CN109803966B - Novel amine-based compound and organic light emitting device using the same - Google Patents

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

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CN109803966B
CN109803966B CN201780060444.6A CN201780060444A CN109803966B CN 109803966 B CN109803966 B CN 109803966B CN 201780060444 A CN201780060444 A CN 201780060444A CN 109803966 B CN109803966 B CN 109803966B
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CN109803966A (en
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车龙范
全相映
赵然缟
金渊焕
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Abstract

The present invention relates to a novel amine-based compound represented by chemical formula 1 and an organic light emitting device including the same. The compound provides improved efficiency, low driving voltage, and improved lifetime characteristics of an organic light emitting device. [ chemical formula 1]
Figure DDA0002011163330000011

Description

Novel amine-based compound and organic light emitting device using the same
Technical Field
The present application claims priority and benefit from korean patent application No. 10-2017-0012952, filed on 26.1.2017 and korean patent application No. 10-2017-0149677, filed on 10.11.2017, the disclosures of which are incorporated herein by reference in their entireties.
The present invention relates to a novel amine-based compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon is a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon has characteristics such as a wide viewing angle, a fast response time, and excellent contrast, brightness, driving voltage, and response speed, and thus many studies have been made.
An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer generally has a multi-layer structure including different materials to improve efficiency and stability of the organic light emitting device, and for example, the organic material layer may be formed of 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 the organic light emitting device, 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, and when the injected holes and electrons meet, excitons are formed and light is emitted when the excitons fall to a ground state.
There is a continuing need to develop new materials for the organic materials used in the above-described organic light emitting devices.
[ Prior art documents ]
[ patent literature ] A
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to a novel amine-based compound and an organic light emitting device including the same.
Technical scheme
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure GDA0003425928980000021
Wherein, in chemical formula 1,
x is O or S, and X is O or S,
a and B are each independently hydrogen; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
at least one of a and B is not hydrogen,
l is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from O, N, Si and S2-60A heteroarylene group, a heteroaryl group,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 to 3 heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
R1is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60An 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 one or more heteroatoms selected from N, O and S2-60A heterocyclic group; and
a1 is an integer from 0 to 4.
The present invention also provides an organic light emitting device including a first electrode; a second electrode disposed to face the first electrode; and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by chemical formula 1.
Advantageous effects
The compound represented by chemical formula 1 as described above may be used as a material of an organic material layer of a light emitting device, and when applied to an organic light emitting device, can improve efficiency, low driving voltage, and/or improve lifetime characteristics.
Drawings
Fig. 1 shows an example of an organic light emitting device comprising 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 device 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
Hereinafter, the present invention will be described in more detail to help understanding the present invention.
In this specification, the symbols
Figure GDA0003425928980000031
Means a bond to another substituent, and a single bond means that there is no separate atom present at the moiety represented by L.
As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: 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; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; 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 a heterocyclic group containing at least one of N, O and S atoms, or a substituent unsubstituted or linked by two or more of the exemplified substituents. For example, "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a compound having the following structure, but is not limited thereto.
Figure GDA0003425928980000041
In the present specification, the ester group may have a structure in which 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 ester group may be a compound having the following structure, but is not limited thereto.
Figure GDA0003425928980000042
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 imide group may be a compound having the following structure, but is not limited thereto.
Figure GDA0003425928980000043
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 and iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof 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 yet another embodiment, the alkyl group has 1 to 6 carbon atoms. 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-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, 1-ethyl-butyl, pentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3, 2-dimethylbutyl, heptyl, 1-methylhexyl, cyclohexyl, octyl, 1-methyl-pentyl, 2-pentyl, and the like, 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 thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof 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, 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 thereof is preferably 3 to 60. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include 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, but are not limited thereto.
In the present specification, the aryl group is not particularly limited, but preferably has 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. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Examples of polycyclic aromatic groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, perylene,
Figure GDA0003425928980000052
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present specification, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro ring structure. In the case of substituted fluorenyl radicals, may form
Figure GDA0003425928980000061
And the like. However, the structure is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure GDA0003425928980000062
Azolyl group,
Figure GDA0003425928980000063
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl, and benzoxazolyl
Figure GDA0003425928980000064
Azolyl, benzimidazolyl, benzothiazolyl,Benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Figure GDA0003425928980000065
Azolyl group,
Figure GDA0003425928980000066
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group of the aralkyl group, aralkenyl group, alkylaryl group and arylamine group is the same as the example of the aforementioned 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 example of the aforementioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group may be the same as that described for the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the aforementioned alkenyl group. In the present specification, the foregoing description of aryl groups may be applied, except that arylene groups are divalent groups. In this specification, the foregoing description of heterocyclic groups may be applied, except that heteroarylene is a divalent group. In the present specification, the foregoing description of aryl or cycloalkyl groups may be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present specification, the foregoing description of the heterocyclic group may be applied except that the heterocyclic group is not a monovalent group but is formed by combining two substituents.
Meanwhile, the present invention provides a compound represented by chemical formula 1.
