CN113039183A

CN113039183A - Novel compound and organic light emitting device comprising same

Info

Publication number: CN113039183A
Application number: CN202080006172.3A
Authority: CN
Inventors: 韩修进; 李东勋; 张焚在; 徐尚德; 郑珉祐; 李征夏; 朴瑟灿; 黄晟现
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2019-06-27
Filing date: 2020-06-12
Publication date: 2021-06-25
Anticipated expiration: 2040-06-12
Also published as: KR20210001936A; CN113039183B; KR102447007B1

Abstract

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

Description

Novel compound and organic light emitting device comprising same

Technical Field

Cross reference to related applications

The present application claims priority based on korean patent application No. 10-2019-0077351, 27, 6-month-2019 and korean patent application No. 10-2020-0069692, 9-month-2020, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel compound and an organic light emitting device comprising 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 device 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 device generally has a structure including an anode and a cathode, and an organic layer 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 device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.

For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.

Documents of the prior art

Patent document

(patent document 1) Korean patent laid-open No. 10-2000-0051826

Disclosure of Invention

Technical subject

The present invention relates to a novel organic light emitting material 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 above-described chemical formula 1,

l is linked to carbon number 1, carbon number 2 or carbon number 3,

l is a single bond, or substituted or unsubstituted C_6-60An arylene group, a cyclic or cyclic alkylene group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S_2-60(ii) a heteroaryl group, wherein,

R₁each independently is hydrogen; deuterium; substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S_2-60(ii) a heteroaryl group, wherein,

R₂each independently is substituted or unsubstituted C_6-60Aryl, benzofuranyl, benzothienyl, dibenzofuranyl or phenylbenzothiophenyl,

p is an integer of 0 to 5,

q is an integer of 1 to 8.

In addition, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 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 device in which improvement of efficiency, low driving voltage, and/or improvement of life span characteristics may 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 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

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

Detailed Description

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

Represents a bond to other substituents.

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; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio (Alkyl thio); arylthio (Aryl thio); alkylsulfonyl (Alkyl sulfonyl); arylsulfonyl (Aryl sulfonyl); 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 1 or more substituents of 1 or more heteroaryl groups containing N, O and S atoms, or substituted or unsubstituted 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 present specification, 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 specifically includes 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, as examples of the halogen group, there are fluorine, chlorine, bromine or 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-, 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. 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 triphenyl 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,

And a fluorenyl group, but 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 be

And the like. But is not limited thereto.

In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,

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), isoquinoyl

Oxazolyl, 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 examples of the 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 heteroaryl 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 in addition thereto, the above description about the aryl group can be applied. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heteroaryl 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 heteroaryl group is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the heteroaryl group can be applied.

Preferably, the above chemical formula 1 may be represented by the following chemical formulae 1-1 to 1-3:

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

In the above chemical formulas 1-1 to 1-3,

for L, Ar₁、Ar₂、R₁、R₂The descriptions of p and q are the same as those in the above chemical formula 1.

Preferably, L may be a single bond, or a substituted or unsubstituted C_6-20An arylene group, a cyclic or cyclic alkylene group,

more preferably, L may be a single bond, phenylene or naphthylene.

Preferably, Ar₁And Ar₂May each independently be substituted or unsubstituted C_6-20An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

more preferably, Ar₁And Ar₂May each independently be phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl substituted with 5 deuterium, carbazolylphenyl or phenylbenzothiophenyl,

most preferably, Ar₁And Ar₂May each independently be any one selected from the following groups:

preferably, R₁May each independently be hydrogen; deuterium; substituted or unsubstituted C_6-20An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

more preferably, R₁May each independently be hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.

Preferably, R₂May each independently be substituted or unsubstituted C_6-20Aryl, benzofuranyl, benzothienyl, dibenzofuranyl or phenylbenzothiophenyl,

more preferably, R₂May each independently be any one selected from the following groups:

preferably, q may be 1 or 2.

Representative examples of the compound represented by the above chemical formula 1 are as follows:

as an example, the compound represented by the above chemical formula 1 may be produced by a production method as shown in the following reaction formula 1, and the remaining compounds except for this may be produced by a similar method.

[ reaction formula 1]

In the above reaction scheme 1, L, Ar₁、Ar₂、R₁、R₂P and q are as defined in the above chemical formula 1, and X₁And X₂Each independently of the other being halogen, X₁And X₂Preferably fluorine, chlorine or bromine.

