WO2019216743A1 - Novel heterocyclic compound and organic light emitting diode using same - Google Patents

Abstract

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

Description

 2019/216743 1 »（： 1 ^ 1 {2019/006002

[Name of invention]

 Novel heterocyclic compound and organic light emitting device using the same

 Technical Field

 This application claims the benefit of priority based on Korean Patent Application No. 10-2018-0054366 of May 11, 2018, and Korean Patent Application No. 10-2019-0054491 of May 9, 2019, and the Korean Patent Application All content disclosed in the literature is incorporated as part of this specification.

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

[Technique to become background of invention]

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, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted. 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. In order to increase the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multi-layered structure composed of different materials. For example, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. 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 layer, and excitons (6X (^ 1011) are formed when the injected holes and the electrons meet each other. When the excitons fall back to the ground state, light is emitted, and there is a continuous demand for the development of new materials for the organic materials used in the organic light emitting devices as described above. 2019/216743 1 »（： 1 ^ 1 {2019/006002

[Patent literature]

 (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

[Content of invention]

 Problem to be solved

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

[Measures of problem]

 The present invention provides a compound represented by the following formula (1).

 [Formula 1]

¾ 내지 ¾ 중 1개 이상은 이고，

At least one of ¾ to ¾ is

내지 九 중 1개 이상은 이고， To ¾ are each independently

At least one of 九 is

 0 is 0 or £,

! ₅ to ₅ each independently represent a substituted or unsubstituted 0 _6-60 aryl; 0 _1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, 比 and 0, show ₅ is adjacent to each other 2019/216743 1 »（： 1 ^ 1 {2019/006002

Combine with a group to form a condensed ring,

Or each independently, a single bond; Substituted or unsubstituted (: _{6-60 arylten} ; or 0 _1-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted 0 and unsubstituted,

¾ to ¾ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 0 _1-60 alkyl; Substituted or unsubstituted 0 _1-60 haloalkyl; Substituted or unsubstituted 0 _1-60 alkoxy; Substituted or unsubstituted 0 _1-60 haloalkoxy; Substituted or unsubstituted 0 ₃ -60 cycloalkyl; Substituted or unsubstituted 0 _2-60 alkenyl; Substituted or unsubstituted aryl; Substituted or unsubstituted 0 ₆ -60 aryloxy; Or 0 _{! -60} heteroaryl containing one or more heteroatoms selected from the group consisting of substituted and unsubstituted 0 and

 111 is an integer from 0 to 4,

 112 is an integer from 0 to 3,

 Is an integer of 0 to 4. In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. to provide.

【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, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.

【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. As shown in FIG.

2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9. And with cathode (4) 2019/216743 1 »（： 1 ^ 1 {2019/006002

An example of an organic light emitting device is shown.

[Specific contents to carry out invention]

 Hereinafter, the present invention will be described in more detail to help understand the present invention. The present invention provides a compound represented by Chemical Formula 1.

본 명세서에 있어서， 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄， 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다. In the present specification, + means a bond connected to another substituent. As used herein, the term `` substituted or unsubstituted '' is deuterium; Halogen group; Cyano 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 group; Aryl sulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine group; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl including one or more of 0 and o atoms, or two or more substituents connected to the substituents exemplified above. For example, when "a substituent to which two or more substituents are linked" is a biphenyl group, the biphenyl may be interpreted as an aryl group substituted with one phenyl group or a substituent to which two phenyl groups are linked. Is not particularly limited, but is preferably 1 to 40. Specifically, the compound may be a compound having the following structure, but is not limited thereto. 2019/216743 1 »（： 1 ^ 1 {2019/006002

In the present specification, the oxygen of 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.

