JP2019501120A - Compound and organic electronic device containing the same - Google Patents

Abstract

  The present specification relates to a compound represented by Chemical Formula 1 and an organic electronic device including the compound.

Description

  This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0037220 filed with the Korean Patent Office on March 28, 2016, the entire contents of which are incorporated herein.

  The present specification relates to a compound and an organic electronic device including the compound.

  A typical example of an organic electronic device is an organic light emitting device. In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting device utilizing an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer often has a multilayer structure composed of different materials, for example, a hole injection layer, a hole transport layer, a light emitting layer. , An electron transport layer, an electron injection layer, and the like. In such an organic light emitting device structure, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. Excitons are formed and emit light when the excitons fall back to the ground state.

  Development of new materials for the organic light emitting device as described above continues to be required.

  The present specification provides a compound and an organic electronic device including the compound.

前記化学式１において、
Ｑは、炭素数１０〜３０の縮合多環芳香族基；または単環もしくは多環のヘテロ環基であり、
Ｌ_１およびＬ_２は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基であり、
Ａｒ_１およびＡｒ_２は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
Ｒ_１〜Ｒ_３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；シアノ基；置換もしくは非置換のアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
ａは、１〜４の整数であり、
ｂは、１〜４の整数であり、
ｃは、１〜４の整数であり、
ａが２以上の場合、２以上のＲ_１は、互いに同一または異なり、
ｂが２以上の場合、２以上のＲ_２は、互いに同一または異なり、
ｃが２以上の場合、２以上のＲ_３は、互いに同一または異なる。 The present specification provides a compound represented by Formula 1 below.

In Formula 1,
Q is a condensed polycyclic aromatic group having 10 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group;
L ₁ and L ₂ are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group And
R _{1 to} R ₃ are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; An aryl group,
a is an integer of 1 to 4,
b is an integer of 1 to 4,
c is an integer of 1 to 4,
when a is 2 or more, two or more R _{1 s} are the same or different from each other;
when b is 2 or more, two or more R _{2 s} are the same or different from each other;
When c is 2 or more, two or more R _{3 s} are the same or different from each other.

  In addition, the present specification describes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode. An organic electronic device including at least one of the organic layers includes the aforementioned compound.

  The compound according to an embodiment of the present specification is used in an organic electric element including an organic light emitting element, thereby reducing the driving voltage of the organic electric element, improving the light efficiency, and thermal stability of the compound. Thus, the lifetime characteristics of the element can be improved.

1 shows an organic electronic device 10 according to an embodiment of the present specification. 1 shows an organic electronic device 11 according to another embodiment of the present specification.

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

  The present specification provides a compound represented by Formula 1.

  The compound of Formula 1 may have characteristics suitable for use in an organic material layer used in an organic light emitting device by introducing various substituents into the core structure. Specifically, it is as follows.

  In the present specification, examples of the substituent are described below, but are not limited thereto.

は、連結される部位を意味する。 In this specification,

Means the site | part connected.

  The term “substituted” means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substituted position is the position where the hydrogen atom is substituted, that is, the substituent can be substituted. The position is not limited, 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” refers to deuterium, halogen group, cyano group, nitro group, hydroxy group, carbonyl group, ester group, imide group, amino group, alkyl group, cycloalkyl group, An alkenyl group; an amine group; an aryl phosphine group; a phosphine oxide group; an aryl group; a silyl group; and a heterocyclic group containing one or more of N, O, S, Se, and Si atoms. Means substituted with one or more substituents, or two or more of the exemplified substituents are substituted with linked substituents, or have no substituents. To do.

  In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but one having 1 to 50 is preferable. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl. , Isopentyl, neopentyl, tert-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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- Propyl, 1,1-dimethyl-propyl, iso Hexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl there are such as, but not limited to.

  In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, Examples include, but are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

  In the present specification, when the aryl group is a monocyclic aryl group, the carbon number is not particularly limited, but those having 6 to 30 carbon atoms are preferable. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, or the like, but is not limited thereto.

  When the aryl group is a polycyclic aryl group, the carbon number is not particularly limited, but those having 6 to 30 carbon atoms are preferable. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrycenyl group, fluorenyl group, or the like, but is not limited thereto.

  In the present specification, the fluorenyl group may be substituted, or adjacent substituents may be bonded to each other to form a ring.

、

、

、

、

、

などになってもよいが、これらに限定されるものではない。 When the fluorenyl group is substituted,

,

,

,

,

,

However, it is not limited to these.

  In the present specification, a heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the number of carbon atoms is not particularly limited. 50 is preferred. Examples of heteroaryl groups include thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, triazole groups, pyridyl groups, bipyridyl groups, pyrimidyl groups, triazine groups, triazole groups, and acridyl groups. Group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole Group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, o Sajiazoriru group, thiadiazolyl group, benzothiazolyl group, and the like dibenzofuranyl group, but is not limited to only these.

