CN107840835B - Novel heterocyclic compound and organic light-emitting element using same - Google Patents

Novel heterocyclic compound and organic light-emitting element using same Download PDF

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CN107840835B
CN107840835B CN201710623704.8A CN201710623704A CN107840835B CN 107840835 B CN107840835 B CN 107840835B CN 201710623704 A CN201710623704 A CN 201710623704A CN 107840835 B CN107840835 B CN 107840835B
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许东旭
李东勋
朴胎润
许净午
张焚在
韩美连
郑珉祐
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Abstract

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

Description

Novel heterocyclic compound and organic light-emitting element using same
Technical Field
The present invention relates to a novel heterocyclic compound and an organic light-emitting element comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed properties, and thus, a great deal of research has been conducted on the organic light emitting element.
An organic light emitting element generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. The organic material layer has a multi-layered structure composed of different materials, respectively, to improve efficiency and stability of the organic light emitting element, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting element, if a voltage is applied between two electrodes, holes are injected from an anode into an organic material layer and electrons are injected from a cathode into the organic material layer, excitons are formed when the injected holes and the electrodes meet, and light is emitted when the excitons return to the ground state again.
As for the organic materials for the organic light emitting element as described above, new materials are continuously required to be developed.
Prior art documents
Patent document 1: korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention provides a novel heterocyclic compound and an organic light-emitting device comprising the same.
Technical scheme
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure BDA0001362296420000021
In the chemical formula 1, the first and second organic solvents,
x is O or S, and X is O or S,
R1to R4At least two ofEach is the same as-L-Ar, and the remainder are hydrogen,
l is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing O, N, Si and one or more of S atoms2-60A hetero-arylene group,
ar is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing O, N, Si and one or more of S atoms2-60(ii) a heteroaryl group, wherein,
however, Ar is not pyridyl.
In addition, the present invention provides an organic light emitting element including: a first electrode; a second electrode opposite the first electrode; and one or more organic material layers between the first electrode and the second electrode, one or more of the organic material layers including the compound represented by chemical formula 1.
Effects of the invention
The compound represented by chemical formula 1 may be used as a material of an organic material layer of an organic light emitting element, and may improve efficiency, and low driving voltage and/or lifetime performance in the organic light emitting element. In particular, the compound represented by chemical formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
Drawings
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
Detailed Description
To facilitate an understanding of the invention, it is described in more detail below.
The present invention provides a compound represented by the chemical formula 1.
In the context of the present specification,
Figure BDA0001362296420000031
or
Figure BDA0001362296420000032
Meaning a bond to another substituent.
In the present specification, the term "substituted or unsubstituted" is intended to be 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 phosphino group; an alkoxy group; an aryloxy group; alkylsulfoxy (alkylthioaxy group); an arylsulfenoxy group; alkylsulfonyl (alkylsulfonylxy group); an arylsulfonyl group; silyl (silyl group); a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or one or more substituents in a heterocyclic group containing one or more of N, O and the S atom, or substituted or unsubstituted with the intent that two or more substituents in the exemplified substituents are linked. For example, the "substituent to which two or more substituents are linked" may be a biphenyl group. In other words, it is understood that the biphenyl group may be an aryl group, or may be a substituent to which two phenyl groups are attached.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but the number of carbon atoms is preferably 1 to 40. Specifically, the compound may include the following structure, but is not limited thereto.
Figure BDA0001362296420000041
In the present specification, with respect to the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkane group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound of the following structural formula may be included, but not limited thereto.
Figure BDA0001362296420000042
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may include the following structure, but is not limited thereto.
Figure BDA0001362296420000043
In the present specification, the silyl group specifically includes, but is 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, a phenylsilyl group and the like.
