WO2019139233A1

WO2019139233A1 - Heterocyclic compound and organic light emitting element using same

Info

Publication number: WO2019139233A1
Application number: PCT/KR2018/013120
Authority: WO
Inventors: 하재승; 김연환; 이성재
Original assignee: 주식회사 엘지화학
Priority date: 2018-01-09
Filing date: 2018-10-31
Publication date: 2019-07-18

Abstract

The present invention provides a novel heterocyclic compound and an organic light emitting element using the same.

Description

2019/139233 1 »（1 ^ 1 {2018/013120

[Name of invention]

Heterocyclic compound and organic light emitting device using the same

Citation with Related Application (s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2018-0002875 dated January 9, 2018 and Korean Patent Application No. 10-2018-0124557 dated October 18, 2018. All content disclosed in the literature is included as part of this specification.

The present invention relates to a heterocyclic compound and an organic light emitting device including the same.

Background Art

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent researches on the luminance, driving voltage and response speed. The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. The organic layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons ( ₆ X ^ 1: ₀₁₁₎ are formed when the injected holes and the electrons meet each other. It will glow when the excitons fall back to the ground. There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices. 0 2019/139233 1 »(： 1 ^ 1 {2018/013120

Detailed Description of the Invention

[Technical problem]

The present invention relates to a heterocyclic compound compound and an organic light emitting device comprising the same.

Technical Solution

In one embodiment of the present invention, a compound represented by the following Chemical Formula 1 is provided:

[Formula 1]

In Chemical Formula 1,

Or any one of

One of the remaining excluding XI to XI is ¾, and the remaining excluding the medium to ¾ are hydrogen, respectively.

And ¾ are each independently represented by the following Chemical Formula 2 or 3, and at least one of ¾ is represented by the following Chemical Formula 2,

(If ₃ is represented by formula (2) represented by the formula (3); And 九 are represented by the formula (2), except when represented by the formula (3).

[Formula 2]

[Formula 3]

-（1_ ₄ ） ₅ -Yarn ₃

In Chemical Formulas 2 and 3, 2019/139233 1 »（： 1 ^ 1 {2018/013120

¾ to ¾ are each independently 0 or N, at least one of ¾ to ¾ is ^,

1 to 14 are each independently, bound; Or substituted or unsubstituted 0 _6-60 arylene,

₃ to ₃ each independently represent a substituted or unsubstituted 0 ₆ -60 ⁶ _ aryl group; Or a 0 ₂ -60 heteroaryl group including one or more of 0, 比 and substituted or unsubstituted,

I, ₁ , ..., and ₃ are each independently an integer of 0-3. Further, in another embodiment of the present invention, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1.

【Effects of the Invention】

The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode according to one embodiment of the present invention, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. .

In particular, the compound represented by Formula 1, in another embodiment of the present invention, may be grooved with a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.

【Brief Description of Drawings】

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. [Best Mode for Implementation of the Invention] 2019/139233 1 »（1 ^ 1 {2018/013120

Advantages and features of the embodiments of the present invention and how to achieve them will become apparent with reference to the embodiments described below in detail. However, the present invention is not limited to the embodiments disclosed below, but can be embodied in various forms, and the present embodiments are merely to make the disclosure of the present invention complete, and are common in the art to which the present invention pertains. It is provided to inform those skilled in the art to the fullest extent of the invention and the invention is defined only by the scope of the claims. Hereinafter, before the detailed description of the embodiments of the present invention, the expressions, terms, and the like commonly used in the present specification are defined. Hereinafter, the present invention will be described in more detail to help understand the present invention.

4-In this specification, *-and ¾ each mean a bond connected to another substituent. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of 0 and £ atoms, or two or more substituents in the above-described substituents are substituted or unsubstituted. For example, the "substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may be interpreted as a substituent to which two phenyl groups are linked. In this specification, the carbon number of the carbonyl group is not particularly limited. ， It is preferable to have 1 to 40 carbon atoms. Specifically, the compound may have the following structure, but is not limited thereto. 2019/139233 1 »（： 1 ^ 1 {2018/013120

In the present specification, the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, 1 butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited to this. 2019/139233 1 »（： 1 ^ 1 {2018/013120

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, 1-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group and the like, but is not limited thereto. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine. In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups are methyl, ethyl, propyl, ₁₁ _ propyl, isopropyl, butyl, I: tert-butyl, isobutyl, La-butyl, t-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, ₁₁ _ Pentyl, isopentyl, neopentyl, horatinpanyl, nuclear chamber, ₁₁ -nuclear chamber, 1 -methylpentyl, 2 -methylpentyl, 4 -methyl-2 -pentyl, 3,3-dimethylbutyl, 2 -ethylbutyl, heptyl, _11-heptyl, 1-methyl haeksil, cyclopentylmethyl, cyclohexyl haektil methyl, octyl, - octyl, 1 ₆₁寸-octyl, 1-methylheptyl,

2-ethylnuclear chamber, 2-propylpentyl, _11- nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1, 1-dimethyl-propyl, isonuclear chamber, 2-methylpentyl, 4-methylnuclear chamber, 5- Methyl nucleus, and the like, but is not limited thereto. In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl,

2 -pentenyl, 3 -pentenyl, 3 -methyl- 1 -butenyl, 1,3-butadienyl, allyl, 1 -phenylvinyl 1- day, 2 -phenylvinyl-1 -day, 2,2 -Diphenylvinyl- 1-yl, 2-phenyl- 2- (naphthyl-l-yl) vinyl-l-yl, 2,2-bis (diphenyl-l-yl) vinyl-l-yl, stilbe But there's a nil group, styrenyl group, 2019/139233 1 »（： 1 ^ 1 {2018/013120

It is not limited. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclonuclear chamber, 3-methylcyclonuclear chamber, 4-methylcyclonuclear chamber, 2,3-dimethylcyclonuclear chamber, 3, 4,5-trimethyl-bicyclo haeksil, 4 Ah ₆₁寸_ butyl cycloalkyl include but haeksil, cycloheptyl, cyclooctyl, and the like. In the present specification, the aryl group is not particularly limited, but preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be, for example, a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