본 명세서에 있어서， 이미드기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

본 명세서에 있어서， 실릴기는 구체적으로 트리메틸실릴기， 트리에틸실릴기 ,

부틸디메틸실릴기， 비닐디메틸실릴기 , 프로필디메틸실릴기， 트리페닐실릴기， 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. 2019/216743 1»（：1^1{2019/006002

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group,

Butyl dimethyl silyl group, vinyl dimethyl silyl group, propyl dimethyl silyl group, triphenyl silyl group, diphenyl silyl group, phenyl silyl group and the like, but is not limited thereto. 2019/216743 1 »（： 1 ^ 1 {2019/006002

In the present specification, the boron group is specifically trimethyl boron group, triethyl boron group, butyl dimethyl boron group, triphenyl boron group, 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 the alkyl group include methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, 11-butyl, isobutyl, ratchetbutyl, 3-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, 11 -Pentyl, isopentyl, neopentyl, kopentyl, nuclear chamber, 11-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4 -methyl- 2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, II-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, -octyl, 1 ₆ generation_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-yl, 2 -phenylvinyl-l-yl, 2, 2 -Diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2019/216743 1 »（： 1 ^ 1 {2019/006002

2, 2-bis (diphenyl- 1-yl) vinyl- 1-yl, stilbenyl group, styrenyl group and the like, but is not limited to these. 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-trimethylcyclonuclear chamber, 4,6-butylcyclonuclear chamber, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. In the present specification, the aryl group is not particularly limited, but preferably has 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 a monocyclic aryl group, but may be 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, peryleneyl group, chrysenyl group, or the like, but is not limited thereto. In the present specification, heteroaryl is a heteroaryl containing one or more of 0, and £ as a dissimilar element, carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl 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, acridil group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, 2019/216743 1 »（： 1 ^ 1 {2019/006002

Dibenzothiophene group, benzofuranyl group, phenanthrosline group (6113111; 11101), isooxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto. In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of 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 heteroaryl amine may be applied to the description of the aforementioned heteroaryl. 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, except that the arylene is a divalent group, the description of the aryl group described above may be applied. In the present specification, the description of the aforementioned heteroaryl may be applied except that the heteroarylene is a divalent group. 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 heterocycle is not a monovalent group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding. On the other hand, in Formula 1, Show to ₃ may be each independently a substituted or unsubstituted 0 _6-60 aryl. For example, the Shows ₃ and ₃ may be phenyl. Preferably, in Chemical Formula 1, I, to each independently, a single bond; Or substituted or unsubstituted Ce-60 arylene. For example, may be a single bond. Preferably, Formula 1 may be any one of the compounds of Formulas 2 to 5. 2019/216743 1 »（： 1/10 公 019/006002

[Formula 2]

[Formula 4] 2019/216743 1 ^» （： 1 ^ 1 {2019/006002

In the above, descriptions of ¾ to ¾, to = 0, ₄ , ₅ , 112 and! 13 are as defined above. Preferably, in Formula 1, ₄ and ₅ are each independently, substituted or unsubstituted 0 _6-60 aryl, or ₄ and 紅₅ may be combined with groups adjacent to each other to form a condensed ring. Preferably, in Formula 1, may be a single bond, phenylene, pyridinediyl, biphenyldiyl, or naphthylene. 2019/216743 1 »（： 1/10 公 019/006002

For example, the compound may be selected from the group consisting of the following compounds:

 2019/216743 1 »（： 1 ^ 1 {2019/006002

On the other hand, the compound represented by the formula (1) can be prepared by the same production method as in Scheme 1 below.

Scheme 1

X is halogen and more preferably bromo or chloro. The reaction is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The manufacturing method may be more specific in the production examples to be described later. 2019/216743 1 »（： 1 ^ 1 {2019/006002

In addition, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Formula 1; to provide. 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, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. 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 material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of 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 diode 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. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9. And an example of an organic light-emitting device composed of a cathode (4). In such a structure, the compound represented by Formula 1 is the hole injection layer, hole transport layer, electron 2019/216743 1 »（： 1 ^ 1 {2019/006002

It may be included in one or more layers of the blocking layer, the light emitting layer, the electron transport layer and the electron injection layer. Specifically, the organic material layer may include a light emitting layer, and the light emitting layer may include two or more host materials. In this case, the two or more host materials may include a compound represented by Chemical Formula 1. 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. At this time, such as sputtering or e-beam evaporat ion

Using a physical vapor deposit ion (PVD) method, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer are formed thereon. After forming the organic layer, 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 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, spray method, roll coating and the like, but is not limited thereto. 2019/216743 1 »（： 1 ^ 1 {2019/006002

