CN113166131A

CN113166131A - Novel compound and organic light emitting device comprising same

Info

Publication number: CN113166131A
Application number: CN202080006642.6A
Authority: CN
Inventors: 李征夏; 李东勋; 张焚在; 徐尚德; 郑珉祐; 韩修进; 朴瑟灿; 黄晟现
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2019-05-23
Filing date: 2020-05-25
Publication date: 2021-07-23
Anticipated expiration: 2040-05-25
Also published as: KR20200135228A; KR102392658B1; CN113166131B

Abstract

The invention provides a novel compound and an organic light emitting device using 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. 10-2019-0060569, 23/5/2019 and korean patent application No. 10-2020-0061904, 22/5/2020, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel compound and an organic light emitting device using 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 0001) Korean patent laid-open publication No. 10-2013-073537

Disclosure of Invention

Technical subject

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

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,

X₁、X₂、X₃、X'₁、X'₂and X'₃Each independently is N or CR₁Provided that X is₁To X₃Is N, X'₁To X'₃One or more of them is N,

R₁each independently of the others is hydrogen, cyano, or with Ar selected from adjacent₁、Ar₂、Ar'₁And Ar'₂Any of which are combined to form a fused ring,

L₁and L'₁Each independently is a direct bond; substituted or unsubstituted C_6-60An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S_5-60Arylene of heteroaryleneThe base group is a group of a compound,

L₁to 1 or 2, provided that L₁L 'when linked to 1'₁To any one of 2', 3' and 4', L₁L 'when linked to 2'₁Is connected with the 3 'or the 4',

Ar₁、Ar₂、Ar'₁and Ar'₂Each independently is substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S_5-60A heteroaryl group.

In addition, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound of the present invention.

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 suppression layer 7, a light-emitting layer 3, an electron transport layer 8, an electron transport layer 9, and a cathode 4.

Detailed Description

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

(description of wording)

In the context of the present specification,

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 heterocyclic groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents being bonded. 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, a3, 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-propylpentyl group, a n-nonyl group, a2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a1, 1-dimethyl-propyl group, a 1-propyl group, a tert-pentyl group, a 2-pentyl group, a hexyl, 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 number of carbon atoms of the cycloalkyl group is 3 to 30. 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,

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. When the fluorenyl group is substituted, the compound may be

And the like. But is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms. 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, thiazolyl, isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, 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 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 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 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 in addition to this, the above description on the heterocyclic group can be applied.

(Compound (I))

[ chemical formula 1]

In the above-described chemical formula 1,

L₁and L'₁Each independently is a direct bond; substituted or unsubstituted C_6-60An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S_5-60A heteroarylene group, a heteroaryl group,

Ar₁、Ar₂、Ar'₁and Ar'₂Each independently is a substitutionOr unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S_5-60A heteroaryl group.

Preferably, the compound represented by the above chemical formula 1 is any one selected from the group consisting of:

in the above compounds, Y₁、Y₂、Y₃、Y'₁、Y'₂、Y'₃Each independently is N or CR'₁Provided that, in each formula, Y₁To Y₃One or more of N, Y'₁To Y'₃Is N, R'₁Each independently of the other is hydrogen or cyano,

L₁、L'₁、Ar₁、Ar₂、Ar'₁and Ar'₂As defined above.

Preferably, Ar as a terminal substituent of the above-mentioned triazine substituent₁、Ar₂、Ar'₁And Ar'₂Each independently further substituted with one or more deuterium. In the case where the terminal substituent is further substituted with deuterium, the lifetime characteristics can be improved when applied to an organic light-emitting device, and thus is preferable.

Preferably, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formulae 2 to 6:

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

[ chemical formula 5]

[ chemical formula 6]

In the above-mentioned chemical formulas 2 to 6,

X₁、X₂、X₃、X'₁、X'₂、X'₃、L₁、L'₁、Ar₁、Ar₂、Ar'₁and Ar'₂As defined above.

Preferably, L₁And L'₁Each independently being a direct bond, a phenylene group or a dimethylfluorenylene group.

Or, L₁And L'₁Each independently is a direct bond.

Preferably according to L₁And L'₁The linking position of (a), the structure of the linking group is selected as follows.

