阅读说明：本技术 新型化合物及利用其的有机发光元件 (Novel compound and organic light-emitting element using same ) 是由 李征夏 赵圣美 郑珉祐 李东勳 朴胎润 金曙渊 于 2018-11-16 设计创作，主要内容包括：本发明提供新型化合物及利用其的有机发光元件。(The invention provides a novel compound and an organic light-emitting element using the same.)

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

each X is independently N, S or CR₁Wherein at least two of X are N,

R₁is hydrogen, or substituted or unsubstituted C_6-60An aryl group, a heteroaryl group,

y is S, O or C (CH)₃)₂，

L is a single bond; substituted or unsubstituted C_6-60Arylene group: or substituted or unsubstituted C containing more than 1 of O, N, Si and S_2-60A heteroarylene group, a heteroaryl group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 of O, N, Si and S_2-60(ii) a heteroaryl group, wherein,

Ar₃is hydrogen; substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 of O, N, Si and S_2-60(ii) a heteroaryl group, wherein,

Ar₄is hydrogen, substituted or unsubstituted C_6-60And (4) an aryl group.

2. The compound of claim 1, wherein X is N.

3. The compound of claim 1, wherein L is a single bond, phenylene, biphenyldiyl, dibenzofurandiyl, or pyridyldiyl.

4. The compound of claim 1, wherein Ar₁And Ar₂Each independently is phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl.

5. The compound of claim 4, wherein Ar₁And Ar₂At least one of which is phenyl.

6. The compound of claim 1, wherein Ar₃Is hydrogen.

7. The compound of claim 1, wherein Ar₄Is hydrogen.

8. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the following structures:

9. an organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 8.

10. The organic light-emitting element according to claim 9, wherein the organic layer containing the compound is a light-emitting layer.

11. The organic light-emitting element according to claim 10, wherein the light-emitting layer contains 2 kinds of hosts, and 1 kind of the hosts is the compound.

Technical Field

Cross reference to related applications

The present application claims priority based on korean patent application No. 10-2017-0154284, 11/17/2017, the entire contents of which are incorporated herein by reference.

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

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.

An organic light-emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.

Development of new materials for organic materials used in the organic light-emitting devices described above is continuously demanded.

Disclosure of Invention

Problems to be solved

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

Means for solving the problems

The present invention provides a compound represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above,

each X is independently N, S or CR₁Wherein at least two of X are N,

R₁is hydrogen, or substituted or unsubstituted C_6-60An aryl group, a heteroaryl group,

y is S, O or C (CH)₃)₂，

L is a single bond; substituted or unsubstituted C_6-60Arylene group: or substituted or unsubstituted C containing more than 1 of O, N, Si and S_2-60A heteroarylene group, a heteroaryl group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 of O, N, Si and S_2-60(ii) a heteroaryl group, wherein,

Ar₃is hydrogen; substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 of O, N, Si and S_2-60(ii) a heteroaryl group, wherein,

Ar₄is hydrogen, substituted or unsubstituted C_6-60And (4) an aryl group.

In addition, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the chemical formula 1.

Effects of the invention

The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting element in which improvement of efficiency, lower driving voltage, and/or improvement of life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.

Drawings

Fig. 1 shows an example of an organic light-emitting element 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 element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.

Fig. 3 shows an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 10, and a cathode 4.

Modes for carrying out the invention

Hereinafter, the present invention will be described in more detail to assist understanding thereof.

The present invention provides a compound represented by the above chemical formula 1.

In the context of the present specification,

or

Refers to a bond to another substituent.

In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; phosphine oxideA group; an alkoxy group; an aryloxy group; alkylthio radicals (A), (B), (C), (D), (

Alkyl thio xy); arylthio radicals (A), (B), (C

Aryl thio xy); alkylsulfonyl (

Alkyl sulfo xy); arylsulfonyl (

Aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or one or more substituents of N, O and one or more heterocyclic groups containing S atoms, or substituted or unsubstituted by being linked by 2 or more substituents of the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.

In the ester group, 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, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, 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.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,

A group, a fluorenyl group and the likeHowever, the present invention is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may beAnd the like. But is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least 1 of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoylOxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.

In the above chemical formula 1, the following chemical formulas 1-1 to 1-4 may be represented according to the binding position:

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

Preferably, X are both N.

Preferably, L is a single bond, phenylene, biphenyldiyl, dibenzofurandiyl, or pyridinediyl.

