JP2019507738A - Heterocyclic compound and organic electroluminescent device containing the same - Google Patents

Abstract

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

Description

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

  This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0017264 filed with the Korean Patent Office on February 15, 2016, the entire contents of which are incorporated herein.

  An electroluminescent element is a kind of self-luminous display element, which has an advantage of not only a wide viewing angle and excellent contrast but also a high response speed.

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

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

  In order to improve the performance, lifetime or efficiency of organic electroluminescent devices, the development of organic thin film materials continues to be sought.

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

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およびｃは、０〜３の整数であり、ｂ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 the following Chemical Formula 1.
[Chemical Formula 1]

In Formula 1, Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
L1 to L3 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 divalent heterocyclic group;
R1 to R3 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group,
a and c are integers of 0 to 3, b is an integer of 0 to 4, and when a to c are 2 or more, the substituents in parentheses are the same or different.

  The present application also includes 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 electroluminescence device including the organic electroluminescence device, wherein at least one of the organic layers includes 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 lifetime characteristics of the device by the thermal stability of the compound. Can be improved.

An example of an organic electroluminescent element in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated is shown. An example of an organic electroluminescent element 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 laminated is shown. 2 is an LC / MS spectrum of Chemical Formula 1A in Reaction Formula 1. 2 is an LC / MS spectrum of Compound 1 of Synthesis Example 1. 2 is an LC / MS spectrum of Compound 2 of Synthesis Example 2. 7 is an LC / MS spectrum of Compound 7 of Synthesis Example 7.

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

  The present specification provides a heterocyclic compound represented by Formula 1.

  In the present specification, examples of the substituent are described below, but 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 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, phosphine oxide group, silyl group, alkyl group, cycloalkyl group, alkenyl group, alkoxy group. Substituted with one or more substituents selected from the group consisting of: an aryl group; and a heterocyclic group, or two or more substituents of the above exemplified substituents are substituted with linked substituents; Or does not have any substituents. 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.

  In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

  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, the alkoxy group may be a straight chain, a branched chain or a ring chain. Although carbon number of an alkoxy group is not specifically limited, A C1-C20 thing is preferable. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3, Although it may become 3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., it is not limited to these.

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

  In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but those having 6 to 25 carbon atoms are preferable. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl 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 10 to 24 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.

、

になってもよいが、これ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 this.

）、
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 one or more atoms that are not carbon atoms and hetero atoms, and specifically, the hetero atoms are selected from the group consisting of O, N, Se, Si, S, and the like. One or more selected atoms can be included. Although carbon number of a heterocyclic group is not specifically limited, A C2-C60 thing is preferable. Examples of heterocyclic groups include thiophenyl, furanyl, pyrrole, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridyl, hydroacridyl Group (for example,

),
Pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indole, carbazolyl, benzoxazolyl, benzimidazolyl Group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group; benzosilole group; dibenzosilole group; phenanthrolinyl group ), Isoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxazinyl group, and condensed structures thereof, but are not limited thereto. Other examples of the heterocyclic group include heterocyclic structures containing a sulfonyl group, such as

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 to the substituent. For example, as a condensed ring of benzimidazole,

However, it is not limited to these.

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

  In the present specification, an “adjacent” group means a substituent substituted by an atom directly linked to an atom to which the substituent is substituted, or another substituent substituted by an atom to which the substituent is substituted. Can mean. For example, two substituents substituted in the ortho position on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring are interpreted as “adjacent” groups to each other.

  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 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, Ar 1 and Ar 2 are the same as or different from each other, and each independently represents 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 represents 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, and each independently represents an aryl group-substituted or unsubstituted phenyl group; an aryl group-substituted or unsubstituted biphenyl group; an aryl group-substituted or Unsubstituted terphenyl group; aryl group substituted or unsubstituted triphenylene group; aryl group substituted or unsubstituted dimethylfluorene group; aryl group substituted or unsubstituted dibenzofuran group; aryl group substituted or unsubstituted dibenzo A thiophene group; or an aryl group substituted or unsubstituted carbazole group.