For example, L₁Is connected with 1, and L'₁When linked to any one selected from the group consisting of 2', 3' and 4', L₁And L'₁Each independently being a direct bond, a phenylene group or a dimethylfluorenylene group.

L₁Is connected with 2, and L'₁When 3' is linked, L₁And L'₁Are all directly bonded.

L₁Is connected with 2, and L'₁When attached to 4', L₁And L'₁Is a direct bond, phenylene or dimethylfluorenylene.

Preferably, Ar₁、Ar₂、Ar'₁And Ar'₂May each independently be any one selected from the following groups:

in the formula (I), the compound is shown in the specification,

d is deuterium, CN represents cyano,

n is an integer of 1 to 3,

m is an integer of 0 to 2,

a is an integer of 0 to 3,

b is an integer of 0 to 4,

c is an integer of 0 to 5,

e is an integer of 0 to 6,

f is an integer of 0 to 7,

g is an integer of 0 to 8,

h is an integer from 0 to 9.

Preferably, the compound represented by the above chemical formula 1 may be any one selected from the following compounds:

the compound represented by chemical formula 1 according to the present invention may have high efficiency, low driving voltage, high luminance, and long life characteristics when applied to an organic light emitting device by including a triazine-based substituent at a specific position in each of the benzene rings on both sides of dibenzothiophene.

The compound represented by the above chemical formula 1 can be produced through the following reaction formula a.

[ reaction formula A ]

In the above-mentioned reaction formula a,

except for Z₁、Z₂And Z₃The other groups are as defined above, Z₁、Z₂And Z₃Is halogen, each independently is bromine or chlorine.

In the reaction formula a, the functional group, catalyst, solvent, and the like used may be appropriately changed depending on the target product. The method for producing the compound of chemical formula 1 can be further embodied in the production examples described below.

(organic light emitting device)

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: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound represented by 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 suppression 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 device 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 above chemical formula 1.

In addition, the organic layer may include an electron inhibiting layer including 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. Preferably, the compound represented by chemical formula 1 in the light-emitting layer may be a host compound, and the light-emitting layer may further include a dopant compound.

In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer simultaneously performing electron transport and electron injection, and 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 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 suppression layer 7, a light-emitting layer 3, an electron transport layer 8, an electron transport layer 9, 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, electron suppression layer, light emitting layer, electron transport layer, and electron injection 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, in the case where 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. This can be produced as follows: 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 can 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 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 electron inhibiting layer is a layer interposed between the hole transporting layer and the light emitting layer in order to prevent electrons injected from the cathode from being transferred to the hole transporting layer without being recombined in the light emitting layer, and is also referred to as an electron blocking layer. The electron-inhibiting layer is preferably a substance having a smaller electrophilic ability than the electron-transporting layer.

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 (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene)A group) (PPV) polymer; spiro (spiroo) compounds; a polyfluorene; rubrene, etc., but 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 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.

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,

Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. 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 that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons from the cathode well and transfer the electrons to the light emitting layer, and a substance having a high electron mobility is preferable. 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, as a suitable anionExamples of polar substances are the usual substances with a low work function 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: 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 described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.

Production example 1

Production example 1-1: synthesis of intermediate A4

1) Production of intermediate A1

1-bromo-3-iodo-2- (methylthio) benzene (100g, 304mmol) and (2-chlorophenyl) boronic acid (47.5g, 304mmol) were added to 1500ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, sodium carbonate (96.6g, 911.9mmol) was dissolved in 97ml of water and charged, and after sufficiently stirring, tetrakistriphenylphosphine-palladium (7g, 6.1mmol) was charged. After the reaction for 8 hours, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer, and then the organic layer was distilled. This was again dissolved in 948ml 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 silica gel column using chloroform and ethyl acetate to obtain compound a1(78.7g, 83%, MS: [ M + H ] + ═ 312.9).

2) Production of intermediate A2

After compound A1(78.7g, 252.3mmol) was dissolved in 750ml of acetic acid under nitrogen atmosphere, it was cooled to 0 ℃. 35% hydrogen peroxide (8.6g, 252.3mmol) was charged, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, water was added to neutralize the reaction solution, the organic layer was separated with ethyl acetate, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure to obtain compound a2(72g, 87%, MS: [ M + H ] + ═ 328.9).