This can be However, it is not limited to this. 2019/139233 1 »（： 1 ^ 1 {2018/013120

In the present specification, the heterocyclic group is a heterocyclic group including one or more of 0, rain, and the like as a dissimilar element. Although the carbon number is not particularly limited, it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group,

Thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group, but are not limited to these. In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description about the aryl group described above may be applied except that the arylten is a divalent group. In the present specification, except that the heteroarylene is a divalent group, the description of the aforementioned heterocyclic group may be applied. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic ring is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding. Compound represented by Formula 1 Hereinafter, provided by one embodiment of the present invention, represented by the following Formula 1 2019/139233 1 »（： 1 ^ 1 {2018/013120

The compound is described in detail. However, definitions of substituents and the like which are not described in detail below will be clearly understood with reference to the above.

[Formula 1]

The compound represented by the above formula (1), to the type of the heterocyclic compound quinoline ½ ₀ 1 ₁₁比比₆₎ to the linker (Nishi此D), it will have the same or different two substituents are combined structure to each other.

Here, two substituents which are the same or different from each other are defined as ¾ and ¾. Specifically,

And ¾ are each independently represented by Formula 2 or 3,

And at least one of ¾ is represented by the following Chemical Formula 2. Provided that ¾ is represented by Formula 2 and 人 is represented by Formula 3; And it is represented by the formula (2) and except the case represented by the formula (3).

[Formula 2]

[Formula 3]

( ₃ ) When the compound represented by the formula (1) is used as a material of the organic layer of the organic light emitting device, by introducing quinoline into the linker to improve the electron attracting ability to have a high battery, affinity and excellent electron transfer and Have the ability to regulate. Accordingly, the compound represented by Chemical Formula 1 may contribute to improving efficiency, low driving voltage and / or lifespan of the organic light emitting diode. 2019/139233 1 »（： 1 ^ 1 {2018/013120

Specifically, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-21, depending on the bonding position of 11 and ¾. Formulas 1-1 to 1-21 illustrate the case where all the rest except hydrogen, to medium, and ¾ are hydrogen:

[Formula 1-1]

[Formula

[Formula 1-7] 2019/139233 1 »（： 1 ^ 1 {2018/013120

[Formula 1-14] 2019/139233 1 »（： 1 ^ 1 {2018/013120

[Formula 1-21] 2019/139233 1 »（： 1 ^ 1 {2018/013120

When the compound represented by Chemical Formula 1 is represented by Chemical Formula 1-2, is represented by Chemical Formula 2, and Chemical Formula ¾ is represented by Chemical Formula 2 or 3.

Independently, the compound represented by Formula 1 described above is

When represented by 1-4, is represented by the formula (2), the formula ¾ is represented by the formula (2) or 3.

Independently, when the compound represented by Chemical Formula 1 is represented by Chemical Formulas 1-1, 1-3, and 1-5 to 1-21, 1 ′ and ¾ are each independently represented by Chemical Formula 2 or 3 Although it is represented, at least one of 1 'and 1 ₂ is represented by the formula (2). On the other hand, the following description, regardless of whether the formula 1 is represented by any one of the following formula 1-1 to 1-21. In addition, each of the following descriptions are independent, and merely presented specific examples of one embodiment of the present invention, and one embodiment of the present invention is not limited by the following description. In Formula 2, at least two of ¾, ¾, and ¾ may be: Specifically, ¾, ¾, and ¾ may be all. In Chemical Formulas 2 and 3, to may be each independently a bond or phenylene. Specifically, in Formula 2, ni may be phenylene. ! To 紅₃ are each independently phenyl unsubstituted or substituted with any one substituent selected from the group consisting of 0 _1-4 alkyl, halogen, cyano, and tri ( _-4 alkyl) silyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethyl fluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl. Specifically, at least one of ₁ and ₂ may be a phenyl group. \ ¥ 0 2019/139233 1 »（： 1 ^ 1 {2018/013120

2 _! And ¾ may be represented by Formula 2, and the other may be represented by Formula 3.

A specific example than _5, the compound represented by Formula 1 is any one selected from the number of days doeneungun configured to.

2019/139233 1 »（： 1/10 公 018/013120

Compound represented by the formula (1). It can be prepared by the same method as in Scheme 1. The preparation method is more specific in the preparation examples to be described later. 2019/139233 1 »（： 1 ^ 1 {2018/013120

Can be. Organic light emitting device using the compound represented by Formula 1

₅ or less, provided by another embodiment of the present invention will be described in detail an organic light emitting element. This is an organic light emitting device including the compound represented by Chemical Formula 1 in at least one layer of the organic layer, and the configurations, structures, and the like except for the compound represented by Chemical Formula 1 may be the same as those generally known in the art. have.

10

For example, the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.

_{There is 15} . However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting the hole, the hole injection layer, the hole transport layer, or

₂₀ A layer for simultaneously injecting and transporting a hole includes the compound represented by Chemical Formula 1. In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

₂₅₂₅

In addition, the organic layer may include an electron transport layer or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).