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

  In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents 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, L 1 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, L 1 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 A substituted or unsubstituted divalent fluorenyl group.

  In one embodiment of the present specification, L1 is a direct bond; an alkyl group-substituted or unsubstituted phenylene group; an alkyl group-substituted or unsubstituted divalent dibenzofuranyl group; an alkyl group-substituted or unsubstituted. 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 and are 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 and are 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 and are each independently a direct bond; or a phenylene group.

  In one embodiment of the present specification, R1-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 which concerns on one embodiment of this specification is manufactured with the manufacturing method mentioned later.
[Reaction Formula 1]

1) Production of Chemical Formula 1-a 100.00 g (1.0 eq) of 9H-carbazole and 100.74 g (1.5 eq) of KOtBu were placed in 1 L of DMF (dimethylformamide) and heated and stirred. At the start of reflux, 149.33 g (1.2 eq) of 1-bromo-3-chloro-2-fluorobenzene was added. When the reaction was completed after 5 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in CHCl ₃ and washed with water, and the pressure was reduced again to remove the solvent, which was purified using column chromatography. 191.22 g (yield 90%) of the chemical formula 1-a was obtained. [M + 2H] = 356

2) Production of Chemical Formula 1A Pd (t-Bu ₃ P) ₂ 1.19 g (0.005 eq) and K ₂ CO ₃ 129.74 g (2.00 eq) were added to Chemical Formula 1-a 191.22 g (1.0 eq). It put into 1 L of dimethylacetamide (Dimethylacetamide), and it recirculate | refluxed and stirred. After 3 hours, the reaction was poured into water, the crystals were dropped and filtered. The filtered solid was completely dissolved in ethyl acetate and then washed with water. The product-dissolved solution was concentrated under reduced pressure and purified using column chromatography. 107.15 g (83% yield) of Chemical Formula 1A was obtained. [M] = 275

  Moreover, this specification provides the organic electroluminescent element containing the compound mentioned above.

  In one embodiment of the present application, the first electrode, the second electrode provided to face the first electrode, and one or more organic substances provided between the first electrode and the second electrode An organic electroluminescent device including a layer, wherein at least one of the organic layers includes the heterocyclic 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 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 laminated. For example, as a typical example of the organic electroluminescent device of the present invention, the organic electroluminescent 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, and the like as an organic material layer. be able to. However, the structure of the organic electroluminescent element 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 1 to 1000 mm.

  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 hole transport layer includes the heterocyclic compound.

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

  In one embodiment of the present application, 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 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 element 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 heterocyclic compound.

  In one embodiment of the present application, 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. Also 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 included in one of the two or more electron transport layers, or each of the two or more electron transport layers. May be included.

  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 excluding the heterocyclic compound may be the same as or different from each other. .

  In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport including a compound including an arylamino group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic layer including the heterocyclic compound. It further includes a layer.

  In another embodiment, the organic electroluminescent device may be an organic electroluminescent device having a structure in which an anode, one or more organic 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 an organic electroluminescent device according to one embodiment of the present application is illustrated in FIGS.

  FIG. 1 illustrates the structure of an organic electroluminescent element in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated. 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. Yes. In this structure, the heterocyclic compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

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

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

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

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

  For example, the organic electroluminescent element of the present application 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). To form an anode, and then form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then deposit a material to be used as a cathode thereon. Manufactured by. In addition to this method, an organic electroluminescent device can be formed by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate.

  In addition, the heterocyclic compound of Formula 1 is formed on the organic material layer by a solution coating method as well as a vacuum deposition method at the time of manufacturing the organic electroluminescent 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 electroluminescent device can be formed 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); 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.

The cathode material is preferably a material having a small work function so that it is easy to inject electrons into the organic material layer. Specific examples of the cathode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF / Al or LiO ₂ / There are materials having a multilayer structure such as Al, but the material is not limited thereto.

