KR102126884B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Heterocyclic compounds and organic light emitting devices using the same {HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts 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, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

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

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

[Formula 1]

In Chemical Formula 1,

Any one of Y ₁ to Y ₇ is Z ₁ ,

Any one of Z ₁ to Y ₇ other than Z ₁ is Z ₂ ,

The rest of Z ₁ and Z ₂ among Y ₁ to Y ₇ are each hydrogen.

Z ₁ and Z ₂ are each independently represented by the following Formula 2 or 3, but at least one of Z ₁ and Z ₂ is represented by the following Formula 2,

(However, Y ₃ When represented by Formula 2 and Y ₁ is represented by Formula 3; And Y ₅ Formula 2, except when Y ₁ is represented by Formula 3)

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

X ₁ to X ₃ are each independently CR ₁ or N, wherein at least one of X ₁ to X ₃ is N,

L1 to L4 are each independently a bond; Or substituted or unsubstituted C _6-60 arylene,

Ar ₁ to Ar ₃ are each independently a substituted or unsubstituted C _6-60 aryl group; Or a substituted or unsubstituted C _2-60 heteroaryl group containing one or more of O, N, Si and S,

p, q, r, and s are each independently an integer from 0 to 3.

In addition, 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 layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by the formula (1). .

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

Particularly, the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material in another embodiment of the present invention.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light emitting device comprising 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 Did.

Advantages and features of embodiments of the present invention, and a method of achieving them, will be clarified with reference to embodiments described below in detail. However, the present invention is not limited to the embodiments disclosed below, but may be implemented in various different forms, and only the embodiments allow the disclosure of the present invention to be complete, and are conventional in the art to which the present invention pertains. It is provided to fully inform the knowledgeable person of the scope of the invention, and the invention is only defined by the scope of the claims.

Hereinafter, prior to a detailed description of embodiments of the present invention, expressions, terms, and the like commonly used herein are defined.

Hereinafter, it will be described in more detail in order to help the understanding of the present invention.

및

는 각각, 다른 치환기에 연결되는 결합을 의미한다. In this specification,

And

Each represents a bond connected to a different substituent.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted with a straight chain, 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, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-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 straight chain or branched chain, and 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 are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styrenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary 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, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups and dibenzofuranyl groups, and the like, but are not limited thereto.

In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, the description of the heteroaryl group among the heteroarylamines described above may be applied. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this specification, the heterocycle 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, a compound represented by the following Chemical Formula 1 provided in one embodiment of the present invention will be described in detail. However, definitions of substituents, etc., which are not described in detail below, will be clearly understood with reference to the foregoing.

[Formula 1]

The compound represented by Chemical Formula 1 has a structure in which two substituents, which are the same or different from each other, are bonded to each other by using quinoline, a type of heterocyclic compound, as a linker.

Here, two substituents which are the same or different from each other are defined as Z ₁ and Z ₂ . Specifically, Z ₁ and Z ₂ are each independently represented by Formula 2 or 3, but at least one of Z ₁ and Z ₂ is represented by Formula 2 below. However, Y ₃ When represented by Formula 2 and Y ₁ is represented by Formula 3; And Y ₅ It is represented by the formula (2) and Y ₁ is represented by the formula (3).

[Formula 2]

[Formula 3]

When the compound represented by Chemical Formula 1 is used as a material of an organic material layer of an organic light emitting device, quinoline is introduced as a linker to improve electron withdrawing ability to have high electron affinity and to have excellent electron transport and control ability. . Accordingly, the compound represented by Chemical Formula 1 may contribute to improving the efficiency of the organic light emitting device, low driving voltage, and/or lifetime characteristics.

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 Z ₁ and Z ₂ . The following Chemical Formulas 1-1 to 1-21 exemplify a case in which all of Y ₁ to Y ₇ except Z ₁ and Z ₂ are all hydrogen:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Formula 1-14]

[Formula 1-15]

[Formula 1-16]

[Formula 1-17]

[Formula 1-18]

[Formula 1-19]

[Formula 1-20]

[Formula 1-21]

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

Independently, when the compound represented by Chemical Formula 1 is represented by Chemical Formula 1-4, Z ₁ is represented by Chemical Formula 2, and Chemical Formula Z ₂ is represented by Chemical Formula 2 or 3.

In addition, independently, when the compound represented by Formula 1 is represented by Formula 1-1, 1-3, and 1-5 to 1-21, Z ₁ and Z ₂ are each independently Formula 2 or 3 However, at least one of Z ₁ and Z ₂ is represented by Chemical Formula 2.

Meanwhile, the following description is applied irrespective of whether Formula 1 is represented by any one of the following Formulas 1-1 to 1-21. In addition, each of the following descriptions are independent, and only specific examples of one embodiment of the present invention are presented, and one embodiment of the present invention is not limited by the following description.

In Formula 2, at least two of X ₁ , X ₂ and X ₃ may be N. Specifically, X ₁ , X ₂ and X ₃ may all be N.

In Chemical Formulas 2 and 3, L ₁ to L ₄ may be each independently a bond or phenylene. Specifically, L ₃ in Formula 2 may be phenylene.