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 thereto. 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 (⑴, indium zinc oxide (1å0); combinations of metals and oxides such as ¾0: hour or £ 炯₂ : 況; poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (則: For example, conductive polymers such as polypyrrole and polyaniline, etc., but are not limited thereto. It is preferable that the material has a small work function to facilitate electron injection, and 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 an alloy thereof, a multi-layered material such as LiF / Al or Li¾Ml, etc. The hole injection layer is a layer for injecting holes from an electrode, As the particle material, it has the ability to transport holes, and has an effect of hole injection at the anode, excellent hole injection effect on the light emitting layer or light emitting material, and prevents the excitons generated in the light emitting layer from moving to the electron injection layer or electron injection material. In addition, it is preferable that a compound having excellent thin film formation ability is preferred, wherein the highest occupied molecul ar orbital (H0M0) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic matter. Examples are metal porphyr (porphyr in), oligothiophene, arylamine-based organic matter, 2019/216743 1 »（： 1 ^ 1 {2019/006002

Nucleonitrilenuxazatriphenylene-based organics, quinacridone-based organics, perylene-based organics, anthraquinones and polyaniline and polythiophene-based conductive polymers, but are limited to these It is not. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. The hole transport layer is a material capable of transporting holes from the anode or the hole injection layer and transferring the holes to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. 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. Specific 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; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. The heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, as an aromatic amine derivative 2019/216743 1 »（： 1 ^ 1 {2019/006002

Examples of the bamboo aromatic ring derivative having a substituted or unsubstituted arylamino group include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound includes at least one of substituted or unsubstituted arylamines. As the compound in which the arylvinyl group is substituted, a substituent selected from one or two or more selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and 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, a platinum complex, and the like. The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include a complex of 8-hydroxyquinoline; Complexes containing four quarters; 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, etherboom and samarium, each followed by an aluminum layer or a silver layer. The electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a 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. 2019/216743 1 »(： 1 ^ 1 {2019/006002

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 [biquinolina] SAT beryllium bis (10-hydroxybenzo [biquinolinato] zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) （0-cresolato Gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc., but are not limited thereto. . The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission 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. Preparation of the compound represented by Chemical 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 only for illustrating the present invention, and the scope of the present invention is not limited thereto. Preparation Example 1 Preparation of Intermediate

2-Chloro-4- (4-chlorophenyl) -6-phenyl-l, 3,5-triazine (for 30.0, 99.7

1_) 1) and 2,4-diphenyl-6- (2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- 2019/216743 1 ^» （： 1 ^ 1 {2019/006002

Yl) phenyl) -1,3,5-triazine (43.4 g, 99.7 mmol) in tetrahydrofuran (300 rnL), followed by 2 M aqueous potassium carbonate (aq. K ₂ C0 ₃ ) (150 mL) Tetrakistriphenylphosphinopalladium [Pd (PPh ₃ ) ₄ ] (3.5 g, 3 mol%) was added thereto, followed by stirring and reflux for 12 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized with tetrahydrofuran and ethyl acetate, filtered and dried to give compound 1A (33.7 g, 59% yield).

MS: [M + H] ⁺ = 575 Preparation Example 2 Preparation of Intermediate VII

2-chloro-4- (3-chlorophenyl) -6-phenyl-l, 3,5_triazine (30.0 g, 99.7 ■ o1) and 2,4-dipheny1-6- (2- (4,4,5,5 -tetramethy1-1,3,2_dioxaboro1an-2-yl) phenyl) -1,3,5-tr ^. Disperse iazine (43.4 g, 99.7 mmol) in tetrahydrofuran (300 mL), then add 2 M aqueous potassium carbonate solution (aq. K ₂ CO ₃ ) (150 mL) and add tetrakistriphenylphosphinopalladium [Pd (PPh ₃ ) ₄ ] (3.5 g, 3 mol%) was added thereto, followed by stirring and reflux for 12 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized with tetrahydrofuran and ethyl acetate, filtered and dried to give compound 1BC28.0 g, yield 49%).