  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. As the hole transport material, the light emitting layer receives hole transport from the anode or the hole injection layer. A substance that can be transferred to the group and has a 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 nonconjugated portion.

The light-emitting substance is a substance that can emit 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 good quantum efficiency for fluorescence and phosphorescence. Substances 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.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer, and the electron transporting material is a material that can be well received by the electron injection from the cathode and transferred to the light emitting layer. A substance having high mobility with respect to 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-hydroxyquinolinatolithium, 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-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum Bis (2-methyl-8-quinolinato) (2-naphth Acrylate), and the like gallium, but are not limited to these.

  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 electroluminescent device according to the present specification may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

  Hereinafter, the present specification will be described in detail by way of examples in order to specifically describe the present specification. However, the examples according to the present specification can be modified in various different forms, and the scope of the present application is not construed to be limited to the examples described in detail below. The examples in this application are provided to provide a more thorough explanation of the present specification to those skilled in the art.

化学式１Ａ１０．０ｇ（１．０ｅｑ）、Ｎ−（［１，１'：３'，１''−ターフェニル］−５'−イル）ジベンゾ［ｂ，ｄ］フラン−４−アミン１１．１９ｇ（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２０．５６ｇ（収率８７％）得た。［Ｍ＋Ｈ］＝６５１ Synthesis Example 1 Compound 1

10.0 g (1.0 eq) of chemical formula 1A, N-([1,1 ′: 3 ′, 1 ″ -terphenyl] -5′-yl) dibenzo [b, d] furan-4-amine 11.19 g ( 1.1 eq), NaOtBu 6.98 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.09 g (0.005 eq) were 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 and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 20.56 g (yield 87%) of Compound 1. [M + H] = 651

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）−［１，１'−ビフェニル］−４−アミン１１．１９ｇ（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２０．１６ｇ（収率８２％）得た。［Ｍ＋Ｈ］＝６７７ Synthesis Example 2 Compound 2

10.0 g (1.0 eq) of chemical formula 1A, N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl)-[1,1′-biphenyl] -4-amine 11.19 g (1 0.1 eq), NaOtBu 6.98 g (2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.09 g (0.005 eq) were 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 and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 20.16 g (yield 82%) of Compound 2. [M + H] = 677

化学式１Ａ１０．０ｇ（１．０ｅｑ）、Ｎ−（４−（ジベンゾ［ｂ，ｄ］フラン−２−イル）フェニル）−［１，１'：３'，１''−ターフェニル］−５'−アミン１１．１９ｇ（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２２．７０ｇ（収率８６％）得た。［Ｍ］＝７２６ Synthesis Example 3 Compound 3

10.0 g (1.0 eq) of chemical formula 1A, N- (4- (dibenzo [b, d] furan-2-yl) phenyl)-[1,1 ′: 3 ′, 1 ″ -terphenyl] -5 ′ -11.19 g (1.1 eq) of amine, 6.98 g (2.0 eq) of NaOtBu, 0.09 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 90 ml of xylene, refluxed and stirred. did. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 22.70 g (yield 86%) of compound 3. [M] = 726

化学式１Ａ１０．０ｇ（１．０ｅｑ）、（４−（［１，１'：３'，１''−ターフェニル］−５'−イル（４−（ジベンゾ［ｂ，ｄ］フラン−３−イル）フェニル）アミノ）フェニル）ボロン酸２４．２８ｇ（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４を２５．０８ｇ（収率８６％）得た。［Ｍ＋Ｈ］＝８０３ Synthesis Example 4 Compound 4

10.0 g (1.0 eq) of chemical formula 1A, (4-([1,1 ′: 3 ′, 1 ″ -terphenyl] -5′-yl (4- (dibenzo [b, d] furan-3-yl ) Phenyl) amino) phenyl) boronic acid 24.28 g (1.1 eq), K ₃ PO ₄ dissolved in 40 ml of water 15.43 g (2.0 eq), Pd (t-Bu ₃ P) ₂ 0.09 g (0 0.005 eq) was 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 and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 25.08 g of Compound 4 (yield 86%). [M + H] = 803