Ar ₁ to Ar ₃ are each independently, unsubstituted or substituted with any substituent selected from the group consisting of C _1-4 alkyl, halogen, cyano, and tri(C _1-4 alkyl)silyl. Phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl. Specifically, at least one of Ar ₁ and Ar ₂ may be a phenyl group.

One of Z ₁ and Z ₂ may be represented by Chemical Formula 2, and the other one may be represented by Chemical Formula 3.

For a more specific example, the compound represented by Formula 1 may be any one selected from the group consisting of:

The compound represented by Formula 1 is. It can be prepared in the same manner as in Scheme 1 below. The manufacturing method may be more specific in the manufacturing examples to be described later.

Organic light-emitting device using the compound represented by the formula (1)

Hereinafter, an organic light emitting device provided in another embodiment of the present invention will be described in detail. This is an organic light emitting device including the compound represented by Formula 1 in at least one layer of the organic material layer, and the rest of the structures, structures, etc., except for the compound represented by Formula 1, may be the same as those generally known in the art. .

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 multi-layer 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 as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 It includes the compound displayed.

In addition, the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

Further, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.

In addition, the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron transport and electron injection includes a compound represented by Chemical Formula 1.

In addition, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.

Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate. Further, 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 the 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 device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting device comprising 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 Did. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic 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 can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode 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 when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one 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.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic layer is smooth. 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 (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SNO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably 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; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light-emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and 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, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, 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 transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; 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 according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, and bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

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

The preparation of the compound represented by Chemical Formula 1 and the 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 them.

<Production Example 1 (Synthesis of Compounds 1 to 21)>

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

1) Synthesis of A1: 3-Bromo-2-hydroxyquinoline (30g, 133.8mmol), triphenylene-2-ylboronic acid (38.2g, 140.5mmol) was added to tetrahydrofuran (300ml) 2M potassium carbonate aqueous solution (150 ml) was added, and tetrakistriphenyl-phosphino palladium (3.09 g, 2 mol%) was added, followed by stirring for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed to separate the layers. After removal of the solvent, the white solid was recrystallized with ethyl acetate to prepare the C1 (41.2 g, yield 83%).

MS[M+H] ⁺ = 372.44

2) Synthesis of A2: A1 (25g, 67.1mmol) was added to chloroform (400ml) to dissolve and then slowly added dropwise perfluorofutansulfonyl fluoride (30.41g, 100.6mmol) at room temperature for 3 hours at room temperature. It was stirred. After extraction with water and chlroform at room temperature, the white solid was recrystallized with ethyl acetate and hexane to prepare A2 (40.78 g, yield, 93%).

MS[M+H] ⁺ = 654.52

3) Synthesis of A3: Compound A2 (30 g, 45.8 mmol), bis(pinacolato)diboron (12.83 g, 50.5 mmol) and potassium acetate (13.2 g, 137.4 mmol) were mixed in a nitrogen atmosphere, and dioxane ( 300ml) and heated while stirring. In reflux, bis(dibenzylideneacetone)palladium (1.00g, 3mol%) and tricyclohexylphosphine (0.98g, 6mol%) were added and heated and stirred for 3 hours. After the reaction was completed, the temperature was reduced to room temperature and filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with tetrahydrofuran and ethyl acetate produced A3 (18.07 g, 82%).

MS[M+H] ⁺ = 482.40

4) Synthesis of Compound 1: A3 (20g, 41.4mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (14.5g, 42.2mmol) is tetrahydrofuran After adding to (300ml), 2M potassium carbonate aqueous solution (150ml) was added, tetrakistriphenyl-phosphino palladium (0.987g, 2mol%) was added, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed to separate the layers. After removal of the solvent, the white solid was recrystallized from ethyl acetate to prepare the C1 (20.57 g, yield 80%).

MS[M+H] ⁺ = 663.80

(2) Synthesis of Compound 2 (Formula 1-13)

1) Synthesis of B1: In the synthesis of A1, 6-bromo-4-hydroxyquinoline was substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl was substituted for triphenylene-2-ylboronic acid. -6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)1,3,5-triazine except the same Synthesized by method to prepare B1

MS[M+H] ⁺ = 453.52

2) Synthesis of B2: B2 was synthesized by the same method except that B1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 735.60

3) Synthesis of B3: B3 was synthesized by the same method except that B2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 563.48

4) Synthesis of Compound 2: In the synthesis of Compound 1, B3 was substituted for A3, and 4-(4-chlorophenyl was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-2,6-Diphenylpyrimidine was synthesized in the same manner, except that Compound 2 was prepared.

MS[M+H] ⁺ = 743.89

(3) Synthesis of Compound 3 (Formula 1-9)

1) Synthesis of C1: In the synthesis of A1, 6-bromo-3-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and [1,1'- is substituted for triphenylene-2-ylboronic acid. C1 was prepared by synthesizing in the same manner except that biphenyl]-4-ylboronic acid was used.

