JP6705586B2 - Heterocyclic compound and organic electroluminescent device containing the same - Google Patents

Description

The present specification relates to a heterocyclic compound and an organic electroluminescent device including the same.

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0017271 filed with the Korean Patent Office on February 15, 2016, the entire contents of which are incorporated herein.

The electroluminescent device is a kind of self-luminous display device, and has the advantages of wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, the electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as required.

The material of the organic thin film can have a light emitting function as needed. For example, as the organic thin film material, a compound which itself constitutes the light emitting layer may be used, or a compound which functions as a host or a dopant of the host-dopant-based light emitting layer may be used. In addition, a compound that plays a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection may be used as a material of the organic thin film.

In order to improve the performance, life or efficiency of organic electroluminescent devices, the development of materials for organic thin films continues to be required.

The present specification provides a heterocyclic compound and an organic electroluminescent device including the same.

前記化学式１において、Ａｒ１およびＡｒ２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リール基；または置換もしくは非置換のヘテロ環基であり、
Ｌ１〜Ｌ３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２価のヘテロ環基であり、
Ｒ１〜Ｒ３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シリル基；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環基であり、ａは、０〜２の整数であり、ｂおよびｃは、０〜４の整数であり、ａ〜ｃが２以上の場合、括弧内の置換基は、同一または異なる。 The present application provides a heterocyclic compound represented by Chemical Formula 1 below.
[Chemical formula 1]

In the above chemical formula 1, Ar1 and Ar2 are the same or different from each other, each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
L1 to L3 are the same or different from each other, each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,
R1 to R3 are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or It is a substituted or unsubstituted heterocyclic group, a is an integer of 0 to 2, b and c are integers of 0 to 4, and when a to c are 2 or more, the substituent in the parentheses is , Same or different.

Further, the present application provides a first electrode, a second electrode provided so as to face the first electrode, and one or more organic material layers provided between the first electrode and the second electrode. An organic electroluminescent device including the organic electroluminescent device, wherein one or more layers of the organic material layers include the heterocyclic compound described above.

The heterocyclic compound according to one embodiment of the present application is used in an organic electroluminescent device, reduces the driving voltage of the organic electroluminescent device, improves the light efficiency, and improves the life characteristics of the device by the thermal stability of the compound. Can be improved.

1 shows an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 are sequentially laminated. 1 shows an example of an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked. 3 is an LC/MS spectrum of Chemical Formula 1-c of Reaction Formula 1. 3 is an LC/MS spectrum of Chemical Formula 1A of Reaction Formula 1. 3 is an LC/MS spectrum of Compound 2 of Synthesis Example 2. 3 is an LC/MS spectrum of Compound 3 of Synthesis Example 3. 5 is an LC/MS spectrum of Compound 5 of Synthesis Example 5.

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

The present specification provides the heterocyclic compound represented by Chemical Formula 1.

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

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

In the present specification, the term “substituted or unsubstituted” includes deuterium; halogen group; cyano group; nitro group; hydroxy group; alkyl group; cycloalkyl group; alkenyl group; alkoxy group; aryl group; and heterocycle. Substituted with one or two or more substituents selected from the group consisting of groups, substituted with two or more substituents among the exemplified substituents linked with a substituent, or any substitution It means that it also has no group. For example, the “substituent in which two or more substituents are linked” may be a biphenyl group. That is, the biphenyl group may be an aryl group, and is interpreted as a substituent in which two phenyl groups are linked.

Examples of halogen groups herein include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be linear or branched and the carbon number is not particularly limited, but one having 1 to 50 carbon atoms 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- Examples include, but are not limited to, propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

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

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

In the present specification, the alkenyl group may be linear or branched and the carbon number is not particularly limited, but is preferably 2 to 40. Specific examples are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-. Butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1- Examples include, but are not limited to, yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but one having 6 to 25 carbon atoms is preferable. Specifically, the monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, or the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but one having 10 to 24 carbon atoms is preferable. Specifically, the polycyclic aryl group may be, but is not limited to, a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group and the like.

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, the present invention is not limited to these.

