CN113631553A - Novel compound and organic light emitting device using the same - Google Patents

Novel compound and organic light emitting device using the same Download PDF

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CN113631553A
CN113631553A CN202080019617.1A CN202080019617A CN113631553A CN 113631553 A CN113631553 A CN 113631553A CN 202080019617 A CN202080019617 A CN 202080019617A CN 113631553 A CN113631553 A CN 113631553A
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CN113631553B (en
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朴瑟灿
李东勋
张焚在
徐尚德
郑珉祐
李征夏
韩修进
黄晟现
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LG Chem Ltd
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Abstract

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

Description

Novel compound and organic light emitting device using the same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0113117, 11, 2019 and korean patent application No. 10-2020-0111895, 9, 2, 2020, the entire contents of the documents containing the korean patent application are included as part of the present specification.
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 the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
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 compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure BDA0003251826530000021
In the above-described chemical formula 1,
X1to X3Each independently is CH or N, and X1To X3At least one of which is N,
Y1and Y2Each independently of the other is O or S,
Ar1are identical to each other and are substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
Ar2are identical to each other and are substituted or unsubstituted C6-60Aryl radicals(ii) a Or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
each R is independently hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; a silyl group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60An aryloxy group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
n is an integer of 1 to 5.
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 represented by 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, an organic 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 8, a hole suppression layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
(definition of wording)
In the context of the present specification,
Figure BDA0003251826530000031
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 radicals (A), (B), (C), (D), (C), (D), (E), (D), (E) and (D)
Figure BDA0003251826530000041
Alkyl thio xy); arylthio radicals (A), (B), (C)
Figure BDA0003251826530000042
Figure BDA0003251826530000043
Aryl thio xy); alkylsulfonyl (
Figure BDA0003251826530000044
Alkyl sulfo xy); arylsulfonyl (
Figure BDA0003251826530000045
Aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituents formed by connecting 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.
Figure BDA0003251826530000046
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.
Figure BDA0003251826530000047
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.
Figure BDA0003251826530000051
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-propylpentyl group, a n-nonyl group, a 2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a 1, 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,
Figure BDA0003251826530000061
And a fluorenyl group, 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 hetero element, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Figure BDA0003251826530000062
Azolyl group,
Figure BDA0003251826530000063
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Figure BDA0003251826530000064
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Figure BDA0003251826530000065
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, and arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group 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 exemplified above for the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
(Compound (I))
The present invention provides a compound represented by the above chemical formula 1.
Preferably, in the above chemical formula 1, X1To X3Are all N.
Preferably, Y1And Y2Both O or both S.
Preferably, Ar1Identical to each other and is phenyl substituted or unsubstituted by deuterium.
Preferably, Ar2Identical to each other and is phenyl substituted or unsubstituted by deuterium.
Preferably, Ar1And Ar2Is substituted with deuterium.
Preferably, Ar1And Ar2Are identical to each other.
Preferably, R is hydrogen, in which case n is an integer of 5.
Specifically, the compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-10, wherein, preferably, may be represented by the following chemical formula 1-1:
[ chemical formula 1-1]
Figure BDA0003251826530000081
[ chemical formulas 1-2]
Figure BDA0003251826530000082
[ chemical formulas 1-3]
Figure BDA0003251826530000083
[ chemical formulas 1 to 4]
Figure BDA0003251826530000091
[ chemical formulas 1 to 5]
Figure BDA0003251826530000092
[ chemical formulas 1 to 6]
Figure BDA0003251826530000093
[ chemical formulas 1 to 7]
Figure BDA0003251826530000094
[ chemical formulas 1 to 8]
Figure BDA0003251826530000101
[ chemical formulas 1 to 9]
Figure BDA0003251826530000102
[ chemical formulas 1-10]
Figure BDA0003251826530000103
In the above chemical formulas 1-1 to 1-10,
X1to X3、Y1、Y2、Ar1、Ar2R and n are the same as defined in the above chemical formula 1.
Preferably, in the above chemical formula 1 and chemical formulae 1-1 to 1-10, two Ar' s1May be bonded to each other at the ortho (ortho), meta (meta) or para (para) position in the benzene ring to which they are bonded.