3) Production of intermediate A3

Compound A2(72.0g, 219.6mmol) and 290ml of sulfuric acid were charged into a flask at 5 ℃ and stirred while warming slowly, and stirred at room temperature for 1.5 hours. After the reaction, the reaction mixture was added dropwise in the reverse direction to 3000ml of ice water, and then neutralized with an aqueous potassium carbonate solution, the organic layer was separated with ethyl acetate, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure to obtain compound a3(40.3g, 62%, MS: [ M + H ] + ═ 296.9).

4) Production of Compound A4

After compound A3(40.3g, 143.1mmol) was dissolved in tetrahydrofuran (630ml), the temperature was lowered to-78 ℃ and 2.5M t-butyllithium (t-BuLi) (57.8ml, 144.6mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropyl borate (49.5ml, 214.7mmol) was added, and the mixture was stirred for 3 hours while gradually raising the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid (400ml), and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether in this order, and dried under vacuum to give intermediate A4(32.8g, yield 92%; MS: [ M + H ])]⁺＝263)。

Production examples 1 and 2: synthesis of intermediate B4

1) Production of Compound B1

Compound B1(82.5g, yield 87%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A1 of preparation example 1-1, except that (4-chlorophenyl) boronic acid (47.5g, 304mmol) was used in place of (2-chlorophenyl) boronic acid]⁺＝312)。

2) Production of Compound B2

Compound B2(72g, yield 83%; MS: [ M + H ]; (M + H); Compound A2) was prepared in the same manner as in the preparation of Compound A2, except that Compound B1(82.5g, 264.5mmol) was used in place of Compound A1]⁺＝328)。

3) Production of Compound B3

Compound B3(42.2g, yield 65%; MS: [ M + H ]; (M + H); MS) was prepared in the same manner as in the preparation of Compound A3, except that Compound B2(72.5g, 219.6mmol) was used in place of Compound A2]⁺＝296)。

4) Production of Compound B4

Using compoundsCompound B4(33.6g, yield 90%; MS: [ M + H ]; (M + H); Compound A4 was prepared in the same manner as for compound A4, except that B3(42.2g, 142.6mmol) was used in place of compound A3]⁺＝263)。

Production examples 1 to 3: synthesis of intermediate C4 Compound

1) Preparation of Compound C1

Compound C1(85.3g, yield 90%; MS: [ M + H ] was prepared by the same method as that for preparing Compound A1 of preparation example 1-1, except that (3-chlorophenyl) boronic acid (47.5g, 304mmol) was used instead of (2-chlorophenyl) boronic acid]⁺＝312)。

2) Preparation of Compound C2

Compound C2(75.3g, yield 84%; MS: [ M + H ]; (M + H); was prepared by the same method as that for the preparation of Compound A2, except that Compound C1(85.3g, 273.5mmol) was used in place of Compound A1]⁺＝328)。

3) Preparation of Compound C3

Compound C3(46.9g, 69% yield; MS: [ M + H ]; (M + H); MS) was prepared in the same manner as in the preparation of Compound A3, except that Compound C2(75.3g, 229.6mmol) was used in place of Compound A2]⁺＝296)。

4) Preparation of Compound C4

Compound C4(39.5g, yield 95%; MS: [ M + H ]; (M + H); Compound A4 was prepared in the same manner as in the preparation of Compound A4, except that Compound C3(46.9g, 158.5mmol) was used in place of Compound A3]⁺＝263)。

Production examples 1 to 4: synthesis of intermediate D4

1) Production of Compound D1

4-bromo-1-iodo-2- (methylthio) benzene (100g, 304mmol) was used as a starting materialCompound D1(77.7g, yield 82%; MS: [ M + H ] was prepared in a similar manner to the preparation of Compound A1 of preparation example 1-1, except that 1-bromo-3-iodo-2- (methylthio) benzene was used]⁺＝312)。

2) Production of Compound D2

Compound D2(69.0g, yield 80%; MS: [ M + H ]; (M + H); Compound A2) was prepared in the same manner as in the preparation of Compound A2, except that Compound D1(82.0g, 262.9mmol) was used in place of Compound A1]⁺＝328)。

3) Production of Compound D3

Compound D3(39.2g, yield 63%; MS: [ M + H ]; (M + H); was prepared by the same method as that for the preparation of Compound A3, except that Compound D2(69.0g, 210.4mmol) was used in place of Compound A2]⁺＝296)。