Preferably, Ar₁And Ar₂Each independently is phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl. More preferably, Ar₁And Ar₂At least one of which is phenyl.

Preferably, Ar₃Is hydrogen.

Preferably, Ar₄Is hydrogen.

Representative examples of the compound represented by the above chemical formula 1 are shown below:

in addition, the present invention provides a method for producing a compound represented by the above chemical formula 1, as shown in the following reaction formula 1:

[ reaction formula 1]

In the above reaction formula 1, the definitions other than X 'are the same as those described above, and X' is halogen, preferably chlorine or bromine.

The above reaction is suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the suzuki coupling reaction may be modified according to techniques well known in the art. The above-described manufacturing method can be further embodied in a manufacturing example to be described later.

In addition, the present invention provides an organic light emitting element comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the chemical formula 1.

The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element 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, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the chemical formula 1.

In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1. In particular, the compounds according to the invention can be used as hosts for light-emitting layers. In addition, the light emitting layer may include 2 kinds of hosts, and in this case, 1 kind of the hosts uses the compound represented by the chemical formula 1.

In addition, the organic layer may include an electron transport layer or an electron injection layer including the compound represented by the chemical formula 1.

In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection includes the compound represented by the above chemical formula 1.

In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.

In addition, the organic light emitting element according to the present invention may be an organic light emitting element having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting element according to the present invention may be an inverted (inverted) type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure example of an organic light emitting element according to an embodiment of the present invention is shown in fig. 1 and 2.

Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.

Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in one or more layers among the above hole injection layer, hole transport layer, light emitting layer, and electron transport layer.

Fig. 3 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 10, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in one or more layers among the above hole injection layer, hole transport layer, light emitting layer, and electron transport layer.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

For example, the organic light emitting element according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.

In addition, when the compound represented by the above chemical formula 1 is used to manufacture an organic light emitting device, the organic layer may be formed not only by a vacuum deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and indium zinc oxide (IZ O); such as ZnO: al or SNO₂: a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting species is between the work function of the anode species and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerizedstyryl) compounds;BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

Pyrimidine derivatives, etc., but are not limited thereto.

As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,Diindenoperene (Periflanthene) and the like, as the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

The electron transporting layer is a layer which receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and serves as an electron transporting material,the material is a material capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: the organic light-emitting device has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injection layer, and has excellent thin-film formation ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The organic light emitting element according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.

The production of the compound represented by the above chemical formula 1 and the organic light emitting element comprising the same is specifically described 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 thereto.

[ production example ]

Production example 1: production of Compound A

1) Production of Compound A-1

In a 2000mL round bottom flask, a mixture of methyl 3-aminobenzo-thiophene-2-carboxylate (65.0g, 313.6mmol) and urea (84.8g, 1.41mol) was stirred at 200 ℃ for 2 hours. After the reaction mixture was cooled to normal temperature, poured into sodium hydroxide solution, and after impurities were filtered and removed, the reaction was acidified (HCl, 2N), and the obtained precipitate was dried to obtain compound a-1(52.6g, yield 77%).

2) Production of Compound A

In a 1000mL round bottom flask, a mixture of Compound A-1(52.6g, 0.24mol) and phosphorus oxychloride (750mL) was stirred under reflux for 7.5 hours. The reaction mixture was cooled to room temperature and poured into ice/water with vigorous stirring to form a precipitate. The thus-obtained reaction product was filtered to obtain compound a (51.0g, yield 83%, white solid).

Production example 2: production of Compound B

1) Production of Compound B-1

In a 2000mL round bottom flask, a mixture of methyl 3-aminobenzofuran-2-carboxylate (65.0g, 340.0mmol) and urea (91.9g, 1.5mol) was stirred at 200 ℃ for 2 hours. After the reaction mixture was cooled to normal temperature, poured into sodium hydroxide solution, and after impurities were filtered and removed, the reaction was acidified (HCl, 2N), and the obtained precipitate was dried to obtain compound B-1(49.4g, yield 72%).

2) Production of Compound B

In a 1000mL round bottom flask, a mixture of Compound B-1(49.4g, 0.24mol) and phosphorus oxychloride (720mL) was stirred under reflux for 7.5 hours. The reaction mixture was cooled to room temperature and poured into ice/water with vigorous stirring to form a precipitate. The thus-obtained reaction product was filtered to obtain compound B (45.1g, yield 77%, white solid).