Preferably, in the above chemical formula 1 and chemical formulae 1-1 to 1-10, two Ar' s2May be bonded to each other at the ortho-, meta-or para-position in the benzene ring to which they are bonded.
Preferably, in the above chemical formula 1 and chemical formulae 1-1 to 1-10, Ar1And Ar2May be combined at positions corresponding to each other.
As an example, the compound represented by the above chemical formula 1 or chemical formula 1-1 may be represented by any one of the following chemical formulae 1-1-1 to 1-1-6, wherein, preferably, may be represented by 1-1-2:
Figure BDA0003251826530000111
in the above chemical formulas 1-1-1 to 1-1-6,
X1to X3、Y1、Y2、Ar1、Ar2R and n are the same as defined in the above chemical formula 1.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
Figure BDA0003251826530000121
Figure BDA0003251826530000131
Figure BDA0003251826530000141
Figure BDA0003251826530000151
Figure BDA0003251826530000161
Figure BDA0003251826530000171
Figure BDA0003251826530000181
on the other hand, the present invention provides, as an example, a method for producing a compound represented by the above chemical formula 1, as shown in the following reaction formula 1:
[ reaction formula 1]
Figure BDA0003251826530000191
In the above reaction scheme 1, R, X1～X3And n is as defined above.
In the above reaction formula 1, Ar is Ar1Or are all Ar2Specifically, Ar's are the same as each other and are substituted or unsubstituted C6-60Aryl radicals(ii) a Or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60Heteroaryl, Y is Y1Or Y2Specifically O or S, and the above Ar is Ar1When Y is Y1Ar is Ar2When Y is Y2，Z1And Z2Each independently is a halogen group such as chlorine or bromine, and W is a boron-containing organic group such as a boronic acid group, a boronic ester group, or a boronic acid pinacol ester (boronic acid pinacol ester) group.
Specifically, among the compounds represented by chemical formula 1, the compound represented by chemical formula 1a, in which two substituents bound to the parent structure are identical to each other, can be produced by a production method including the steps of: a Suzuki coupling reaction is carried out in the presence of a base and a palladium-based catalyst between a compound (I) having a core structure and a compound (II) having a substituent structure bonded to the core structure and a boron-containing organic group.
Examples of the palladium-based catalyst include bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), Pd (P-tBu)3)2) Tetrakis (triphenylphosphine) palladium (0), Pd (PPh)3)4) Tris (dibenzylideneacetone) dipalladium, Pd2(dba)3) Bis (triphenylphosphine) palladium chloride (bis (triphenylphoshine) palladium chloride, Pd (PPh)3)2Cl2) Bis (acetonitrile) palladium (II) chloride (bis (acetonitrile) palladium (II) chloride, Pd (CH)3CN)2Cl2) Palladium (II) acetate (Pd (OAc))2) Palladium (II) acetylacetonate (Palladium (II) acetylacetate, Pd (acac)2) Allyl palladium (II) chloride dimer, [ Pd (allyl) Cl]2) Palladium on carbon (Pd/C), or Palladium (II) chloride (PdCl)2) And the like, and either one or a mixture of two or more of them may be used.
In addition, as the base, sodium tert-butoxide (sodium tert-but)Inorganic bases such as oxide, NaOtBu), potassium tert-butoxide (potassium tert-butoxide), sodium tert-amylate (sodium tert-pentoxide), sodium ethoxide (sodium ethoxide), sodium carbonate (sodium carbonate), potassium carbonate (potassium carbonate), cesium carbonate (sodium carbonate), sodium hydride (sodium hydride), lithium hydride (lithium hydride), or potassium hydride (potassium hydride); tetraethylammonium hydroxide (Et)4Organic bases such as NOH), bis (tetraethyl) ammonium carbonate, and triethylamine; any one or a mixture of two or more of these inorganic salts can be used.