_In addition, the electron transport layer, the electron injection layer, or the layer for the electron transport and the electron injection at the same time includes the compound represented by the formula (1). In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1. In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic layers and a cathode are sequentially stacked on a substrate. The organic light emitting device according to the present invention may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, metal or conductive metal oxides or alloys thereof on a substrate using a method of physical vapor deposition (PVD), such as sputtering or e-beam evaporat ion, To form an anode, 2019/139233 1 »（： 1 ^ 1 {2018/013120

After forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material 0 2003/012890). However, the manufacturing method is not limited to this. For example, the first electrode is an anode, the second electrode is a cathode, or 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 generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide 110, indium zinc oxide 1a0; Combinations of metals and oxides, such as ¾0: hour or 3 炯_{2: ¾} ; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene], polypyrrole and polyaniline, and the like, but are not limited thereto. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; ᆻ 1 or Multilayer materials such as Li¾Ml, but not limited to them. The hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. It is preferable that H0M0 (highest occupied molecul ar orbital) of the hole injection material be between the work function of the anode material and the HOMO of the surrounding organic matter. Specific examples of the hole injection material include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but not limited to these. The hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer. A hole transporting material is a material capable of receiving holes from an anode or a hole injection layer and transferring the holes to the light emitting layer. Suitable. Specific examples include arylamine-based organics, conductive polymers, and block copolymers having both conjugated and non-conjugated portions, but are not limited thereto. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Concrete examples thereof include 8-hydroxyquinoline aluminum complex (Alq _3); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (p-phenylene vinylene) (PPV) family; Spi ro compounds; Polyfluorene, rubrene, etc., but not limited to these. 2019/139233 1 »（： 1 ^ 1 {2018/013120

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and gluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder type. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound is substituted or unsubstituted. A compound in which at least one arylvinyl group is substituted with a substituted arylamine, wherein the aryl group, silyl group,. A substituent selected from the group consisting of an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, styryl amine, styryl diamine, styryl triamine, styryl tetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex and a platinum complex. The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable. Specific examples thereof include a complex of 8-hydroxyquinoline; Complexes containing urine 1 _¾ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having 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, the effect of electron injection from the cathode, the light emitting layer or light emission 2019/139233 1 »（： 1 ^ 1 {2018/013120

The compound which has the outstanding electron injection effect with respect to a material, prevents the movement of the excitons produced | generated in the light emitting layer to the hole injection layer, and is excellent in thin film formation ability is preferable _. Specifically, fluorenone _, anthraquinodimethane, diphenoquinone _, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto. Examples of the metal complex compound include 8-hydroxyquinolinatolium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, Tris (2-methyl-8-hydroxyquinolinato) aluminum, Tris (8-hydroxyquinolinato) gallium _, bis ( ₁₀ -hydroxybenzo ¾] qui Nolinato) beryllium, bis (10-hydroxybenzo [biquinolinato] zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) （ _0- cresol Rato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, etc., are not limited to this. Do not. The organic light emitting device according to the present invention may be a front light emitting type, a back light emitting type or a double light emitting type depending on the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. [Form for implementation of the invention]

Preparation of the compound represented by Formula ₁ and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by these as described above.

<Production Example 1 (Synthesis of Compound 1 21)> 2019/139233 1 »(： 1/10 公 018/013120

(1) Synthesis of Compound 1 (Formula 1-1)

1) Synthesis: 3-bromo-2-hydroxyquinoline (30 133.8_01 _), triphenylene-2-ylboronic acid (38.2 _§ , 140.5_01 ₎ and tetrahydrofuran (30 (加 1) 2 potassium carbonate aqueous solution (150 _US1 ) was added, followed by addition of tetrakistriphenyl-phosphinopalladium (3.09 yo, ¾ _101¾>) , followed by heating and stirring for 10 hours. The aqueous solution of potassium carbonate was removed and the layers were separated. After removing the solvent, the white solid was recrystallized from ethyl acetate to obtain 01 (41.2).

Yield 83%) was prepared.

One to one] ⁺ = 372.44

2) Synthesis of 2 shows: (fluoride perfluoro Fu tanseol sulfonyl flow at room temperature was added and dissolved in chloroform (400), 67.1_ ₀₁ for ₂₅₎ (dropwise addition of 30.41 _§, 100. & ^ ₀₁₎ slowly, and Stir at room temperature for 3 hours. After extraction with water and 此 11 ₁₀ ™ at room temperature, the white solid was recrystallized with ethyl acetate and nucleic acid to prepare Show 2 (for 40.78, yield, 93%).

¾ 梅 [¾1 + ratio ⁺ = 654.52 2019/139233 1 »（： 1 ^ 1 {2018/013120

3) Synthesis of 3 shows: The compounds show bis 2 (, for 45.8_01 30), in a nitrogen atmosphere (pinacolato) di boron (12.83 _§, 50.5_ ₀₁₎ and potassium acetate (13.2 _§, 137.4 _{■ 01)} the Mix, add dioxane (300), and heat with stirring. In the state of reflux, bis (dibenzylideneacetone) palladium (per 1.00, 3 rice ₀₁ 1) and tricyclonuclear phosphine (0.98 s01 _% ) were added thereto, followed by heating and stirring for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, extraction was performed with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was recrystallized from tetrahydrofuran and ethyl acetate to prepare the Show 3 (18.07 _2, 82%).

[¾! +}!] ⁺ = 482.40

4) Synthesis of Compound 1: Shows 3 (2¾, 41.4_ _01), 2- (3-triazine (14.5 I, ₀₁ 42.2_) - chlorophenyl) - 4,6-diphenyl-1,3,5 After addition to tetrahydrofuran (300 US1), 21 potassium carbonate aqueous solution (150 ₀₁₁ ) was added, and tetrakistriphenyl-phosphinopalladium (0.987 yo, ¾ _01% ) was added thereto, followed by heating and stirring for 10 hours. . After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed and the layers were separated. After removing the solvent, the white solid was recrystallized from ethyl acetate.

Yield 80%) was prepared.

Within 1] ⁺ = 663.80 (2) Synthesis of Compound 2 (Formula 1-13)

2019/139233 1 »(： 1/10 公 018/013120

1) Synthesis of bar: 6-bromo-4-hydroxyquinoline in place of 3-bromo-2-hydroxyquinoline in the synthesis of I-1, 2,4-di instead of triphenylene-2-ilboronic acid Phenyl-6-

₅ （4- （4,4,5,5-tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl） synthesis by the same method, except that 1,3,5-triazine is used. Manufactured

3 units] ⁺ = 453.52

2) Synthesis of 32: 62 was prepared by synthesizing in the same manner, except that in the synthesis of Y2, instead of yarn was used.

₁₀ 3 +} {] ⁺ = 735.60

3) Synthesis of 63: In the synthesis of Show 3, 63 was prepared in the same manner except that seedling 2 was used instead of Show 2.