Step 1 of the above reaction formula 1 is preferably carried out as a suzuki coupling reaction in the presence of a palladium catalyst and a base, and the reactive group used for the suzuki coupling reaction can be changed according to a technique known in the art. Further, step 2 of the above reaction formula 1 is preferably carried out in the presence of a palladium catalyst and a base as an amine substitution reaction, and the reactive group for the amine substitution reaction can be changed according to a technique known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later. .

In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 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 have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as an organic layer, but the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the compound represented by the chemical formula 1. In particular, the compound according to the present invention can be used as a host of a light emitting layer.

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

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

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

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

Fig. 1 illustrates an example of an organic light-emitting device composed of 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 device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, 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 contained in 1 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 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting device 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 device according to the present invention may be manufactured by sequentially stacking 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 PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (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 device.

In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. 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 device may be manufactured by depositing a cathode material, an organic 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 (IZO); ZnO-Al or SnO₂A 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: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance 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 substance is a substance 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 substance 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 electron blocking layer is a layer interposed between the hole transport layer and the light emitting layer in order to prevent electrons injected from the cathode from being transferred to the hole transport layer without being recombined in the light emitting layer, and is also referred to as an electron blocking layer. In the electron blocking layer, a substance having a smaller electron affinity than that of the electron transport layer is preferably used.

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 is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

Azole, 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. As the host material, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto. Preferably, the compound represented by the above chemical formula 1 may be contained as a host material.

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 arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,

And diindenopyrene, and the like, and the styrylamine compound is a compound substituted with at least 1 arylvinyl group in a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine 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 hole blocking layer is a layer interposed between the electron transport layer and the light emitting layer in order to prevent holes injected from the anode from being transferred to the electron transport layer without being recombined in the light emitting layer, and is also referred to as a hole inhibiting layer. A substance having a large ionization energy is preferably used for the hole blocking layer.

The electron transport layer isThe electron transporting substance is a substance which can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a substance 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. In particular, examples of suitable cathode materials include those having a low work function and accompanied by an aluminum layer or a 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: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming 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 device 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 device.

The manufacture of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated 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 1: production of Compound 1

Step 1) production of Compound 1-a

2-bromo-4-chloro-1-fluorobenzene (50g, 238.7mmol) and phenylboronic acid (29.1g, 238.7mmol) were added to 1000ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (99g, 716.2mmol) was dissolved in 99ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (8.3g, 7.2mmol) was charged. After the reaction for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. The obtained product was again charged into 20 times 987ml of chloroform and dissolved, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce compound 1-a (34.5g, 70%, MS: [ M + H ] + ═ 207.6) as a white solid.

Step 2) production of Compound 1-b

Under nitrogen atmosphere, compound 1-a (30g, 145.2mmol) and bis (pinacolato) bisBoron (36.9g, 145.2mmol) was added to 600ml of bis

In an alkane (Diox), stirred and refluxed. Then, potassium acetate (92.5g, 435.5mmol) was added thereto, followed by well stirring, and then Pd (dba) was added thereto₂(2.5g, 4.4mmol) and tricyclohexylphosphine (2.4g, 8.7 mmol). After the reaction for 3 hours, the reaction mixture was cooled to normal temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. The obtained product was again poured into 10 times 433ml of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give 1-b (34.2g, 79%, MS: [ M + H ]: as a white solid]+＝299.2)。

Step 3) production of Compound 1-c

Under nitrogen, compound 1-b (50g, 167.7mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (44.9g, 167.7mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (69.5g, 503.1mmol) was dissolved in 70ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (5.8g, 5mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. The obtained product was again poured into and dissolved in 20 times 1353ml of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce compound 1-c (47.4g, 70%, MS: [ M + H ] + ═ 404.5) as a white solid.

Step 4) production of Compound 1

Under nitrogen atmosphere, compound 1-c (20g, 43.4mmol) and 3-phenyl-9H-carbazole (10.6g, 43.4mmol) were added to 400ml of dimethylformamide, stirred and refluxed. Cesium carbonate (42.4g, 130.3mmol) was then charged, heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 30 times 817ml of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to produce compound 1(20.1g, 74%, MS: [ M + H ] + ═ 627.8) as a yellow solid.

Production example 2: production of Compound 2

Compound 2 was produced by the same production method as that of compound 1, except that (phenyl-d 5) boronic acid was used instead of phenylboronic acid in production example 1. (MS: [ M + H ] + ═ 632.3).