In chemical formula 1, a and B may each independently be hydrogen or selected from any one of the following. That is, in chemical formula 1, one of a and B is hydrogen and the other is selected from the following, or both a and B may be selected from the following:
Figure GDA0003425928980000071
wherein, the first and the second end of the pipe are connected with each other,
Y1is O, S or CZ4Z5，
Z1To Z5Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; c1-20An alkyl group; c1-20A haloalkyl group; c6-20An aryl group; or C containing one or more heteroatoms of O or S2-20Heteroaryl, and
n1 to n3 are each independently an integer of 0 to 3.
For example, a and B are each independently hydrogen or selected from any one of the following:
Figure GDA0003425928980000081
specifically, in chemical formula 1, in the case of an organic light emitting device manufactured using a compound in which both a and B are hydrogen as an electron blocking layer or a hole transporting layer, there are limitations that the efficiency is reduced by 10% or more and the lifetime is reduced by 30% or more. Therefore, in chemical formula 1, when a and B each independently satisfy hydrogen or are selected from any one of the foregoing, the efficiency of the device may be improved and, at the same time, the stability may be greatly improved.
Further, L is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted spiro-fluorenylene group.
For example, L may be a single bond or selected from any of the following:
Figure GDA0003425928980000082
specifically, for example, L may be a single bond or any one selected from the group consisting of:
Figure GDA0003425928980000091
when L has a long chain as described below, since the distance between the core and the arylamine group in chemical formula 1 becomes too far, the characteristics of the organic light emitting device may be greatly deteriorated:
Figure GDA0003425928980000092
further, Ar1And Ar2Each independently may be substituted or unsubstituted C6-20An aryl group; or C which is substituted or unsubstituted and contains 1 to 3 heteroatoms of O or S2-20A heteroaryl group.
For example, Ar1And Ar2May each independently be any one selected from:
Figure GDA0003425928980000093
wherein the content of the first and second substances,
Y2is O, S or CZ14Z15，
Z11To Z15Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; a silyl group; c1-20An alkyl group; c1-20A haloalkyl group; c6-20An aryl group; or C containing one or more heteroatoms of O or S2-20Heteroaryl with the proviso that Z14And Z15May be linked to each other to form a monocyclic ring or a polycyclic ring, and
m1 to m3 are each independently an integer of 0 to 3.
Here, Z11To Z13Each independently hydrogen, deuterium, halogen, cyano, trimethylsilyl, methyl, tert-butyl, phenyl, naphthyl, triphenylene, dibenzofuranyl or dibenzothiophenyl,
Z14And Z15Each independently a methyl group, or rings linked to each other to form a monocyclic ring or a polycyclic ring, and
m1 to m3 are each independently 0 or 1.
Specifically, for example, Ar1And Ar2May each independently be any one selected from:
Figure GDA0003425928980000101
Figure GDA0003425928980000111
Figure GDA0003425928980000121
Figure GDA0003425928980000131
furthermore, R1Can be hydrogen, deuterium, halogen, cyano, nitro, C1-20Alkyl or C6-20And (4) an aryl group.
For example, R1May be hydrogen, deuterium, halogen, cyano, nitro, methyl or phenyl, and a1 may be 0 or 1.
Herein, a1 represents R1And when a1 is 2 or more, two or more of R1 may be the same as or different from each other. The description of n1 to n3 and m1 to m3 can be understood with reference to the description of a1 and the structure of chemical formula 1.
Meanwhile, the compound may be represented by the following chemical formula 1A or 1B:
[ chemical formula 1A ]
Figure GDA0003425928980000141
[ chemical formula 1B ]
Figure GDA0003425928980000142
Wherein, in chemical formulas 1A and 1B,
X、A、B、L、Ar1and Ar2The same as defined in chemical formula 1 above.
For example, the compound may be any one selected from the group consisting of:
Figure GDA0003425928980000151
Figure GDA0003425928980000161
Figure GDA0003425928980000171
Figure GDA0003425928980000181
Figure GDA0003425928980000191
Figure GDA0003425928980000201
Figure GDA0003425928980000211
Figure GDA0003425928980000221
Figure GDA0003425928980000231
Figure GDA0003425928980000241
Figure GDA0003425928980000251
Figure GDA0003425928980000261
Figure GDA0003425928980000271
Figure GDA0003425928980000281
Figure GDA0003425928980000291
Figure GDA0003425928980000301
Figure GDA0003425928980000311
Figure GDA0003425928980000321
Figure GDA0003425928980000331
Figure GDA0003425928980000341
Figure GDA0003425928980000351
Figure GDA0003425928980000361
the compound represented by chemical formula 1 has a structure in which a or B and an arylamine substituent are connected to a specific position of a dibenzofuran/dibenzothiophene core, and thus, an organic light emitting device using the same may have high efficiency, low driving voltage, high luminance, and a long lifetime.
Meanwhile, the compound represented by chemical formula 1A may be prepared, for example, by the preparation method shown in the following reaction scheme 1, and the compound represented by chemical formula 1B may be prepared, for example, by the preparation method shown in the following reaction scheme 2.
[ reaction scheme 1]
Figure GDA0003425928980000371
[ reaction scheme 2]
Figure GDA0003425928980000381
In reaction schemes 1 and 2, X, A, B, L, Ar1And Ar2The same as defined in chemical formula 1 above.