The Suzuki coupling reaction may be carried out in water, an organic solvent, or a mixed solvent thereof, and examples of the organic solvent include diethyl ether, tetrahydrofuran, and 1, 4-bis (ether)
Figure BDA0003251826530000202
Ether solvents such as alkane, ethylene glycol diethyl ether, dimethoxyethane, bis (2-methoxyethyl) ether, diethylene glycol diethyl ether, tetrahydrofuran, or anisole; aromatic hydrocarbon solvents such as benzene, toluene or xylene; halogenated aromatic solvents such as chlorobenzene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethylimidazolidinone, or acetonitrile; or a sulfoxide-based solvent such as dimethyl sulfoxide (DMSO), and any one of them or a mixture of two or more thereof may be used.
As another example, the present invention provides a method for producing a compound represented by the above chemical formula 1 by a 2-step reaction as shown in the following reaction formula 2:
[ reaction formula 2]
Figure BDA0003251826530000201
In the above reaction formula 2, Ar1、Ar2、R、X1～X3、Y1、Y2、Z1、Z2And n is as defined above, W1And W2Each independently a boronic acid group, a boronic ester group, a boronic pinacol ester group or the likeAn organic group.
Specifically, among the compounds represented by the above chemical formula 1, the compound represented by the above chemical formula 1b, in which two substituents bound to the parent nucleus structure are different from each other, can be produced by a production method including the steps of: a first step (S1) of subjecting a compound (I) including a parent-nucleus structure, a compound (II-1) including any one of substituent structures bonded to the parent-nucleus structure, and a boron-containing organic group to a first suzuki coupling reaction in the presence of a base and a palladium-based catalyst; a second step (S2) of subjecting the intermediate compound (1 b') produced as a product, the compound (II-2) containing the boron-containing organic group and the remaining one of the substituent structures bonded to the above parent nucleus structure to a second suzuki coupling reaction in the presence of a base and a palladium-based catalyst.
In the above reaction formula 2, it is suggested that the reaction with the compound (II-2) is carried out after the reaction with the compound (II-1), but the reaction with the compound (II-1) may be carried out after the reaction with the compound (II-2) by changing the reaction order.
In the reaction formula 2, the alkali and palladium-based catalyst and the suzuki coupling reaction in the first and second steps are the same as described above, and can be carried out by the same method.
On the other hand, a reaction substance used in the production of the compound (1) of the above chemical formula 1; the compounds (I), (II-1) and (II-2) can be produced by a usual organic reaction, or can be used by being purchased commercially.
(organic light emitting device)
In another aspect, 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 include, in addition to the light-emitting layer, one or more layers selected from a hole injection layer, a hole transport layer, and an electron suppression layer between the first electrode and the light-emitting layer; or a structure in which at least one of a hole-inhibiting layer, an electron-transporting layer, and an electron-injecting layer is provided as an organic layer between the light-emitting layer and the second electrode. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger 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 may include the compound represented by the above chemical formula 1.
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. The light-emitting layer may further include a compound represented by the following chemical formula 2.
[ chemical formula 2]
Figure BDA0003251826530000221
In the above-described chemical formula 2,
Ar4and Ar5Each independently is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R4and R5Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60(ii) a heteroaryl group, wherein,
a and b are each independently an integer of 0 to 7.
More specifically, Ar4And Ar5Each independently is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl or dimethylfluorenyl, R4And R5May all be hydrogen.
The compound represented by the above chemical formula 2 may be any one selected from the following compounds:
Figure BDA0003251826530000231
Figure BDA0003251826530000241
Figure BDA0003251826530000251
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, an organic layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above organic layer 3.
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 8, a hole suppression layer 9, an electron transport layer 10, an electron injection layer 11, 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 5, hole transport layer 6, electron suppression layer 7, light emitting layer 8, hole suppression layer 9, electron transport layer 10, and electron injection layer 11.
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. 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 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, alloys thereof, and mixtures 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. The hole-transporting substance may be a compound represented by the above chemical formula 1, an arylamine organic substance, a conductive polymer, a block copolymer in which a conjugated portion or a non-conjugated portion is present, or the like, but is not limited thereto.