）、
ピリダジニル基、ピラジニル基、キノリニル基、キナゾリニル基、キノキサリニル基、フタラジニル基、ピリドピリミジニル基、ピリドピラジニル基、ピラジノピラジニル基、イソキノリニル基、インドール基、カルバゾリル基、ベンズオキサゾリル基、ベンズイミダゾリル基、ベンゾチアゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、ベンゾチオフェニル基、ジベンゾチオフェニル基、ベンゾフラニル基、ジベンゾフラニル基；ベンゾシロール基；ジベンゾシロール基；フェナントロリニル基（ｐｈｅｎａｎｔｈｒｏｌｉｎｙｌ ｇｒｏｕｐ）、イソオキサゾリル基、チアジアゾリル基、フェノチアジニル基、フェノキサジニル基、およびこれらの縮合構造などがあるが、これらにのみ限定されるものではない。その他にも、ヘテロ環基の例として、スルホニル基を含むヘテロ環構造、例えば、

などがある。 In the present specification, the heterocyclic group includes an atom which is not carbon and one or more hetero atoms, and specifically, the hetero atom is selected from the group consisting of O, N, Se and S. Can include one or more atoms. The number of carbon atoms of the heterocyclic group is not particularly limited, but those having 2 to 60 carbon atoms are preferable. Examples of the heterocyclic group are thiophenyl group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, acridyl group, hydroacridyl group. Groups (eg,

),
Pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group Group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group; benzosilole group; dibenzosilole group; phenanthrolinyl group ), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a phenoxazinyl group, and a condensed structure thereof, but are not limited thereto. In addition, as an example of the heterocyclic group, a heterocyclic structure containing a sulfonyl group, for example,

and so on.

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。 In the present specification, the condensed structure may be a structure in which an aromatic carbon hydrogen ring is condensed with the substituent. For example, as a fused ring of benzimidazole,

However, the present invention is not limited to these.

In the present specification, the arylene group means an aryl group having two bonding positions, that is, a divalent group. The above description of the aryl group is applicable to these, except that they are each a divalent group.

In the present specification, the “adjacent” group means a substituent substituted on the atom directly connected to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. Can mean For example, two substituents substituted in the ortho position on the benzene ring and two substituents on the same carbon on the aliphatic ring are taken to be "adjacent" groups to one another.

In one embodiment of the present specification, Ar 1 and Ar 2 are the same or different from each other, and each independently, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted hetero group having 2 to 60 carbon atoms. It is a cyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted hetero group having 2 to 30 carbon atoms. It is a cyclic group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently, a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; An unsubstituted triphenylene group; a substituted or unsubstituted dimethylfluorene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, each independently, a phenyl group substituted or unsubstituted with an aryl group; a biphenyl group substituted or unsubstituted with an aryl group; Unsubstituted terphenyl group; Triphenylene group substituted or unsubstituted with aryl group; Dimethylfluorene group substituted or unsubstituted with aryl group; Dibenzofuran group substituted or unsubstituted with aryl group; Dibenzo substituted or unsubstituted with aryl group A thiophene group; or a carbazole group substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, each independently, a phenyl group substituted or unsubstituted by a phenyl group; a biphenyl group substituted or unsubstituted by a phenyl group; Unsubstituted terphenyl group; phenyl group-substituted or unsubstituted triphenylene group; phenyl group-substituted or unsubstituted dimethylfluorene group; phenyl group-substituted or unsubstituted dibenzofuran group; phenyl group-substituted or unsubstituted dibenzo A thiophene group; or a carbazole group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently, a phenyl group substituted or unsubstituted with a phenyl group; a biphenyl group; a terphenyl group; a triphenylene group; A substituted dimethylfluorene group; a phenyl group-substituted or unsubstituted dibenzofuran group; a phenyl group-substituted or unsubstituted dibenzothiophene group; or a phenyl group-substituted or unsubstituted carbazole group.

In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent dibenzofuranyl group; a substituted or unsubstituted divalent dibenzothiophenyl group; or It is a substituted or unsubstituted divalent fluorenyl group.