MS: [M + H] ⁺ = 575 Production Example 3 Preparation of Intermediate 1 2019/216743 1 ^» （： 1 ^ 1 {2019/006002

 2-ch 1 or o-4-(2-ch 1 or opheny 1) -6-pheny 1-1, 3, 5-t r i az i ne (30.0 g,

99.7 mmol) and 2, 4-diphenyl-6- (2- (4, 4, 5, 5-tetramethy 1-1,3, 2-dioxaborol an-2-yl) phenyl) -l, 3,5- triazine (43.4 g, 99.7 mmol) was dispersed in tetrahydrofuran (300 mL), then 2M aqueous potassium carbonate solution (aq. K ₂ CO ₃ ) (150 mL) was added and tetrakistriphenylphosphinopalladium [Pd (PPh ₃ ) ₄ ] (3.5 g, 3 mol%) was added thereto, followed by stirring and reflux for 12 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized with tetrahydrofuran and ethyl acetate, filtered and dried to give compound 1C (30.3 g, yield 53%).

MS: [M + H] ⁺ = 575

Compound 1A (20.0 g, 34.8 mmol) and dibenzo [b, d] furan_ 4 -ylboronic acid (11.1 g, 52.3 mmol) were added to dioxane (200 mL) in a nitrogen atmosphere, and the mixture was stirred and refluxed. This potassium potassium carbonate (14.4 g, 104.5 mmol) was dissolved in water (60 mL) and sufficiently stirred, followed by bis (tri-1-butylphosphine) palladium (0) (0.5 g, 1.0 mmol). After the reaction for 2 hours, the temperature was lowered to room temperature and filtered. 2019/216743 1 »（： 1 ^ 1 {2019/006002

The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and then recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to prepare compound 1 (17.5 _§ , yield 71%).

3: _] ⁺ = 707

디벤조［ 비퓨란 -4 -일보론산 대신 디벤조［13,(1］퓨란 -3 -일보론산을 사용한 것을 제외하고 실시예 1에서 화합물 1을 제조하는 방법과 동일한 방법으로 상기 화합물

66%)를 제조하였다.

The compound was prepared in the same manner as in the method of preparing Compound 1, except that dibenzo [13, (1] furan-3-ylboronic acid was used instead of dibenzo [bifuran-4-ylboronic acid.

66%) was prepared.

13: _] ⁺ = 707

디벤조［1₎,₍1］퓨란 -4 -일보론산 대신 디벤조［ 則퓨란- 2 -일보론산을 사용한 것을 제외하고 실시예 1에서 화합물 1을 제조하는 방법과 동일한 2019/216743 1»（：1^1{2019/006002

Same as the method for preparing compound 1 in Example 1, except that dibenzo [則 furan-2-ylboronic acid was used instead of dibenzo [1 ₎ and ₍ 1] furan-4-ylboronic acid 2019/216743 1 »（： 1 ^ 1 {2019/006002

70%）를 제조하였다.By the above method

70%) was prepared.

3: [¾1 unit] ⁺ = 707 Example 4: Preparation of compound 4

 Compound 4 (10.3 yo, 42%) by the same method as the method for preparing compound 1 in Example 1, except that dibenzo [則 furan-1-ylboronic acid was used instead of dibenzo [] furan-4-ylboronic acid Was prepared.

3: _] ⁺ = 707

디벤조［13 ,（1］퓨란 -4 -일보론산 대신 디벤조［1）,（1］티오펜- 4 -일보론산을 사용한 것을 제외하고 실시예 1에서 화합물 1을 제조하는 방법과 동일한 2019/216743 1»（：1^1{2019/006002

Except for using dibenzo [1], (1] thiophene-4-ylboronic acid in place of dibenzo [13, (1] furan-4-ylboronic acid, the same method as in Example 1 for preparing Compound 1 2019/216743 1 »（： 1 ^ 1 {2019/006002

Compound 5 (for 16.6, 66%) was prepared by the method.

디벤조［ 비퓨란- 4 -일보론산 대신 디벤조［13,(1］티오펜- 3 -일보론산을 사용한 것을 제외하고 실시예 1에서 화합물 1을 제조하는 방법과 동일한 방법으로 상기 화합물

78%)를 제조하였다. _] ⁺ = 723 Example 6: Preparation of compound 6

The compound was prepared in the same manner as in the method of preparing compound 1, except that dibenzo [13, (1] thiophene-3-ylboronic acid was used instead of dibenzo [bifuran-4-ylboronic acid.

78%) was prepared.