Production example 3: production of Compound 3

Compound 3 was produced by the same production method as that of compound 1, except that 4- (phenyl-d 5) -9H-carbazole was used instead of 3-phenyl-9H-carbazole in production example 1. (MS [ M + H)]⁺＝632)。

Production example 4: production of Compound 4

In production example 1, 4- (dibenzo [ b, d ] was used]Compound 4 was produced by the same production method as that of compound 1 except that furan-2-yl) -9H-carbazole was used instead of 3-phenyl-9H-carbazole. (MS [ M)+H]⁺＝717)。

Production example 5: production of Compound 5

Compound 5 was produced by the same production method as that of compound 1, except that 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole in production example 1. (MS [ M + H)]⁺＝716)。

Production example 6: production of Compound 6

In production example 1, 2-chloro-4- (dibenzo [ b, d ] was used]Compound 6 was produced by the same production method as that of compound 1 except that thiophen-4-yl) -6-phenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole were substituted for 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole. (MS [ M + H)]⁺＝733)。

Production example 7: production of Compound 7

In production example 1, 2-chloro-4- (dibenzo [ b, d ] was used]Furan-4-yl) -6- (dibenzo [ b, d)]Compound 7 was produced by the same production method as that of compound 1 except that thiophen-4-yl) -1,3, 5-triazine was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine. (MS [ M + H)]⁺＝823)。

Production example 8: production of Compound 8

In production exampleCompound 8 was produced by the same production method as that of compound 1 except that (3- (9H-carbazol-9-yl) phenyl) boronic acid was used instead of phenylboronic acid in 1. (MS [ M + H)]⁺＝792)。

Production example 9: production of Compound 9

Compound 9 was produced by the same production method as that of compound 1, except that 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole in production example 1. (MS [ M + H)]⁺＝703)。

Production example 10: production of Compound 10

In preparation example 1,2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 2- (9H-carbazol-4-yl) benzo [ d ] were used]Compound 10 was produced by the same production method as that of compound 1 except that thiazole was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole. (MS [ M + H)]⁺＝760)。

Production example 11: production of Compound 11

Step 1) production of Compound 11-a

1-bromo-4-chloro-2-fluorobenzene (50g, 238.7mmol) and phenylboronic acid (29.1g, 238.7mmol) were added to 1000ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (99g, 716.2mmol) was dissolved in 99ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (8.3g, 7.2mmol) was charged. After the reaction for 1 hour, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. The obtained product was again charged into 20 times 987ml of chloroform and dissolved, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce compound 11-a (30.1g, 61%, MS: [ M + H ] + ═ 207.6) as a white solid.

Step 2) production of Compound 11-b

Under nitrogen, compound 11-a (30g, 145.2mmol) and bis (pinacolato) diboron (36.9g, 145.2mmol) were added to 600ml of bis

In an alkane, stirred and refluxed. Then, potassium acetate (92.5g, 435.5mmol) was added thereto, and well-stirred Pd (dba) was added thereto₂(2.5g, 4.4mmol) and tricyclohexylphosphine (2.4g, 8.7 mmol). After 6 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. The obtained product was again poured into 10 times 433ml of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give a white solid compound 11-b (32g, 74%, MS: [ M + H ]]+＝299.2)。

Step 3) production of Compound 1-c

Under nitrogen, 11-b (50g, 167.7mmol) and 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine (45.7g, 167.7mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (69.5g, 503.1mmol) was dissolved in 70ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (5.8g, 5mmol) was charged. After the reaction for 1 hour, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. The obtained product was again put into 20 times 1370ml of chloroform and dissolved, washed with water 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce compound 11-c (48.6g, 71%, MS: [ M + H ] + ═ 409.5) as a white solid.

Step 4) production of Compound 11

Under a nitrogen atmosphere, compound 11-c (20g, 49mmol) and 4-phenyl-9H-carbazole (11.9g, 49mmol) were added to 400ml of dimethylformamide, stirred and refluxed. Cesium carbonate (47.9g, 146.9mmol) was then charged, heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was poured into 30 times 928ml of chloroform and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by passing through a silica gel column using chloroform and ethyl acetate, to thereby produce compound 11(21.7g, 70%, MS: [ M + H ] + ═ 632.8) as a yellow solid.