The electron-suppressing layer is a layer including: the hole transport layer is preferably formed on the hole transport layer, and is preferably provided in contact with the light emitting layer, and serves to prevent excessive electron transfer by adjusting hole mobility, thereby increasing the probability of hole-electron combination, and improving the efficiency of the organic light emitting device. The electron-suppressing layer contains an electron-suppressing substance, and examples of such electron-suppressing substances include, but are not limited to, the compound represented by chemical formula 1, and arylamine-based organic substances.
The light-emitting layer may contain a host material and a dopant material as described above. The host material may include an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like, in addition to the compound of chemical formula 1. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds: (
Figure BDA0003251826530000281
Figure BDA0003251826530000282
) And pyrimidine derivatives, but are not limited thereto.
Further, 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,
Figure BDA0003251826530000283
BisindeneAnd pyrene, etc., and the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on 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 inhibiting layer is a layer including: the organic light emitting device is preferably formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, and functions to improve the efficiency of the organic light emitting device by adjusting the electron mobility to prevent excessive hole migration and increase the hole-electron bonding probability. The hole-inhibiting layer contains a hole-inhibiting substance, and examples of such hole-inhibiting substances include pyrimidine derivatives, triazine derivatives, triazole derivatives, and the like,
Figure BDA0003251826530000284
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
An electron transport layer is formed on the light-emitting layer or the hole-inhibiting layer. The electron transport layer is a layer that receives electrons from the cathode or an electron injection layer described below and transports the electrons to the light emitting layer. The electron-transporting substance is a substance that 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. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: 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 LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Figure BDA0003251826530000291
Azole,
Figure BDA0003251826530000292
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.
On the other hand, the electron transport layer and the electron injection layer may be provided in the form of an electron injection and transport layer that transports the received electrons to the light-emitting layer and functions as the electron transport layer and the electron injection layer.
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 fabrication of the above-described organic light emitting device 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.
Synthesis example 1: synthesis of intermediate A
Figure BDA0003251826530000301
Step 1) Synthesis of intermediate A-1
Under nitrogen atmosphere, 6,8-dibromo-1-chlorodibenzo [ b, d ] is added]Furan (6,8-dibromo-1-chlorodibenzo [ b, d)]furan) (30g, 83.2mmol) and phenylboronic acid (20.2g, 166.4mmol) were added to 600ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (34.5g, 249.7mmol) was dissolved in 35ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (2.9g, 2.5mmol) was charged. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again charged into 20-fold 591mL 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 recrystallized from chloroform and ethyl acetate to give Compound A-1(16.5g, 56%, MS: [ M + H ])]+＝355.8)。
Step 2) Synthesis of intermediate A
A-1(30g, 84.5mmol) and bis (pinacolato) diboron (21.5g, 84.5mmol) were added to 600ml of bis under nitrogen
Figure BDA0003251826530000302
In an alkane (Diox), stirred and refluxed. Then, potassium acetate (24.9g, 253.6mmol) was charged, and after sufficiently stirring, palladium dibenzylideneacetone palladium (1.5g, 2.5mmol) and tricyclohexylphosphine (1.4g, 5.1mmol) were charged. After reacting for 3 hours, the reaction mixture was cooled to normal temperature, and the organic layer was filtered to remove salts, and the organic layer obtained by filtration was distilled. Dissolving the extract in 10 times of 377ml of chloroform, washing with water for 2 times, separating organic layer, adding anhydrous magnesium sulfate, stirring, filtering, and filteringThe solution was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give a white solid compound A (26g, 69%, MS: [ M + H ]]+＝447.4)。