4) Production of Compound D4

Compound D4(32.6g, yield 94%; MS: [ M + H ]; (M + H); Compound A4 was prepared in the same manner as in the preparation of Compound A4, except that Compound D3(39.2g, 132.5mmol) was used in place of Compound A3]⁺＝263)。

Production examples 1 to 5: synthesis of intermediate E4

1) Preparation of Compound E1

Compound E1(84.4g, yield 89%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A1 of preparation example 1-1, except that 4-bromo-1-iodo-2- (methylthio) benzene (100g, 304mmol) and (3-chlorophenyl) boronic acid (47.5g, 304mmol) were used in place of 1-bromo-3-iodo-2- (methylthio) benzene and (2-chlorophenyl) boronic acid]⁺＝312)。

2) Preparation of Compound E2

Compound E2(73.6g, yield 83%; MS: [ M + H ]; (M + H); Compound A2 was prepared in a similar manner to the method for preparing Compound A2, except that Compound E1(84.4g, 270.6mmol) was used in place of Compound A1]⁺＝328)。

3) Preparation of Compound E3

Compound E3(41.2g, yield 62%; MS: [ M + H ]; (M + H); Compound A3 was prepared in a similar manner to the method for preparing Compound A3, except that Compound E2(73.6g, 224.4mmol) was used in place of Compound A2]⁺＝296)。

4) Preparation of Compound E4

Compound E4(32.8g, yield 90%; MS: [ M + H ]; (M + H); Compound A4 was prepared in the same manner as in the preparation of Compound A4, except that Compound E3(41.2g, 139.2mmol) was used in place of Compound A3]⁺＝263)。

Production example 2

Production example 2-1: synthesis of intermediate A5

1) Production of Compound A5-1

A4(10g, 38.2mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.2g, 38.2mmol) were added to 200ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (15.8g, 114.5mmol) was dissolved in 16ml of water and charged, and after sufficiently stirring, tetrakis (triphenyl-phosphine) palladium (1.3g, 1.1mmol) was charged. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was put into 514ml of tetrahydrofuran and dissolved, washed with water 2 times, 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 tetrahydrofuran and ethyl acetate to give compound a5-1(14.9g, 87%, MS: [ M + H ] + ═ 450.1) as a solid.

2) Production of Compound A5

A5-1(14.9g, 33.2mmol) and bis (pinacolato) diboron (10.1g, 39.8mmol) were added to 298ml of bis under a nitrogen atmosphere

In an alkane (Diox), stirred and refluxed. Then, potassium acetate (9.6g, 99.5mmol) was added thereto, and after sufficiently stirring, bis (dibenzylideneacetone) was added thereto) Palladium (0.6g, 1mmol) and tricyclohexylphosphine (0.6g, 2 mmol). After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was put into 539ml 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 Compound A5(13.8g, 77%, MS: [ M + H ]]+＝542.2)。

Production example 2-2: synthesis of intermediate A6

Compound a6(MS [ M + H ] + ═ 632) was produced in the same production method as that of compound a5, except that in production example 2-1, 2-chloro-4- (dibenzofuran-3-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine.

Production examples 2 to 3: synthesis of intermediate A7

Compound a7(MS [ M + H ] + -707) was produced by the same production method as that of compound a5, except that 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -3-phenyl-9H-carbazole was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 4: synthesis of intermediate B5

Compound B5(MS [ M + H ] + ═ 648) was produced by the same production method as that for compound a5, except that compound B4 and 2-chloro-4- (dibenzothiophen-4-yl) -6-phenyl-1, 3, 5-triazine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 5: synthesis of intermediate B6

Compound B6(MS [ M + H ] + -631) was produced by the same production method as that for compound a5, except that compound B4 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 6: synthesis of intermediate B7

Compound B7(MS [ M + H ] + ═ 541) was produced in the same production method as that of compound a5, except that compound B4 and 4-chloro-2, 6-diphenylpyrimidine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 7: synthesis of intermediate C5 Compound

Compound C5(MS [ M + H ] + ═ 632) was produced by the same production method as that for compound a5, except that compound C4 and 2-chloro-4- (dibenzofuran-4-yl) -6-phenyl-1, 3, 5-triazine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 8: synthesis of intermediate C6 Compound