MS[M+H] ⁺ = 298.36

2) Synthesis of C2: C2 was synthesized by the same method except that C1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 580.44

3) Synthesis of C3: C3 was synthesized by the same method except that C2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 408.32

4) Synthesis of Compound 3: In the synthesis of Compound 1, C3 was substituted for A3, and 2-(4-chlorophenyl was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner, except that the compound 3 was prepared.

MS[M+H] ⁺ = 589.71

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

1) Synthesis of D1: In the synthesis of A1, 3-bromo-4-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl is substituted for triphenylene-2-ylboronic acid. -6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)1,3,5-triazine except the same Synthesis by the method to prepare D1

MS[M+H] ⁺ = 453.52

2) Synthesis of D2: D2 was prepared by synthesizing in the same manner, except that D1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 735.60

3) Synthesis of D3: D3 was synthesized by the same method except that D2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 563.48

4) Synthesis of Compound 4: In the synthesis of Compound 1, D3 was substituted for A3, and 4'-bromo-[ instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 4 was synthesized by the same method except that 1,1'-biphenyl]-4-carbonitrile was used.

MS[M+H] ⁺ = 614.72

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

1) Synthesis of E1: In the synthesis of A1, 7-bromo-4-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline and 4,6-diphenyl is substituted for triphenylene-2-ylboronic acid. E1 was synthesized by the same method except that 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)pyrimidine was used. Prepared

MS[M+H] ⁺ = 452.53

2) Synthesis of E2: E2 was synthesized by the same method except that E1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 734.61

3) Synthesis of E3: E3 was synthesized by the same method except that E2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 562.49

4) Synthesis of Compound 5: In the synthesis of Compound 1, E3 is substituted for A3, and 2-(4-chlorophenyl is substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner, except that the compound 5 was prepared

MS[M+H] ⁺ = 743.89

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

1) Synthesis of F1: In the synthesis of A1, 8-bromo-4-hydroxyquinoline was substituted for 3-bromo-2-hydroxyquinoline, and triphenylene-2-ylboronic acid was substituted for (4-(dibenzo F1 was synthesized by the same method except that [b,d]furan-4-yl)phenyl)boronic acid was used.

MS[M+H] ⁺ = 388.44

2) Synthesis of F2: E2 was synthesized by the same method except that F1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 670.52

3) Synthesis of F3: In the synthesis of A3, F3 was synthesized by the same method except that F2 was used instead of A2.

MS[M+H] ⁺ = 498.40

4) Synthesis of Compound 6: In the synthesis of Compound 1, F3 is substituted for A3, and 2-(4-chlorophenyl is substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4- (naphthalen-2-yl)-6-phenyl-1,3,5-triazine was synthesized in the same manner except for using to prepare compound 6

MS[M+H] ⁺ = 729.86

(7) Synthesis of Compound 7 (Formula 1-21)

1) Synthesis of G1: In the synthesis of A1, 7-bromo-8-hydroxyquinoline was substituted for 3-bromo-2-hydroxyquinoline, and triphenylene-2-ylboronic acid was substituted for (4-(9H- G1 was synthesized by the same method except that carbazole-9-yl)phenyl)boronic acid was used.

MS[M+H] ⁺ = 387.45

2) Synthesis of G2: G2 was synthesized by the same method except that G1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 669.53

3) Synthesis of G3: G3 was synthesized by the same method except that G2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 497.42

4) Synthesis of Compound 7: In the synthesis of Compound 1, G3 was substituted for A3, and 2-(4-chlorophenyl was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine was synthesized in the same manner, except that Compound 7 was prepared.

MS[M+H] ⁺ = 728.87

(8) Synthesis of Compound 8 (Formula 1-18)

1) Synthesis of H1: In the synthesis of A1, 8-bromo-5-hydroxyquinoline was substituted for 3-bromo-2-hydroxyquinoline, and 4'-(4, instead of triphenylene-2-ylboronic acid. 4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-[1,1'-diphenyl]-4-carbonitrile was synthesized in the same manner except that H1 was prepared

MS[M+H] ⁺ = 323.37

2) Synthesis of H2: H2 was synthesized by the same method except that H1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 605.45

3) Synthesis of H3: In the synthesis of A3, H3 was synthesized by the same method except that H2 was used instead of A2.

MS[M+H] ⁺ = 433.33

4) Synthesis of Compound 8: In the synthesis of Compound 1, H3 was substituted for A3, and 2,4-diphenyl- was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Same method except using 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)1,3,5-triazine Synthesized to prepare Compound 8

MS[M+H] ⁺ = 614.72

(9) Synthesis of Compound 9 (Formula 1-4)

1) Synthesis of I1: In the synthesis of A1, 2-chloro-6-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline and 9-(4-(4 is substituted for triphenylene-2-ylboronic acid. -Phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)1,3,5-triazin-2-yl) I1 was synthesized by the same method except that phenyl)9H-carbazole was used.