Synthesis example 2: synthesis of intermediate B
Figure BDA0003251826530000311
In step 1 of Synthesis example 1,2, 4-dibromo-7-chlorodibenzo [ b, d ] was used]Furan (2,4-di broomo-7-chlorodibenzo [ b, d ]]furan) instead of 6,8-dibromo-1-chlorodibenzo [ b, d ]]Except for furan, intermediate B was produced by the same method as the method for producing intermediate a. (MS: [ M + H ]]+＝447.4)
Synthesis example 3: synthesis of intermediate C
Figure BDA0003251826530000312
In step 1 of Synthesis example 1, 3-dibromo-7-chlorodibenzo [ b, d ] was used]Furan (1,3-di broomo-7-chlorodibenzo [ b, d ]]furan) instead of 6,8-dibromo-1-chlorodibenzo [ b, d ]]Except for furan, intermediate C was produced by the same method as the production method of intermediate a. (MS: [ M + H ]]+＝447.4)
Synthesis example 4: synthesis of intermediate D
Figure BDA0003251826530000321
In step 1 of Synthesis example 1,2, 4-dibromo-6-chlorodibenzo [ b, d ] was used]Furan (2,4-di broomo-6-chlorodibenzo [ b, d ]]furan) instead of 6,8-dibromo-1-chlorodibenzo [ b, d ]]Except for furan, intermediate D was produced by the same method as the production method of intermediate a. (MS: [ M + H ]]+＝447.4)
Synthesis example 5: synthesis of intermediate E
Figure BDA0003251826530000322
Intermediate E was produced in the same manner as the production method of intermediate a except that (phenyl-d5) boronic acid was used instead of phenylboronic acid in step 1 of synthesis example 1. (MS: [ M + H ]]+＝457.4)
Synthesis example 6: synthesis of intermediate F
Figure BDA0003251826530000323
In step 1 of Synthesis example 1,2, 4-dibromo-7-chlorodibenzo [ b, d ] was used]Furan (2,4-di broomo-7-chlorodibenzo [ b, d ]]furan) instead of 6,8-dibromo-1-chlorodibenzo [ b, d ]]Intermediate F was produced by the same method as the production method of intermediate a except that furan was used instead of phenylboronic acid (phenyl-d5) boronic acid. (MS: [ M + H ]]+＝457.4)
Synthesis example 7: synthesis of intermediate G
Figure BDA0003251826530000331
In step 1 of Synthesis example 1, 6,8-dibromo-1-chlorodibenzo [ b, d ] was used]Thiophene (6,8-di bromo-1-chlorodibenzo [ b, d)]thiophene) instead of 6,8-dibromo-1-chlorodibenzo [ b, d ]]Except for furan, intermediate G was produced by the same method as the production method of intermediate a. (MS: [ M + H ]]+＝463.4)
Synthesis example 8: synthesis of Compound 1
Figure BDA0003251826530000332
2,4-dichloro-6-phenyl-1,3,5-triazine (2, 4-dichoro-6-phenyl-1, 3,5-triazine) (15g, 66.4mmol) and intermediate A (59.2g, 132.8mmol) were added to 300ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (27.5g, 199.1mmol) was dissolved in 83ml of water and chargedAfter stirring sufficiently, bis (tri-tert-butylphosphine) palladium (0) (1g, 2mmol) was added. After 7 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The final product was dissolved in 2634ml of chloroform which was 50 times the volume of the product, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a fluorescent solid compound 1. (26.9g, 51%, MS: [ M + H ]]+＝794.9)
Synthesis example 9: synthesis of Compound 2
Figure BDA0003251826530000341
Compound 2 was produced by the same method as the production method of compound 1, except that intermediate B was used instead of intermediate a in synthesis example 8. (MS: [ M + H ]]+＝794.9)
Synthesis example 10: synthesis of Compound 3
Figure BDA0003251826530000342
Compound 3 was produced by the same method as the production method of compound 1, except that intermediate C was used instead of intermediate a in synthetic example 8. (MS: [ M + H ]]+＝794.9)
Synthesis example 11: synthesis of Compound 4
Figure BDA0003251826530000343
Compound 4 was produced by the same method as the production method of compound 1, except that intermediate D was used instead of intermediate a in synthesis example 8. (MS: [ M + H ]]+＝794.9)
Synthesis example 12: synthesis of Compound 5
Figure BDA0003251826530000351
Compound 5 was produced by the same method as the production method of compound 1, except that intermediate E was used instead of intermediate a in synthesis example 8. (MS: [ M + H ]]+＝814.4)
Synthesis example 13: synthesis of Compound 6