Compound C6(MS [ M + H ] + -707) was produced by the same production method as that of compound a5, except that compound C4 and 2- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 9: synthesis of intermediate C7 Compound

Compound C7(MS [ M + H ] + -618) was produced in the same manner as the production method of compound a5, except that compound C4 and 2- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 10: synthesis of intermediate D5

Compound D5(MS [ M + H ] + ═ 632) was produced in the same manner as in the production method of compound a5, except that compound D4 and 2-chloro-4- (dibenzofuran-1-yl) -6-phenyl-1, 3, 5-triazine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 11: synthesis of intermediate D6

Compound D6(MS [ M + H ] + -707) was produced in the same production method as that of compound a5, except that compound D4 and 4- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 12: synthesis of intermediate D7

Compound D7(MS [ M + H ] + ═ 541) was produced in the same production method as that of compound a5, except that compound D4 and 2-chloro-4, 6-diphenylpyrimidine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 13: synthesis of intermediate E5

Compound E5(MS [ M + H ] + -542) was produced by the same production method as that of compound a5, except that compound E4 was used instead of compound a4 in production example 2-1.

Production examples 2 to 14: synthesis of intermediate E6

Compound E6(MS [ M + H ] + ═ 632) was produced in the same production method as that for compound a5, except that compound E4 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

Production examples 2 to 15: synthesis of intermediate E7

Compound E7(MS [ M + H ] + -707) was produced by the same production method as that of compound a5, except that compound E4 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -2-phenyl-9H-carbazole were used instead of compound a4 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in production example 2-1.

[ examples ]

Example 1: production of Compound 1

A5(4g, 7.4mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (2g, 7.4mmol) were added to 120ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (3.1g, 22.2mmol) was dissolved in 3ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0.1g, 0.1mmol) was charged. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was put into 382ml of dichlorobenzene and dissolved, washed with water for 2 times, 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 dichlorobenzene and ethyl acetate to produce compound 1(4.2g, 88%, MS: [ M + H ] + ═ 647.2) as a white solid.

Example 2: production of Compound 2

Using 2- ([1,1' -biphenyl)]Compound 2(3.8g, yield 72%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound 1 in example 1, except that (E) -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used in place of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝723)。

Example 3: production of Compound 3

Compound 3(3.3g, yield 61%, MS: [ M + H ] was prepared in the same manner as in preparation of Compound 1 of example 1, except that 2-chloro-4- (dibenzofuran-4-yl) -6- (phenyl-d 5) -1,3, 5-triazine was used in place of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝741)。

Example 4: production of Compound 4

Compound 4(3.2g, yield 69%, MS: [ M + H ]: 4 was produced by the same method as the production of compound 1 of example 1 except that compound A6 and 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine were used in place of compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝741)。

Example 5: production of Compound 5

Compound 5(3.6g, yield 79%, MS: [ M + H ] was prepared by the same method as that for the preparation of compound 1 of example 1, except that compound A7 and 2-chloro-4, 6-diphenylpyrimidine were used in place of compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝811)。

Example 6: production of Compound 6

Compound 6(3.8g, yield 81%, MS: [ M + H ]: M + H) was produced in the same manner as in the production of compound 1 in example 1, except that compound B5 and 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine were used in place of compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝758)。

Example 7: production of Compound 7

Using compound B6 and 2- ([1,1' -biphenyl)]-4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine instead of Compound A5 and 2-chloro-4, 6Compound 7(3.9g, yield 75%, MS: [ M + H ] was produced in the same manner as in the production of Compound 1 in example 1, except that diphenyl-1, 3, 5-triazine]⁺＝812)。

Example 8: production of Compound 8

Compound 8(3.4g, yield 63%, MS: [ M + H ] was prepared in the same manner as in preparation of Compound 1 of example 1, except that Compound B7 and 22- (3-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine were used in place of Compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝722)。

Example 9: production of Compound 9

Compound 9(4.3g, yield 72%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound 1 of example 1 except that Compound B7 and 3- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole were used in place of Compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝811)。

Example 10: production of Compound 10

Compound 10(3.5g, yield 76%, MS: [ M + H ] was produced in the same manner as in the production of Compound 1 in example 1, except that Compound C5 was used in place of Compound A5]⁺＝737)。