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, examples of the halogen group include 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 number of carbon atoms of the alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is from 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-methylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is from 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl (stilbenyl group), styryl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms is preferably 3 to 60. According to one embodiment, the number of carbon atoms of said cycloalkyl group is between 3 and 30. According to another embodiment, the number of carbon atoms of said cycloalkyl group is from 3 to 20. According to yet another embodiment, the number of carbon atoms of said cycloalkyl group is from 3 to 6. Specifically, the compound includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-methylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but the number of carbon atoms is preferably 6 to 60, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 30. According to another embodiment, the number of carbon atoms of the aryl group is from 6 to 20. The monocyclic aryl group may include phenyl, biphenyl, terphenyl, and the like, but is not limited thereto. The polycyclic aromatic groups may include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, perylene, and the like,
Figure BDA0001362296420000062
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. When the fluorenyl group is substituted, it may contain
Figure BDA0001362296420000061
And the like, but are not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are 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 aforementioned aryl example. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, alkylamino group is the same as the aforementioned examples of the alkyl group. In this specification, the foregoing description of heterocyclic groups may apply to heteroaryl groups in heteroarylamine groups. In the present specification, the alkenyl group in the aralkenyl group is the same as the aforementioned examples of the alkenyl group. In this specification, the foregoing description of aryl groups may apply to arylene groups with the exception of divalent groups. In this specification, the foregoing description of heterocyclic groups applies to heteroarylene groups with the exception of divalent groups. In the present specification, the foregoing description of aryl or cycloalkyl groups may be applied to hydrocarbon rings except those formed by bonding of non-monovalent groups and two substituents. In the present specification, the foregoing description of a heterocyclic group may be applied to a heterocyclic ring except for a monovalent group and a group formed by bonding two substituents.
Preferably, R1To R4Two in the process areThe same-L-Ar, the remainder being hydrogen. That is, the compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-6.
[ chemical formula 1-1]
Figure BDA0001362296420000071
[ chemical formulas 1-2]
Figure BDA0001362296420000081
[ chemical formulas 1-3]
Figure BDA0001362296420000082
[ chemical formulas 1 to 4]
Figure BDA0001362296420000083
[ chemical formulas 1 to 5]
Figure BDA0001362296420000084
[ chemical formulas 1 to 6]
Figure BDA0001362296420000085
Preferably, L is a single bond, or any one selected from the group,
Figure BDA0001362296420000091
more preferably, L is 1, 3-phenylene, 1, 4-phenylene, or biphenyl-4,4 '-diyl (biphenyl-4, 4' -diyl).
Preferably, Ar is any one selected from the group,
Figure BDA0001362296420000092
in the chemical formula, the compound represented by the formula,
X1、X2and X3Are each independently CH or N,
X4and X5Each independently S, O, or NH,
X6and X7Are each independently CH or N,
X8to X10At least one of which is N and the others are CH,
R1to R7Are each independently hydrogen, C6-60Aryl, or C containing one or more atoms of O, N, Si and S2-60A heteroaryl group.
In the above, when X1To X7When NH or CH, H in place of NH or CH may be bonded
Figure BDA0001362296420000101
Or by substitution of R1To R4。
Preferably, R1To R7Each independently hydrogen, phenyl, biphenyl, naphthyl, or pyridyl.
More preferably, Ar is any one selected from the group,
Figure BDA0001362296420000111
preferably, the compound represented by the chemical formula 1 is any one selected from the group consisting of,
Figure BDA0001362296420000121
Figure BDA0001362296420000131
Figure BDA0001362296420000141
Figure BDA0001362296420000151
Figure BDA0001362296420000161
Figure BDA0001362296420000171
Figure BDA0001362296420000181
Figure BDA0001362296420000191
Figure BDA0001362296420000201
Figure BDA0001362296420000211
Figure BDA0001362296420000221
Figure BDA0001362296420000231
Figure BDA0001362296420000241
Figure BDA0001362296420000251
Figure BDA0001362296420000261
Figure BDA0001362296420000271
Figure BDA0001362296420000281
Figure BDA0001362296420000291
the compound represented by the chemical formula 1 may be prepared by a preparation method as shown in the following reaction formula 1. The production method is more specifically described in the production examples described later.
[ reaction formula 1]
Figure BDA0001362296420000301
In the reaction scheme 1, the reaction is carried out,
X、R1、R2、R3、R4l and Ar are as defined above,
R′1to R'4At least two of which are 4,4,5,5-tetramethyl-1,3, 2-dioxaborolan-yl (4,4,5,5-tetramethyl-1,3, 2-dioxaborolan) and the remainder are hydrogen, X 'is halogen or R'1To R'4At least two of which are halogens and the remainder hydrogen,x' is 4,4,5,5-tetramethyl-1,3,2-dioxaborolan (4,4,5,5-tetramethyl-1,3, 2-dioxaborolan).