In one embodiment of the present specification, L1 is a direct bond; a phenylene group substituted or unsubstituted with an alkyl group; a divalent dibenzofuranyl group substituted or unsubstituted with an alkyl group; A divalent dibenzothiophenyl group; or a divalent fluorenyl group substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, L1 is a direct bond; a phenylene group; a divalent dibenzofuranyl group; a divalent dibenzothiophenyl group; a divalent fluorenyl group; or a divalent dimethylfluorenyl group. is there.

In one embodiment of the present specification, L2 and L3 are the same or different from each other, each independently a direct bond or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L2 and L3 are the same or different from each other, each independently a direct bond or an arylene group.

In one embodiment of the present specification, L2 and L3 are the same or different from each other, each independently a direct bond or a phenylene group.

In one embodiment of the present specification, R1 to R3 are the same or different from each other, each independently hydrogen; or deuterium.

In one embodiment of the present specification, R1 to R3 are hydrogen.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following structural formulas.

The compound according to one embodiment of the present specification is produced by the production method described below.

１）化学式１−ｃの製造
４−ブロモ−１−クロロ−２−ヨードベンゼン２００．００ｇ（１．００ｅｑ）、（２−ニトロフェニル）ボロン酸（（２−ｎｉｔｒｏｐｈｅｎｙｌ）ｂｏｒｏｎｉｃ ａｃｉｄ）１０５．７８ｇ（１．０ｅｑ）、Ｐｄ（ＰＰｈ_３）_４ ７．３１ｇ（０．０１ｅｑ）をＴＨＦ１．５Ｌに溶かして撹拌した後、Ｋ_２ＣＯ_３ １１３．７８ｇ（１．３ｅｑ）を水４００ｍｌに溶かして添加、これを６０℃で撹拌した。２時間後に反応が終了すると、有機層を分離した後、減圧して溶媒を除去した。生成物をＣＨＣｌ_３に完全に溶かしてから水で洗い、溶液を５０％程度減圧濃縮し、エタノールを入れて、結晶を落として濾過した。この後、カラムクロマトグラフィーを用いて精製した。化学式１−ｃを１７１．３０ｇ（収率８７％）得た。［Ｍ＋Ｈ］＝３１０ [Reaction formula 1]

1) Preparation of Chemical Formula 1-c 4-bromo-1-chloro-2-iodobenzene 200.00 g (1.00 eq), (2-nitrophenyl)boronic acid ((2-nitrophenyl)boronic acid) 105.78 g( 1.0 eq), Pd(PPh ₃ ) ₄ 7.31 g (0.01 eq) were dissolved in 1.5 L of THF and stirred, and then K ₂ CO ₃ 113.78 g (1.3 eq) was dissolved in 400 ml of water and added. This was stirred at 60°C. When the reaction was completed after 2 hours, the organic layer was separated and then depressurized to remove the solvent. The product was completely dissolved in CHCl ₃ and washed with water, the solution was concentrated under reduced pressure by about 50%, ethanol was added, crystals were dropped, and the mixture was filtered. After that, it was purified using column chromatography. 171.30 g (yield 87%) of Chemical Formula 1-c was obtained. [M+H]=310

2) Production of Chemical Formula 1-b Chemical Formula 1-c 171.30 g (1.0 eq) was dissolved in 500 mL of triethylphosphite (P(OEt) ₃ ) and refluxed and stirred. When the reaction was completed after 3 hours, the pressure was reduced under vacuum to remove about 50% of the solvent and the crystals were dropped by cooling. After filtration, it was completely dissolved in ethyl acetate and washed with water. The solution was concentrated under reduced pressure by about 70%, cooled to remove crystals, and filtered. After that, it was purified using column chromatography. 124.48 g (yield 81%) of Chemical Formula 1-b was obtained. [M+H]=279

3) Production of Chemical Formula 1-a Chemical Formula 1-b 124.48 g (1.0 eq), iodobenzene 100.10 g (1.1 eq), CuI 25.49 g (0.3 eq), K ₂ CO ₃ 12.34 g (2. 0 eq) was put in 1 L of dioxane, 30 ml of ethylenediamine was added dropwise, and the mixture was stirred at 80°C. When the reaction is completed, after cooling at room temperature, the solution in which the product is dissolved is depressurized to remove all the solvent, completely dissolved in CHCl ₃ and washed with water, and depressurized again to remove the solvent. This was purified using column chromatography. 123.56 g (yield 78%) of Chemical Formula 1-a was obtained. [M+H]=355