化学式１Ａ１０．０ｇ（１．０ｅｑ）、（４−（［１，１'−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８．３９ｇ（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２２．７０ｇ（収率８３％）得た。［Ｍ＋Ｈ］＝７５３ Synthesis Example 5 Compound 5

10.0 g (1.0 eq) of chemical formula 1A, (4-([1,1′-biphenyl] -4-yl (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) amino) phenyl) Boronic acid 8.39 g (1.1 eq), K ₃ PO ₄ 15.43 g (2.0 eq) dissolved in water 40 ml, Pd (t-Bu ₃ P) ₂ 0.09 g (0.005 eq) in dioxane 90 ml Dissolved, 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 and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 22.70 g (yield 83%) of compound 5. [M + H] = 753

化学式１Ａ１０．０ｇ（１．０ｅｑ）、（４−（［１，１'−ビフェニル］−４−イル（４−（ジベンゾ［ｂ，ｄ］フラン−４−イル）フェニル）アミノ）フェニル）ボロン酸９．８９ｇ（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２２．４４ｇ（収率８５％）得た。［Ｍ＋Ｈ］＝７２７ Synthesis Example 6 Compound 6

10.0 g (1.0 eq) of chemical formula 1A, (4-([1,1′-biphenyl] -4-yl (4- (dibenzo [b, d] furan-4-yl) phenyl) amino) phenyl) boronic acid 9.89 g (1.1 eq), 15.43 g (2.0 eq) of K ₃ PO ₄ dissolved in 40 ml of water, 0.09 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 90 ml of dioxane. , 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 and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 22.44 g (yield 85%) of Compound 6. [M + H] = 727

化学式１Ａ１０．０ｇ（１．０ｅｑ）、（４−（（４−（ジベンゾ［ｂ，ｄ］フラン−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６．１３ｇ（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７を２３．２７ｇ（収率８０％）得た。［Ｍ＋Ｈ］＝８０１ Synthesis Example 7 Compound 7

Chemical Formula 1A 10.0 g (1.0 eq), (4-((4- (dibenzo [b, d] furan-4-yl) phenyl) (triphenylene-2-yl) amino) phenyl) boronic acid 6.13 g (1 0.1 eq), K ₃ PO ₄ 15.43 g (2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.09 g (0.005 eq) 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 and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. By column chromatography, 23.27 g (yield 80%) of compound 7 was obtained. [M + H] = 801

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２４．３３ｇ（収率８１％）得た。［Ｍ＋Ｈ］＝８２７ Synthesis Example 8 Compound 8

10.0 g (1.0 eq) of chemical formula 1A, (4-((4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) (triphenylene-2-yl) amino) phenyl) boronic acid 25.24 g (1.1 eq), K ₃ PO ₄ 15.43 g (2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.09 g (0.005 eq) dissolved in 40 ml of water were dissolved in 90 ml of dioxane and refluxed. Stir. When the reaction was completed after 1 hour, the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ and washed with water, and the pressure was reduced again to remove about 50% of the solvent. Ethyl acetate was added again in a reflux state, the crystals were dropped and cooled, and then filtered. This was subjected to column chromatography to obtain 24.33 g (yield 81%) of Compound 8. [M + H] = 827

<Comparative example>
A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 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 manner, hexanitrile hexaazatriphenylene (HAT-CN) having the following chemical formula was thermally vacuum deposited to a thickness of 150 mm 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 thickness of 150 mm to form an electron blocking layer. Next, the following BH and BD were vacuum-deposited at a weight ratio of 25: 1 to a thickness of 30 mm on the electron blocking layer 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 injecting and transporting layer having a thickness of 360 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 electroluminescent device.

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

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

<Experimental Example 1-3>
In the comparative example, 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.