The compound represented by chemical formula 1 may be prepared by appropriately replacing starting materials according to the structure of the compound to be prepared with reference to reaction schemes 1 and 2.
Meanwhile, the present invention provides an organic light emitting device comprising the compound represented by chemical formula 1. In one example, the present invention provides an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by chemical formula 1.
The organic material layer may include a hole injection layer, a hole transport layer, or a layer that performs both hole injection and hole transport.
In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer may include the compound represented by chemical formula 1.
In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer that performs both electron transport and electron injection.
In addition to the organic material layer, the organic light emitting device may further include an Electron Blocking Layer (EBL) disposed between the hole transport layer and the light emitting layer and/or a Hole Blocking Layer (HBL) disposed between the light emitting layer and the electron transport layer. The electron blocking layer and the hole blocking layer may be organic layers adjacent to the light emitting layer, respectively.
In this case, the compound represented by chemical formula 1 may be included in the hole transport layer and/or the electron blocking layer.
The organic material layer of the organic light emitting device according to the present invention may have a single layer structure, or alternatively, may have a multi-layer structure in which at least two organic material layers are stacked. For example, the organic light emitting device of the present invention may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as organic material layers. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic material layers may be included.
The organic material layer of the organic light emitting device according to the present invention may have a single layer structure, or alternatively, may have a multi-layer structure in which at least two organic material layers are stacked. For example, the organic light emitting device of the present invention may further include a hole injection layer and a hole transport layer disposed between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer disposed between the light emitting layer and the second electrode, in addition to the light emitting layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a greater number of organic material layers may be included.
In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is shown in fig. 1 and 2.
Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in the light emitting layer.
Fig. 2 shows an example of an organic light emitting device 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 chemical formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by the following process: an anode is formed by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, 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 be used as a cathode is deposited on the organic material layer. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, the compound represented by chemical formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (international publication WO 2003/012890). However, the manufacturing method is not limited thereto.
For 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.
As the anode material, in general, a material having a large work function is preferably used 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, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO Al or SNO2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.
As the cathode material, in general, it is preferable to use a material having a small work function so that electrons can be easily injected into the organic material 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, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al; and the like, but are not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: it has an ability to transport holes and thus has an effect of injecting holes in the anode, and has an excellent hole injection effect on the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the electron injecting layer or the electron injecting material, and 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 metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, polythiophene-based conductive polymer, and the like, but are not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large mobility to holes, which can receive holes from the anode or the hole injection layer and transport the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion coexist, and the like, but are not limited thereto.
The light emitting material is a material capable of emitting light in a visible light region by combining holes and electrons respectively transported from a hole transport layer and an electron transport layer and having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzene
Figure GDA0003425928980000411
Oxazole, benzothiazole-based and benzimidazole-based compounds; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; a polyfluorene; rubrene; and the like, but are not limited thereto.
The light emitting layer may comprise a host material and a dopant material as described above. The host material may further include a fused aromatic ring derivative, a heterocyclic ring-containing compound, and the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specific examples of the aromatic amine derivative include substituted or unsubstituted fused aromatic ring derivatives having an arylamino group, and examples thereof include pyrene, anthracene, having an arylamino group,
Figure GDA0003425928980000412
And diindenopyrene, and the like. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one 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 are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrriamine, styryltretramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.
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 electron transport material is a material that can well receive electrons from the cathode and transport the electrons to the light emitting layer, and a material having a large mobility to electrons is suitable. Specific examples thereof include 8-hydroxyquinoline Al complexes; comprising Alq 3The complex of (1); an organic radical compound; a hydroxyflavone-metal complex; and the like, but are not limited thereto. The electron transport layer may be used with a predetermined desired cathode material as used according to the prior art. Examples of suitable cathode materials are, in particular, general materials having a low work function and are followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, and in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and such a compound is preferable: it is provided withAn ability to transport electrons, an effect to inject electrons from a cathode, and an excellent electron injection effect to a light emitting layer or a light emitting material, prevent excitons generated in the light emitting layer from moving to a hole injection layer, and have an excellent thin film forming ability. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,
Figure GDA0003425928980000421
Azole,
Figure GDA0003425928980000422
Oxadiazoles, triazoles, imidazoles, perylene tetracarboxylic acids, fluorenylidene methanes, anthrones, and the like, and derivatives thereof; a metal complex compound; a nitrogen-containing 5-membered ring derivative; and the like, but are not limited thereto.
Examples of the metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolino) (o-cresol), aluminum bis (2-methyl-8-quinolino) (1-naphthol), gallium bis (2-methyl-8-quinolino) (2-naphthol), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a front side light emitting type, a rear side light emitting type, or a double side light emitting type, depending on the material used.
In addition, the compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The preparation of the compound represented by chemical formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only, and the scope of the present invention is not limited thereto.