MS[M+H] ⁺ = 618.71

2) Synthesis of I2: I2 was synthesized by the same method except that I1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ =900.79

3) Synthesis of Compound 9: In the synthesis of Compound 1, I3 was substituted for A3, and phenylboronic acid was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. It was synthesized in the same manner except for Compound 9

MS[M+H] ⁺ = 678.81

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

1) Synthesis of J1: In the synthesis of A1, 8-chloro-2-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl- is substituted for triphenylene-2-ylboronic acid. Same method except using 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)1,3,5-triazine Synthesized to prepare J1

MS[M+H] ⁺ = 453.52

2) Synthesis of J2: In the synthesis of A2, J2 was synthesized by the same method except that J1 was used instead of A1.

MS[M+H] ⁺ = 735.60

3) Synthesis of J3: J3 was prepared by synthesizing in the same manner, except that J2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 563.48

10) Synthesis of Compound 10: In the synthesis of Compound 1, J3 instead of A3, 2-(4-chlorophenyl instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner, except that the compound 10 was prepared.

MS[M+H] ⁺ = 744.87

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

1) Synthesis of K1: In the synthesis of A1, 2-chloro-4-hydroxyquinoline was substituted for 3-bromo-2-hydroxyquinoline, and 2-([1.1'- instead of triphenylene-2-ylboronic acid. Biphenyl]-3-yl)-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3,5-tri K1 was prepared by synthesizing in the same manner except that azine was used.

MS[M+H] ⁺ = 529.62

2) Synthesis of K2: In the synthesis of A2, K2 was synthesized by the same method except that K1 was used instead of A1.

MS[M+H] ⁺ = 811.69

3) Synthesis of Compound 11: In the synthesis of Compound 1, K2 is substituted for A3, and biphenyl-4-boronic acid is substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 11 was synthesized in the same manner except for using

MS[M+H] ⁺ = 665.81

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

1) Synthesis of L1: In the synthesis of A1, 2-chloro-5-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl- is substituted for triphenylene-2-ylboronic acid. Same method except using 6-(3-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine Synthesized to prepare L1

MS[M+H] ⁺ = 453.52

2) Synthesis of L2: In the synthesis of A2, K2 was synthesized by the same method except that L1 was used instead of A1.

MS[M+H] ⁺ = 735.60

3) Synthesis of Compound 12: In the synthesis of Compound 1, L2 instead of A3, 3-(9H-carbazole instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Compound 9 was synthesized by the same method except that -9-yl)phenyl)boronic acid was used.

MS[M+H] ⁺ = 678.81

(13) Synthesis of Compound 13 (Formula 1-5)

1) Synthesis of M1: In the synthesis of A1, 2-bromo-7-chloroquinoline was substituted for 3-bromo-2-hydroxyquinoline, and (4'-cyano- was substituted for triphenylene-2-ylboronic acid. [1,1'-biphenyl]-4-yl) M1 was prepared by synthesizing in the same manner except that boronic acid was used.

MS[M+H] ⁺ = 341.81

2) Synthesis of M2: In the synthesis of A3, M2 was synthesized by the same method except that M1 was used instead of A2.

MS[M+H] ⁺ = 433.33

3 ) Synthesis of Compound 13: In the synthesis of Compound 1, M2 was substituted for A3, and 2-(4-chlorophenyl was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner, except that the compound 13 was prepared.

MS[M+H] ⁺ = 614.72

(14) Synthesis of Compound 14 (Formula 1-8)

1) Synthesis of N1: In the synthesis of A1, 3-bromo-5-chloroquinoline was substituted for 3-bromo-2-hydroxyquinoline, and 2-([1,1] was substituted for triphenylene-2-ylboronic acid. '-Biphenyl]-4-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)- N1 was prepared by synthesizing in the same manner except that 1,3,5-triazine was used.

MS[M+H] ⁺ = 390.88

2) Synthesis of N2: In the synthesis of A3, N2 was synthesized by the same method except that N1 was used instead of A2.

MS[M+H] ⁺ = 482.40

3) Synthesis of Compound 14: In the synthesis of Compound 1, N2 was substituted for A3, and 2-bromotriphenylene was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 14 was synthesized by the same method except for using

MS[M+H] ⁺ = 739.89

(15) Synthesis of Compound 15 (Formula 1-10)

In the synthesis of Compound 1, 3-bromo-7-quinoline was substituted for A3, and 2,4-diphenyl- was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Same method except using 6-(3-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine Synthesized to prepare Compound 15

MS[M+H] ⁺ = 744.87

(16) Synthesis of Compound 16 (Formula 1-11)

1) Synthesis of O1

In the synthesis of A1, 3-bromo-8-chloroquinoline is substituted for 3-bromo-2-hydroxyquinoline, and (4-(naphthalen-1-yl)phenyl)boro is substituted for triphenylene-2-ylboronic acid. O1 was prepared by synthesizing in the same manner, except that nitric acid was used.

MS[M+H] ⁺ = 366.86

2) Synthesis of O2

O2 was synthesized by the same method except that O1 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 458.37

3) Synthesis of Compound 16: In the synthesis of Compound 1, O2 was substituted for A3, and 2-(4-chlorophenyl was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner, except that the compound 16 was prepared.