Production example 3: production of Compound 3

1) Production of Compound C-1

1-bromo-3-chloro-2-methoxybenzene (35.0g, 0.16mol) was dissolved in tetrahydrofuran (350mL), the temperature was lowered to-78 deg.C, and 2.5M t-butyllithium (t-BuLi) (66.4mL, 0.17mmol) was slowly added dropwise. After stirring at the same temperature for 1 hour, triisopropyl borate (B (OiPr)₃) (54.7mL, 0.24mol), the temperature was slowly raised to ambient temperature while stirring for 3 hours. To the reaction mixture was added 2N aqueous hydrochloric acid (60mL), and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and then ether (ethyl ether) and dried in vacuo. After drying, it was recrystallized from chloroform and ethyl acetate and dried to obtain Compound C-1(25.1g, yield 85%; MS: [ M + H ]]⁺＝230)。

2) Production of Compound C-2

1-bromo-3-fluoro-2-iodobenzene (38g, 125mmol), compound C-1(25.1g, 125mmol) were dissolved in tetrahydrofuran (280 mL). Adding sodium carbonate (Na) thereto₂CO₃)2M solution (180mL), tetrakis (triphenylphosphine) palladium (0) (1.44g, 1.25mmol), reflux 10 h. Cooling to normal temperature after the reaction is finished, and separating waterThe layers were removed, dried over anhydrous magnesium sulfate, and the mixture concentrated under reduced pressure was recrystallized from chloroform and ethanol to give Compound C-2(31.6g, yield 55%; MS: [ M + H ]]⁺＝314)。

3) Production of Compound C-3

Compound C-2(31.6g, 100mmol) was dissolved in 380mL of dichloromethane and cooled to 0 ℃. Boron tribromide (10.0mL, 105.2mmol) was slowly added dropwise and stirred for 12 hours. After the completion of the reaction, the reaction mixture was washed with water 3 times, and the filtrate dried over magnesium sulfate and filtered was distilled under reduced pressure and purified by column chromatography to obtain Compound C-3(29.0g yield 96%; MS: [ M + H ]]⁺＝300)。

4) Production of Compound C-4

Compound C-3(29.0g, 96mmol) and calcium carbonate (39.8g, 283.5mol) were dissolved in N-methyl-2-pyrrolidone (175mL), and the mixture was stirred under heating for 2 hours. The temperature was reduced to normal temperature, reverse precipitated in water and filtered. After completely dissolving in methylene chloride, the mixture was washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized from ethanol and dried to obtain Compound C-4(21.1g, yield 78%; MS: [ M + H ]]⁺＝280)。

5) Production of Compound C-5

After compound C-4(21.1g, 74.8mmol) was dissolved in tetrahydrofuran (170mL), the temperature was lowered to-78 deg.C and 2.5M t-butyllithium (t-BuLi) (30.2mL, 75.5mmol) was slowly added dropwise. After stirring at the same temperature for 1 hour, triisopropyl borate (25.9mL, 112.2mmol) was added, and the temperature was slowly raised to room temperature while stirring for 3 hours. To the reaction mixture was added 2N aqueous hydrochloric acid (150mL), and the mixture was stirred at room temperature for 1 hour. The resulting precipitate was filtered, washed with water and ether (ethyl ethereal) in this order, and dried under vacuum to give Compound C-5(17.2g, yield 93%; MS: [ M + H ])]⁺＝247)。

6) Production of Compound C-6

After compound C-5(17.2g, 69.8mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (18.7g, 69.8mmol) were dissolved in tetrahydrofuran (250mL), potassium carbonate (28.9g, 0.21mol) was dissolved in water (80mL) and added, tetrakis (triphenylphosphine) palladium (2.42g,21mmol), the mixture was stirred for 10 hours. The temperature was lowered to room temperature, the aqueous layer was separated and removed, dried over anhydrous magnesium sulfate, and the mixture concentrated under reduced pressure was recrystallized from chloroform and ethanol to give Compound C-6(25.1g, yield 83%; MS: [ M + H ])]⁺＝434)。

7) Production of Compound C

Mixing compound C-6(25.1g, 56.5mmol), 4,5, 5-tetramethyl- [1,3, 2]]Dioxaborane (15.8g, 62.2mmol), Pd (dba)₂(0.98g，1.7mmol)、PCy₃(0.95g, 3.4mmol) KOAc (16.6g, 0.17mol) was added to the mixtureIn an alkane (dioxane; 350mL), the mixture was stirred under reflux for 8 hours. The temperature is reduced to normal temperature, and the solvent is decompressed and concentrated. Dissolving the concentrated solution in CHCl completely₃Then, the reaction mixture was washed with water, and the resultant solution was concentrated under reduced pressure and purified by column chromatography. Compound C (23.0g, 77% yield) was obtained.