Preparation example A: preparation of intermediate compound A
Figure GDA0003425928980000423
Preparation example B: preparation of intermediate compound B
Figure GDA0003425928980000431
Preparation example C: preparation of intermediate compound C
Figure GDA0003425928980000432
Preparation example D: preparation of intermediate compound D
Figure GDA0003425928980000433
Preparation example E: preparation of intermediate compound E
Figure GDA0003425928980000441
Preparation example F: preparation of intermediate compound F
Figure GDA0003425928980000442
Preparation example G: preparation of intermediate compound G
Figure GDA0003425928980000451
Preparation example H: preparation of intermediate compound H
Figure GDA0003425928980000452
Preparation example I: preparation of intermediate compound I
Figure GDA0003425928980000453
Preparation example J: preparation of intermediate Compound J
Figure GDA0003425928980000461
Preparation example K: preparation of intermediate compound K
Figure GDA0003425928980000462
Preparation example L: preparation of intermediate Compound L
Figure GDA0003425928980000463
Preparation example M: preparation of intermediate compound M
Figure GDA0003425928980000471
Preparation example 1: preparation of Compound 1
[ Compound 1]
Figure GDA0003425928980000472
Compound A (7.56g, 31.11mmol) and bis ([1, 1' -biphenyl ] -4-yl) amine (10.99g, 34.22mmol) were completely dissolved in 220ml xylene in a 500ml round bottom flask under nitrogen atmosphere, cesium carbonate (12.13g, 37.33mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.08g, 0.16mmol) were added thereto, and the mixture was heated and stirred for 3 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 180ml of ethyl acetate to prepare compound 1(12.46g, yield: 71%).
MS[M+H]+＝564
Preparation example 2: preparation of Compound 2
[ Compound 2]
Figure GDA0003425928980000473
Compound A (8.22g, 33.83mmol) and N- ([1, 1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (13.43g, 37.21mmol) were completely dissolved in 250ml of xylene in a 500ml round-bottom flask under nitrogen atmosphere, to which was added cesium carbonate (13.19g, 40.59mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.17mmol), and the mixture was heated and stirred for 2 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 130ml of ethyl acetate to prepare Compound 2(10.45g, yield: 51%).
MS[M+H]+＝604
Preparation example 3: preparation of Compound 3
[ Compound 3]
Figure GDA0003425928980000481
Compound A (6.73g, 27.70mmol) and N- (4- (dibenzo [ b, d ] furan-4-yl) phenyl) -9, 9-dimethyl-9H-fluoren-2-amine (13.74g, 30.47mmol) were completely dissolved in 300ml of xylene in a 500ml round-bottomed flask under nitrogen atmosphere, to which was added cesium carbonate (10.80g, 33.23mmol) and bis (tri-tert-butylphosphino) palladium (0) (0.07g, 0.14mmol), and the mixture was heated and stirred for 6 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 260ml of tetrahydrofuran to prepare compound 3(13.29g, yield: 69%).
MS[M+H]+＝694
Preparation example 4: preparation of Compound 4
[ Compound 4]
Figure GDA0003425928980000491
Compound B (4.96g, 15.55mmol) and bis ([1, 1' -biphenyl ] -4-yl) amine (5.49g, 17.10mmol) were completely dissolved in 260ml xylene in a 500ml round bottom flask under nitrogen atmosphere. To this was added cesium carbonate (6.06g, 18.66mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.04g, 0.08mmol), and the mixture was heated and stirred for 6 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate to prepare compound 4(7.19g, yield: 67%).
MS[M+H]+＝640
Preparation example 5: preparation of Compound 5
[ Compound 5]
Figure GDA0003425928980000492
Compound B (4.96g, 15.55mmol) and N-phenyl- [1, 1': 4', 1 "-terphenyl ] -4-amine (5.49g, 17.10mmol) was completely dissolved in 260ml of xylene in a 500ml round bottom flask, cesium carbonate (6.06g, 18.66mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.04g, 0.08mmol) were added thereto, and then the mixture was heated and stirred for 5 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 250ml of ethyl acetate to prepare compound 5(6.08g, yield: 56%).
MS[M+H]+＝640
Preparation example 6: preparation of Compound 6
[ Compound 6]
Figure GDA0003425928980000501
Compound C (5.13g, 17.51mmol) and bis ([1, 1' -biphenyl ] -4-yl) amine (6.18g, 19.26mmol) were completely dissolved in 190ml of xylene in a 500ml round bottom flask under nitrogen atmosphere, to which was added cesium carbonate (6.83g, 21.01mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.04g, 0.09mmol), and the mixture was heated and stirred for 4 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 250ml of ethyl acetate to prepare Compound 6(7.82g, yield: 73%).
MS[M+H]+＝614
Preparation example 7: preparation of Compound 7
[ Compound 7]
Figure GDA0003425928980000502
Compound C (4.29g, 14.64mmol) and N- ([1, 1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (5.81g, 16.11mmol) were completely dissolved in 280ml of xylene in a 500ml round bottom flask under nitrogen atmosphere, to which was added cesium carbonate (5.71g, 17.57mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.04g, 0.07mmol), and the mixture was heated and stirred for 3 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 130ml of ethyl acetate to prepare compound 7(5.17g, yield: 58%).
MS[M+H]+＝604
Preparation example 8: preparation of Compound 8
[ Compound 8]
Figure GDA0003425928980000511
Compound D (7.38g, 15.19mmol) and phenylboronic acid (2.13g, 17.46mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (120ml) and tetrakis- (triphenylphosphine) palladium (0.62g, 0.58mmol), and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to prepare compound 8(6.27g, yield: 73%).