MS[M+H] ⁺ = 739.89

(17) Synthesis of Compound 17 (Formula 1-12)

1) Synthesis of P1: In the synthesis of A1, 3-bromo-8-chloroquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl- is substituted for triphenylene-2-ylboronic acid. Same method except using 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)1,3,5-triazine Synthesized to prepare P1

MS[M+H] ⁺ = 471.96

2) Synthesis of P2: In the synthesis of A3, P2 was synthesized by the same method except that P1 was used instead of A2.

MS[M+H] ⁺ = 563.48

3) Synthesis of Compound 17: In the synthesis of Compound 1, P2 is substituted for A3, and 4-(4-chlorophenyl is substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-2,6-diphenylpyrimidine was synthesized in the same manner, except that Compound 17 was prepared.

MS[M+H] ⁺ = 743.89

(18) Synthesis of Compound 18 (Formula 1-16)

1) Synthesis of Q1: In the synthesis of A1, 5-chloro-6-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl- is substituted for triphenylene-2-ylboronic acid. Same method except using 6-(3-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine Synthesized to prepare Q1

MS[M+H] ⁺ = 453.52

2) Synthesis of Q2: In the synthesis of A2, Q2 was synthesized by the same method except that Q1 was used instead of A1.

MS[M+H] ⁺ = 735.60

3) Synthesis of Q3: Q3 was synthesized by the same method except that Q2 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 563.48

3) Synthesis of Compound 18: In the synthesis of Compound 1, Q3 was substituted for A3, and 3-bromobiphenyl was substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Compound 18 was prepared by synthesizing in the same manner except that

MS[M+H] ⁺ = 589.71

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

1) Synthesis of R1: In the synthesis of A1, 5-bromo-7-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 4,6-diphenyl is substituted for triphenylene-2-ylboronic acid. R1 was synthesized by the same method except that 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)pyrimidine was used. Prepared

MS[M+H] ⁺ = 452.52

2) Synthesis of R2: R2 was synthesized by the same method except that R1 was used instead of A1 in the synthesis of A2.

MS[M+H] ⁺ = 734.61

3) Synthesis of R3: In the synthesis of A3, R3 was synthesized by the same method except that R2 was used instead of A2.

MS[M+H] ⁺ = 562.49

4) Synthesis of Compound 19: In the synthesis of Compound 1, R3 is substituted for A3, and 2-(2-chlorophenyl is substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner except that the compound 19 was prepared.

MS[M+H] ⁺ = 743.89

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

1) Synthesis of S1: In the synthesis of A1, 6-bromo-7-chloroquinoline is substituted for 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl- is substituted for triphenylene-2-ylboronic acid. Synthesis was conducted in the same manner as S6, except that 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)pyrimidine was used. Did

MS[M+H] ⁺ = 470.97

2) Synthesis of S2: S2 was synthesized by the same method except that S1 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 562.49

3) Synthesis of Compound 20: In the synthesis of Compound 1, S2 is substituted for A3, and 2-(3-chlorophenyl is substituted for 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. )-4,6-diphenyl-1,3,5-triazine was synthesized in the same manner except that the compound 20 was prepared.

MS[M+H] ⁺ = 743.89

(21) Synthesis of Compound 21 (Formula 1-20)

1) Synthesis of T1: In the synthesis of A1, 6-bromo-8-chloroquinoline is substituted for 3-bromo-2-hydroxyquinoline and 2-([1,1] is substituted for triphenylene-2-ylboronic acid. '-Biphenyl]-4-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl-1 T1 was prepared by synthesizing in the same manner, except that 3,5-triazine was used.

MS[M+H] ⁺ = 548.06

2) Synthesis of T2: T2 was prepared by synthesizing in the same manner, except that T1 was used instead of A2 in the synthesis of A3.

MS[M+H] ⁺ = 639.58

3) Synthesis of Compound 21: T2 instead of A3 in the synthesis of Compound 1, 2-bromotriphenylene instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Compound 21 was synthesized in the same manner except for using

MS[M+H] ⁺ = 739.89

<Example 1>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and distilled water was used for Millipore Co. Distilled water, which was second filtered as a product filter, was used. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HI-1) was thermally vacuum-deposited to a thickness of 500 Pa to form a hole injection layer. Then, HT1 (900 kPa), a material for transporting holes, was vacuum-deposited, and then HT2 was vacuum-deposited to a thickness of 50 kPa on the hole transport layer to form a hole control layer. As a compound emitting layer, a host BH1 and a dopant BD1 compound (25:1) were vacuum deposited to a thickness of 300 Pa. Then, the ETM1 compound (50Å) was formed as an electron control layer and co-deposited with Compound 2 synthesized in Preparation Example 1 and LiQ (1:1, 310Å) to sequentially form an electron transport layer. On the electron transport layer, lithium fluoride (LiF) and Mg and Ag (10:1, 150 Å) having a thickness of 10 순차적 were sequentially deposited, and an aluminum having a thickness of 1,000 증착 was formed to form a cathode, thereby producing an organic light emitting device.

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

<Example 2>

In Example 1, the same experiment was performed except that Compound 4 was used instead of Compound 2 as the electron transport layer.