Production example 12: production of Compound 12

Compound 12 was produced by the same production method as that of compound 11, except that 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole and 2-phenyl-9H-carbazole were used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole in production example 11. (MS [ M + H)]⁺＝760)。

Production example 13: production of Compound 13

In preparation example 11, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 4- (dibenzo [ b, d ] were used]Compound 13 was produced by the same production method as that of compound 11, except that furan-2-yl) -9H-carbazole was used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole. (MS [ M + H)]⁺＝717)。

Production example 14: production of Compound 14

In preparation example 11, 2- (3-chlorophenyl) -4- (dibenzo [ b, d ] was used]Compound 14 was produced by the same production method as that of compound 11, except that thiophen-4-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine. (MS [ M + H)]⁺＝809)。

Production example 15: production of Compound 15

Compound 15 was produced by the same production method as that of compound 11, except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3, 6-diphenyl-9H-carbazole were used instead of 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine and 4-phenyl-9H-carbazole in production example 11. (MS [ M + H)]⁺＝703)。

Production example 16: production of Compound 16

Step 1) production of Compound 16-a

2-bromo-1-chloro-3-fluorobenzene (50g, 238.7mmol) and phenylboronic acid (29.1g, 238.7mmol) were added to 1000ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (99g, 716.2mmol) was dissolved in 99ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (8.3g, 7.2mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. The obtained product was again charged into 20 times 987ml of chloroform and dissolved, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound 16-a (29.6g, 60%, MS: [ M + H ] + ═ 207.6).

Step 2) production of Compound 16-b

Compound 16-a (30g, 145.2mmol) and bis (pinacolato) diboron (36.9g, 145.2mmol) were added to 600ml of bis under nitrogen

In an alkane, stirred and refluxed. Then, potassium acetate (92.5g, 435.5mmol) was added thereto, followed by well stirring, and then Pd (dba) was added thereto₂(2.5g, 4.4mmol) and tricyclohexylphosphine (2.4g, 8.7 mmol). After 7 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. The obtained product was again poured into 10 times 433ml of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give 16-b (33.3g, 77%, MS: [ M + H ]: as a white solid]+＝299.2)。

Step 3) production of Compound 1-c

Under nitrogen, compound 16-b (50g, 167.7mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (44.9g, 167.7mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (69.5g, 503.1mmol) was dissolved in 70ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (5.8g, 5mmol) was charged. After the reaction for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. The obtained product was again poured into and dissolved in 20 times 1353ml of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound 16-c (52.1g, 77%, MS: [ M + H ] + ═ 404.5).

Step 4) production of Compound 16

Compound 16-c (20g, 49.6mmol) and 2-phenyl-9H-carbazole (12.1g, 49.6mmol) were added to 400ml of dimethylformamide under nitrogen atmosphere, stirred and refluxed. Cesium carbonate (48.5g, 148.7mmol) was then charged, heated and stirred. After 3 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 30 times 932ml of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by means of a silica gel column using chloroform and ethyl acetate, to thereby produce compound 16(23g, 74%, MS: [ M + H ] + ═ 627.8) as a yellow solid.

Production example 17: production of Compound 17

In production example 16, 2-chloro-4- (dibenzo [ b, d ] was used]Thiophen-4-yl) -6-phenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 2-phenyl-9H-carbazole, in addition to this, by reaction with compound 16Compound 17 was produced by the same production method. (MS [ M + H)]⁺＝733)。

Production example 18: preparation of Compound 18

Compound 18 was produced by the same production method as that of compound 16, except that 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 3-phenyl-9H-carbazole were used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 2-phenyl-9H-carbazole in production example 16. (MS [ M + H)]⁺＝703)。

Production example 19: production of Compound 19

Compound 19 was produced by the same production method as that of compound 16, except that 4- (phenyl-d 5) -9H-carbazole was used instead of 2-phenyl-9H-carbazole in production example 16. (MS [ M + H)]⁺＝632)。

Production example 20: production of Compound 20

In production example 16, (4- (dibenzo [ b, d ]) was used]Compound 20 was produced by the same production method as that of compound 16 except that phenylboronic acid, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole were replaced with thiophen-4-yl-phenyl) -4, 6-diphenyl-1, 3, 5-triazine and 4-phenyl-9H-carbazole. (MS [ M + H)]⁺＝885)。

Example 1

Indium Tin Oxide (ITO) and a process for producing the same

Is coated in a thickness ofThe glass substrate with the thin film formed thereon was put into distilled water in which a detergent was dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, the following compound HT-A and the following compound PD were mixed in a weight ratio of 95:5 in such a manner that