MS[M+H]+＝564
Preparation example 9: preparation of Compound 9
[ Compound 9]
Figure GDA0003425928980000512
Compound D (7.38g, 15.19mmol) and naphthalen-2-ylboronic acid (2.13g, 17.46mmol) were completely dissolved in 280ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (140ml) and tetrakis- (triphenylphosphine) palladium (0.61g, 0.57mmol), and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to prepare compound 9(7.01g, yield: 75%).
MS[M+H]+＝614
Preparation example 10: preparation of Compound 10
[ Compound 10]
Figure GDA0003425928980000521
Compound E (7.38g, 15.19mmol) and phenylboronic acid (2.13g, 17.46mol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (120ml) and tetrakis- (triphenylphosphine) palladium (0.49g, 0.46mmol), and the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 240ml of ethyl acetate to prepare compound 10(8.26g, yield: 79%).
MS[M+H]+＝604
Preparation example 11: preparation of Compound 11
[ Compound 11]
Figure GDA0003425928980000522
Compound F (7.77g, 13.49mmol) and phenylboronic acid (1.89g, 15.51mol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under a nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (100ml) and tetrakis- (triphenylphosphine) palladium (0.47g, 0.40mmol), and the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 260ml of ethyl acetate to prepare compound 11(8.26g, yield: 79%).
MS[M+H]+＝654
Preparation example 12: preparation of Compound 12
[ Compound 12]
Figure GDA0003425928980000531
Compound G (6.64G, 11.22mmol) and (9, 9-dimethyl-9H-fluoren-2-yl) boronic acid (3.07G, 12.90mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under a nitrogen atmosphere, 2M aqueous potassium carbonate (120ml) and tetrakis- (triphenylphosphine) palladium (0.39G, 0.34mmol) were added thereto, and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310ml of ethyl acetate to prepare compound 12(8.26g, yield: 79%).
MS[M+H]+＝786
Preparation example 13: preparation of Compound 13
[ Compound 13]
Figure GDA0003425928980000532
Compound H (5.39g, 20.81mmol) and N- ([1, 1 '-biphenyl ] -4-yl) - [1, 1': 4', 1 "-terphenyl ] -4-amine (9.17g, 23.10mmol) was completely dissolved in 250ml of xylene in a 500ml round bottom flask, cesium carbonate (8.66g, 27.05mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.11g, 0.21mmol) were added thereto, and then the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 250ml of tetrahydrofuran to prepare compound 13(11.67g, yield: 70%).
MS[M+H]+＝656
Preparation example 14: preparation of Compound 14
[ Compound 14]
Figure GDA0003425928980000541
Compound I (7.16g, 20.81mmol) and N-phenyl- [1, 1' -biphenyl ] -4-amine (5.81g, 23.72mmol) were completely dissolved in 300ml xylene in a 500ml round bottom flask under nitrogen atmosphere, to which was added cesium carbonate (8.89g, 27.79mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.11g, 0.21mmol), and the mixture was heated and stirred for 3 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 200ml of tetrahydrofuran to prepare compound 14(8.88g, yield: 72%).
MS[M+H]+＝580
Preparation example 15: preparation of Compound 15
[ Compound 15]
Figure GDA0003425928980000542
Compound I (4.28g, 13.85mmol) and N- ([1, 1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (5.55g, 15.37mmol) were completely dissolved in 280ml of xylene in a 500ml round-bottom flask under nitrogen atmosphere, to which was added cesium carbonate (5.76g, 18.01mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.07g, 0.14mmol), and the mixture was heated and stirred for 4 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 220ml of tetrahydrofuran to prepare compound 15(4.39g, yield: 46%).
MS[M+H]+＝696
Preparation example 16: preparation of Compound 16
[ Compound 16]
Figure GDA0003425928980000551
Compound K (9.68g, 19.28mmol) and phenylboronic acid (2.61g, 21.40mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (120ml) and tetrakis- (triphenylphosphine) palladium (0.67g, 0.58mmol), and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the aqueous layer was removed and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220ml of ethyl acetate to prepare compound 16(6.09g, yield: 54%).
MS[M+H]+＝580
Preparation example 17: preparation of Compound 17
[ Compound 17]
Figure GDA0003425928980000552
Compound A (5.32g) and (4- (bis ([1, 1' -biphenyl ] -4-yl) amino) phenyl) boronic acid (10.72g, 24.30mmol) were completely dissolved in 240ml tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (120ml) and tetrakis- (triphenylphosphine) palladium (0.76g, 0.66mmol), and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to prepare compound 17(7.12g, yield: 51%).
MS[M+H]+＝640
Preparation example 18: preparation of Compound 18
[ Compound 18]
Figure GDA0003425928980000561
Compound A (6.67g, 27.45mmol) and (4- ([1, 1' -biphenyl ] -4-yl (9, 9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid (10.72g, 24.30mol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round-bottomed flask under a nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (120ml) and tetrakis- (triphenylphosphine) palladium (0.76g, 0.66mmol), and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the aqueous layer was removed and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to prepare compound 18(7.12g, yield: 51%).