¾ ^ [¾1 state] ⁺ = 563.48

4) Synthesis of Compound 2: 83-Lule, 2-instead of Show 3, in the synthesis of Compound 1

Synthesis was carried out in the same manner, except that 4- (4-chlorophenyl) -2,6_diphenylpyrimidine was used instead of ₁₅ (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Compound 2 was prepared \ ¥ 0 2019/139233 （1/10 公 018/013120

[¾! ⁺ = 743.89

1) Synthesis of 01: 6-bromo-3-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline in the above synthesis, [1，1′-rather than triphenylene-2-ylboronic acid; Synthesis was carried out in the same manner, except that phenyl] _ 4 -ylboronic acid was used, thereby preparing 01.

1 «+ rain ^{+ ::} 298.36

2) Synthesis of 02: Synthesis of 02 was carried out in the same manner as in Synthesis of Show 2 except that Da was used instead of Sa.

¾6 [¾｝] ⁺ = 580.44

3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 02 was used instead of Yo2.

11 [11 + 11] ⁺ = 408.32

4) Synthesis of Compound 3: In the synthesis of Compound 1, 03 was substituted instead of Show 3,

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the synthesis in the same manner to prepare compound 3

3 [1 «+ ratio ⁺ = 589.71 2019/139233 1 »（： 1/10 公 018/013120

(4) Synthesis of Compound 4 (Formula 1-7)

1) Synthesis of 1) 1: 3 -bromo-4 -hydroxyquinoline instead of 3 -bromo-2 -hydroxyquinoline in the synthesis of I-1, 2,4 instead of triphenylene-2 -ilboronic acid -Diphenyl-6-

(4- (4,4,5,5-Tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl) Synthesis in the same manner except using 1,3,5-triazine 1) 1 was manufactured

] \ 1 +} {] ⁺ = 453.52

2) Synthesis of 02: Synthesis of 02 was carried out in the same manner, except that Synthesis of Show 2 was used instead.

13 [in ¾1] ⁺ = 735.60

3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 2 was used instead of Show 2.

Oh + rain 563.48

4) Synthesis of Compound 4: In the synthesis of Compound 1, 03 instead of Show 3, 2 −

The same method except using 4'-bromo- [1,1'-biphenyl] -4-carbonitrile instead of (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 4 was prepared by synthesizing with.

1 child1 \ 1 + 11] ⁺ = 614.72 2019/139233 1 »（： 1/10 公 018/013120

(5) Synthesis of Compound 5 (Formula 1-14)

1) Synthesis: 7-bromo-4-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline and 4,6-diphenyl instead of triphenylene-2-ylboronic acid in the synthesis of Show 1 -2_

Except for using (4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-2-yl) phenyl) pyrimidine, the synthesis was carried out in the same manner to prepare.

¾ [引; ¾! + ¾ ⁺ = 452.53

2) Synthesis of Grave 2: In the synthesis of Show 2, £ 2 was produced in the same way, except that instead of 4 was used.

¾ 犯 [¾! +}!] ⁺ = 734.61

3) Synthesis of Mystery 3: Synthesis of £ 3 was made in the same manner, except that Table 2 was used instead of Show2 in the synthesis of Show3.

¾ 犯 [! «+}!] ⁺ = 562.49

4) Synthesis of Compound 5: £ 3 instead of 3 in the synthesis of Compound 1, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the synthesis of the compound 5 in the same manner

¾1 ¾ «1] ⁺ = 743.89

(6) Synthesis of Compound 6 (Formula 1-15)

1) Synthesis of 1: Instead of 3-bromo-2-hydroxyquinoline in the synthesis of / \ 1, 8-bromo-4-hydroxyquinoline was substituted for triphenylene-2-ylboronic acid (4-

Synthesis was carried out in the same manner, except that (dibenzo [lipuran-4-yl) phenyl) boronic acid was used.

Manufactured

[¾! + !!] ⁺ = 388.44 2）

Synthesis of Seed 2 was prepared in the same manner as in Exhibit 2, except that instead of 4 was used. 2019/139233 1 »(： 1/10 公 018/013120 + rain 670.52

3）

Synthesis of: Synthesis of Show 3 was carried out in the same manner as in Synthesis of Show 3 except that F 2 was used instead of Show 2.

¾13¾ + 11] ⁺ = 498.40

4) Synthesis of Compound 6: In the synthesis of Compound 1, 3 rule instead of Show 3, 2-

(3-chlorophenyl) -4,6-diphenyl- 1,2- (4-chlorophenyl) instead of 1,3,5-triazine

Compound 6 was prepared in the same manner except for using (naphthalene-2-yl) -6-phenyl-1,3,5-triazine.

¾13 + ratio ⁺ = 729.86

1) Synthesis of A: In the synthesis of I-1, 7-bromo-8-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and triphenylene-2-ilboronic acid is used instead of (4- Carbazol _ 9 -yl) phenyl) Boronic acid was synthesized in the same manner, except that it was prepared.

¾ ^ [¾! + Ratio ⁺ = 387.45 2019/139233 1 »（： 1 ^ 1 {2018/013120

2) Synthesis of 02: Synthesis of G2 was carried out in the same manner as in Synthesis of Show 2 except that A was used instead of S.

3 [in 1 \ 1] ⁺ = 669.53

3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 02 was used instead of Show 2.

¾6 [¾1 + ratio ⁺ = 497.42

4) Synthesis of Compound 7: 3, instead of show 3 in the synthesis of Compound 1, 2 −

(3-chlorophenyl) -4,6-diphenyl 2-, 4-chlorophenyl instead of 1,3,5-triazine

Compound 7 was prepared in the same manner except for using (naphthalene-1-yl) -6-phenyl-1,3,5-triazine.

