CN111918867B - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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Abstract
The application provides a compound and an organic light emitting device including the same.
Description
Technical Field
Cross Reference to Related Applications
The present application claims the benefits of korean patent application No. 10-2018-0096138 filed on 8 months 17 in 2018 and korean patent application No. 10-2019-0074232 filed on 21 months 6 in 2019, the contents of which are incorporated herein by reference in their entireties.
The present application relates to a compound and an organic light emitting device including the same.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage, and response speed, and thus many researches have been conducted thereon.
The 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-layered structure including different materials to enhance efficiency and stability of the organic light emitting device, 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, electrons are injected from a cathode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall back to a ground state.
There is a continuing need to develop new materials for organic materials used in these organic light emitting devices.
[ Prior Art literature ]
[ patent literature ]
(patent document 1) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
An object of the present application is to provide an organic light emitting material and an organic light emitting device including the same.
Technical proposal
In one aspect of the present application, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in the chemical formula 1,
m and n are each independently integers of 0 to 4, provided that at least one of them is an integer of 1 to 4,
L 1 and L 2 Each independently is a single bond, or a substituted or unsubstituted C 6-60 Arylene group, and
a and B are each independently selected from the group consisting of:
wherein, in the above group,
X 1 、X 2 and X 3 Each independently CH or N, provided that X 1 、X 2 And X 3 At least one of which is N, and
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C comprising at least one of O and S 2-60 Heteroaryl groups.
In another aspect of the present application, there is provided an organic light emitting device including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the one or more layers of the organic material layers include a compound represented by chemical formula 1.
Advantageous effects
The compound represented by chemical formula 1 described above may be used as a material of an organic material layer of an organic light emitting device, and may increase efficiency, achieve a low driving voltage, and/or improve lifetime characteristics in the organic light emitting device. In particular, the above compound represented by chemical formula 1 may be used as a material for hole injection, hole transport, hole blocking, light emission, electron transport, or electron injection.
Drawings
Fig. 1 shows an example of an organic light emitting device 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 device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron transport layer 9, and a cathode 4.
Detailed Description
Hereinafter, the present application will be described in more detail to aid understanding of the present application.
In one embodiment of the present application, there is provided a compound represented by chemical formula 1.
As used herein, a symbolMeaning a bond to another substituent.
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; alkylthio; arylthio; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and a heterocyclic group comprising at least one of N, O and an S atom, or a substituent which is unsubstituted or linked via two or more of the substituents exemplified above. For example, a "substituent to which two or more substituents are attached" may be a biphenyl group. That is, biphenyl may also be aryl, and may be interpreted as two phenyl-linked substituents.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40.
Specifically, the carbonyl group may be a compound having the following structural formula, but is not limited thereto.
In the present specification, the ester group may have a linear, branched or cyclic alkyl group in which oxygen of the ester group may be substituted with 1 to 25 carbon atoms; or an aryl substituted structure having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a compound having the following structural formula, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group and phenylboron group, 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 straight 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 a carbon number of 1 to 20. According to another embodiment, the alkyl group has a carbon number of 1 to 10. According to another embodiment, the alkyl group has a carbon number of 1 to 6. Specific examples of the alkyl group include, but are not limited to, 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, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be straight 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 a carbon number of 2 to 10. According to yet another embodiment, the alkenyl group has a carbon number of 2 to 6. 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- (naphthalen-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl,Radical, styryl, etc., but is 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 a carbon number of 3 to 30. According to another embodiment, the cycloalkyl group has a number of carbon atoms of 3 to 20. According to yet another embodiment, the cycloalkyl group has a number of carbon atoms of 3 to 6. 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-t-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 a carbon number of 6 to 30. According to another embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, an aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,A radical, a fluorenyl radical, etc., but is 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 structure. In the case where fluorenyl groups are substituted, it is possible to formEtc. However, the structure is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing one or more 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 heterocyclyl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, and benzoFuryl, phenanthroline group, iso ∈ ->Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In this specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as the foregoing examples of the aryl groups. In this specification, the alkyl groups in the aralkyl group, alkylaryl group, and alkylamino group are the same as the aforementioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroarylamine group may employ the foregoing description of the heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as the aforementioned examples of alkenyl groups. In the present specification, the foregoing description of aryl groups can be applied, except that arylene groups are divalent groups. In this specification, the foregoing description of heterocyclic groups may be applied, except that the heteroarylene group is a divalent group. In the present specification, the foregoing description of aryl or cycloalkyl groups can 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 ring is not a monovalent group but is formed by combining two substituents.
Preferably, m and n may each independently be 0 or 1, provided that at least one of the two may be 1.
More preferably, m may be 1 and n may be 0.
Preferably L 1 And L 2 May each independently be a single bond, or a substituted or unsubstituted C 6-20 Arylene groups.
More preferably L 1 And L 2 May each independently be a single bond, phenylene, biphenylene, terphenylene, tetrabiphenyl, naphthylene, anthracenylene, fluorenylene, phenanthrylene, pyrenylene, or triphenylene.
Most preferably L 1 And L 2 May each independently be a single bond, phenylene, or biphenylene.
Preferably Ar 1 And Ar is a group 2 Can be independently of each otherStanding by C which is substituted or unsubstituted 6-20 Aryl, or substituted or unsubstituted C comprising at least one of O and S 6-20 Heteroaryl groups.