MS[M+H]+＝680
Preparation example 19: preparation of Compound 19
[ Compound 19]
Figure GDA0003425928980000571
Compound C (7.75g, 27.45mmol) and (4- ([1, 1' -biphenyl ] -4-yl (9, 9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid (13.41g, 30.42mol) were completely dissolved in 280ml of tetrahydrofuran in a 500ml round-bottomed flask under a nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (140ml) and tetrakis- (triphenylphosphine) palladium (0.92g, 0.79mmol), and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to prepare compound 19(15.26g, yield: 84%).
MS[M+H]+＝690
Preparation example 20: preparation of Compound 20
[ Compound 20]
Figure GDA0003425928980000572
Compound L (5.47g, 17.15mmol) and bis ([1, 1' -biphenyl ] -4-yl) amine (6.33g, 19.72mmol) were completely dissolved in 180ml of xylene in a 500ml round bottom flask under nitrogen atmosphere, to which was added cesium carbonate (8.38g, 25.72mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.17mmol), and the mixture was heated and stirred for 6 hours. After the temperature was reduced to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 250ml of ethyl acetate to prepare compound 20(6.77g, yield: 62%).
MS[M+H]+＝640
Preparation example 21: preparation of Compound 21
[ Compound 21]
Figure GDA0003425928980000581
Compound M (7.54g, 22.51mmol) and N- ([1, 1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (9.34g, 25.88mmol) were completely dissolved in 220ml xylene in a 500ml round bottom flask under nitrogen atmosphere, to which was added cesium carbonate (11.00g, 33.76mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.12g, 0.23mmol), and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature, the reaction mixture was filtered to remove the base. Then, xylene was concentrated under reduced pressure and recrystallized from 180ml of ethyl acetate to prepare compound 21(10.07g, yield: 64%).
MS[M+H]+＝696
Examples 1 to 1
Is coated thereon with a thickness of
Figure GDA0003425928980000582
The ITO (indium tin oxide) as a glass substrate of the thin film was put in distilled water in which a detergent was dissolved, and ultrasonic washing was performed. In this case, a product made of Fischer co is used as a cleaning agent, and utilization is usedDistilled water was filtered twice by a filter manufactured by Millipore co. After washing the ITO for 30 minutes, ultrasonic washing was performed twice using distilled water for 10 minutes each time. After the completion of the washing with distilled water, ultrasonic washing was performed using solvents of isopropyl alcohol, acetone and methanol, and then it was dried and transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum depositor.
On the ITO transparent electrode thus prepared, to
Figure GDA0003425928980000583
Is thermally vacuum deposited to form a hole injection layer of hexanitrile Hexaazatriphenylene (HAT) of the following formula.
[HAT]
Figure GDA0003425928980000591
The following compound HT1 as a hole transporting material was vacuum deposited on the hole injection layer
Figure GDA0003425928980000592
To form a hole transport layer.
[HT1]
Figure GDA0003425928980000593
Then, the compound 1 prepared in preparation example 1 was vacuum-deposited on the hole transport layer to a film thickness of
Figure GDA0003425928980000594
To form an electron blocking layer.
Next, the following BH and BD were vacuum deposited on the electron blocking layer at a weight ratio of 25:1 to a film thickness of
Figure GDA0003425928980000595
To form a light emitting layer.
[BH]
Figure GDA0003425928980000596
[BD]
Figure GDA0003425928980000601
[ET]
Figure GDA0003425928980000602
[LiQ]
Figure GDA0003425928980000603
Vacuum-depositing the above compound ET and the above compound LiQ (lithium quinolinate) on the light-emitting layer at a weight ratio of 1:1 to form a layer having a thickness of
Figure GDA0003425928980000604
The electron transport layer of (1). Sequentially depositing on the electron transport layer to a thickness of
Figure GDA0003425928980000605
With a thickness of lithium fluoride (LiF) of
Figure GDA0003425928980000606
To form an electron injection layer and a cathode.
In the above process, the deposition rate of the organic material is maintained at
Figure GDA0003425928980000607
To
Figure GDA0003425928980000608
Maintaining the deposition rate of lithium fluoride at the cathode
Figure GDA0003425928980000609
Maintaining the deposition rate of aluminum at
Figure GDA00034259289800006010
Figure GDA00034259289800006011
And the degree of vacuum during deposition was maintained at 2X 10-7Hold in the palm to 5 x 10-6And thus an organic light emitting device was manufactured.
Examples 1-2 to examples 1-15
Organic light-emitting devices of examples 1-2 to 1-15 were respectively manufactured in the same manner as in example 1-1, except that compound 1 was changed to those shown in table 1 below when the electron blocking layer was formed.
Comparative example 1-1
An organic light-emitting device was fabricated in the same manner as in example 1-1, except that EB-1 shown below was used instead of compound 1 in forming the electron blocking layer.
[EB-1]
Figure GDA0003425928980000611
Comparative examples 1 to 2
An organic light-emitting device was fabricated in the same manner as in example 1-1, except that EB-2 shown below was used in place of compound 1 in forming the electron blocking layer.
[EB-2]
Figure GDA0003425928980000612
Comparative examples 1 to 3
An organic light-emitting device was fabricated in the same manner as in example 1-1, except that EB-3 shown below was used in place of compound 1 in forming the electron blocking layer.