The reaction is preferably carried out in the presence of potassium carbonate. Furthermore, the reaction is preferably carried out under a tetrakistriphenylphosphine palladium (tetrakisphenyl-phosphinopallidium) catalyst. The reaction is preferably carried out for 1 to 10 hours, and after the reaction, washing and/or drying may be carried out as necessary.
In addition, the present invention provides an organic light emitting element comprising the compound represented by chemical formula 1. As one example, the present invention provides an organic light-emitting element comprising: a first electrode; a second electrode opposite the first electrode; and one or more organic material layers between the first electrode and the second electrode, one or more of the organic material layers including the compound represented by chemical formula 1.
The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer, but the structure of the organic light emitting element is not limited thereto, and may include fewer organic layers.
In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the chemical formula 1.
In addition, the organic material layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the organic material layer may include an electron transport layer, or an electron injection layer, which includes the compound represented by chemical formula 1.
Further, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron injection and electron transport includes the compound represented by the chemical formula 1. In particular, the compound represented by chemical formula 1 according to the present invention has excellent thermal stability, a deep HOMO level of 6.0eV or more, a high triplet Energy (ET), and hole stability. Also, when the compound represented by the chemical formula 1 is used for an organic material layer that can simultaneously perform electron injection and electron transport, an n-type dopant used in the industry may be used in combination.
In addition, the organic material layer may include a light emitting layer and an electron transport layer including the compound represented by chemical formula 1.
In addition, the organic light emitting element of the present invention may be an organic light emitting element having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate. Further, the organic light emitting device of the present invention may be an organic light emitting device having a cathode, one or more organic material layers, and an inverted structure (inverted type) in which an anode is sequentially laminated on a substrate. For example, fig. 1 and 2 show the structure of an organic light emitting device according to an embodiment of the present invention.
Fig. 1 is a schematic view of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In such a structure, the compound represented by the chemical formula 1 may be included in the light emitting layer.
Fig. 2 is a schematic view of an organic light-emitting element including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In such a structure, the compound represented by the chemical formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
The organic light emitting element of the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic material layers include the compound represented by chemical formula 1. Further, when the organic light emitting element includes a plurality of organic material layers, the organic material layers may be formed of the same or different materials.
For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (e-beam evaporation) method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a material that can serve as a cathode is deposited on the organic material layer. In addition to such a method, an organic light emitting element can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, when the organic light emitting element is manufactured, the compound represented by the chemical formula 1 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution coating method. The solution coating method refers to spin coating, dip coating, knife coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.
In addition to the method described, an organic light emitting element can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing 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 generally preferably a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or 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 are not limited thereto.
The cathode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer. The cathodeSpecific examples of the material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF/Al or LiO2A multi-layer structure material such as Al, etc., but not limited thereto.
The hole injection layer is a layer for injecting holes from an electrode, and a compound having the following ability is preferably used as a hole injection material: is capable of transporting holes, thereby having a hole injection effect at the anode and an excellent hole injection effect to the light emitting layer or the light emitting material, and preventing excitons generated in the light emitting layer from being transferred to the electron injection layer or the electron injection material, and also has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic materials, hexanitrile-hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-and polythiophene-based conductive polymers, and the like.
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 following materials are suitably used as the hole transport material: holes can be received from the anode or the hole injection layer and transferred to the light emitting layer, and have high mobility to the holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which both conjugated portions and non-conjugated portions are present.
The light-emitting material is a material that can emit light in the visible light region by receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and a material having a quantum efficiency favorable for fluorescence or phosphorescence is preferably used as the light-emitting material. Specific examples include 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a Carbazole-based compounds; dimeric styrene (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) based polymers; spiro (spiroo) compounds; polyfluorene and redFluorene, and the like, but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material contains a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene (pentacene) derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic group-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
The dopant material includes an aromatic amine derivative, a styrene amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group and contains pyrene, anthracene, having an arylamino group,
Figure BDA0001362296420000341
And a styrylamine compound is a compound in which at least one aryl vinyl group is substituted with a substituted or unsubstituted arylamine, and one or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the styrylamine compound includes, but is not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like. Preferably, as the dopant material, a compound represented by the following chemical formula 2 may be used.