<Example 3>

In Example 1, the same experiment was performed except that Compound 5 was used instead of Compound 2 as the electron transport layer.

<Example 4>

In Example 1, the same experiment was performed except that Compound 7 was used instead of Compound 2 as the electron transport layer.

<Example 5>

In Example 1, the same experiment was performed except that Compound 8 was used instead of Compound 2 as the electron transport layer.

<Example 6>

In Example 1, the same experiment was performed except that Compound 10 was used instead of Compound 2 as the electron transport layer.

<Example 7>

In Example 1, the same experiment was performed except that Compound 11 was used instead of Compound 2 as the electron transport layer.

<Example 8>

In Example 1, the same experiment was performed except that Compound 13 was used instead of Compound 2 as the electron transport layer.

<Example 9>

In Example 1, the same experiment was performed except that Compound 15 was used instead of Compound 2 as the electron transport layer.

<Example 10>

In Example 1, the same experiment was performed except that Compound 19 was used instead of Compound 2 as the electron transport layer.

<Example 11>

In Example 1, the same experiment was performed except that Compound 20 was used instead of Compound 2 as the electron transport layer.

<Example 12>

In Example 1, the same experiment was performed except that Compound 7 was used instead of Compound 2 as the electron transporting layer, and the ratio of Compound 7 and LiQ was 2:1 instead of 1:1.

<Example 13>

In Example 1, the same experiment was performed except that Compound 13 was used instead of Compound 2 as the electron transport layer, and the ratio of Compound 13 and LiQ was 1:2 instead of 1:1.

<Example 14>

In Example 1, the same experiment was performed except that Compound 20 was used instead of Compound 2 as the electron transport layer, and the ratio of Compound 20 and LiQ was 2:1 instead of 1:1.

<Comparative Example 1>

The electron transport layer in Example 1 was tested in the same manner, except that ET1 was used instead of Compound 2.

<Comparative Example 2>

In Example 1, the electron transport layer was tested in the same manner, except that ET2 was used instead of Compound 2.

<Comparative Example 3>

In Example 1, the electron transport layer was tested in the same manner, except that ET2 was used instead of Compound 2 and the ratio of the electron transport layer and LiQ was 2:1 instead of 1:1.

<Comparative Example 4>

In Example 1, the electron transporting layer was tested in the same manner, except that ET2 was used instead of Compound 2 and the ratio of the electron transporting layer and LiQ was 1:2 instead of 1:1.

<Comparative Example 5>

In Example 1, the electron transport layer was tested in the same manner, except that ET5 below was used instead of Compound 2.

ET5

<Comparative Example 6>

In Example 1, the electron transport layer was tested in the same manner, except that ET6 was used instead of Compound 2.

ET6

<Experimental Example 1>

Table 1 shows the results of experiments of the organic light emitting device manufactured by using each compound as an electron transport layer material, as in Examples 1 to 14 and Comparative Examples 1 to 6.

No Electronic control layer Electron transport layer: LiQ Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinate
(x,y) life span
(T95, h)
(@20mA/cm ² ) Example 1 ETM1 Compound 2: LiQ = 1:1 3.51 6.71 (0.135, 0.138) 49.0 Example 2 ETM1 Compound 4: LiQ = 1:1 3.45 6.63 (0.134, 0.137) 50.2 Example 3 ETM1 Compound 5: LiQ = 1:1 3.41 6.58 (0.135, 0.138) 55.2 Example 4 ETM1 Compound 7: LiQ = 1:1 3.34 6.82 (0.134, 0.138) 51.2 Example 5 ETM1 Compound 8: LiQ = 1:1 3.42 6.72 (0.136, 0.139) 48.9 Example 6 ETM1 Compound 10: LiQ = 1:1 3.31 6.52 (0.135, 0.138) 48.5 Example 7 ETM1 Compound 11: LiQ = 1:1 3.42 6.68 (0.134, 0.137) 50.2 Example 8 ETM1 Compound 13: LiQ = 1:1 3.38 6.77 (0.135, 0.138) 52.2 Example 9 ETM1 Compound 15: LiQ = 1:1 3.45 6.72 (0.134, 0.138) 49.5 Example 10 ETM1 Compound 19: LiQ = 1:1 3.33 6.81 (0.136, 0.139) 48.8 Example 11 ETM1 Compound 20: LiQ = 1:1 3.47 6.77 (0.135, 0.138) 50.1 Example 12 ETM1 Compound 7: LiQ = 2: 1 3.71 6.68 (0.134, 0.138) 51.2 Example 13 ETM1 Compound 13: LiQ = 1: 2 3.30 6.58 (0.136, 0.139) 53.5 Example 14 ETM1 Compound 20: LiQ = 2: 1 3.68 6.64 (0.135, 0.138) 54.1 Comparative Example 1 ETM1 ET1: LiQ = 1:1 4.01 5.89 (0.134, 0.138) 38.1 Comparative Example 2 ETM1 ET2: LiQ = 1:1 3.82 5.71 (0.134, 0.138) 33.5 Comparative Example 3 ETM1 ET2: LiQ = 2: 1 3.88 5.48 (0.134, 0.138) 35.2 Comparative Example 4 ETM1 ET2: LiQ = 1: 2 3.68 5.55 (0.134, 0.138) 34.8 Comparative Example 5 ETM1 ET5: LiQ = 1:1 3.78 5.61 (0.134, 0.138) 38.2 Comparative Example 6 ETM1 ET6: LiQ = 1:1 3.72 5.35 (0.134, 0.138) 37.1