¾1 _] ⁺ = 723

디벤조比,₍1］퓨란 -4 -일보론산 대신 디벤조［13,(1］티오펜- 2 -일보론산을 사용한 것을 제외하고 실시예 1에서 화합물 1을 제조하는 방법과 동일한 방법으로 상기 화합물

29%)를 제조하였다.

The compound was prepared in the same manner as in the method for preparing compound 1 in Example 1, except that dibenzo [13, (1] thiophene-2-ylboronic acid was used instead of dibenzoby, ₍ 1] furan-4-ylboronic acid.

29%) was prepared.

13: [¾1 bet ⁺ = 723 2019/216743 1 »(： 1 ^ 1 {2019/006002 Example 8 Preparation of Compound 8

디벤조［ 퓨란- 4 -일보론산 대신 디벤조［ 티오펜- 1 -일보론산을 사용한 것을 제외하고 실시예 1에서 화합물 1을 제조하는 방법과 동일한 방법으로 상기 화합물 8（11.0 _§, 44%）를 제조하였다.

Compound 8 (11.0 _§ , 44%) was prepared in the same manner as in the preparation of Compound 1 in Example 1, except that dibenzo [thiophen-1-ylboronic acid was used instead of dibenzo [furan-4-ylboronic acid. Prepared.

¾13: ¾] ⁺ = 723

］퓨란

Furan

4-ilboronic acid （11. 1 dragon, 52.3 _ ₀ 1) was placed in dioxane (200 kPa) and stirred and refluxed. This potassium carbonate (14.4 yo, 104.5 _ ₀ 1) was dissolved in water (60 kPa). 2019/216743 1 »（： 1 ^ 1 {2019/006002

After sufficient stirring, bis (tri-1 -butylphosphine) palladium (0) (0.5 g, 1.0 mmol) was added thereto. After the reaction for 2 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and then recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to prepare compound 9 (16.2 g, yield 66%).

MS: [M + H] ⁺ = 707 Example 10: Preparation of Compound 10

디벤조比 ]퓨란 -4 -일보론산 대신 디벤조比 ]퓨란 -3 -일보론산을 사용한 것을 제외하고 실시예 9에서 화합물 9을 제조하는 방법과 동일한 방법으로 상기 화합물 10(9.3용, 38%)를 제조하였다.

Compound 10 (for 9.3, 38%) in the same manner as in the method for preparing compound 9 in Example 9, except for using dibenzo 比] furan-3-ylboronic acid instead of dibenzo 比] furan-4-ylboronic acid Was prepared.

13: _] ⁺ = 707 Example 11: Preparation of Compound 11

2019/216743 1»(：1/10公019/006002

대신 디벤조比，(1］퓨란 -1 -일보론산을 사용한 것을 제외하고 실시예 9에서 화합물 9을 제조하는 방법과 동일한 방법으로 상기 화합물

60%)를 제조하였다.

2019/216743 1 »(： 1/10 公 019/006002

Instead of using the compound in the same manner as in Example 9 except for using dibenzobi ， (1] furan-1-ylboronic acid

60%) was prepared.

_] ⁺ = 707 Example 12: Preparation of Compound 12

디벤조比 ］퓨란 -4 -일보론산 대신 디벤조［ 則티오펜- 4 -일보론산을 사용한 것을 제외하고 실시예 9에서 화합물 9을 제조하는 방법과 동일한 방법으로 상기 화합물 12(17.4요， 69%)를 제조하였다. 실시예 13: 화합물 13의 제조

Compound 12 (17.4, 69%) in the same manner as in the method for preparing compound 9 in Example 9, except that dibenzo [thiothiophene-4-ylboronic acid was used instead of dibenzo 比] furan-4-ylboronic acid ) Was prepared. Example 13: Preparation of Compound 13

2019/216743 1»（：1^1{2019/006002

2019/216743 1 »（： 1 ^ 1 {2019/006002

4-Iboronic acid (11.1 g, 52.3 ol) was added to dioxane (200 mL) and stirred and refluxed. This potassium potassium carbonate (14.4 g, 104.5 mmol) was dissolved in water (60 mL) and sufficiently stirred, followed by bis (tri-1-butylphosphine) palladium (0) (0.5 g, 1.0 mmol). After the reaction for 2 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and then recrystallized using a tetrahydrofuran and ethyl acetate mixed solution. The resulting solid was filtered and dried to prepare compound 13 (17.2 g, yield 70%).