  In the present specification, the heterocycle may be selected from the above-mentioned examples of the cycloalkyl group, aryl group, or heteroaryl group, except that it is a monovalent group, monocyclic or polycyclic, It may be aliphatic or aromatic, or a condensed form thereof, but is not limited thereto.

  In the present specification, the aromatic ring group may be monocyclic or polycyclic, and may be selected from the examples of the aryl group except that it is not monovalent.

  In the present specification, the condensed polycyclic aromatic group means an aromatic hydrocarbon ring, and examples thereof include, but are not limited to, naphthylene, anthracene, phenanthrene, and pyrene.

  In the present specification, a monocyclic or polycyclic heterocyclic group means a ring containing one or more of N, O, or S atoms as a heteroatom. For example, pyridine, pyrimidine, pyridazine, triazine , Pyran, thiopyran, diazine, or pyrazine, which may be selected from the examples of the heteroaryl group, but is not limited thereto.

  In the present specification, an arylene group means an aryl group having two bonding positions, that is, a divalent group. Except for these being each a divalent group, the above description of the aryl group is applicable.

  In the present specification, the heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. Except for these being a divalent group, the above description of the heteroaryl group is applicable.

  In one embodiment of the present specification, Q is a condensed polycyclic aromatic group having 10 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group.

  In one embodiment herein, Q is substituted or unsubstituted naphthylene.

  In one embodiment of the present specification, Q is substituted or unsubstituted phenanthrene.

  In one embodiment herein, Q is naphthylene.

  In one embodiment herein, Q is phenanthrene.

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L ₁ and L ₂ are substituted or unsubstituted phenylene groups.

In one embodiment of the present specification, L ₁ and L ₂ are phenylene groups.

In one embodiment of the present specification, L ₁ and L ₂ are substituted or unsubstituted biphenylene groups.

In one embodiment of the present specification, L ₁ and L ₂ are biphenylene groups.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted N-containing heteroaryl group It is.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 10 to 30 carbon atoms; or substituted or unsubstituted N is 3 or less. It is a heteroaryl group containing.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each independently an aryl group having 10 to 30 carbon atoms; or a heterogeneous group containing 3 or less N substituted or unsubstituted with an aryl group An aryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted Or it is an unsubstituted triphenylene group or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents an aryl group-substituted or unsubstituted pyridine group, an aryl group-substituted or unsubstituted pyrimidine group, or an aryl group. A substituted or unsubstituted triazine group, a triphenylene group, or a carbazole group;

In one embodiment of the present specification, Ar ₁ is a pyridine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyridine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyridine group.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a triazine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a triazine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₁ is a carbazole group.

In another embodiment, Ar ₁ is a triphenylene group.

In one embodiment of the present specification, Ar ₂ is a pyridine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyridine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyridine group.

In one embodiment of the present specification, Ar ₂ is a pyrimidine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyrimidine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a triazine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a triazine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₂ is a carbazole group.

In another embodiment, Ar ₂ is a triphenylene group.

In one embodiment of the present specification, R _{1 to} R ₃ are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl. A group; or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R _{1 to} R ₃ are the same or different from each other and are each independently hydrogen.

前記化学式１−Ａおよび１−Ｂにおいて、
Ｑ、Ｌ_１、Ｌ_２、Ａｒ_２、Ｒ_１〜Ｒ_３、およびａ〜ｃに関する定義は、前記化学式１で定義したものと同じであり、
Ｘ_１〜Ｘ_３のうちの少なくとも１つは、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
Ｘ_４〜Ｘ_６のうちの少なくとも１つは、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
Ａｒ_３〜Ａｒ_６は、互いに同一または異なり、それぞれ独立に、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基である。 In an embodiment of the present specification, the Chemical Formula 1 may be represented by the following Chemical Formula 1-A or 1-B.

In the chemical formulas 1-A and 1-B,
The definitions for Q, L ₁ , L ₂ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Formula 1.
At least one of X _{1 to} X ₃ is N, and the rest are the same or different from each other, each independently N or CR;
At least one of X _{4 to} X ₆ is N, and the rest are the same or different from each other, each independently N or CR;
Ar _{3 to} Ar ₆ are the same or different from each other, and each independently represents hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Of the heteroaryl group.

In one embodiment of the present specification, Ar _{3 to} Ar ₆ are the same or different from each other and are each independently hydrogen; or a substituted or unsubstituted aryl group.

In another embodiment, Ar _{3 to} Ar ₆ are the same or different from each other and are each independently hydrogen; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In still another embodiment, Ar _{3 to} Ar ₆ are the same or different from each other and are each independently hydrogen; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In still another embodiment, Ar _{3 to} Ar ₆ are the same or different from each other and are each independently hydrogen; or an aryl group having 6 to 30 carbon atoms.

In yet another embodiment, Ar _{3 to} Ar ₆ are the same or different from each other and are each independently hydrogen; or a phenyl group.

