative pole 5‧‧‧ Hole injection layer 6‧‧‧Hole transmission layer 7‧‧‧Electron transport layer

FIG. 1 illustrates an example of an organic light emitting element in which a substrate 1, a positive electrode 2, a light emitting layer 3, and a negative electrode 4 are sequentially stacked. FIG. 2 illustrates an example of an organic light-emitting element in which a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a positive electrode 4 are sequentially stacked.

1‧‧‧Substrate

2‧‧‧Positive

3‧‧‧Light-emitting layer

4‧‧‧Negative pole

Claims (17)

A compound represented by the following chemical formula 1:

In Chemical Formula 1, z is Si, X ₁ to X ₃ are the same or different from each other, and at least one of X ₁ to X ₃ is N, and the others are CR, and L is a direct bond; substituted or unsubstituted Arylene; or substituted or unsubstituted divalent heterocyclic group, R is hydrogen; deuterium; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted A substituted heterocyclic group, Ar ₁ and Ar ₂ are the same or different from each other, and are each independently unsubstituted or selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, Cycloalkyl substituted with at least one of the group consisting of C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to C ₄₀ heterocyclic group; unsubstituted Or selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to C ₄₀ heterocyclic group At least one substituted aryl group; or unsubstituted or selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C ₁ to C ₄₀ alkyl, A heterocyclic group substituted with at least one of the group consisting of C ₆ to C ₄₀ cycloalkyl, C ₆ to C ₄₀ aryl, and C ₂ to C ₄₀ heterocyclic group, R ₁ to R ₄ are the same or different from each other, and Each independently is hydrogen; deuterium; C ₁ to C ₁₀ alkyl; or C ₆ to C ₁₂ aryl, n is an integer of 0 to 4, and when n is an integer of 2 or greater, multiple Ls are the same as each other Or different, p is an integer from 0 to 4, and when p is 2 or an integer greater than 2, multiple R ₁ are the same or different from each other, and q, r, and s are integers from 0 to 5, and when q, When r and s are each 2 or an integer greater than 2, a plurality of R ₂ to R ₄ are the same or different from each other, wherein the compound represented by Chemical Formula 1 is asymmetric, and the substituted or unsubstituted is One or two substituents selected from the group consisting of deuterium, halogen, cyano, nitro, hydroxy, alkyl, alkenyl, alkoxy, cycloalkyl, amine, aryl, and heterocyclic group It is substituted by one or more substituents, substituted by a substituent to which two or more of the substituents are attached, or has no substituent. The compound described in item 1 of the scope of patent application, wherein X ₁ to X ₃ are N. The compound described in item 1 of the scope of the patent application, wherein L is a direct bond; or a substituted or unsubstituted C ₁ to C ₂₀ arylene group. The compound described in item 1 of the scope of patent application, wherein Ar ₁ and Ar ₂ are the same or different from each other, and are each independently a substituted or unsubstituted C ₆ to C ₂₀ aryl group; or substituted or unsubstituted的 C ₂ to C ₂₀ heterocyclic group. The compound described in item 1 of the scope of patent application, wherein R ₁ to R ₄ are hydrogen. The compound described in item 1 of the scope of patent application, wherein the compound represented by Chemical Formula 1 is any one selected from the following structural formulae:

An organic electronic component, comprising: a first electrode; a second electrode arranged to face the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, One or more of the organic material layers contains the compound described in any one of items 1 to 6 in the scope of the patent application. The organic electronic device according to claim 7, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound. The organic electronic device according to the seventh item of the patent application, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound. The organic electronic element according to the seventh item of the patent application, wherein the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer contains the compound. The organic electronic device described in item 7 of the scope of patent application further includes: one layer or two or more layers selected from the group consisting of: hole injection layer, hole transport layer, electron transport layer, electron Injection layer, electron blocking layer and hole blocking layer. The organic electronic component according to item 9 of the scope of patent application, wherein the organic electronic component is selected from the group consisting of organic light-emitting components, organic phosphorescent components, organic solar cells, organic photoconductors (OPC) and organic transistors . The organic electronic element according to the seventh item of the patent application, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains a compound represented by the following chemical formula A-1: [Chemical formula A-1]

In the chemical formula A-1, m is 1 or an integer greater than 1, and Ar3 is a substituted or unsubstituted monovalent or higher valence benzol; substituted or unsubstituted monovalent or higher fluoranthene group ; Substituted or unsubstituted monovalent or higher pyrene group; or substituted or unsubstituted monovalent or higher

Group, L1 is a direct bond; substituted or unsubstituted arylene group; or substituted or unsubstituted heteroaryl group, Ar4 and Ar5 are the same or different from each other, and are each independently substituted or unsubstituted Aryl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted arylalkyl group; or substituted or unsubstituted heterocyclic group; or each other Combine to form a substituted or unsubstituted ring, and when m is 2 or greater than 2, two or more structures in the parentheses are the same or different from each other, wherein the substituted or unsubstituted is selected from deuterium , Halogen group, cyano group, nitro group, hydroxyl group, alkyl group, alkenyl group, alkoxy group, cycloalkyl group, amino group, aryl group, and heterocyclic group consisting of one substituent or two or more The substituent is substituted by a substituent to which two or more substituents in the substituent are attached, or it has no substituent. The organic electronic device described in item 13 of the scope of patent application, wherein L1 is a direct bond, Ar3 is a divalent pyrene group, and Ar4 and Ar5 are the same or different from each other, and are each independently unsubstituted or substituted by an alkyl group The silyl substituted aryl group of, and m is 2. The organic electronic element according to the seventh item of the scope of patent application, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains a compound represented by the following chemical formula A-2:

In the chemical formula A-2, Ar6 and Ar7 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group, and G1 to G8 are each other The same or different, and each independently is hydrogen; substituted or unsubstituted monocyclic aryl; or substituted or unsubstituted polycyclic aryl, wherein the substituted or unsubstituted is selected from deuterium , Halogen, cyano, nitro, hydroxy, alkyl, alkenyl, alkoxy, cycloalkyl, amino, aryl, and heterocyclic group consisting of one substituent or two or more The substituent is substituted by a substituent to which two or more substituents in the substituent are attached, or it has no substituent. The organic electronic device described in item 15 of the scope of patent application, wherein Ar6 and Ar7 are 1-naphthyl groups, and G1 to G8 are hydrogen. The organic electronic device as described in item 13 of the scope of patent application, wherein the light-emitting layer contains a compound represented by the following chemical formula A-2:

In the chemical formula A-2, Ar6 and Ar7 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group, and G1 to G8 are each other The same or different, and each independently is hydrogen; substituted or unsubstituted monocyclic aryl; or substituted or unsubstituted polycyclic aryl, wherein the substituted or unsubstituted is selected from deuterium , Halogen group, cyano group, nitro group, hydroxyl group, alkyl group, alkenyl group, alkoxy group, cycloalkyl group, amino group, aryl group, and heterocyclic group consisting of one substituent or two or more Substituent substitution is substituted by a substituent to which two or more substituents in the substituent are attached, or there is no substituent therein.

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