[EB-3]
Figure GDA0003425928980000621
Comparative examples 1 to 4
An organic light-emitting device was fabricated in the same manner as in example 1-1, except that EB-4 shown below was used instead of compound 1 in forming the electron blocking layer.
[EB-4]
Figure GDA0003425928980000622
Experimental example 1
Voltage, efficiency, luminance, color coordinates, and lifetime were measured by applying current to the organic light emitting devices manufactured in examples 1-1 to 1-15 and comparative examples 1-1 to 1-4, and the results are shown in table 1 below. T95 means the time it takes for the luminance to decrease to 95% of the initial luminance (650 nits).
[ Table 1]
Figure GDA0003425928980000631
Figure GDA0003425928980000641
Figure GDA0003425928980000651
As shown in table 1, it was confirmed that the organic light emitting device manufactured by using the compound according to the present invention as an electron blocking layer exhibited superior performance in terms of driving voltage, current efficiency, lifespan, and stability, as compared to the organic light emitting device of the comparative example.
Specifically, in the case of an organic light-emitting device manufactured by using the compound of comparative examples 1-1 to 1-3, which has the same structure as the core of the present invention but has no substituent in the 1 st and 3 rd directions, as an electron blocking layer, it resulted in a 10% or more reduction in efficiency and a 30% or more reduction in lifetime, as compared to examples.
On the other hand, the compounds of comparative examples 1 to 4 showed the results that: the distance between the core and the arylamine group is too far, and thus the characteristics of the organic light emitting device are greatly deteriorated.
Thus, it was determined that in the case of the compounds of the examples of the present invention, the efficiency of the device increased while the stability increased significantly.
Example 2-1
Is coated thereon with a thickness of
Figure GDA0003425928980000652
The ITO (indium tin oxide) as a glass substrate of the thin film was put in distilled water in which a detergent was dissolved, and ultrasonic washing was performed. In this case, a product manufactured by Fischer co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed twice using distilled water for 10 minutes each time. After the completion of the washing with distilled water, ultrasonic washing was performed using solvents of isopropyl alcohol, acetone and methanol, and then it was dried and transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum depositor.
On the ITO transparent electrode thus prepared, to
Figure GDA0003425928980000653
Thermal vacuum deposition of HAT to form a hole injection layer.
The compound prepared in preparation example 1 as a hole transporting material was vacuum-deposited on the hole injection layer to a film thickness of
Figure GDA0003425928980000661
To form a hole transport layer.
Subsequently, vacuum deposition is carried out on the hole transport layer toThe lower compound EB was to a film thickness of
Figure GDA0003425928980000662
To form an electron blocking layer.
[EB]
Figure GDA0003425928980000663
Next, BH and BD were vacuum deposited on the electron blocking layer at a weight ratio of 25:1 to a film thickness of
Figure GDA0003425928980000664
To form a light emitting layer.
Vacuum depositing the above compound ET and the above compound LiQ (lithium quinolinate) on the light emitting layer at a weight ratio of 1:1 to form a thickness of
Figure GDA0003425928980000665
The electron transport layer of (1). Sequentially depositing on the electron transport layer to a thickness of
Figure GDA0003425928980000666
With a thickness of lithium fluoride (LiF) of
Figure GDA0003425928980000667
To form an electron injection layer and a cathode.
In the above process, the deposition rate of the organic material is maintained at
Figure GDA0003425928980000668
To
Figure GDA0003425928980000669
Maintaining the deposition rate of lithium fluoride at the cathode
Figure GDA00034259289800006610
Maintaining the deposition rate of aluminum at
Figure GDA00034259289800006611
Figure GDA00034259289800006612
And the degree of vacuum during deposition was maintained at 2X 10-7Hold in the palm to 5 x 10-6And thus an organic light emitting device was manufactured.
Example 2-2 to example 2-12
Organic light-emitting devices of examples 2-2 to 2-12 were each manufactured in the same manner as in example 2-1, except that compound 1 was changed to those shown in table 2 below when the hole transport layer was formed.
Comparative example 2-1
An organic light-emitting device was fabricated in the same manner as in example 2-1, except that, in forming the hole transport layer, HT-1 shown below was used instead of compound 1 as the electron transport material.
[HT-1]
Figure GDA0003425928980000671
Comparative examples 2 to 2
An organic light-emitting device was fabricated in the same manner as in example 2-1, except that, in forming the hole transport layer, HT-2 shown below was used instead of compound 1 as the electron transport material.
[HT-2]
Figure GDA0003425928980000672
Comparative examples 2 to 3
An organic light-emitting device was fabricated in the same manner as in example 2-1, except that, in forming the hole transport layer, HT-3 shown below was used instead of compound 1 as the electron transport material.
[HT-3]
Figure GDA0003425928980000681
Comparative examples 2 to 4
An organic light-emitting device was fabricated in the same manner as in example 2-1, except that, in forming the hole transport layer, HT-4 shown below was used instead of compound 1 as the electron transport material.
[HT-4]
Figure GDA0003425928980000682
Experimental example 2
Voltage, efficiency, luminance, color coordinates, and lifetime were measured by applying current to the organic light emitting devices manufactured in examples 2-1 to 2-12 and comparative examples 2-1 to 2-4, and the results are shown in table 2 below. T95 means the time it takes for the luminance to decrease to 95% of the initial luminance (650 nits).