[ chemical formula 2]
Figure BDA0001362296420000351
In the chemical formula 2,
R8to R15Each independently is hydrogen, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-10Cycloalkyl, substituted or unsubstituted C3-30Alkylsilyl, substitutedOr unsubstituted C8-30Arylsilyl, substituted or unsubstituted C1-20Alkoxy, substituted or unsubstituted C6-20Aralkyl, or substituted or unsubstituted C6-10An aryl group, a heteroaryl group,
Ar1to Ar4Each independently is substituted or unsubstituted C6-30Aryl group except said Ar1To Ar4At least one of which is independently C1-20Alkyl, cyano, halogen, nitro, or carbonyl substitution.
Preferably, R8To R15In R9And R13Each independently is substituted or unsubstituted C1-20Alkyl and the remainder hydrogen. More preferably, R8To R15In R9And R13Is isopropyl and the remainder is hydrogen.
Preferably, Ar1To Ar4Is a quilt C1-20Alkyl or cyano substituted phenyl. More preferably, Ar1And Ar3Is a quilt C1-20Alkyl-substituted phenyl, Ar2And Ar4Is phenyl substituted by cyano.
Representative examples of the compound represented by the chemical formula 2 are as follows:
Figure BDA0001362296420000352
the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the following materials are suitably used as the electron transport material: can receive electrons from the cathode and transfer them to the light-emitting layer, and has high mobility to electrons. Specific examples include 8-hydroxyquinoline aluminum complexes; containing Alq3A complex compound; an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. As used in the prior art, the electron transport layer may be used with any cathode material desired. In particular, examples of suitable cathode materials are conventional materials having a small work function and accompanying an aluminum or silver layer. In particular, the cathode material comprises cesium, barium, calcium, ytterbium and samarium, in each case withWith an aluminum layer or a silver layer.
The electron injection layer is a layer for injecting electrons from an electrode, and a compound having the following ability is preferably used as an electron injection material: capable of transporting electrons to have an electron injection effect from a cathode and an excellent electron injection effect to a light emitting layer or a light emitting material, and preventing excitons generated in the light emitting layer from being transferred to a hole injection layer, and also having an excellent thin film forming ability. Specifically, the electron injection material includes fluorenone (fluoroenone), anthraquinodimethane (anthraquinodimethane), diphenoquinone (diphenoquinone), thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like, but is not limited thereto.
The metal complex includes lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinoline) chloride, gallium bis (2-methyl-8-quinoline) (o-cresol), aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol), and the like, but is not limited thereto.
The organic light-emitting element of the present invention may be of a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
In addition, the compound represented by the chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.
The preparation of the compound represented by the chemical formula 1 and the organic light emitting element including the same will be described in detail in the following examples. However, the following embodiments are merely to illustrate the present invention, and the scope of the present invention is not limited to the following embodiments.
Example 1(E1)
Figure BDA0001362296420000371
After completely dissolving the compound represented by the chemical formula A (10.0g, 23.8mmol) and the compound represented by the chemical formula B (12.7g, 47.6mmol) in THF (100mL), a solution of potassium carbonate (9.9g, 71.4mmol) dissolved in 50mL of water was added. Tetratriphenylphosphine palladium (825mg, 0.71mmol) was added thereto, and the mixture was stirred under heating for 8 hours. And (3) reducing the temperature to normal temperature to finish the reaction, and filtering the potassium carbonate solution to obtain a white solid. The white solid obtained by the filtration was washed twice with THF and ethyl acetate, respectively, to prepare the compound represented by the formula E1 (13.4g, yield 89%).