Production example 4: production of Compound 1-1

After compound A (10g, 39.2mmol) and 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine (17.1g, 39.2mmol) were dissolved in tetrahydrofuran (150mL) under a nitrogen atmosphere, potassium carbonate (16.3g, 0.11mol) was dissolved in water (50mL) and added, and after adding tetrakis (triphenylphosphine) palladium (1.35g, 1.18mmol), it was heated and stirred for 9 hours. Compound 1-1(16.8g, yield 81%, MS: [ M + H ]: was prepared by cooling to room temperature, filtering, washing with water and ethanol, and drying]⁺＝528)。

Production example 5: production of Compound 1-2

Compound 1-2 was produced by the same method as the method for producing compound 1-1, except that 2, 4-diphenyl-6- (3- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine was used instead of 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine.

Production example 6: production of Compounds 1 to 3

Compound 1-3P1 was produced by the same method as the method for producing compound 1-1, except that (3-bromophenyl) boronic acid was used instead of 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine. Subsequently, compound 1-3 was produced by the same method as the method for producing compound 1-1, using compound 1-3P1 in place of compound A.

Production example 7: production of Compounds 1 to 4

Compound 1-4P1 was produced by the same method as the method for producing compound 1-1, except that (4-bromophenyl) boronic acid was used instead of 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine. Subsequently, compound 1-4 was produced by the same method as the method for producing compound 1-1, using compound 1-4P1 in place of compound A.

Production example 8: production of Compounds 1 to 5

1) Production of Compounds 1-5P1

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (20g, 74.7mmol) and (5-bromopyridin-2-yl) boronic acid (15.1g, 74.7mmol) were dissolved in tetrahydrofuran (250mL) under a nitrogen atmosphere, potassium carbonate (31.0g, 0.22mol) was dissolved in water (90mL) and added, tetrakis (triphenylphosphine) palladium (2.59g, 2.24mmol) was added, and the mixture was heated and stirred for 5 minutesAnd (4) hours. The temperature was lowered to room temperature, and the mixture was filtered, washed with water and ethanol, and dried to give compound 1-5P1(25.1g, yield 86%, MS: [ M + H ]]⁺＝389)。

2) Production of Compounds 1-5P2

Mixing compound 1-5P1(25.1g, 64.5mmol), 4,5, 5-tetramethyl- [1,3, 2%]Dioxaborane (16.4g, 64.5mmol), Pd (dba)₂(1.11g，1.93mmol)、PCy₃(1.08g, 3.87mmol) KOAc (22.1g, 0.22mol) was added to the mixture

In an alkane (dioxane; 300mL), the mixture was stirred under reflux for 10.5 hours. The temperature is reduced to normal temperature, and the solvent is decompressed and concentrated. Dissolving the concentrated solution in CHCl completely₃Then, the reaction mixture was washed with water, and the solution containing the product was concentrated under reduced pressure and purified by column chromatography to obtain compound 1-5P2(22.1g, yield 79%).

3) Production of Compounds 1 to 5

Compound 1-5 was produced by the same method as the method for producing compound 1-1, except that compound 1-5P2 was used instead of 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine.

Production example 9: production of Compounds 1 to 6

Compound 1-6 was produced by the same method as the method for producing compound 1-1, except that compound C was used instead of 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenyl) -1,3, 5-triazine.

Production example 10: production of Compound 2-1

Compound 2-1 was produced by the same method as that for producing Compound 1-1, except that Compound B was used instead of Compound A.

Production example 11: production of Compound 2-2

Compound 2-2 was produced by the same method as the method for producing compound 1-1, except that compound B and 2, 4-diphenyl-6- (3- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine were used instead of compound a and 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine, respectively.

Production example 12: production of Compound 2-3

Compound 2-3 was produced by the same method as the method for producing compound 1-5, except that compound B was used instead of compound a.

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