4) Preparation of Chemical Formula 1A Chemical Formula 1-a 123.55 g (1.0 eq), Pd(t-Bu ₃ P) ₂ 0.75 g (0.005 eq), K ₂ CO ₃ 126.05 g (2.00 eq) in dimethyl It was put in 800 mL of acetamide (Dimethylacetamide), refluxed and stirred. After 3 hours, the reaction was poured into water to remove crystals and filtered. The filtered solid was completely dissolved in ethyl acetate and then washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 86.90 g (yield 83%) of Chemical Formula 1A was obtained. [M]=275

In addition, the present specification provides an organic electroluminescent device including the compound described above.

In one embodiment of the present application, a first electrode, a second electrode provided so as to face the first electrode, and one or more layers of organic material provided between the first electrode and the second electrode. An organic electroluminescent device including a layer, wherein at least one layer of the organic material layers includes the heterocyclic compound.

As used herein, when a member is positioned “on” another member, this is not only the case where one member is in contact with another member, but also between other members. It also includes the case where members exist.

In this specification, when a portion is “comprising” a component, this does not exclude the other component or the inclusion of the other component, unless specifically stated to the contrary. To do.

The organic material layer of the organic electroluminescent element of the present application may have a single-layer structure, but may also have a multilayer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic electroluminescence device of the present invention, the organic electroluminescence device has 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 an organic material layer. be able to. However, the structure of the organic electroluminescent device is not limited to this, and may include a smaller number of organic layers.

In one embodiment of the present application, the organic layer has a thickness of 1Å to 1000Å.

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

In one 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 heterocyclic compound.

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

In one embodiment of the present application, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.

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

In one embodiment of the present application, the organic electroluminescent device includes a first electrode, a second electrode facing the first electrode, and a gap between the first electrode and the second electrode. And a light emitting layer, and two or more organic material layers 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 materials are included. At least one of the layers comprises said heterocyclic compound.

In one embodiment of the present application, the two or more organic layers are two or more 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. Good.

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

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

In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transporting layer including a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic material layer containing the heterocyclic compound. Further includes layers.

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

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

For example, the structure of the organic electroluminescent device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.

FIG. 1 illustrates the structure of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the heterocyclic compound may be included in the light emitting layer 3.

FIG. 2 illustrates the structure of an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked. There is. In this structure, the heterocyclic compound may be contained 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 this structure, the heterocyclic compound may be included in at least one of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic electroluminescent device of the present application is manufactured by the materials and methods known in the art, except that one or more of the organic layers include the compound of the present application, that is, the heterocyclic compound. ..

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

The organic electroluminescent device of the present application is a material known in the art, except that one or more of the organic material layers include the heterocyclic compound, that is, the heterocyclic compound represented by Chemical Formula 1. And manufactured by the method.

For example, the organic electroluminescent 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. At this time, a PVD (Physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) is used to form a metal or a conductive metal oxide or an alloy thereof on the substrate. To form an anode 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 substance used as a cathode is deposited thereon. Manufactured by. In addition to this method, an organic electroluminescent device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Chemical Formula 1 is formed in the organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the organic electroluminescent device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.

In addition to this method, an organic electroluminescent device can 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 application, 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.

As the anode material, a material having a large work function is usually preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material 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); ZnO: Al or _SnO 2: combination of a metal oxide such as Sb; conductive poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, but not limited thereto.

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 the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF/Al or LiO ₂ / There is a material having a multi-layered structure such as Al, but the material is not limited thereto.