MS[M+H]+＝631
Example 2(E2)
Figure BDA0001362296420000381
A compound represented by the chemical formula E2 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝783
Example 3(E3)
Figure BDA0001362296420000382
A compound represented by the chemical formula E3 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝783
Example 4(E4)
Figure BDA0001362296420000391
A compound represented by the chemical formula E4 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝721
Example 5(E5)
Figure BDA0001362296420000392
A compound represented by the chemical formula E5 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝781
Example 6(E6)
Figure BDA0001362296420000401
A compound represented by the chemical formula E6 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝799
Example 7(E7)
Figure BDA0001362296420000402
A compound represented by the chemical formula E7 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝729
Example 8(E8)
Figure BDA0001362296420000411
A compound represented by the chemical formula E8 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝783
Example 9(E9)
Figure BDA0001362296420000412
A compound represented by the chemical formula E9 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝781
Example 10(E10)
Figure BDA0001362296420000421
A compound represented by the chemical formula E10 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝539
Example 11(E11)
Figure BDA0001362296420000422
A compound represented by the chemical formula E11 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝693
Example 12(E12)
Figure BDA0001362296420000431
A compound represented by the chemical formula E12 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝693
Example 13(E13)
Figure BDA0001362296420000432
A compound represented by the chemical formula E13 was prepared by the same method as example 1, except that each starting material was the same as the reaction formula.
MS[M+H]+＝625
Experimental example 1
Will be coated with a thickness of
Figure BDA0001362296420000433
The glass substrate of the ITO (indium tin oxide) thin film of (1) was placed in distilled water in which a cleaning agent was dissolved and subjected to ultrasonic cleaning. In this case, a product of Fischer company was used as the cleaning agent, and distilled water obtained by twice filtration through a Filter (Filter) manufactured by Millipore company was used as the distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water, the mixture is ultrasonically cleaned and dried with solvents of isopropanol, acetone and methanol, and then transferred to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum deposition apparatus.
On the ITO transparent electrode thus prepared, a HI-A compound was formed to a thickness of
Figure BDA0001362296420000441
The hole injection layer of (1). On the hole injection layer, HAT compounds described below were deposited by vacuum deposition in this order
Figure BDA0001362296420000442
And the following HT-A compounds
Figure BDA0001362296420000443
A hole transport layer is formed.
Then, on the hole transport layer, the following BH compound and BD compound were vacuum-deposited at a weight ratio of 25:1 to form a film thickness of
Figure BDA0001362296420000444
The light emitting layer of (1).
On the light-emitting layer, by mixing at a ratio of 1:1Compound E1 of example 1 and the LiQ compound described below were vacuum deposited by weight ratio to form a thickness of
Figure BDA0001362296420000445
The electron injection and transport layer of (1). On the electron injection and transport layer, by sequentially depositing to a thickness of
Figure BDA0001362296420000446
With a thickness of lithium fluoride (LiF) of
Figure BDA0001362296420000447
To form the cathode.
During the process, the deposition rate of the organic material is maintained
Figure BDA0001362296420000448
To
Figure BDA0001362296420000449
Lithium fluoride deposition rate maintenance for cathodes
Figure BDA00013622964200004410
Aluminum deposition rate maintenance
Figure BDA00013622964200004411
And the vacuum degree is kept at 1X 10 during deposition-7To 5X 10-5torr, thereby an organic light emitting element was manufactured.
Figure BDA0001362296420000451
Experimental examples 2 to 13
An organic light-emitting element was manufactured by the same method as the experimental example 1, except that the compounds E2 to E13 of examples 2 to 13 were used instead of the compound E1 of example 1.
Comparative Experimental examples 1 to 12
An organic light-emitting element was produced by the same method as in mutexperimental mutexample 1, mutexcept that the following compounds ET-a to ET-L were used in place of compound E1 of mutexample 1.
Figure BDA0001362296420000461
The organic light-emitting elements manufactured in the experimental examples and comparative experimental examples were set at 10mA/cm2Was measured for the driving voltage and the luminous efficiency at a current density of 20mA/cm2The time (T90) to reach 90% with respect to the initial brightness was measured at the current density of (c), and the results are shown in tables 1 and 2 below.
[ TABLE 1]
Figure BDA0001362296420000462
Figure BDA0001362296420000471
[ TABLE 2]
Figure BDA0001362296420000472
From the above table 1, it can be confirmed that the compound represented by chemical formula 1 of the present invention can be used for an organic material layer capable of simultaneously performing electron injection and electron transport of an organic light emitting element.