MS: _] ⁺ = 707 Example 14 Preparation of Compound 14

66%)를제조하였다. 14 Compound described above in the same manner as in the method for preparing compound 13 in Example 13, except that dibenzo [13, (1] furan-3-ylboronic acid was used instead of 14 dibenzo 比] furan-4-ylboronic acid

66%) was prepared.

디벤조［ 到퓨란 -4 -일보론산 대신 디벤조比 ］퓨란 -1 -일보론산을 사용한 것을 제외하고 실시예 13에서 화합물 13을 제조하는 방법과 동일한 방법으로 상기 화합물

24%)를 제조하였다. ^ 13: [1 \ «1] ⁺ = 707 Example 15 Preparation of Compound 15 2019/216743 1 »（： 1 ^ 1 {2019/006002

The compound was prepared in the same manner as in the method of preparing compound 13, except that dibenzo [] furan-1-ylboronic acid was used instead of dibenzo [[chi] furan-4-ylboronic acid.

24%) was prepared.

디벤조比 ］퓨란 -4 -일보론산 대신 디벤조!; 비티오펜- 4 -일보론산을 사용한 것을 제외하고 실시예 13에서 화합물 13을 제조하는 방법과 동일한 방법으로 상기 화합물

19%)를 제조하였다. 실험예 1

Dibenzo non] dibenzo! Instead of furan-4-ilboronic acid; The compound in the same manner as the compound 13 in Example 13, except that bithiophene-4-ylboronic acid was used.

19%) was prepared. Experimental Example 1

A glass substrate coated with a thin film of I0 (indium tin oxide) having a thickness of 1,300 A was put in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as distilled water. After washing IT0 for 30 minutes, the ultrasonic cleaning was performed twice with distilled water for 10 minutes. Distilled water 2019/216743 1 »（： 1 ^ 1 {2019/006002

After the washing, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The following bar-1 compound was thermally vacuum deposited to a thickness of 50 kPa on the 110 transparent electrode prepared as above to form a hole injection layer. The following _1 compound was vacuum-deposited to a thickness of 250 to form a hole transport certificate on the hole injection layer, and the following 1′-2 compound was vacuum deposited to a thickness of 50 particles on the hole transport layer to form an electron blocking layer. Compound 1, the following X-1 compound, and phosphorescent dopant 61) -1, which were prepared in Example 1 as a light emitting layer on the electron blocking layer, were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 particles. . The following £ 1 ^ 1 compound was vacuum deposited to a thickness of 250 shows to form an electron transport certificate, and the following seed compound and a needle were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron having a thickness of 100 shows. An injection layer was formed. Aluminum was deposited on the electron injection layer to a thickness of 1000 particles to form a cathode.

2019/216743 1 »（： 1 ^ 1 {2019/006002

상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 떼를 유지하였고, 알루미늄은 2

증착 속도를 유지하였으며， 증착시 진공도는 1 X 10^-7 ~ 5 X 10一⁸ 1；017를 유지하였다. 실험예 2내지 16

In the above process, the deposition rate of organic material was maintained at 0.4 to 0.7, and aluminum was 2

The deposition rate was maintained, and the vacuum degree during deposition was maintained at 1 × 10 ⁻⁷ to 5 × 10 1 ⁸ 1; 017. Experimental Examples 2 to 16

Instead of compound 1 of Example 1 in Experimental Example 1 described in Table 1 below 2019/216743 1 »（： 1 ^ 1 {2019/006002

Except for using the compound, an organic light emitting device was manufactured in the same manner as in Experimental Example 1. Comparative Experiments 1 to 5

 An organic light emitting diode was manufactured according to the same method as Experimental Example 1, except that Compound 1 of Example 1 was used instead of Compound 1 of Example 1 in Experimental Example 1.

2019/216743 1»（：1^1{2019/006002

2019/216743 1 »（： 1 ^ 1 {2019/006002

The experimental examples and comparative experimental examples were measured voltage and efficiency at a current density of 11/011 ² An organic light emitting device in, by measuring the lifetime at a current density of 50 / (Re ² is shown in Table 1 to the result. In this case,] ₉₅ means the time which becomes 95% of initial luminance.