Figure BDA0003251826530000352
Compound 6 was produced by the same method as the production method of compound 1, except that intermediate F was used instead of intermediate a in synthesis example 8. (MS: [ M + H ]]+＝814.4)
Synthesis example 14: synthesis of Compound 7
Figure BDA0003251826530000361
Step 1) Synthesis of intermediate 7-1
2,4-dichloro-6-phenyl-1,3,5-triazine (15g, 66.4mmol) and intermediate B (29.6g, 66.4mmol) were added to 300ml of tetrahydrofuran under nitrogen and stirred at 50 ℃. Then, potassium carbonate (27.5g, 199.1mmol) was dissolved in 83ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (2.3g, 2mmol) was charged. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The final extract was dissolved in 1692ml of chloroform 50 times the volume of the extract, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid compound intermediate 7-1(18.3g, 54%, MS: [ M + H ]]+＝511)。
Step 2) Synthesis of Compound 7
Under nitrogen atmosphere, intermediate 7-1(15g, 29.4mmol) and intermediate D (13.1g, 29.4mmol) were added to 300ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (12.2g, 88.2mmol) was dissolved in 37ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (O) (0.5g, 0.9mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. The final product was dissolved in 1168ml of chloroform 50 times the volume of the product, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce compound 7 as a white solid. (17.5g, 75%, MS: [ M + H ]]+＝794.9)
Synthesis example 15: synthesis of Compound 8
Figure BDA0003251826530000371
Compound 8 was produced by the same method as the production method of compound 1, except that intermediate G was used instead of intermediate a in synthetic example 8. (MS: [ M + H ]]+＝826.1)
< device example >
Example 1
Indium Tin Oxide (ITO) and a process for producing the same
Figure BDA0003251826530000372
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. Further, after the substrate was cleaned for 5 minutes by oxygen plasma, the substrate was transferredSending to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HT-A was mixed with 5% by weight of PD to prepare a mixture
Figure BDA0003251826530000373
Is subjected to thermal vacuum evaporation to form a hole injection layer, and then only the HT-A substance is added
Figure BDA0003251826530000374
The hole transport layer is formed by evaporation. On the hole transport layer, as an electron inhibiting layer, the following HT-B and
Figure BDA0003251826530000375
thermal vacuum evaporation is performed on the thickness. Next, Compound 1 as a first host and GH-A as a second host were mixed at a weight ratio of 40:60 to constitute a host, and GD as a dopant was mixed in an amount of 15 wt% based on the total weight of the host, and the mixture was doped with a dopant such that
Figure BDA0003251826530000376
The thickness of (2) is vacuum-evaporated to form a light-emitting layer. N mutext, on the light-emitting layer, as a hole-suppressing layer, the following ET-A and
Figure BDA0003251826530000377
vacuum evaporation is performed to a thickness of (1). Next, as an electron transporting layer, ET-B and Liq were added at a ratio of 2:1
Figure BDA0003251826530000378
Is subjected to thermal vacuum evaporation, and then LiF and magnesium are mixed in a ratio of 1:1
Figure BDA0003251826530000379
The electron injection layer is formed by vacuum evaporation. On the electron injection layer, magnesium and silver are mixed at a ratio of 1:4
Figure BDA00032518265300003710
Thickness ofThe cathode was formed by vapor deposition, and an organic light-emitting device was manufactured.
Figure BDA0003251826530000381
Examples 2 to 8 and comparative examples 1 to 3
Organic light-emitting devices of examples 2 to 8 and comparative examples 1 to 3 were produced in the same manner as in example 1, except that the first host material was changed to the compound described in table 1 below.
Figure BDA0003251826530000391
Experimental example: evaluation of device characteristics
The organic light emitting devices fabricated in examples 1 to 8 and comparative examples 1 to 3 were heat-treated in an oven at 100 ℃ for 30 minutes, then taken out, and applied with a current to measure voltage, efficiency, and lifetime (T95), and the results are shown in table 1 below. At this time, the voltage and efficiency were 10mA/cm2T95 means at a current density of 20mA/cm2Time (hr) when initial brightness decreased to 95%.