Example 11: production of Compound 11

Compound 11(2.8g, yield 62%, MS: [ M + H ] was prepared by the same method as that for the preparation of Compound 1 in example 1, except that Compound C6 was used in place of Compound A5]⁺＝812)。

Example 12: production of Compound 12

Compound 12(3.4g, yield 73%, MS: [ M + H ] was prepared by the same method as that for the preparation of Compound 1 in example 1, except that Compound C7 was used in place of Compound A5]⁺＝723)。

Example 13: production of Compound 13

Compound 13(4.7g, yield 88%, MS: [ M + H ] was produced by the same method as the production of Compound 1 of example 1 except that Compound C7 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole-1, 3,4,5,6,8-d6 were used in place of Compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝818)。

Example 14: production of Compound 14

Using compound D5 and 2- ([1,1' -biphenyl)]Compound 14(3.2g, yield 63%, MS: [ M + H ] M + H) was produced in the same manner as in the production of Compound 1 in example 1, except that (E) -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used in place of Compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝813)。

Example 15: production of Compound 15

Compound 15 was produced in the same manner as in the production of Compound 1 in example 1 except that Compound D6 was used in place of Compound A5 (3.3 yield 71MS: [ M + H ]]⁺＝812)。

Example 16: production of Compound 16

Compound 16(3.5g, yield 63%, MS: [ M + H ]: 16 was prepared in the same manner as in the preparation of Compound 1 in example 1 except that Compound D7 and 2-chloro-4- (dibenzothiophen-4-yl) -6-phenyl-1, 3, 5-triazine were used in place of Compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝752)。

Example 17: production of Compound 17

Compound 17(3.8g, yield 64%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound 1 of example 1 except that Compound E5 and 2- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole were used in place of Compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝812)。

Example 18: preparation of Compound 18

Compound 18(3.8g, yield 84%, MS: [ M + H ] was produced by the same method as the production of compound 1 of example 1, except that compound E5 and 2-chloro-4-phenylquinazoline were used instead of compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝620)。

Example 19: production of Compound 19

Compound 19(3.6g, yield 77%, MS: [ M + H ] was produced by the same production method as that of Compound 1 of example 1, except that Compound E6 was used in place of Compound A5]⁺＝737)。

Example 20: production of Compound 20

Compound 20(3.5g, yield 75%, MS: [ M + H ]: M + H) was produced by the same production method as that of compound 1 of example 1, except that compound E7 and 2-chloro-4-phenyl-6- (phenyl-d 5) -1,3, 5-triazine were used instead of compound A5 and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine]⁺＝817)。

[ Experimental example ]

Experimental example 1

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

The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is 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 hexanitrile Hexaazatriphenylene (HAT) compound was added

The hole injection layer is formed by thermal vacuum deposition. On the above hole injection layer, an HT-1 compound is added

Is subjected to thermal vacuum evaporation, and HT-2 compounds are sequentially added to

The hole transport layer is formed by vacuum evaporation. Then, compound 1 produced as a host, the following H1 compound, and phosphorescent dopant GD were co-evaporated at a weight ratio of 47:47:6 on the hole transport layer to form a hole transport layer

A thick light emitting layer. On the above-mentioned luminescent layer an ET-1 substance is added

Is formed by vacuum evaporation to a thickness of (2) to form a hole blocking layer, and an ET-2 substance and LiQ (8-hydroxyquinoline Lithium) are vacuum evaporated to a weight ratio of 1:1 to form the hole blocking layer

The electron transport layer of (1). On the electron transport layer, sequentially

Depositing lithium fluoride (LiF) in a thickness on the lithium fluoride

Aluminum is deposited to form a cathode.

In the above-mentioned process, the first step,maintenance of deposition rate of organic material

Lithium fluoride maintenance of cathode

Deposition rate of (3), aluminum maintenance

The vacuum degree is maintained at 1X 10 during the vapor deposition^-7～5×10^-8And (4) supporting.

Experimental examples 2 to 20

Organic light-emitting devices of experimental examples 2 to 20 were each produced in the same manner as in experimental example 1, except that compounds shown in table 1 below were used instead of compound 1 as a host in forming the light-emitting layer.

Comparative Experimental examples 1 to 5

Organic light-emitting devices of comparative examples 1 to 5 were each produced in the same manner as in example 1, except that compounds 1 were replaced with C1 to C5 shown below, respectively, as shown in table 1 below.