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

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

The light emitting substance is a substance capable of emitting light in the visible light region by receiving and coupling holes and electrons from the hole transport layer and the electron transport layer, respectively, and has a high quantum efficiency for fluorescence and phosphorescence. The substance is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compound; dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzoxazole, benzthiazole, And benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based 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. The host material includes a fused aromatic ring derivative or a heterocycle-containing compound. Specifically, the condensed aromatic ring derivative includes anthracene derivative, pyrene derivative, naphthalene derivative, pentacene derivative, phenanthrene compound, fluoranthene compound, and the like, and the heterocycle-containing compound includes compound, dibenzofuran derivative, ladder-type furan compound. , Pyrimidine derivatives and the like, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is a material that receives electron injection from the cathode and can be transferred to the light emitting layer. A substance having high mobility with respect to is preferable. Specific examples thereof include, but are not limited to, 8-hydroxyquinoline Al complex; Alq ₃ -containing complex; organic radical compound; hydroxyflavone-metal complex. The electron transport layer can be used with any desired cathode material, such as those used by the prior art. In particular, examples of suitable cathode materials are the usual materials which have a low work function, followed by an aluminum or silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, in each case 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, an excellent electron injection effect for a light emitting layer or a light emitting material, and a light emitting layer. Compounds which prevent the excitons generated in (2) from moving to the hole injection layer and have excellent thin film forming ability are preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and their derivatives, metal complex compounds, And nitrogen-containing 5-membered ring derivatives, but not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, and tris(8-hydroxyquino). Linato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]. Quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholate)aluminum , Bis(2-methyl-8-quinolinato)(2-naphtholate)gallium, and the like, but are not limited thereto.

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 thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

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

化学式１Ａ１０．０ｇ（１．０ｅｑ）、Ｎ−（４−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）フェニル）ビフェニル−４−アミン１４．４４ｇ（１．１ｅｑ）、ＮａＯｔＢｕ６．９８ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をキシレン（Ｘｙｌｅｎｅ）９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物１を１７．２４ｇ（収率７９％）得た。［Ｍ＋Ｈ］＝６７７ Synthesis example 1. Compound 1

Chemical formula 1A 10.0 g (1.0 eq), N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)biphenyl-4-amine 14.44 g (1.1 eq), NaOtBu 6.98 g ( 2.0 eq) and 0.09 g (0.005 eq) of Pd(t-Bu ₃ P) ₂ were dissolved in 90 ml of xylene and refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. By subjecting this to column chromatography, 17.24 g (yield 79%) of Compound 1 was obtained. [M+H]=677

化学式１Ａ１０．０ｇ（１．０ｅｑ）、Ｎ−（ビフェニル−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−３−アミン１７．４８ｇ（１．１ｅｑ）、ＮａＯｔＢｕ６．９８ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をキシレン（Ｘｙｌｅｎｅ）９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物２を１９．９１ｇ（収率８１％）得た。［Ｍ］＝６００ Synthesis example 2. Compound 2

Chemical formula 1A 10.0 g (1.0 eq), N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-3-amine 17.48 g (1.1 eq), NaOtBu 6.98 g (2.0 eq) , Pd(t-Bu ₃ P) ₂ 0.09 g (0.005 eq) was dissolved in 90 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. This was subjected to column chromatography to obtain 19.91 g of Compound 2 (yield 81%). [M]=600

化学式１Ａ１０．０ｇ（１．０ｅｑ）、Ｎ−（４−（ジベンゾ［ｂ，ｄ］フラン−４−イル）フェニル）ビフェニル−４−アミン１４．４４ｇ（１．１ｅｑ）、ＮａＯｔＢｕ６．９８ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をキシレン（Ｘｙｌｅｎｅ）９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物３を１６．８０ｇ（収率７７％）得た。［Ｍ＋Ｈ］＝６５１ Synthesis example 3. Compound 3

Chemical formula 1A 10.0 g (1.0 eq), N-(4-(dibenzo[b,d]furan-4-yl)phenyl)biphenyl-4-amine 14.44 g (1.1 eq), NaOtBu 6.98 g (2. 0 eq) and 0.09 g (0.005 eq) of Pd(t-Bu ₃ P) ₂ were dissolved in 90 ml of xylene and refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. This was subjected to column chromatography to obtain 16.80 g of Compound 3 (yield 77%). [M+H]=651

化学式１Ａ１０．０ｇ（１．０ｅｑ）、Ｎ−（４−（ジベンゾ［ｂ，ｄ］チオフェン−３−イル）フェニル）ビフェニル−４−アミン１６．４４ｇ（１．１ｅｑ）、ＮａＯｔＢｕ６．９８ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をキシレン（Ｘｙｌｅｎｅ）９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物４を１９．６２ｇ（収率８３％）得た。［Ｍ］＝６６６ Synthesis example 4. Compound 4