[ Table 1]
Figure BDA0003251826530000392
When the compounds CE1 to CE3 of comparative examples 1 to 3 were compared with the compounds of examples 1 to 8, it was found that the organic light emitting devices including the compounds of examples 1 to 8 exhibited more excellent long life characteristics due to Ar substituents. Further, when examples 1 and 5 and examples 2 and 6 are compared, it is found that the lifetime characteristics are further improved when deuterium is substituted.
From the results, when the compound of chemical formula 1 is used as a light emitting layer of an organic electroluminescent device, advantages in terms of voltage and efficiency are obtained, and in particular, a device having long life characteristics can be obtained.
[ description of symbols ]
1: substrate 2: anode
3: organic material layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: luminescent layer
9: hole-inhibiting layer 10: electron transport layer
11: an electron injection layer.

Claims (19)

1. A compound represented by the following chemical formula 1:
chemical formula 1
Figure FDA0003251826520000011
In the chemical formula 1, the first and second organic solvents,
X1to X3Each independently is CH or N, and X1To X3At least one of which is N,
Y1and Y2Each independently of the other is O or S,
Ar1are identical to each other and are substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
Ar2are identical to each other and are substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
each R is independently hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; a silyl group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60An aryloxy group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
n is an integer of 1 to 5.
2. The compound of claim 1, wherein X1To X3Are all N.
3. The compound of claim 1, wherein Y1And Y2Both O or both S.
4. The compound of claim 1, wherein Ar1Identical to each other and is phenyl substituted or unsubstituted by deuterium.
5. The compound of claim 1, wherein Ar1Are bonded to each other in adjacent, inter or paired positions.
6. The compound of claim 1, wherein Ar2Identical to each other and is phenyl substituted or unsubstituted by deuterium.
7. The compound of claim 1, wherein Ar2Are bonded to each other in adjacent, inter or paired positions.
8. The compound of claim 1, wherein Ar1And Ar2Is substituted with deuterium.
9. The compound of claim 1, wherein Ar1And Ar2Are identical to each other.
10. The compound of claim 1, wherein Ar1And Ar2Are bonded at positions symmetrical to each other.
11. The compound of claim 1, wherein R is hydrogen.
12. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the following chemical formulae 1-1 to 1-10:
chemical formula 1-1
Figure FDA0003251826520000021
Chemical formula 1-2
Figure FDA0003251826520000022
Chemical formulas 1 to 3
Figure FDA0003251826520000031
Chemical formulas 1 to 4
Figure FDA0003251826520000032
Chemical formulas 1 to 5
Figure FDA0003251826520000033
Chemical formulas 1 to 6
Figure FDA0003251826520000034
Chemical formulas 1 to 7
Figure FDA0003251826520000041
Chemical formulas 1 to 8
Figure FDA0003251826520000042
Chemical formulas 1 to 9
Figure FDA0003251826520000043
Chemical formulas 1 to 10
Figure FDA0003251826520000044
In the chemical formulas 1-1 to 1-10,
X1to X3、Y1、Y2、Ar1、Ar2R and n are as defined in claim 1.
13. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
Figure FDA0003251826520000051
Figure FDA0003251826520000061
Figure FDA0003251826520000071
Figure FDA0003251826520000081
Figure FDA0003251826520000091
Figure FDA0003251826520000101
Figure FDA0003251826520000111
14. 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 13.
15. The organic light emitting device of claim 14, wherein the organic layer is a light emitting layer.
16. The organic light emitting device according to claim 15, wherein the light emitting layer further comprises a compound represented by the following chemical formula 2:
chemical formula 2
Figure FDA0003251826520000121
In the chemical formula 2,
Ar4and Ar5Each independently is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R4and R5Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or notSubstituted C1-60An alkyl group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C2-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60(ii) a heteroaryl group, wherein,
a and b are each independently an integer of 0 to 7.
17. The organic light emitting device of claim 16, wherein Ar4And Ar5Each independently is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
18. The organic light emitting device of claim 16, wherein R4And R5Are all hydrogen.
19. The organic light emitting device according to claim 16, wherein the compound represented by chemical formula 2 is any one selected from the group consisting of:
Figure FDA0003251826520000131
Figure FDA0003251826520000141
Figure FDA0003251826520000151
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