In addition, as can be seen from the comparison between the experimental examples of table 1 above and the comparative experimental examples 1,2, 3, and 6 of table 2 above, the compound of formula 1 according to the present invention in which dibenzofuran or dibenzothiophene is substituted with the same two substituents is significantly superior in terms of driving voltage, efficiency, and lifetime of the organic light emitting element, as compared with the compound substituted with different substituents.
In addition, comparing the experimental examples of table 1 above and the comparative experimental example 5 of table 2 above, it was confirmed that the performance of the organic light emitting element was improved as compared with the case of having a substituent such as pyridine which is poor in electron transport ability.
In addition, as can be seen from the comparison between the experimental examples of table 1 above and the comparative experimental examples 4 and 7 to 12 of table 2 above, the organic light emitting device of formula 1 according to the present invention has significantly superior driving voltage, efficiency, and lifetime compared to the compound in which the same substituent is substituted on one side of the phenyl group in the dibenzofuran and dibenzothiophene skeleton, as compared to the compound in which the same substituent is substituted on a different phenyl group.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light-emitting layer 8: electron transport layer

Claims (9)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure FDA0002788943700000011
In the chemical formula 1, the first and second organic solvents,
x is O or S, and X is O or S,
R1to R4At least two of which are the same as-L-Ar, the remainder being hydrogen,
l is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing O, N, Si and one or more of S atoms2-60A hetero-arylene group,
ar is any one selected from the group consisting of:
Figure FDA0002788943700000012
in the chemical formula, the compound represented by the formula,
X1、X2and X3Are each independently CH or N,
X4and X5Are respectively and independently S,O, or NH, in the presence of oxygen,
X6and X7Are each independently CH or N,
X8to X10At least one of which is N and the remainder are CH, and
R1to R7Each independently is hydrogen, C6-60Aryl, or C containing one or more atoms of O, N, Si and S2-60(ii) a heteroaryl group, wherein,
however, Ar is not pyridyl.
2. The compound of claim 1, wherein,
R1to R4Two of them are the same-L-Ar, and the remainder are hydrogen.
3. The compound of claim 1, wherein,
l is a single bond, or any one selected from the group,
Figure FDA0002788943700000021
4. the compound of claim 1, wherein,
l is 1, 3-phenylene, 1, 4-phenylene, or biphenyl-4, 4' -diyl.
5. The compound of claim 1, wherein,
ar is any one selected from the group consisting of,
Figure FDA0002788943700000031
6. the compound of claim 1, wherein,
the compound represented by the chemical formula 1 is any one selected from the group consisting of,
Figure FDA0002788943700000041
Figure FDA0002788943700000051
Figure FDA0002788943700000061
Figure FDA0002788943700000071
Figure FDA0002788943700000081
Figure FDA0002788943700000091
Figure FDA0002788943700000101
Figure FDA0002788943700000111
Figure FDA0002788943700000121
Figure FDA0002788943700000131
Figure FDA0002788943700000141
Figure FDA0002788943700000151
Figure FDA0002788943700000161
Figure FDA0002788943700000171
Figure FDA0002788943700000181
Figure FDA0002788943700000191
7. an organic light-emitting element comprising: a first electrode; a second electrode opposite the first electrode; and one or more layers of organic material between the first electrode and the second electrode, one or more of the layers of organic material comprising a compound of any one of claims 1 to 6.
8. The organic light-emitting element according to claim 7,
the organic material layer containing the compound is an electron injection layer; an electron transport layer; or a layer that performs both electron injection and electron transport.
9. The organic light-emitting element according to claim 7,
the organic light emitting element includes a light emitting layer including a compound represented by the following chemical formula 2 as a dopant,
[ chemical formula 2]
Figure FDA0002788943700000201
In the chemical formula 2,
R8to R15Each independently is hydrogen, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-10Cycloalkyl, substituted or unsubstituted C3-30Alkylsilyl, substituted or unsubstituted C8-30Arylsilyl, substituted or unsubstituted C1-20Alkoxy, substituted or unsubstituted C6-20Aralkyl, or substituted or unsubstituted C6-10An aryl group, a heteroaryl group,
Ar1to Ar4Each independently is substituted or unsubstituted C6-30Aryl group except said Ar1To Ar4At least one of which is independently C1-20Alkyl, cyano, halogen, nitro, or carbonyl substitution.
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