<Example 15>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and distilled water was used for Millipore Co. Distilled water, which was second filtered as a product filter, was used. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HI-1) was thermally vacuum-deposited to a thickness of 500 Pa to form a hole injection layer. Then, HT1 (900 kPa), a material for transporting holes, was vacuum-deposited, and then HT2 was vacuum-deposited to a thickness of 50 kPa on the hole transport layer to form a hole control layer. As a compound emitting layer, a host BH1 and a dopant BD1 compound (25:1) were vacuum deposited to a thickness of 300 Pa. Then, Compound 1 (50 화합물) synthesized in Preparation Example 1 was formed as an electron control layer, and co-deposited with ETM2 and LiQ (1:1, 310Å) to sequentially form an electron transport layer. On the electron transport layer, lithium fluoride (LiF) and Mg and Ag (10:1, 150 Å) having a thickness of 10 순차적 were sequentially deposited, and an aluminum having a thickness of 1,000 증착 was formed to form a cathode, thereby producing an organic light emitting device.

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

<Example 16>

In Example 15, the same experiment was performed except that Compound 3 was used instead of Compound 1 as the electron control layer.

<Example 17>

In Example 15, the same experiment was performed except that Compound 6 was used instead of Compound 1 as the electron control layer.

<Example 18>

In Example 15, the same experiment was performed except that Compound 7 was used instead of Compound 1 as the electron control layer.

<Example 19>

In Example 15, the same experiment was performed except that Compound 9 was used instead of Compound 1 as the electron control layer.

<Example 20>

In Example 15, the same experiment was performed except that Compound 10 was used instead of Compound 1 as the electron control layer.

<Example 21>

In Example 15, the same experiment was performed except that Compound 11 was used instead of Compound 1 as the electron control layer.

<Example 22>

In Example 15, the same experiment was performed except that Compound 12 was used instead of Compound 1 as the electron control layer.

<Example 23>

In Example 15, the same experiment was performed except that Compound 14 was used instead of Compound 1 as the electron control layer.

<Example 24>

In Example 15, the same experiment was performed except that Compound 16 was used instead of Compound 1 as the electron control layer.

<Example 25>

In Example 15, the same experiment was performed except that Compound 17 was used instead of Compound 1 as the electron control layer.

<Example 26>

In Example 15, the same experiment was performed except that Compound 18 was used instead of Compound 1 as the electron control layer.

<Example 27>

In Example 15, the same experiment was performed except that Compound 21 was used instead of Compound 1 as the electron control layer.

<Example 28>

In Example 1, the electron-adjusting layer was used in the same manner except that Compound 6 was used instead of Compound 1, and the ratio of ETM2 and LiQ was 2:1 instead of 1:1 as the electron transporting layer.

<Example 29>

In Example 1, the electron-controlling layer was used in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1, and the ratio of ETM2 and LiQ was 1:2 instead of 1:1 as the electron transporting layer.

<Example 30>

The same experiment was performed in Example 1 except that Compound 17 was used instead of Compound 1 and the ratio of ETM2 and LiQ was 2:1 instead of 1:1 as the electron transport layer.

<Comparative Example 7>

In Example 7, the same experiment was performed except that ET3 was used instead of Compound 1 as the electron control layer.

<Comparative Example 8>

In Example 7, the same experiment was performed except that ET4 was used instead of Compound 1 as the electron control layer.

<Comparative Example 9>

In Example 7, the same experiment was performed except that ET4 was used instead of Compound 1 as the electron control layer, and the ratio of the electron transport layer and LiQ was 2:1 instead of 1:1.

<Comparative Example 10>

In Example 7, the same experiment was performed except that ET3 was used instead of Compound 1 as the electron control layer, and the ratio of the electron transport layer and LiQ was 1:2 instead of 1:1.

<Comparative Example 11>

In Example 7, the electron control layer was tested in the same manner, except that ET7 was used instead of Compound 1.

ET7

<Comparative Example 12>

In Example 7, the electron control layer was tested in the same manner, except that ET8 was used instead of Compound 1.

ET8

<Experimental Example 2>

Table 2 shows the results of experiments of the organic light emitting device manufactured by using each compound as an electron transport layer material, as in Examples 15 to 30 and Comparative Examples 7 to 11.