3 [¾1 + ratio ⁺ = 728.87

(8) Synthesis of Compound 8 (Formula 1-1 ⁸ )

2019/139233 1 »（： 1/10 公 018/013120

1) Synthesis: 8-bromo-5-hydroxyquinoline in place of 3-bromo-2-hydroxyquinoline in the synthesis of 4 '-(4, 4, instead of triphenylene-2-ylboronic acid 5,5-Tetramethyl-l, 3,2-dioxabolorane-2-yl)-[1,1'-diphenyl] -4-carbonitrile was synthesized in the same manner, except that it was prepared.

1 Ma ¾1 + ratio ⁺ = 323.37

2) Synthesis of 112: In the synthesis of Show 2, 112 was synthesized in the same manner except for using Ta instead of Sa.

1 child¾1 +} 1] ⁺ :: 605.45

3) Synthesis of 113: In the synthesis of Show 3, 112 was used instead of Show 2. Except for the synthesis in the same way to manufacture

[¾! + ¾ ⁺ = 433.33

4) Synthesis of Compound 8: In the synthesis of Compound 1, 113 instead of Show 3 and 2,4-diphenyl instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazane. -6- (4- (4,4,5,5_tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl) 1,3,5-triazine in the same manner except Compound 8 was prepared by synthesis.

Oh + rain 614.72

1) Synthesis of 11: In the synthesis of the above compound, 2-chloro-6-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline, and 9- (4- (4) instead of triphenylene-2-ylboronic acid. -Phenyl-6- (4- （4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-2-yl) phenyl) l, 3,5-triazin-2-yl) II was prepared in the same manner except for using phenyl) 페닐 -carbazole. 2019/139233 1 »（： 1 ^ 1 {2018/013120 A¾1 + ratio ⁺ = 618.71

2) Synthesis of 12: In the synthesis of Show 2, 12 was prepared by synthesizing in the same manner except that I I was used instead of Show 1.

¾ 保 [in ¾1] ⁺ = 900.79

3) Synthesis of Compound 9: In the synthesis of Compound 1, 13 was used instead of Show 3, and phenylboronic acid instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Compound 9 was prepared in the same manner except for preparing compound 9

1 1 \ 1 + ¾ ⁺ = 678.81

(10) Synthesis of Compound 10 (Formula 1-6)

1) Synthesis of II: In the synthesis of Show 1, 8-chloro-2-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl instead of triphenylene-2-ylboronic acid 6- (4- (4, 4, 5,5-Tetramethyl-l, 3,2-dioxabolorane-2-yl) phenyl) except for using 1,3,5-triazine Was synthesized to prepare II.

Within 13] ⁺ = 453.52

2) Synthesis of 12: using instead of in the synthesis of 2019/139233 1 »（： 1/10 公 018/013120 Except for 1/10

¾! £ [¾! +}!] ⁺ = 735.60

3) Synthesis of] 3 Synthesis of 13 was carried out in the same manner as in Synthesis of Show 3, except that 犯 was used instead of Show 2.

¾13¾ + 11] ⁺ = 563.48

10) Synthesis of Compound 10: In the synthesis of Compound 1, 13 (L) instead of Show 3, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-chloro) Phenyl) -4,6-diphenyl-1,3,5-triazine was synthesized in the same manner to prepare compound 10.

3 [¾1 + ratio ⁺ = 744.87

(11) Synthesis of Compound 11 (Formula 1-2)

2019/139233 1 »（： 1/10 公 018/013120

1) Synthesis of XI: Instead of 3-bromo-2-hydroxyquinoline in the synthesis of I-1

2- (chloro-)-hydroxyquinoline was replaced with 2-([1.1'-biphenyl] -3-yl)-4-phenyl-6- (4, 4, 5, instead of triphenylene-2-ylboronic acid. 5-tetramethyl-1,3,2-dioxabolorane-2-yl) _ 1,3,5-triazine was synthesized in the same manner except that

3 units] ⁺ = 529.62

2) Synthesis: In the synthesis of Show 2, 1 (2) was prepared by synthesizing in the same manner except that 1 (1) was used instead.

13_] ⁺ = 811.69

3) Synthesis of Compound 11: In the synthesis of Compound 1, biphenyl-4 instead of show 3 instead of 2-, 3- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. A compound 11 was prepared by the same method except for using boronic acid.

¾ 3 [¾1] ⁺ = 665.81

(12) Synthesis of Compound 12 (Formula 1-3)

1) 1 Synthesis: 2-Chloro-5-hydroxyquinoline in place of 3-bromo-2-hydroxyquinoline in the above synthesis, 2,4-diphenyl-6 in place of triphenylene-2-ylboronic acid -(3-4, 4, 5, 5--tetramethyl-l, 3,2-dioxabolorane-2-yl) phenyl)-1,3,5-triazine Except for the use, it was synthesized in the same way and manufactured.

1 ¾1 + 11] ⁺ = 453.52

2) Synthesis of 12: In the synthesis of Show 2, 1 ^ 2 was prepared by synthesizing in the same manner except that 1 instead of 4 was used.

¾6 [¾1 + 11] ⁺ = 735.60

3) Synthesis of Compound 12 In the synthesis of Compound 1, 12 instead of 3, 2 −

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead _. Compound 12 was prepared in the same manner except for using 3- (VII! -Carbazol-9-yl) phenyl) boronic acid, to prepare Compound 12.

¾1 and 1 \ «{] ⁺ = 678.81

1) Synthesis: Instead of 3-bromo-2-hydroxyquinoline in the synthesis of the above

2 -bromo-7 -chloroquinoline instead of triphenylene-2-ylboronic acid (4'-cyano-

Except that [1，1′-biphenyl] -4-yl) boronic acid was used.

2019/139233 1 »（： 1/10 公 018/013120

3) Synthesis of Compound 13: In the synthesis of Compound 1, ¾12 instead of Show 3 was substituted with 2- (4-chloro instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Phenyl) -4,6-diphenyl-1,3,5-triazine was synthesized in the same manner to prepare compound 13

1) Synthesis: 3-bromo-5-chloroquinoline in place of 3-bromo-2-hydroxyquinoline in the synthesis of the above compound, 2-([1,1'-) in place of triphenylene-2-ylboronic acid Biphenyl]-4-yl)-4-phenyl-6- (4- (4, 4, 5, 5--tetramethyl- 1, 3, 2- dioxaborolane- 2-yl) phenyl) -1, Except for the use of 3,5-triazines, they were synthesized in the same manner to produce.