[ Table 2]
Figure GDA0003425928980000691
Figure GDA0003425928980000701
Figure GDA0003425928980000711
As shown in table 2, it can be confirmed that the organic light emitting device manufactured by using the compound according to the present invention as a hole transport layer exhibits more excellent performance in terms of current efficiency, driving voltage, lifespan, and stability, as compared to the organic light emitting device of the comparative example.
Specifically, in the case of an organic light-emitting device manufactured by using the compound of comparative examples 2-1 to 2-3, which has the same structure as the core of the present invention but has no substituent in the 1 st and 3 rd directions, as a hole transport layer, it resulted in a 10% or more reduction in efficiency and a 30% or more reduction in lifetime, as compared to the examples.
On the other hand, the compounds of comparative examples 2 to 4 showed the results that: the distance between the core and the arylamine group is too far, and thus the characteristics of the organic light emitting device are greatly deteriorated.
Thus, it was determined that in the case of the compounds of the examples of the present invention, the efficiency of the device increased while the stability increased significantly.
Therefore, it can be seen that the compound according to the present invention is excellent not only in electron blocking ability but also in hole transporting ability, and thus can be applied to an electron blocking layer and/or a hole transporting layer of an organic light emitting device.
Description of the reference numerals
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer
6: hole transport layer
7: luminescent layer
8: electron transport layer

Claims (12)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure FDA0003530041690000011
Wherein, in chemical formula 1,
x is O or S, and X is O or S,
a and B are each independently hydrogen; warp C1-10Alkyl substituted or unsubstituted C6-30An aryl group; or C comprising 1 to 3 heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
at least one of a and B is not hydrogen,
l is a single bond; or via C1-10Alkyl substituted or unsubstituted C6-30An arylene group, a cyclic or cyclic alkylene group,
Ar1and Ar2Each independently is any one selected from the group consisting of:
Figure FDA0003530041690000012
wherein the content of the first and second substances,
Y2is O, S or CZ14Z15，
Z11To Z15Each independently is hydrogen; deuterium; c1-20An alkyl group; c6-20An aryl group; or C containing one or more heteroatoms of O or S2-20Heteroaryl with the proviso that Z14And Z15Optionally linked to each other to form a monocyclic ring or a polycyclic ring, and
m1 to m3 are each independently an integer of 0 to 3,
R1is hydrogen; deuterium; or C1-10An alkyl group;
a1 is an integer from 0 to 4.
2. The compound of claim 1, wherein a and B are each independently hydrogen or selected from any one of the following:
Figure FDA0003530041690000021
wherein the content of the first and second substances,
Y1is O, S or CZ4Z5，
Z1To Z3Each of which is independently hydrogen, is,
Z4And Z5Each independently is hydrogen; or C1-10Alkyl radicals, and
n1 to n3 are each independently an integer of 0 to 3.
3. The compound of claim 2, wherein a and B are each independently hydrogen or selected from any one of the following:
Figure FDA0003530041690000031
4. the compound of claim 1, wherein L is a single bond or is selected from any one of the following:
Figure FDA0003530041690000032
5. the compound of claim 4, wherein L is a single bond or is selected from any one of the following:
Figure FDA0003530041690000033
6. the compound of claim 1, wherein Ar1And Ar2Each independently is any one selected from the group consisting of:
Figure FDA0003530041690000041
Figure FDA0003530041690000051
Figure FDA0003530041690000061
Figure FDA0003530041690000071
7. according to claim1 wherein R is1Is hydrogen, deuterium, or methyl, and a1 is 0 or 1.
8. The compound of claim 1, wherein the compound is represented by the following chemical formula 1A or 1B:
[ chemical formula 1A ]
Figure FDA0003530041690000072
[ chemical formula 1B ]
Figure FDA0003530041690000081
Wherein, in chemical formulas 1A and 1B,
X、A、B、L、Ar1and Ar2As defined in claim 1.
9. A compound selected from any one of the following:
Figure FDA0003530041690000091
Figure FDA0003530041690000101
Figure FDA0003530041690000111
Figure FDA0003530041690000121
Figure FDA0003530041690000131
Figure FDA0003530041690000141
Figure FDA0003530041690000151
Figure FDA0003530041690000161
Figure FDA0003530041690000171
Figure FDA0003530041690000181
Figure FDA0003530041690000191
Figure FDA0003530041690000201
Figure FDA0003530041690000211
Figure FDA0003530041690000221
Figure FDA0003530041690000231
Figure FDA0003530041690000241
Figure FDA0003530041690000251
Figure FDA0003530041690000261
Figure FDA0003530041690000271
Figure FDA0003530041690000281
Figure FDA0003530041690000291
Figure FDA0003530041690000301
10. an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and at least one layer of organic material disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound of claim 1.
11. The organic light-emitting device according to claim 10, wherein the organic material layer containing the compound is a hole injection layer, a hole transport layer, or a layer that performs both hole injection and hole transport functions.
12. An organic light-emitting device according to claim 10, wherein the organic material layer containing the compound is an electron blocking layer.
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