  In one embodiment of the present specification, R is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

  In other embodiments, R is hydrogen.

前記化学式２〜５において、
Ｌ_１、Ｌ_２、Ａｒ_１、Ａｒ_２、Ｒ_１〜Ｒ_３、およびａ〜ｃに関する定義は、前記化学式１で定義したものと同じであり、
Ｒ_４およびＲ_５は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；シアノ基；置換もしくは非置換のアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
ｄは、１〜６の整数であり、
ｅは、１〜８の整数であり、
ｄが２以上の場合、２以上のＲ_４は、互いに同一または異なり、
ｅが２以上の場合、２以上のＲ_５は、互いに同一または異なる。 In an embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 2 to 5.

In the chemical formulas 2 to 5,
The definitions for L ₁ , L ₂ , Ar ₁ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Formula 1.
R ₄ and R ₅ are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; An aryl group,
d is an integer of 1 to 6;
e is an integer from 1 to 8,
when d is 2 or more, two or more R _{4 s} are the same or different from each other;
When e is 2 or more, two or more R _{5 s} are the same or different from each other.

In one embodiment of the present specification, R ₄ and R ₅ are the same or different from each other and are each independently hydrogen.

According to one embodiment of the present specification, the compound of Formula 1 may be any one selected from the following structural formulas.

  The compound which concerns on one embodiment of this specification can be manufactured with the manufacturing method mentioned later. In the production examples to be described later, representative examples are described, but substituents may be added or removed as necessary, and the positions of the substituents may be changed. In addition, starting materials, reactants, reaction conditions, etc. may be altered based on techniques known in the art.

  The present specification also provides an organic electronic device including the aforementioned compound.

  In one embodiment of the present specification, the first electrode, the second electrode provided to face the first electrode, and one or more layers provided between the first electrode and the second electrode An organic electronic device including an organic material layer, wherein at least one of the organic material layers includes the compound.

  In this specification, when a member is located “on” another member, this is not only when the member is in contact with the other member, but also between the two members. This includes cases where members are present.

  In this specification, when a part “includes” a component, this means that the component can further include other components, unless otherwise stated, unless otherwise stated. To do.

  The organic material layer of the organic electronic device of the present specification may have a single layer structure, but may also have a multilayer structure in which two or more organic material layers are laminated. 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, and the like as an organic material layer. it can. However, the structure of the organic electronic device is not limited to this, and may include a smaller number of organic layers.

  According to one embodiment of the present specification, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoreceptor (OPC), and an organic transistor.

  Hereinafter, an organic light emitting device will be exemplified.

  In one embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

  In another embodiment, the organic layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes the compound.

  The host material includes 50 wt% to 99 wt%, preferably 60 wt% to 95 wt%, more preferably 80 wt% to 90 wt%, based on the entire light emitting layer material.

  In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer includes the compound.

  In one embodiment of the present specification, 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 one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.

  In one embodiment of the present specification, the organic light emitting device is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. It further includes one layer or two or more layers.

  The organic layer containing the compound contains the compound as a host and can be used together with an iridium-based (Ir) dopant.

  In one embodiment of the present specification, the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and a gap between the first electrode and the second electrode. And two or more organic layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and the two or more organic materials. At least one of the layers includes the compound. In one embodiment of the present specification, the two or more organic layers are selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, and a hole blocking layer. May be.

  In one 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. Specifically, in one embodiment of the present specification, the compound may be included in one of the two or more electron transport layers, or included in each of the two or more electron transport layers. May be.

  In one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, the other materials except the compound may be the same as or different from each other.

  In one embodiment of the present specification, the organic layer includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic layer including the compound. Further included.

  In another embodiment, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

  When the organic material layer containing the compound of Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. According to an example, the electron transport layer including the compound of Formula 1 may further include LiQ.

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

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

  FIG. 1 illustrates the structure of the organic light emitting device 10 in which the first electrode 30, the light emitting layer 40, and the second electrode 50 are sequentially stacked on the substrate 20. FIG. 1 is an exemplary structure of an organic light emitting device according to an embodiment of the present specification, and may further include another organic material layer.

  In FIG. 2, the first electrode 30, the hole injection layer 60, the hole transport layer 70, the electron blocking layer 80, the light emitting layer 40, the electron transport layer 90, the electron injection layer 100, and the second electrode 50 are formed on the substrate 20. The structure of an organic light emitting device in which are sequentially stacked is illustrated. FIG. 2 is an exemplary structure according to an embodiment of the present specification, and may further include another organic material layer.

  The organic light-emitting device of the present specification can be manufactured by materials and methods known in the art except that one or more of the organic layers contain the compound of the present specification, that is, the compound.

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

  The organic light emitting device of the present specification is a material and method known in the art, except that one or more of the organic layers includes the compound, that is, the compound represented by Formula 1. Can be manufactured.