MS [M + H] ⁺ = 390.88

2) Synthesis of 2: Synthesis of 2 was carried out in the same manner as in the synthesis of Show 3, except that 附 was used instead of Show 2. 2019/139233 1 »（： 1/10 公 018/013120

482.40

3) Synthesis of Compound 14: In the synthesis of Compound 1, 2-bromotriphenyl instead of N 2 rule, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of Show 3 Compound 14 was prepared in the same manner, except that ten was used.

In the synthesis of Compound 1, 3-bromo-7-quinoline is substituted for show 3, and 2,4-diphenyl is substituted for 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. -6- (3-4,4,5,5_tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl)-1,3,5-triazines in the same manner except Compound 15 was prepared by synthesis.

13 + ratio ⁺ 744.87 (16) Synthesis of Compound 16 (Formula 1-11)

1） Synthesis of 01

In the synthesis of the above, 3-bromo-8-chloroquinoline instead of 3-bromo-2-hydroxyquinoline and (4- (naphthalen-1-yl) phenyl) borotrane instead of traphenylene-2-ylboronic acid 01 was prepared by synthesizing in the same manner except for using nic acid.

1 Ma ¾1 + Ratio ⁺ = 366.86

2） Synthesis of 02

Synthesis of 02 was carried out in the same manner, except that 01 was used instead of 2- in the synthesis of Ya-3.

Oh + rain 458.37

3) Synthesis of Compound 16: In place of Show 3 in the synthesis of Compound 1, 02, 2-

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 16 was prepared by the same method except in the same manner.

¾ ^ [¾1] ⁺ = 739.89

(17) Synthesis of Compound 17 (Formula 1-12) 2019/139233 1 »（： 1/10 公 018/013120

3-bromo-8-chloroquinoline was replaced by 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2) instead of triphenylene-2-ylboronic acid. Dioxaborolane 2-yl) phenyl) 1,3, 5- Triazine was synthesized in the same manner except that triazine was used to produce a child.

+ R 471.96

2) Synthesis of? 2: In the synthesis of ^ 3, 2 was synthesized in the same manner except that Ra was used instead of Show 2.

3 [in 1⁄3] ⁺ = 563.48

3) Synthesis of Compound 17: In the synthesis of Compound 1, 2ruL, 2-instead of Show 3

Synthesis in the same manner, except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine was used instead of (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Compound 17 was prepared

財 [] ¾ + ¾ ⁺ = 743.89

(18) Synthesis of Compound 18 (Formula 1-16) 2019/139233 1 »（： 1/10 公 018/013120

1) Synthesis of ¾1: 5 -Chloro-6-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline in the synthesis of Show 1, 2,4-diphenyl instead of triphenylene-2-ylboronic acid 6- (3-4,4,5,5-Tetramethyl-l, 3,2-dioxabolorane-2-yl) phenyl)-except for using 1,3,5-triazine Synthesized with

3¾ + ratio ⁺ = 453.52

2) Synthesis of 02: Synthesis of 02 was carried out in the same manner as in Example 2 except that Ah was used instead to prepare 02.

3¾ units] ⁺ = 735.60

¾ 保 [¾! + ¾ ⁺ = 563.48

3) Synthesis of Compound 18: In the synthesis of Compound 1, 03 instead of Show 3, 3- (bromobiphenyl) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the use, compounds 18 were prepared in the same manner. 2019/139233 1 »（： 1/10 公 018/013120

MS [M + H] ⁺ = 589.71

(19) Synthesis of Compound 19 (Formula 1-17)

1) Synthesis: 5 -bromo-7 -hydroxyquinoline instead of 3 -bromo-2 -hydroxyquinoline in the synthesis of Sangasho 1, 4,6-di instead of triphenylene-2 -alboronic acid Except for using phenyl-2_ (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) phenyl) pyrimidine, the synthesis was carried out in the same manner to prepare.

3 [¾1 + ratio ⁺ = 452.52

2) Synthesis of 1 ~ 2: In the synthesis of Show 2, seedling 2 was prepared by synthesizing in the same manner except that instead of yarn was used.

(¾! + ¾ ⁺ = 734.61 () 2019/139233 1 »(1/10 公 018/013120

3) Synthesis of Key 3: In the synthesis of Show 3, seedling 3 was prepared in the same manner except that seedling 2 was used instead of show 2.

¾ ^ [¾1 + ¾ ⁺ = 562.49

4) Synthesis of Compound 19: In the synthesis of Compound 1, Compound 3 instead of Show 3 was substituted with 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Chlorophenyl) -4,6-diphenyl-1,3,5-triazine was synthesized in the same manner to prepare Compound 19.

3¾ + ratio ⁺ = 743.89

(20) Synthesis of Compound 20 (Formula 1-19)

1) Synthesis: 6-bromo-7-chloroquinoline instead of 3-bromo-2-hydroxyquinoline in the synthesis of Show 1, 2,4-diphenyl- instead of triphenylene-2-ylboronic acid Synthesis was carried out in the same manner, except that 6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) phenyl) pyrimidine was used to prepare. 2019/139233 1 »(： 1/10 公 018/013120

1 child 1 ⁺ 1 ratio ⁺ = 470.97

2) Synthesis of 松: In the synthesis of Show 3, except that Show 2 was used instead, it was synthesized in the same manner to prepare 役.

+ R 562.49

3) Synthesis of Compound 20: In the synthesis of Compound 1, 2 instead of 3, 2-

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the synthesis in the same manner to prepare Compound 20

3 [¾1] ⁺ = 743.89

1) Synthesis of II: In the above synthesis, 6-bromo-8-chloroquinoline instead of 3-bromo-2-hydroxyquinoline and 2-([1,1 '] instead of triphenylene-2-ylboronic acid. -Biphenyl] -4 -yl) -4 -phenyl- 6- (4- (4,4,5,5 -tetramethyl- 1,3,2 -dioxaborolane-2 -yl) phenyl- 1, II was prepared by the same method except that 3,5-triazine was used.