Chemical formula 1A 10.0 g (1.0 eq), N-(4-(dibenzo[b,d]thiophen-3-yl)phenyl)biphenyl-4-amine 16.44 g (1.1 eq), NaOtBu 6.98 g (2. 0 eq) and 0.09 g (0.005 eq) of Pd(t-Bu ₃ P) ₂ were dissolved in 90 ml of xylene and refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. By subjecting this to column chromatography, 19.62 g (yield 83%) of Compound 4 was obtained. [M]=666

化学式１Ａ１０．０ｇ（１．０ｅｑ）、４−（ビフェニル−４−イル（４−（ジベンゾ［ｂ，ｄ］ｔｈｉｏｐｈｅｎ−４−イル）フェニル）アミノ）フェニルボロン酸２１．８８ｇ（１．１ｅｑ）、水４０ｍｌに溶かしたＫ_３ＰＯ_４ １５．４３ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をジオキサン９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物５を２１．８５ｇ（収率８１％）得た。［Ｍ＋Ｈ］＝７４３ Synthesis example 5. Compound 5

Chemical Formula 1A 10.0 g (1.0 eq), 4-(biphenyl-4-yl(4-(dibenzo[b,d]thiophen-4-yl)phenyl)amino)phenylboronic acid 21.88 g (1.1 eq), _K 3 _PO 4 15.43 g dissolved in water 40ml _(2.0eq), Pd a (t-Bu 3 P) 2 0.09g (0.005eq) was dissolved in dioxane 90 ml, was refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. By subjecting this to column chromatography, 21.85 g (yield 81%) of Compound 5 was obtained. [M+H]=743

化学式１Ａ１０．０ｇ（１．０ｅｑ）、４−（ビフェニル−４−イル（４−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）フェニル）アミノ）フェニルボロン酸２２．２８ｇ（１．１ｅｑ）、水４０ｍｌに溶かしたＫ_３ＰＯ_４ １５．４３ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をジオキサン９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物６を２３．２４ｇ（収率８５％）得た。［Ｍ］＝７５２ Synthesis example 6. Compound 6

Chemical formula 1A 10.0 g (1.0 eq), 4-(biphenyl-4-yl(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)amino)phenylboronic acid 22.28 g (1.1 eq) ), 15.43 g (2.0 eq) of K ₃ PO _{4 and} 0.09 g (0.005 eq) of Pd(t-Bu ₃ P) ₂ dissolved in 40 ml of water were dissolved in 90 ml of dioxane, and the mixture was refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. This was subjected to column chromatography to obtain 23.24 g of Compound 6 (yield 85%). [M]=752

化学式１Ａ１０．０ｇ（１．０ｅｑ）、４−（（４−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）フェニル）（トリフェニレン−２−イル）アミノ）フェニルボロン酸２５．２４ｇ（１．１ｅｑ）、水４０ｍｌに溶かしたＫ_３ＰＯ_４ １５．４３ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をジオキサン９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でＥｔｈｙｌ ａｃｅｔａｔｅを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物７を２５．８３ｇ（収率８６％）得た。［Ｍ］＝８２６ Synthesis example 7. Compound 7

Chemical formula 1A 10.0 g (1.0 eq), 4-((4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)(triphenylene-2-yl)amino)phenylboronic acid 25.24 g (1 0.1 eq), 15.43 g (2.0 eq) of K ₃ PO _{4 and} 0.09 g (0.005 eq) of Pd(t-Bu ₃ P) ₂ dissolved in 40 ml of water were dissolved in 90 ml of dioxane and refluxed and stirred. .. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again, and the crystals were dropped and cooled, and then filtered. By subjecting this to column chromatography, 25.83 g (yield 86%) of Compound 7 was obtained. [M]=826