  For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or conductive metal oxide on the substrate or an alloy thereof using a PVD (Physical Vapor Deposition) method such as sputtering or electron beam evaporation (e-beam evaporation). After forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, a material that can be used as a cathode is deposited thereon. Can be manufactured. In addition to this method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

  In addition, the compound of Formula 1 is formed on the 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 means spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

  In addition to this method, an organic light emitting device can also be produced by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited to this.

  In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

  In another embodiment, the first electrode is a cathode and the second electrode is an anode.

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

In general, the cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF / Al or LiO ₂ / Al However, the present invention is not limited to these materials.

  The hole injecting material is a layer that injects holes from the electrode, and the hole injecting material has the ability to transport holes, and the hole injecting effect from the anode, the light emitting layer or the light emitting material A compound having an excellent hole injection effect, preventing the excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and having an excellent thin film forming ability is preferable. It is preferable that the HOMO of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine organic material, hexanitrile hexaazatriphenylene organic material, quinacridone organic material, perylene organic material, Examples include, but are not limited to, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

  The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and as a hole transport material, receives holes from the anode or the hole injection layer to the light emitting layer. A substance that can be transferred and has high mobility for holes is preferable. Specific examples include, but are not limited to, arylamine organic materials, conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion.

  The electron blocking layer is a layer that can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer and improve the lifetime and efficiency of the device, if necessary. In addition, a known material is used to form an appropriate portion between the light emitting layer and the electron injection layer.

The light-emitting substance of the light-emitting layer is a substance that can emit light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and has quantum efficiency for fluorescence and phosphorescence. Good materials are preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzthiazole, And benzimidazole compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

  The light emitting layer may include a host material and a dopant material. Examples of the host material include a condensed aromatic ring derivative or a heterocycle-containing compound. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include compounds, dibenzofuran derivatives, and ladder-type furan compounds. , Pyrimidine derivatives and the like, but not limited thereto.

  Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, pefuranthene having an arylamino group, and a styrylamine compound. Is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and is 1 or 2 from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group The substituent selected above is substituted or unsubstituted. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer, and the electron transport material is a material that can be well injected and transferred to the light emitting layer from the cathode. Thus, a substance having a high mobility for electrons is preferable. Specific examples include 8-hydroxyquinoline Al complex; complexes including Alq _3; organic radical compounds; hydroxy flavone - there are metal complexes, but are not limited to only these. The electron transport layer can be used with any desired cathode material, as used by the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

  The electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, and has an excellent electron injection effect for a light emitting layer or a light emitting material. It is preferable to use a compound that prevents the exciton generated in step 1 from moving to the hole injection layer and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and their derivatives, metal complex compounds, And nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

  Examples of the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8 -Hydroxyquinolinate) 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-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-Naphtalato) aluminum, bis (2-methyl-8) Quinolinate) (2-naphtholato) there are such as gallium, and the like.

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

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

  In one embodiment of the present specification, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

  The compound according to the present specification can act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor.

  Hereinafter, the present specification will be described in detail with reference to examples. However, the examples according to the present specification can be modified in various different forms, and the scope of the present specification is not construed to be limited to the examples described in detail below. The examples herein are provided to more fully explain the present specification to those skilled in the art.

  <Example>

<Synthesis Example 1> -Production of Compound Represented by Intermediate 1

(1) Production of Chemical Formula 1B Under a nitrogen atmosphere, (4-chlorophenyl) (4-hydroxyphenyl) methanone (Compound 1A, 100.0 g, 429.81 mmol) was added to 1000 ml of acetonitrile, and potassium carbonate (118 .8 g, 859.62 mmol) was added to 500 ml of water. After this, 1-butanesulfonyl fluoride (194.8 g, 644.72 mmol) was slowly added while heating in a water bath. Thereafter, the reaction was terminated after the reaction proceeded for about 1 hour. After the completion of the reaction, the temperature was lowered to room temperature, the aqueous layer and the organic layer were separated, and the organic layer was distilled under reduced pressure to produce Compound 1B (210 g, 95%).

(2) Production of Chemical Formula 1C In a nitrogen atmosphere, the compound 1B (210.2 g, 408.36 mmol), bis (pinacolato) diboron (103.7 g, 408.36 mmol), and potassium acetate (120.2 g, 1225.08 mmol) ) Were added to 1000 ml of tetrahydrofuran (THF) and heated with stirring. In a refluxing state, [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (1.8 g, 2.45 mmol) was added, and the mixture was heated and stirred for 24 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with ethanol produced Compound 1C (100.0 g, 72%).

(3) Preparation of Intermediate 1 Under a nitrogen atmosphere, Compound 1C (39.0 g, 145.67 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (Compound 1D, 50.0 g, 145.67 mmol) was placed in 300 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (60.4 g, 437.02 mmol) was dissolved in 200 ml of water and charged, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (5.0 g, 4.37 mmol) was added. After reacting for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to produce Intermediate 1 (52.2 g, 80%).