MS [M + H] ⁺ = 548.06

2) Synthesis of 72: In the above Synthesis of Show 3, it was used instead of Show 2 2019/139233 1 »（： 1 ^ 1 {2018/013120

12 were manufactured in the same way except for the synthesis.

301 + 1!] ⁺ = 639.58

3) Synthesis of Compound 21: In the synthesis of Compound 1, 2-bromotriphenyl instead of 12 rule, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of show 3 Compound 21 was prepared in the same manner except for the use of len.

¾¾ [¾1] ⁺ = 739.89

11X3 (Indium Tin Oxide) thin film is a glass substrate coated with ((1,000 ᅀ thickness: Put ₀₁ 7059 ₁₁ For greater, it was dissolved in distilled water, a dispersant and washed with ultrasonic waves. Detergent was used as the ₃ (土la ¾. Of product, distilled water was used as the secondary distilled water and filtered by filter附11 O ₆ 0 _0. products (D). After washing 0 for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried.

Nuclear nitrile nucleated azatriphenylgirene on the 110 transparent electrode thus prepared

111-1） was vacuum-deposited to a thickness of 500 yaw to form a hole injection layer. Thereafter, 1111 (900 kPa), a material for transporting holes, was vacuum deposited, followed by vacuum deposition of # 2 at a film thickness of 50 kPa on the hole transport layer to form a hole control layer. Host # 1 and the dopant 301 compound (25: 1) were vacuum-deposited at the thickness of 300 pieces with the compound light emitting layer. Then, an E ^: m compound (50 kV) was formed as an electron control layer and the compound synthesized in Preparation Example 1

310 sets) was sequentially formed into an electron transport layer. 10 μm thick Rimium fluoride (Niwa ¾¾ and Shawyong (10: 1, 150 入) was deposited on the electron transport bottle and 1,000 ᅀ thick.

An organic light-emitting device was manufactured by depositing aluminum to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 1 flock, the lithium fluoride was 0.2 入八%, and the aluminum was maintained at the deposition rate of 3-7 phosphorus.

2019/139233 1 »（1 ^ 1 {2018/013120

Except for using the compound 4 instead of compound 2 in the electron transport layer in Example 1 was the same experiment. <Example 3>

Except for using Compound 5 instead of Compound 2 as the electron transport layer in Example 1 was the same experiment.

Except for using the compound 7 instead of compound 2 as the electron transport layer in Example 1 was the same experiment.

Example 5

Except for using compound 8 instead of compound 2 as the electron transport layer in Example 1 was the same experiment.

Except for using the compound 10 instead of compound 2 in the Example 1 electron transport layer was the same experiment.

Except for using the compound 11 instead of compound 2 in the electron transport in Example 1 was the same experiment. <Example 8>

Except for using the compound 13 instead of compound 2 in the electron transport layer in Example 1 and was the same experiment.

Example 9

Except for using Compound 15 instead of Compound 2 as the electron transport layer in Example 1 was the same experiment. 2019/139233 1 »（： 1 ^ 1 {2018/013120

Except for using Compound 19 instead of Compound 2 in the electron transport layer in Example 1 and was the same experiment.

Except for using Compound 20 instead of Compound 2 in the electron transport layer in Example 1 and was the same experiment. <Example 12>

Except for using the compound 7 instead of compound 2 in Example 1, and the ratio of the compound 7 and ni £ 1 1: 1 instead of 1: 1 was the same experiment. Example 13

Except for using compound 13 instead of compound 2 in Example 1, and the ratio of the compound 13 and 110 and 1: 1 instead of 1: 1 was the same experiment.

Except for using compound 20 instead of compound 2 in Example 1, and the ratio of compound 20 and niyo was 2: 1 instead of 1: 1 was the same experiment. Comparative Example 1

In Example 1, the electron transport certificate was tested in the same manner except that £ 11 was used instead of Compound 2.

Comparative Example 2

In Example 1, the electron transport layer was tested in the same manner except that £ 2 was used instead of Compound 2. 2019/139233 1 »（： 1 ^ 1 {2018/013120

In Example 1, the electron transport layer was tested in the same manner except that £ 12 was used instead of Compound 2, and the ratio of the electron transport layer and 110 was 2: 1 instead of 1: 1.

<Rain: 5 己 ^! 4>

In Example 1, the electron transporting layer used £ 2 instead of Compound 2.

The same experiment was carried out.

In Example 1, the electron transport layer was used instead of the compound 5 5 5

牌 6 2019/139233 1 »(： 1 ^ 1 {2018/013120

Experimental Example 1

Table 1 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the electron transporting material as in Examples 1 to 14 and Comparative Examples 1 to 6.

TABLE 1

Example 15

A glass substrate (corning 7059 glass) coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,000 A was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. The detergent used was Fischer Co.'s product. Secondly filtered distilled water was used as a product filter. After washing IT0 for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried.

On the thus prepared IT0 transparent electrode, nucleonitrile nuxaazatriphenylgirene (hexanitrile hexaazat riphenylphenyl, HI-1) was thermally vacuum deposited to a thickness of 500 A to form a hole injection layer. HT1 (900 A), which is a material for transporting holes, was vacuum deposited thereon, followed by vacuum deposition of HT2 with a film thickness of 50 A on the hole transport layer to form a hole control layer. The host BH1 and the dopant BD1 compound (25: 1) were vacuum deposited to a thickness of 300 A as the compound light emitting layer. Then, Compound 1 (50A) synthesized in Preparation Example 1 was formed as an electron control layer and co-deposited with ETM2 and LiQ (1: 1, 310 A) to form an electron transport layer sequentially. Lithium fluoride (LiF), Mg and Ag (10: 1, 150 A) having a thickness of 10 A was sequentially deposited on the electron transport layer, and a cathode was formed by depositing aluminum having a thickness of 1,000 A, thereby manufacturing an organic light emitting device. .