The organic light emitting devices fabricated in the above experimental examples 1 to 18 and comparative examples 1 to 5 were applied with current, and the voltage, efficiency and lifetime were measured, and the results thereof are shown in the following table 1. T95 refers to the time required for the luminance to decrease from the initial luminance to 95%.

[ Table 1]

As shown in table 1 above, it was confirmed that in the case of an organic light-emitting device manufactured using the compound according to the present invention as a host of a light-emitting layer, the voltage, efficiency and life characteristics are excellent, and particularly, the long life characteristics are exhibited, as compared with the organic light-emitting device of the comparative example.

It can be confirmed that the organic light emitting device according to the embodiment shows high efficiency characteristics, particularly, a lifetime increased from about 160% to 200%, as compared to the compound C1, which is a phosphorescent host substance, generally used, with an efficiency increased from about 10% to 20%.

The effect of the organic light emitting device was significantly different depending on the substitution position of the substituent of the compound, and for example, in comparative experimental examples 2 and 3 in which the substitution position of the substituent was different, it was confirmed that the driving voltage was high and the life characteristic was significantly reduced as compared with the examples.

The effect of the organic light emitting device was significantly different depending on the kind of the substituent of the compound, and for example, in comparative example 4 having a different substituent, it was confirmed that the voltage characteristics were significantly higher than those of the examples.

In addition, in comparative example 5 using a dibenzofuran core other than dibenzothiophene, it was confirmed that the voltage characteristics and lifetime characteristics were significantly reduced as compared with experimental examples 1 or 7 of similar structure.

In addition, the voltage and lifetime characteristics were different depending on the connection structure of the substituent, and it was confirmed that the voltage and lifetime characteristics were slightly improved when the triazine-based substituent was directly bonded without a connecting group.

Finally, observing experimental examples 2 and 3 or 19 and 20, it was confirmed that the lifetime characteristics were improved with respect to the compound having deuterium substituted at the terminal.

As described above, it was confirmed that the compound of the present invention showed superior characteristics in terms of voltage, efficiency and lifetime depending on the position of the substituent and the kind of the substituent, compared to the comparative example compound.

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 suppression layer 8: electron transport layer

9: 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,

L₁to 1 or 2, provided that L₁L 'when linked to 1'₁To any one selected from 2', 3' and 4 '; l is₁L 'when linked to 2'₁Is connected with the 3 'or the 4',

2. The compound according to claim 1, wherein the compound represented by chemical formula 1 is a compound represented by the following chemical formulae 2 to 6:

chemical formula 2

Chemical formula 3

Chemical formula 4

Chemical formula 5

Chemical formula 6

In the chemical formulae 2 to 6,

X₁、X₂、X₃、X'₁、X'₂、X'₃、L₁、L'₁、Ar₁、Ar₂、Ar'₁and Ar'₂As defined in claim 1.

3. The compound of claim 1, wherein L₁And L'₁Each independently being a direct bond, a phenylene group or a dimethylfluorenylene group.

4. The compound of claim 1, wherein L₁And L'₁Each independently is a direct bond.

5. According to claim1 wherein Ar is₁、Ar₂、Ar'₁And Ar'₂Each independently is any one selected from the following groups:

in the formula (I), the compound is shown in the specification,

n is an integer of 1 to 3,

m is an integer of 0 to 2,

a is an integer of 0 to 3,

b is an integer of 0 to 4,

c is an integer of 0 to 5,

e is an integer of 0 to 6,

f is an integer of 0 to 7,

g is an integer of 0 to 8,

h is an integer from 0 to 9.

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

7. an organic light emitting device, comprising: a first electrode; a second electrode provided so as to face the first electrode; and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer contain the compound according to any one of claims 1 to 6.

8. The organic light-emitting device according to claim 7, wherein the organic layer containing the compound is a light-emitting layer.

9. The organic light-emitting device according to claim 8, wherein the compound is contained as a host.

10. The organic light emitting device of claim 8, wherein the light emitting layer further comprises a dopant compound.

11. The organic light-emitting device according to claim 7, wherein the organic layer containing the compound is an electron injection layer, an electron transport layer, or a layer in which electron injection and electron transport are performed simultaneously.