化合物２Ａ（３０．０ｇ、１０５．９４ｍｍｏｌ）を無水テトラヒドロフラン５００ｍｌに入れて、−７８℃に冷却した。この後、撹拌しながらｎ−ブチルリチウム（５０．９ｍＬ、１２７．１３ｍｍｏｌ）を３０分かけてゆっくり滴加した後、１時間反応した。この後、前記中間体１（２８．５ｇ、６３．５７）を固体状態で投入し、ゆっくり常温に昇温して４時間反応した。反応後、水を注いで反応終結後、水層と有機層とを分離した後、有機層は減圧蒸留して化合物２Ｂを得た。これを再び酢酸５００ｍｌに入れて撹拌しながら硫酸を１〜２滴触媒として投入した後、還流した。２時間反応した後、生成された固体を濾過し、濾過物を再びクロロホルムに溶かした後、カルシウムカーボネートで飽和した水を用いて中和および抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エタノールを用いて再結晶した。生成された固体を濾過後、乾燥して、中間体２（２６．２ｇ、６５％）を製造した。 <Synthesis Example 2> -Production of Compound Represented by Intermediate 2

Compound 2A (30.0 g, 105.94 mmol) was placed in 500 ml of anhydrous tetrahydrofuran and cooled to -78 ° C. Thereafter, n-butyllithium (50.9 mL, 127.13 mmol) was slowly added dropwise over 30 minutes with stirring, followed by reaction for 1 hour. Then, the said intermediate body 1 (28.5g, 63.57) was thrown in in the solid state, and it heated up to normal temperature slowly, and was reacted for 4 hours. After the reaction, water was poured to terminate the reaction, and after separating the aqueous layer and the organic layer, the organic layer was distilled under reduced pressure to obtain Compound 2B. This was again put into 500 ml of acetic acid, and while stirring, sulfuric acid was added as 1 to 2 drops catalyst, and then refluxed. After reacting for 2 hours, the produced solid was filtered, and the filtrate was dissolved again in chloroform, neutralized and extracted with water saturated with calcium carbonate, and then the organic layer was dried with magnesium sulfate. . Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethanol. The resulting solid was filtered and dried to produce Intermediate 2 (26.2 g, 65%).

窒素雰囲気下、前記中間体２（１０．０ｇ、１５．７７ｍｍｏｌ）とカルバゾール（化合物３Ａ、３．２ｇ、１８．９２ｍｍｏｌ）、ソジウムｔ−ブトキシド（１．８ｇ、１８．９２ｍｍｏｌ）をキシレン１００ｍｌに入れて、撹拌および還流した。この後、ビス（トリ−タートブチルホスフィン）パラジウム（０．２ｇ、０．４７ｍｍｏｌ）を投入した。８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物１（８．４ｇ、７１％）を製造した。 <Synthesis Example 3> -Production of Compound Represented by Compound 1

In a nitrogen atmosphere, the intermediate 2 (10.0 g, 15.77 mmol), carbazole (compound 3A, 3.2 g, 18.92 mmol) and sodium t-butoxide (1.8 g, 18.92 mmol) were placed in 100 ml of xylene. And stirred and refluxed. Thereafter, bis (tri-tertbutylphosphine) palladium (0.2 g, 0.47 mmol) was added. After reacting for 8 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The produced solid was filtered and dried to produce Compound 1 (8.4 g, 71%).

  MS: [M + H] + = 764

窒素雰囲気下、前記中間体２（１０．０ｇ、１５．７７ｍｍｏｌ）と化合物４Ａ（６．７ｇ、１８．９２ｍｍｏｌ）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ポタシウムホスフェート（１０．０ｇ、４７．３１ｍｍｏｌ）を水５０ｍｌに溶かして投入した後、十分に撹拌後、ビス（ジベンジリデンアセトン）パラジウム（０．３ｇ、０．４７ｍｍｏｌ）とトリシクロヘキシルホスフィン（０．３ｍｇ、０．９５ｍｍｏｌ）を投入した。１８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物２（８．３ｇ、６４％）を製造した。 <Synthesis Example 4> -Production of Compound Represented by Compound 2

Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 15.77 mmol) and Compound 4A (6.7 g, 18.92 mmol) were placed in 200 ml of 1,4-dioxane and stirred and refluxed. After this, potassium phosphate (10.0 g, 47.31 mmol) was dissolved in 50 ml of water and charged, and after sufficient stirring, bis (dibenzylideneacetone) palladium (0.3 g, 0.47 mmol) and tricyclohexylphosphine ( 0.3 mg, 0.95 mmol) was added. After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The produced solid was filtered and dried to produce Compound 2 (8.3 g, 64%).