In the above process, the deposition rate of the organic material was maintained at 1 A / sec, the lithium fluoride was maintained at 0.2 A / sec, and the aluminum was maintained at a deposition rate of 3 to 7 A / sec.

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<Example 1 '

Except for using Compound 3 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment. <Example 17>

Except for using the compound 6 instead of compound 1 in the electron control layer in Example 15 was the same experiment.

Except for using compound 7 instead of compound 1 in the electron control layer in Example 15 and was the same experiment.

Except for using the compound 9 instead of compound 1 as the electron control layer in Example 15 was the same experiment.

Except for using the compound 10 instead of compound 1 as the electron control layer in Example 15 was the same experiment.

Except for using compound 11 instead of compound 1 in the electron control layer in Example 15 and was the same experiment. <Example 22>

Except for using Compound 12 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.

Except for using Compound 14 instead of Compound 1 as the electron control layer in Example 15 was the same experiment. 2019/139233 1 »（： 1 ^ 1 {2018/013120

Except for using Compound 16 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.

Except for using Compound 17 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.

₁₀ <Example 26>

Except for using Compound 18 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.

Example 27

₁₅ The same experiment as in Example 15 except for using the compound 21 instead of compound 1 as the electron control layer.

In Example 1, the electron control layer was used in place of Compound 1 Compound 6,

Except for the same experiment.

In Example 1, the electron control layer was used in place of Compound 1 Compound 12,

Except for the same experiment.

In Example 1, the electron control layer was used in place of compound 1 compound 17,

Except for the same experiment. 2019/139233 1 »（： 1 ^ 1 {2018/013120

Comparative Example 7

The same experiment was conducted in Example 7, except that £ 13 instead of 1 was used as the electron adjusting layer.

The same experiment was conducted in Example 7, except that £ 4 instead of 1 was used as the electron adjusting layer. Comparative Example 9

Except for using compound 4 in Example 7 instead of compound 1 in Example 7, and the ratio of the electron transport layer and Nesan 2: 1 instead of 1: 1 was the same experiment. Comparative Example 10

Except for using the compound 13 in Example 7 instead of compound 1 in Example 7, and the same experiment except that the ratio of the electron transport layer and the ni 0 in 1: 2 instead of 1: 1. Comparative Example 11

In Example 7, the electron control layer was tested in the same manner except that 7 was used instead of Compound 1.

牌 7 2019/139233 1 »(： 1 ^ 1 {2018/013120

Comparative Example 12

In Example 7, the electron control layer was tested in the same manner except that £ 18 was used instead of Compound 1.

Experimental Example 2

Table 2 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the electron transporting material as in Examples 15-30 and Comparative Example 7 11.

TABLE 2

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Compound derivative of formula according to the ^invention, is able to control the electron transport and electron role in an organic electronic device including an organic light emitting element, the element according to the invention represents the efficiency, driving voltage, excellent properties in terms of stability.

[Explanation of code]

1 substrate 2 anode

3: light emitting layer 4: cathode

5: hole injection layer 6: hole transport layer

7: light emitting layer 8: electron transport layer

Claims

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[Range of request]

[Claim 11

Compound represented by the following formula ( ₁ ):

[Formula 1]

In Chemical Formula 1,

¥ ₁ to '1 of which is ¾,

1 to ₇ in all but _one of which one is _2, and to _7, each of which except the ¾ and _2, the hydrogen

(Wherein 九 is represented by the formula (2) and represented by the formula (3); And (2) except for the case represented by Formula (2) and represented by Formula (3).

At least one of ¾ to ¾

Or each independently, a bond; Or substituted or unsubstituted 0 _{6-60 arylten} , 2019/139233 1 »（： 1 ^ 1 {2018/013120

Show to ₃ each independently represent a substituted or unsubstituted 0 _6-60 aryl group; Or a 0 _2-60 heteroaryl group containing one or more of 0, 比 and £ substituted or unsubstituted,

I），

I, and ₃ are each independently an integer of 0 to 3.

[Claim 2]

The method of claim 1,

Formula ₁ is represented by any one of the following formula 1-1 to 1-21,

compound:

[Formula 1-1]

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[Formula 1-13] 2019/139233 1 »（： 1 ^ 1 {2018/013120

[Formula 1-20] 2019/139233 1 »（： 1 ^ 1 {2018/013120

[Formula 1-21]

In Chemical Formula 1-2,

¾ is represented by Formula 2, wherein ¾ is represented by Formula 2 or 3,

In Chemical Formula 1-4,

Is represented by Formula 2, wherein Formula ¾ is represented by Formula 2 or 3,

In Chemical Formulas 1-1, 1-3, and 1-5 to 1-21,

1 ′ and ¾ are each independently represented by Formula 2 or 3, and at least one of ¾ is represented by Formula 2.

[Claim 3]

The method of claim 1,

At least two of ¾, ¾, and ¾ are N,

compound.

[Claim 4]

The method of claim 1,

To each independently a bond or phenylene,

compound.

[Claim 5]

The method of claim 1,

! To ₃ are each independently unsubstituted or 0 _1-4 alkyl, 2019/139233 1 »（： 1 ^ 1 {2018/013120

Phenyl substituted with any one substituent selected from the group consisting of halogen, cyano, and tra ( _-4 alkyl) silyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethyl fluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl;

compound.

[Claim 6]

The method of claim 5,

The! And _two popularly least one group,

compound.

[Claim 7]

The method of claim 1,

And one of ¾ is represented by Formula 2, and the other is represented by Formula 3,

compound.

[Claim 8]

The method of claim 1,

The compound represented by Formula 1 is any one selected from the group consisting of

compound:

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[Claim 9]

A first electrode; A second electrode provided to face the first electrode; And the first 2019/139233 1 »(： 1/10 公 018/013120 An organic light-emitting device comprising at least one organic layer provided between an electrode and the second electrode, wherein at least one of the organic layers is one of claims 1 to 8 An organic light emitting device comprising the compound according to any one of claims.