化学式１Ａ１０．０ｇ（１．０ｅｑ）、４−（（４−（ジベンゾ［ｂ，ｄ］チオフェン−４−イル）フェニル）（トリフェニレン−２−イル）アミノ）フェニルボロン酸２４．８４ｇ（１．１ｅｑ）、水４０ｍｌに溶かしたＫ_３ＰＯ_４ １５．４３ｇ（２．０ｅｑ）、Ｐｄ（ｔ−Ｂｕ_３Ｐ）_２ ０．０９ｇ（０．００５ｅｑ）をジオキサン９０ｍｌに溶かして、還流し撹拌した。１時間後に反応が終了すると、減圧して溶媒を除去した。この後、ＣＨＣｌ_３に完全に溶かして水で洗い、再度減圧して溶媒を５０％程度除去した。再度還流状態でエチルアセテートを入れて、結晶を落として冷やした後、濾過した。これをカラムクロマトグラフィーによって、化合物８を２４．６３ｇ（収率８３％）得た。［Ｍ＋Ｈ］＝８１７ Synthesis example 8. Compound 8

Chemical formula 1A 10.0 g (1.0 eq), 4-((4-(dibenzo[b,d]thiophen-4-yl)phenyl)(triphenylene-2-yl)amino)phenylboronic acid 24.84 g (1.1 eq) ), 15.43 g (2.0 eq) of K ₃ PO _{4 and} 0.09 g (0.005 eq) of Pd(t-Bu ₃ P) ₂ dissolved in 40 ml of water were dissolved in 90 ml of dioxane, and the mixture was refluxed and stirred. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water, and decompressed again to remove the solvent by about 50%. Ethyl acetate was put in the reflux state again to drop crystals, and the mixture was cooled and then filtered. This was subjected to column chromatography to obtain 24.63 g (yield 83%) of Compound 8. [M+H]=817

<Comparative example>
A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, as a detergent, a product of Fischer Co. was used, and as distilled water, distilled water secondarily filtered by a filter of a product of Millipore Co. was used. After cleaning ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the washing with distilled water was completed, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, and the resultant was dried and then transported to a plasma cleaning machine. After cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum deposition machine. On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT-CN) represented by the following chemical formula was thermally vacuum-deposited to a thickness of 150 Å to form a hole injection layer. The following compound HT (1150Å), which is a substance that transports holes, was vacuum-deposited on the hole injection layer to form a hole transport layer. Next, the following compound EB was vacuum-deposited on the hole transport layer to a film thickness of 150Å to form an electron blocking layer. Next, the following BH and BD were vacuum-deposited in a thickness ratio of 30:1 on the electron blocking layer at a weight ratio of 25:1 to form a light emitting layer. The compound ET and the compound LiQ (lithium quinolate) were vacuum-deposited on the light emitting layer at a weight ratio of 1:1 to form an electron injection and transport layer having a thickness of 360Å. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode. In the above process, the deposition rate of organic substances was maintained at 0.4 to 0.7 Å/sec, the cathode lithium fluoride was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec. The organic electroluminescent device was manufactured by maintaining the degree of 2×10 ^{−7 to} 5×10 ⁻⁶ torr.

<Experimental example 1-1>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound 1 was used in place of the compound EB in the comparative example.

<Experimental example 1-2>
An organic electroluminescence device was produced in the same manner as in the comparative example except that the compound 2 was used instead of the compound EB in the comparative example.

<Experimental example 1-3>
An organic electroluminescent device was produced in the same manner as in the comparative example, except that the compound 3 was used instead of the compound EB in the comparative example.

<Experimental example 1-4>
An organic electroluminescent device was produced in the same manner as in the comparative example, except that the compound 4 was used instead of the compound EB in the comparative example.

<Experimental example 1-5>
An organic electroluminescent device was produced in the same manner as in the comparative example, except that the compound 5 was used instead of the compound EB in the comparative example.

<Experimental example 1-6>
An organic electroluminescence device was produced in the same manner as in the comparative example except that the compound 6 was used in place of the compound EB in the comparative example.

<Experimental example 1-7>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound 7 was used instead of the compound EB in the comparative example.

<Experimental example 1-8>
An organic electroluminescent device was produced in the same manner as in the comparative example, except that the compound 8 was used instead of the compound EB in the comparative example.