  MS: [M + H] + = 826

窒素雰囲気下、前記中間体２（１０．０ｇ、１５．７７ｍｍｏｌ）と化合物５Ａ（３．８ｇ、１８．９２ｍｍｏｌ）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ポタシウムホスフェート（１０．０ｇ、４７．３１ｍｍｏｌ）を水５０ｍｌに溶かして投入した後、十分に撹拌後、ビス（ジベンジリデンアセトン）パラジウム（０．３ｇ、０．４７ｍｍｏｌ）とトリシクロヘキシルホスフィン（０．３ｍｇ、０．９５ｍｍｏｌ）を投入した。１８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物３（７．９ｇ、６７％）を製造した。 <Synthesis Example 5> -Production of Compound Represented by Compound 3

Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 15.77 mmol) and Compound 5A (3.8 g, 18.92 mmol) were placed in 200 ml of 1,4-dioxane and stirred and refluxed. After this, potassium phosphate (10.0 g, 47.31 mmol) was dissolved in 50 ml of water and charged, and after sufficient stirring, bis (dibenzylideneacetone) palladium (0.3 g, 0.47 mmol) and tricyclohexylphosphine ( 0.3 mg, 0.95 mmol) was added. After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The produced solid was filtered and dried to produce Compound 3 (7.9 g, 67%).

  MS: [M + H] + = 752.

  <Synthesis Example 6> -Production of Compound Represented by Compound 4

窒素雰囲気下、中間体２（３０．０ｇ、４７．３１ｍｍｏｌ）、ビス（ピナコラト）ジボロン（化合物６Ａ、１３．２ｇ，５２．０４ｍｍｏｌ）、および酢酸カリウム（１３．９ｇ、１４１．９２ｍｍｏｌ）を混合し、テトラヒドロフラン（ＴＨＦ）１００ｍｌに添加し、撹拌しながら加熱した。還流する状態で、［１，１'−ビス（ジフェニルホスフィノ）フェロセン］ジクロロパラジウム（ＩＩ）（０．８ｇ、１．４２ｍｍｏｌ）とトリ（シクロヘキシル）ホスフィン（０．８ｇ、２．８４ｍｍｌ）を入れて、２４時間加熱および撹拌した。反応終了後、常温に温度を下げた後、濾過した。濾液に水を注いでクロロホルムで抽出し、有機層を無水硫酸マグネシウムで乾燥した。減圧蒸留後、エタノールで再結晶して、中間体３（２６．４ｇ、７７％）を製造した。 (1) Production of intermediate 3

Intermediate 2 (30.0 g, 47.31 mmol), bis (pinacolato) diboron (compound 6A, 13.2 g, 52.04 mmol), and potassium acetate (13.9 g, 141.92 mmol) were mixed under a nitrogen atmosphere. , Added to 100 ml of tetrahydrofuran (THF) and heated with stirring. Under reflux, [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (0.8 g, 1.42 mmol) and tri (cyclohexyl) phosphine (0.8 g, 2.84 ml) were added. And heated and stirred for 24 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with ethanol produced Intermediate 3 (26.4 g, 77%).

窒素雰囲気下、前記化合物６Ｂ（５．０ｇ、１８．７５ｍｍｏｌ）と前記中間体３（１５．０ｇ、２０．６２ｍｍｏｌ）をテトラヒドロフラン１５０ｍｌに入れて、撹拌および還流した。この後、ポタシウムカーボネート（７．８ｇ、５６．２４ｍｍｏｌ）を２００ｍｌの水に溶かして投入した後、十分に撹拌後、テトラキストリフェニル−ホスフィノパラジウム（０．６ｇ、０．５６ｍｍｏｌ）を投入した。６時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物４（９．０ｇ、５５％）を製造した。 (2) Production of compound 4

Under a nitrogen atmosphere, Compound 6B (5.0 g, 18.75 mmol) and Intermediate 3 (15.0 g, 20.62 mmol) were placed in 150 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (7.8 g, 56.24 mmol) was dissolved in 200 ml of water and charged, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (0.6 g, 0.56 mmol) was added. After reacting for 6 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The produced solid was filtered and dried to produce Compound 4 (9.0 g, 55%).

  MS: [M + H] + = 830

窒素雰囲気下、化合物７Ａ（５．０ｇ、１８．７５ｍｍｏｌ）と中間体３（１５．０ｇ、２０．６２ｍｍｏｌ）をテトラヒドロフラン１５０ｍｌに入れて、撹拌および還流した。この後、ポタシウムカーボネート（７．８ｇ、５６．２４ｍｍｏｌ）を２００ｍｌの水に溶かして投入した後、十分に撹拌後、テトラキストリフェニル−ホスフィノパラジウム（０．６ｇ、０．５６ｍｍｏｌ）を投入した。６時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物５（６．８ｇ、４４％）を製造した。 <Synthesis Example 7> -Production of Compound Represented by Compound 5

Under a nitrogen atmosphere, Compound 7A (5.0 g, 18.75 mmol) and Intermediate 3 (15.0 g, 20.62 mmol) were placed in 150 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (7.8 g, 56.24 mmol) was dissolved in 200 ml of water and charged, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (0.6 g, 0.56 mmol) was added. After reacting for 6 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The produced solid was filtered and dried to produce Compound 5 (6.8 g, 44%).