<Experimental Example 1-4>
In the comparative example, 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.

<Experimental Example 1-5>
In the comparative example, 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.

<Experimental Example 1-6>
In the comparative example, an organic electroluminescent device was produced in the same manner as in the comparative example except that the compound 6 was used instead of the compound EB.

<Experimental Example 1-7>
In the comparative example, an organic electroluminescent element was produced in the same manner as in the comparative example except that the compound 7 was used instead of the compound EB.

<Experimental Example 1-8>
In the comparative example, 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.

<Comparative Example 1>
In the comparative example, an organic electroluminescent element 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.

<Comparative example 2>
In the comparative example, an organic electroluminescent element was produced in the same manner as in the comparative example except that the compound H-2 was used instead of the compound EB.

<Comparative Example 3>
In the comparative example, an organic electroluminescent element 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.

<Comparative example 4>
In the comparative example, an organic electroluminescent element was produced in the same manner as in the comparative example except that the compound of H-4 was used instead of the compound EB.

<Comparative Example 5>
In the comparative example, an organic electroluminescent element 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.

<Comparative Example 6>
In the comparative example, an organic electroluminescence 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.

When current was applied to the organic electroluminescent devices prepared in Experimental Examples 1-1 to 1-8 and Comparative Examples 1 to 6, voltage, current density, luminance, color coordinates, and lifetime were measured. It was shown in 1. T95 means the time required for the luminance to decrease from the initial luminance (650 nit) to 95%.

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

  The core of the present invention exhibits characteristics of low voltage, high efficiency, and long life as compared with an organic electroluminescence device manufactured using the compounds of Comparative Examples 1 to 6 as an electron blocking layer. The voltage was reduced by about 5 to 10%, and the efficiency was increased by 10% or more. The direction of the amine linked to the second, tenth and eleventh positions of the existing indolo [3,2,1-jk] carbazole is linked to the sterically hindered direction (seventh) as in the compound of the present invention. When coupled in the direction in which the conjugation breaks, it has been shown that the properties of efficiency increase, voltage decrease, and long life are exhibited, and the stability of the core indolo [3,2,1-jk] carbazole itself is increased. In addition, since many portions where the core and the amine are connected 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 (12)

Heterocyclic compound represented by the following chemical formula 1:
[Chemical Formula 1]

In Formula 1, Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
L1 to L3 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 divalent heterocyclic group;
R1 to R3 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group,
a and c are integers of 0 to 3, b is an integer of 0 to 4, and when a to c are 2 or more, the substituents in parentheses are the same or different.   The Ar1 and Ar2 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 described in 1.   Ar1 and Ar2 are the same or different from each other, and each independently represents a phenyl group substituted or unsubstituted phenyl group; a phenyl group substituted or unsubstituted biphenyl group; a phenyl group substituted or unsubstituted terphenyl group; Substituted or unsubstituted triphenylene group with phenyl group; substituted or unsubstituted dimethylfluorene group with phenyl group; substituted or unsubstituted dibenzofuran group with phenyl group; substituted or unsubstituted dibenzothiophene group with phenyl group; or substituted with phenyl group Or the heterocyclic compound of Claim 1 which is an unsubstituted carbazole group.   The 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. Heterocyclic compounds.   The heterocyclic compound according to claim 1, wherein L 2 and L 3 are the same or different from each other and are each independently a direct bond; or a phenylene group.   The heterocyclic compound according to claim 1, wherein R1 to R3 are hydrogen. The heterocyclic compound according to claim 1, wherein the compound of the chemical formula 1 is selected from the following structural formulas:

  An organic electroluminescent 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 And at least 1 of the said organic substance layer is an organic electroluminescent element which contains the heterocyclic compound of any one of Claims 1-7.   The organic electroluminescence device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.   The organic electroluminescence device according to claim 8, wherein the organic 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 element according to claim 8, 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 electroluminescence device according to claim 8, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.

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