<Comparative Example 1>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-1 was used instead of the compound EB in the comparative example.

<Comparative example 2>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-2 was used in place of the compound EB in the comparative example.

<Comparative example 3>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-3 was used instead of the compound EB in the comparative example.

<Comparative example 4>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-4 was used in place of the compound EB in the comparative example.

<Comparative Example 5>
An organic electroluminescent device was produced in the same manner as in the comparative example, except that the compound of H-5 was used instead of the compound EB in the comparative example.

<Comparative example 6>
An organic electroluminescent device was produced in the same manner as in the comparative example except that the compound of H-6 was used instead of the compound EB in the comparative example.

When a current was applied to the organic light emitting devices produced in Experimental Examples 1-1 to 1-8 and Comparative Examples 1 to 6, voltage, current density, luminance, color coordinates and lifetime were measured, and the results are shown in Table 1 below. It was shown to. T95 means the time required for the brightness to decrease from the initial brightness (650 nit) to 95%.

As shown in Table 1, the organic electroluminescent device manufactured by using the compound of the present invention as the electron blocking layer was excellent in efficiency, driving voltage and/or stability of the organic electroluminescent device. Show the characteristics.

The core of the present invention exhibits lower voltage, higher efficiency, and longer life than the organic light emitting device manufactured using the compounds of Comparative Examples 1 to 6 as the electron blocking layer. The voltage was lowered by about 5 to 10%, and the efficiency was increased by 10% or more. The existing indolo[3,2,1-jk]carbazole is connected to the 2nd, 10th and 11th linked amines in the direction (1st) having a lot of steric hindrance like the compound of the present invention. It has been found that when the conjugation is performed in the direction in which the conjugation is cut off, it exhibits characteristics of increased efficiency, decreased voltage, and long life, and the stability of the core indolo[3,2,1-jk]carbazole itself is also increased. In addition, since many of the core-amine linked portions are broken, there is an advantage that the thermal stability is also excellent.

1: Substrate 2: Anode 3: Light-emitting layer 4: Cathode 5: Hole injection layer 6: Hole transport layer 7: Electron transport layer

Claims (11)

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

In the above chemical formula 1, Ar1 and Ar2 are the same or different from each other, each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
L1 to L3 are the same or different from each other, each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,
R1 to R3 are the same or different from each other, each independently hydrogen; or deuterium ;
a is an integer of 0 to 2, b and c are integers of 0 to 4, and when a to c are 2 or more, the substituents in parentheses are the same or different. Ar 1 and Ar 2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. The heterocyclic compound according to. Ar1 and Ar2 are the same or different from each other, each independently, a phenyl group substituted or unsubstituted by a phenyl group; a biphenyl group substituted or unsubstituted by a phenyl group; a terphenyl group substituted or unsubstituted by a phenyl group; phenyl Group substituted or unsubstituted triphenylene group; phenyl group substituted or unsubstituted dimethylfluorene group; phenyl group substituted or unsubstituted dibenzofuran group; phenyl group substituted or unsubstituted dibenzothiophene group; or phenyl group substituted Alternatively, the heterocyclic compound according to claim 1, which is an unsubstituted carbazole group. The L 1 is a direct bond; a phenylene group; a divalent dibenzofuranyl group; a divalent dibenzothiophenyl group; a divalent fluorenyl group; or a divalent dimethylfluorenyl group. Heterocyclic compounds. The heterocyclic compound according to claim 1, wherein L 2 and L 3 are the same or different from each other and each independently is a direct bond; or a phenylene group. The heterocyclic compound according to claim 1, wherein the compound of Chemical Formula 1 is selected from the following structural formulas:

An organic electroluminescent device including a first electrode, a second electrode provided to face the first electrode, and one or more organic material layers provided between the first electrode and the second electrode. An organic electroluminescent device, wherein at least one of the organic material layers contains the heterocyclic compound according to any one of claims 1 to 6 . The organic electroluminescent element according to claim 7 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound. The organic electroluminescent element 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 includes the heterocyclic compound. The organic electroluminescent device according to claim 7 , 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 includes the heterocyclic compound. The organic electroluminescent element according to claim 7 , wherein the organic layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.

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