  MS: [M + H] + = 831

  <Example>

<Experimental Example 1-1>
A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1000 mm was placed in distilled water in which a dispersant was dissolved and ultrasonically cleaned. The detergent is Fischer Co. The distilled water is Millipore Co. Distilled water that was secondarily filtered through a product filter was used. After washing ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

  On the ITO transparent electrode thus prepared, a hexanitrile hexaazatriphenylene group was thermally vacuum deposited to a thickness of 500 mm to form a hole injection layer. On top of that, HT1 (400Å), which is a substance that transports holes, was vacuum-deposited, and then a host H1 and a dopant D1 compound were vacuum-deposited to a thickness of 300Å as a light emitting layer. On the light emitting layer, the compound 1 prepared in Synthesis Example 3 and LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 350 mm. On the electron injecting and transporting layer, lithium fluoride (LiF) having a thickness of 12 mm and aluminum having a thickness of 2,000 mm were sequentially deposited to form a cathode.

In the above process, the deposition rate of the organic substance is maintained at 0.4 to 0.7 liter / sec, the cathode lithium fluoride is maintained at 0.3 liter / sec, and the aluminum deposition rate is 2 liter / sec. The degree was maintained at 2 × 10 ^{−7 to} 5 × 10 ⁻⁶ torr to fabricate an organic light emitting device.

<Experimental example 1-2>
An organic light emitting device was produced in the same manner as in Experimental Example 1-1 except that Compound 2 was used instead of Compound 1 as the electron transport layer in Experimental Example 1-1.

<Experimental Example 1-3>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that Compound 3 was used instead of Compound 1 as the electron transport layer in Experimental Example 1-1.

<Experimental Example 1-4>
An organic light emitting device was produced in the same manner as in Experimental Example 1-1 except that Compound 4 was used instead of Compound 1 as the electron transport layer in Experimental Example 1-1.

<Experimental Example 1-5>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that Compound 5 was used instead of Compound 1 as the electron transport layer in Experimental Example 1-1.

<Experimental example 2-1>
A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,500 mm was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, a Fischer Co. product was used as the detergent, and distilled water secondarily filtered with a filter of Millipore Co. product was used as distilled water. After washing ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After cleaning with distilled water, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, and methanol was performed, followed by drying, and then transported to a plasma cleaning machine. In addition, the substrate was cleaned for 5 minutes using oxygen plasma, and then the substrate was transported to a vacuum deposition machine.

On the ITO transparent electrode prepared in this way, hexanitrile hexaazatriphenylene (HAT) having the following chemical formula was thermally vacuum deposited to a thickness of 500 mm to form a hole injection layer.

On the hole injection layer, 400 n of NPB (N, N-Bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1-biphenyl) -4,4-diamine) compound having the following structure is formed. The hole transport layer was formed by thermal vacuum deposition to a thickness of.

Next, on the hole transport layer, the compound 1 manufactured in Synthesis Example 3 with a thickness of 300 mm was used as a host, and vacuum deposition was performed with 10 wt% of Ir (ppy) ₃ dopant to form a light emitting layer. . On the light emitting layer, the following electron transport material was vacuum deposited to a thickness of 200 mm to form an electron injection and transport layer.

  On the electron injecting and transporting layer, lithium fluoride (LiF) having a thickness of 12 mm and aluminum having a thickness of 2,000 mm were sequentially deposited to form a cathode.

In the above process, the deposition rate of the organic substance is maintained at 0.4 to 0.7 liter / sec, the cathode lithium fluoride is maintained at 0.3 liter / sec, and the aluminum deposition rate is 2 liter / sec. The degree was maintained at 2 × 10 ^{−7 to} 5 × 10 ⁻⁸ torr to fabricate an organic light emitting device.

<Experimental example 2-2>
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 2 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

<Experimental Example 2-3>
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 3 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

<Experimental Example 2-4>
An organic light emitting device was produced in the same manner as in Experimental Example 2-1, except that Compound 4 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

<Experimental Example 2-5>
An organic light emitting device was produced in the same manner as in Experimental Example 2-1, except that Compound 5 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

<Comparative Example 1-1>
An organic light emitting device was produced in the same manner as in Experimental Example 1-1 except that the following compound of ET1 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-2>
An organic light emitting device was produced in the same manner as in Experimental Example 1-1 except that the following compound of ET2 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-3>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the following compound of ET3 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-4>
An organic light emitting device was produced in the same manner as in Experimental Example 1-1 except that the following compound of ET4 was used instead of Compound 1 in Experimental Example 1-1.