Is subjected to thermal vacuum deposition, and then only the following compound HT-A is deposited in the presence of a solvent

The hole transport layer is formed by evaporation. On the hole transport layer, the following compound HT-B and

the electron blocking layer is formed by thermal vacuum deposition. On the electron blocking layer, compound 1 produced above and compound GD described below were mixed in a weight ratio of 85:15

The thickness of (2) is vacuum-evaporated to form a light-emitting layer. On the light-emitting layer, the following compound ET-A and

the hole blocking layer is formed by vacuum evaporation. On the hole-blocking layer, the following compound ET-B and the following compound Liq are mixed in a weight ratio of 2:1

Is subjected to thermal vacuum evaporation, and then LiF and magnesium are mixed in a weight ratio of 1:1

The electron transporting and injecting layer is formed by vacuum evaporation. On the electron injection layer, magnesium and silver are mixed at a weight ratio of 1:4

The cathode is formed by vapor deposition to produce an organic light-emitting device.

In the above process, the evaporation speed of the organic material is maintained

Lithium fluoride maintenance of cathode

Deposition rate of (3), silver and magnesium maintenance

The vacuum degree is maintained at 2 x 10 during the vapor deposition^-7To 5 x 10^-6And thus an organic light emitting device was manufactured.

Examples 2 to 25 and comparative examples 1 to 11

An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the compound described in table 1 below was used instead of compound 1.

For reference, in examples 21 to 25 and comparative examples 9 to 11, compounds described in the following table 1 were used in a weight ratio of 1:1 in place of compound 1, thereby fabricating organic light emitting devices. By way of example 21, in example 1, compound 2 and compound H-2 were used in a weight ratio of 1:1 instead of compound 1. In Table 1 below, compounds H-2, C1 through C8 are shown below, respectively.

Examples of the experiments

The organic light emitting devices produced in the examples and comparative examples were measured for voltage, efficiency, and lifetime by applying current (T95), and the results are shown in table 1 below. At this time, the voltage and efficiency were 10mA/cm²Is measured by the current density of (a). Furthermore, T95 in Table 1 below indicates a current density of 20mA/cm²Time measured when the initial brightness decreased to 95%.

[ Table 1]

In the compound according to the present invention, an aryl group is substituted at the ortho position of carbazole, and structural warping occurs, so that charge transfer (charge transfer) cannot be achieved well. Therefore, it is assumed that the molecule has high stability and is advantageous for transporting both holes and electrons. In addition, the precursor of chemical formula 1 of the present invention is further substituted with various aryl and heteroaryl groups, so that electron transport characteristics can be variously adjusted, and thus it is predicted to be advantageous to coordinate charge balance according to the modification of the general-purpose layer.

In table 1 described above, examples 1 to 20 and comparative examples 1 to 8 are examples of organic light emitting devices using a host alone in a light emitting layer, and examples 21 to 25 and comparative examples 9 to 11 are device examples using 2 kinds of hosts in a light emitting layer. It was confirmed that the organic light emitting device of the example using the compound of the present invention has higher efficiency, lower driving voltage, and particularly greatly improved life characteristics than the organic light emitting device of the comparative example, not only in the case of using 1 host but also in the case of using 2 hosts in the light emitting layer.

Therefore, as shown in table 1 above, it was confirmed that the compound of chemical formula 1 exhibits characteristics of low voltage, high efficiency, and long life when used as a host of an organic light emitting device.

Description of the symbols

1: substrate 2: anode

3: light-emitting layer 4: cathode electrode

5: hole injection layer 6: hole transport layer

7: electron blocking layer 8: hole blocking layer

9: electron transport layer 10: an electron injection layer.

Claims

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

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

l is linked to carbon number 1, carbon number 2 or carbon number 3,

p is an integer of 0 to 5,

q is an integer of 1 to 8.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 to chemical formula 1-3:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

In the chemical formulas 1-1 to 1-3,

for L, Ar₁、Ar₂、R₁、R₂The description of p and q is the same as defined in claim 1.

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

4. The compound of claim 1, wherein Ar₁And Ar₂Each independently is phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl substituted with 5 deuterium, carbazolylphenyl, or phenylbenzothiophenyl.

5. The compound of claim 1, wherein R₁Is hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.

6. According to the rightThe compound of claim 1, wherein R₂Each independently is any one selected from the following groups:

7. the compound of claim 1, wherein q is 1 or 2.

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

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