No Electronic
Control layer Electron transport layer: LiQ Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinate
(x,y) life span
(T95, h)
(@20mA/cm ² ) Example 15 Compound 1 ETM2: LiQ = 1:1 3.33 6.89 (0.135, 0.138) 52.0 Example 16 Compound 3 ETM2: LiQ = 1:1 3.42 6.79 (0.134, 0.138) 48.0 Example 17 Compound 6 ETM2: LiQ = 1:1 3.44 6.67 (0.134, 0.138) 46.8 Example 18 Compound 7 ETM2: LiQ = 1:1 3.45 6.58 (0.137, 0.134) 47.1 Example 19 Compound 9 ETM2: LiQ = 1:1 3.52 6.87 (0.138, 0.138) 42.5 Example 20 Compound 10 ETM2: LiQ = 1:1 3.51 6.82 (0.135, 0.139) 46.5 Example 21 Compound 11 ETM2: LiQ = 1:1 3.48 6.78 (0.134, 0.138) 50.2 Example 22 Compound 12 ETM2: LiQ = 1:1 3.55 6.88 (0.134, 0.138) 55.2 Example 23 Compound 14 ETM2: LiQ = 1:1 3.49 6.77 (0.137, 0.134) 48.0 Example 24 Compound 16 ETM2: LiQ = 1:1 3.50 6.42 (0.138, 0.138) 49.2 Example 25 Compound 17 ETM2: LiQ = 1:1 3.38 6.82 (0.135, 0.139) 47.2 Example 26 Compound 18 ETM2: LiQ = 1:1 3.48 6.71 (0.137, 0.134) 46.8 Example 27 Compound 21 ETM2: LiQ = 1:1 3.51 6.77 (0.138, 0.138) 47.2 Example 28 Compound 6 ETM2: LiQ = 2: 1 3.55 6.85 (0.135, 0.139) 48.9 Example 29 Compound 12 ETM2: LiQ = 1: 2 3.32 6.55 (0.134, 0.138) 50.7 Example 30 Compound 17 ETM2: LiQ = 2: 1 3.54 6.48 (0.134, 0.138) 52.2 Comparative Example 7 ET3 ETM2: LiQ = 1:1 3.78 5.66 (0.134, 0.138) 33.0 Comparative Example 8 ET4 ETM2: LiQ = 1:1 3.88 5.82 (0.136, 0.139) 28.0 Comparative Example 9 ET4 ETM2: LiQ = 2: 1 4.01 5.89 (0.134, 0.138) 38.1 Comparative Example 10 ET3 ETM2: LiQ = 1: 2 3.82 5.71 (0.134, 0.138) 33.5 Comparative Example 11 ET7 ETM2: LiQ = 1:1 3.91 5.28 (0.134, 0.138) 35.8 Comparative Example 12 ET8 ETM2: LiQ = 1:1 3.99 5.88 (0.134, 0.138) 38.5

The compound derivative of the formula according to the present invention may play an electron transport and electron regulation role in an organic electronic device including an organic light emitting device, and the device according to the present invention exhibits excellent properties in terms of efficiency, driving voltage, and stability.

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 (9)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
Any one of Y ₁ to Y ₇ is Z ₁ ,
Any one of Z ₁ to Y ₇ other than Z ₁ is Z ₂ ,
The rest of Z ₁ and Z ₂ among Y ₁ to Y ₇ are each hydrogen.
Z ₁ and Z ₂ are each independently represented by the following Formula 2 or 3, but at least one of Z ₁ and Z ₂ is represented by the following Formula 2,
(However, Y ₃ When represented by Formula 2 and Y ₁ is represented by Formula 3; And Y ₅ Formula 2, except when Y ₁ is represented by Formula 3)
[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
X ₁ to X ₃ are each independently CH or N, but at least one of X ₁ to X ₃ is N,
L ₁ to L ₄ are each independently a bond or phenylene,
Ar ₁ to Ar ₃ are each independently, unsubstituted or substituted with any substituent selected from the group consisting of C _1-4 alkyl, halogen, cyano, and tri(C _1-4 alkyl)silyl. Phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl; Or carbazolyl,
p, q, r, and s are each independently an integer from 0 to 3.
According to claim 1,
Formula 1 is represented by any one of the following Formulas 1-1 to 1-21,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Formula 1-14]

[Formula 1-15]

[Formula 1-16]

[Formula 1-17]

[Formula 1-18]

[Formula 1-19]

[Formula 1-20]

[Formula 1-21]

In Chemical Formula 1-2,
Z ₁ is represented by Chemical Formula 2, and Chemical Formula Z ₂ is represented by Chemical Formula 2 or 3,
In Formula 1-4,
Z ₁ is represented by Chemical Formula 2, and Chemical Formula Z ₂ is represented by Chemical Formula 2 or 3,
In Chemical Formulas 1-1, 1-3, and 1-5 to 1-21,
Z ₁ and Z ₂ are each independently represented by Formula 2 or 3, but at least one of Z ₁ and Z ₂ is represented by Formula 2 above.
According to claim 1,
At least two of X ₁ , X ₂ and X ₃ are N,
compound.
delete delete According to claim 1,
At least one of Ar ₁ and Ar ₂ is a phenyl group,
compound.
According to claim 1,
One of Z ₁ and Z ₂ is represented by Formula 2, and the other is represented by Formula 3,
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
compound:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is one of claims 1 to 3, and claims 6 to 8 An organic light emitting device comprising the compound according to any one of the preceding claims.

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