前記実験例１−１〜１−５および比較例１−１〜比較例１−５のようにそれぞれの化合物を電子注入および輸送層物質として用いて製造した有機発光素子を、１０ｍＡ／ｃｍ^２の電流密度で駆動電圧と発光効率を測定し、２０ｍＡ／ｃｍ^２の電流密度で初期輝度対比９８％になる時間（ＬＴ_９８）を測定した。その結果を下記表１に示した。 <Comparative Example 1-5>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the following compound of ET5 was used instead of Compound 1 in Experimental Example 1-1.

Organic light-emitting devices manufactured using the respective compounds as electron injection and transport layer materials as in Experimental Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-5 are 10 mA / cm ² . The driving voltage and the light emission efficiency were measured by the current density, and the time (LT ₉₈ ) when the current density was 20 mA / cm ² was 98% relative to the initial luminance was measured. The results are shown in Table 1 below.

<Comparative Example 2-1>
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that the following compound EM2 was used instead of Compound 1 in Experimental Example 2-1.

<Comparative Example 2-2>
An organic light emitting device was produced in the same manner as in Experimental Example 2-1, except that the following compound of ET3 was used instead of Compound 1 in Experimental Example 2-1.

<Comparative Example 2-3>
An organic light emitting device was produced in the same manner as in Experimental Example 2-1, except that the following compound of ET4 was used instead of Compound 1 in Experimental Example 2-1.

<Comparative Example 2-4>
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that the following compound of ET6 was used instead of Compound 1 in Experimental Example 2-1.

An organic light emitting device manufactured using each compound as a light emitting layer material as in Experimental Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-4 was driven at a current density of 10 mA / cm ^2. And the luminous efficiency was measured, and the time (LT ₉₈ ) when the initial luminance was 98% at a current density of 20 mA / cm ² was measured. The results are shown in Table 1 below.

As is apparent from Table 1, in the case of an organic light emitting device manufactured using the compound of the present specification as an electron transport layer material, the structure is similar to that of the compounds 1, 2 and 5, but each is condensed. It can be seen that, compared with ET3 to ET5 which are compounds having no structure, excellent characteristics are exhibited from the viewpoints of efficiency and lifetime. Moreover, it turns out that Experimental example 1-1 to 1-5 are excellent in current efficiency compared with the comparative example 1-1 which does not have the core structure of this application.
Moreover, it turns out that the organic light emitting element manufactured using the compound of this-application specification as a light emitting layer substance also shows the characteristic outstanding in the lifetime especially compared with the substance of Comparative Examples 2-1 to 2-4.

  Although the preferred embodiments of the present invention have been described above, the present invention is not limited to these embodiments, and various modifications can be made within the scope of the claims and the detailed description of the invention. Yes, this also belongs to the category of the present invention.

DESCRIPTION OF SYMBOLS 10, 11: Organic light emitting element 20: Substrate 30: 1st electrode 40: Light emitting layer 50: 2nd electrode 60: Hole injection layer 70: Hole transport layer 80: Electron blocking layer 90: Electron transport layer 100: Electron injection layer

Claims (12)

Compound represented by the following chemical formula 1:

In Formula 1,
Q is a condensed polycyclic aromatic group having 10 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group;
L ₁ and L ₂ are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group And
R _{1 to} R ₃ are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; An aryl group,
a is an integer of 1 to 4,
b is an integer of 1 to 4,
c is an integer of 1 to 4,
when a is 2 or more, two or more R _{1 s} are the same or different from each other;
when b is 2 or more, two or more R _{2 s} are the same or different from each other;
When c is 2 or more, two or more R _{3 s} are the same or different from each other. Ar ₁ or Ar ₂ is a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted triazine group. The compound of claim 1. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-A or 1-B:

In the chemical formulas 1-A and 1-B,
The definitions for Q, L ₁ , L ₂ , R _{1 to} R ₃ , Ar ₂ and a to c are the same as those defined in Formula 1.
At least one of X _{1 to} X ₃ is N, and the rest are the same or different from each other, each independently N or CR;
At least one of X _{4 to} X ₆ is N, and the rest are the same or different from each other, each independently N or CR;
R is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
Ar _{3 to} Ar ₆ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; A substituted heteroaryl group; The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2 to 5:

In the chemical formulas 2 to 5,
The definitions for L ₁ , L ₂ , Ar ₁ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Formula 1.
R ₄ and R ₅ are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; An aryl group,
d is an integer of 1 to 6;
e is an integer from 1 to 8,
when d is 2 or more, two or more R _{4 s} are the same or different from each other;
When e is 2 or more, two or more R _{5 s} are the same or different from each other. The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

  An organic electronic device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode. Then, one or more of the organic layers is an organic electronic device including the compound according to any one of claims 1 to 5.   The organic electronic device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound.   The organic electronic device according to claim 6, 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 includes the compound.   The organic electronic device according to claim 6, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the compound.   The organic electronic device according to claim 6, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.   The organic electronic device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. The organic electronic device according to claim 6.   The organic electronic device according to claim 6, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoreceptor (OPC), and an organic transistor.

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