[Table 1]

2019/216743 1»（：1^1{2019/006002

2019/216743 1 »（： 1 ^ 1 {2019/006002

As shown in Table 1, when using the compound of the present invention as a light emitting layer material, it was confirmed that the characteristics of the voltage is low, and the efficiency and life is excellent compared to Comparative Experimental Examples 1 to 5. This affects each other as two triazine units are located at 0 ^ 110 of phenyl in the compounds of the present invention, and as dibenzofuran or thiophene is directly or indirectly substituted with one or more triazine units, The excellent stability of the electron transport unit and the material, it can be expected that the voltage of the device is low, and the efficiency and life is excellent. [Explanation of code]

 1 ： Substrate 2 ： Anode

 3: light emitting layer 4: cathode

 5: hole injection layer 6: hole transport layer

 7: electron blockage 8: electron transport layer

 9: electron injection layer

Claims

2019/216743 1 »（： 1 ^ 1 {2019/006002 【claims】 【claim 11】 Compound represented by the following formula (1):  [Formula 1]

 In Chemical Formula 1, ¾ to ¾ are each independently,

At least one of ¾ to ¾ is To ₃ are each independently

At least one of ¾ is  0 is 0 or Show to ₅ each independently represent a substituted or unsubstituted 0 ₆ -60 aryl; Or substituted or unsubstituted 0-, hetero- and 01-60 heteroaryl including one or more selected from the group consisting of: to ₅ is bonded to a group adjacent to each other to form a condensed ring, Or each independently, a single bond; Substituted or unsubstituted ( _6:60 arylene); Or 0 _1-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, ^ and To ¾ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted- ₆₀ alkyl; Substituted or unsubstituted 0 _1-60 haloalkyl; Substituted or unsubstituted 0 _{! -60} alkoxy; Substituted or unsubstituted 0 _1-60 2019/216743 1 »（： 1 ^ 1 {2019/006002 Haloalkoxy; Substituted or unsubstituted 0 _3-60 cycloalkyl; Substituted or unsubstituted 0 ₂ -60 alkenyl; Substituted or unsubstituted aryl; Substituted or unsubstituted 0 ₆ -60 aryloxy; Or 01-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted 0 and £ substituted or unsubstituted,  Is an integer of 0 to 4,  112 is an integer of 0 to 3,  Is an integer of 0 to 4. [Claim 2]  The method of claim 1, ₃ to ₃ are each independently a substituted or unsubstituted 0 _6-60 aryl. [Claim 3]  The method of claim 1, Show to ₃ is phenyl; [Claim 4]  The method of claim 1,  Or each independently, a single bond; Or substituted or unsubstituted 0 ₆ -60 arylene, compound [Claim 5]  The method of claim 1,  To silver is a single bond [Claim 6]  The method of claim 1, Formula 1 is any one of the compounds of Formulas 2 to 5, Compound: 2019/216743 1 »（： 1/10 公 019/006002 [Formula 2]

[Formula 4] 2019/216743 1 ^» （： 1 ^ 1 {2019/006002

In Chemical Formulas 2 to 5, ¾ to ¾, V _! To ¾, Q 1 Ar Ar and the description is as defined in claim 1. [Claim 7]  The method of claim 1, Ar ₄ and ₅ are each independently, substituted or unsubstituted 0 _6-60 aryl, or 4 and ₅ are combined with each other to form a condensed ring. [Claim 8] 2019/216743 1 »（： 1 ^ 1 {2019/006002 The method of claim 1,  Is a single bond, phenylene, pyridinediyl, biphenyldiyl, or naphthylene, [Claim 9]  The method of claim 1, The compound is any one selected from the group consisting of the following compounds:

41

43 2019/216743 1 »（： 1 ^ 1 {2019/006002

[Claim 10]  A first electrode; A second electrode provided to face the first electrode; And at least one organic material increaser provided between the low 11 electrode and the second electrode, wherein at least one of the organic material layers is a compound according to any one of claims 1 to 9. It comprises, an organic light emitting device. [Claim 11]  The method of claim 10,  The organic material layer may include a light emitting layer, and the light emitting layer includes two or more host materials. [Claim 12]  The method of claim 11,  The two or more host materials include a compound represented by Formula 1, an organic light emitting device.