Preferably Ar 1 And Ar is a group 2 May each independently be phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl.
Preferably Ar 1 And Ar is a group 2 At least one of which may be substituted or unsubstituted C 6-60 Aryl groups.
More preferably Ar 1 May be substituted or unsubstituted C 6-60 Aryl groups.
More preferably Ar 1 May be substituted or unsubstituted C 6-20 Aryl groups.
Most preferably Ar 1 May be phenyl, biphenyl or naphthyl.
The compound represented by chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-3:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
Wherein, in chemical formulas 1-1 to 1-3,
l1 and a are the same as defined in chemical formula 1 above.
Representative examples of the compound represented by chemical formula 1 are as follows:
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among the compounds represented by chemical formula 1, the compounds in which m is 0 and n is 1 may be prepared, for example, according to the preparation method as shown in the following reaction scheme 1, and the remaining compounds may be prepared in a similar manner.
Reaction scheme 1
Here, in reaction scheme 1, L 1 And A is the same as defined above, X is halogen, preferably X is chlorine or bromine.
Reaction scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction may be modified as known in the art. The above preparation method can be further specifically illustrated in the preparation examples described below.
In another embodiment of the present application, an organic light emitting device including the compound represented by chemical formula 1 is provided. As an example, there is provided an organic light emitting device, including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the one or more layers of the organic material layers include a compound represented by chemical formula 1.
The organic material layer of the organic light emitting device of the present application may have a single layer structure, or it may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic layers.
Further, the organic material layer may include a light emitting layer, wherein the light emitting layer includes a compound represented by chemical formula 1. In particular, the compounds according to the application can be used as hosts in light-emitting layers.
The organic material layer may include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer may include a compound represented by chemical formula 1.
The electron transport layer, the electron injection layer, or the layer performing both electron transport and electron injection may contain a compound represented by chemical formula 1.
The organic material layer may include a light emitting layer and an electron transporting layer, wherein the electron transporting layer may include a compound represented by chemical formula 1.
The organic material layer may include a hole blocking layer, wherein the hole blocking layer may include a compound represented by chemical formula 1.
The organic material layer may include an electron blocking layer, wherein the electron blocking layer may include a compound represented by chemical formula 1.
The organic light emitting device according to the present application may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present disclosure may be an inverted organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, fig. 1 and 2 illustrate the structure of an organic light emitting device according to an embodiment of the present disclosure.
Fig. 1 shows an example of an organic light emitting device including 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, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron transport layer 9, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron transport layer.
The organic light emitting device according to the present application may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layer include 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 application 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: a metal, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer is formed on the anode, and then a material that can function 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, in manufacturing an organic light emitting device, 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. Herein, the solution coating method means spin coating, dip coating, knife coating, ink jet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
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 (international publication WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.
As the anode material, it is generally preferable to use 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, 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, such as ZnO: al or SnO 2 : sb; conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene)](PEDOT), polypyrrole and polyaniline; etc., but is not limited thereto.
As the cathode material, it is generally 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; multilayer structural materials, e.g. LiF/Al or LiO 2 Al; etc., but is 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 a capability of transporting holes, and thus has an effect of injecting holes in an anode and an excellent hole injection effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and has an excellent capability of forming a thin film. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is 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, hexanitrile hexaazabenzophenanthrene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and 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 high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, and the like, but are not limited thereto.
The luminescent material is preferably such a material: which can receive holes and electrons respectively transferred from the hole transport layer and the electron transport layer and combine the holes and electrons to emit light in the visible light region and have good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light emitting material include: 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; a dimeric styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzoOxazole, benzothiazole-based and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) based polymers; a spiro compound; polyfluorene; rubrene; etc., but is not limited thereto.
The electron blocking layer is a layer provided between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being transferred to the hole transport layer without being recombined in the light emitting layer, and may be referred to as an electron suppressing layer. The electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.
The light emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocycle-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but are not limited thereto. Further, the metal complex includes iridium complex, platinum complex, and the like, but is not limited thereto. />
The hole blocking layer is a layer provided between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being transferred to the electron transport layer without being recombined in the light emitting layer, and may be referred to as a hole suppressing layer. The hole blocking layer is preferably a material having a high ionization energy. Preferably, the compound represented by chemical formula 1 may be included as a material of the hole blocking layer.
The electron transport layer is used for receiving electrons from the electron injection layer and transporting the electrons to the light emitting layerAnd the electron transporting material is suitably such that: which can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and has high electron mobility. Specific examples of the electron transport material include: al complexes of 8-hydroxyquinoline; comprising Alq 3 Is a complex of (a) and (b); an organic radical compound; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials having a low work function followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. Preferably, the compound represented by chemical formula 1 may be included as a material of the electron transport layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that: it has an ability to transport electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated by the light emitting layer from moving to a hole injecting layer, and also has an excellent ability to form a thin film. Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex compound include, but are not limited to, 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 (2-methyl-8-quinoline) chlorogallium, gallium bis (2 v methyl-8-quinoline) (o-cresol), gallium bis (2-methyl-8-quinoline) (1-naphthol) aluminum, gallium bis (2-methyl-8-quinoline) (2-naphthol) and the like.
The organic light emitting device according to the present application may be of a front-side emission type, a rear-side emission type or a double-side emission type depending on the materials used.
In addition, the compound represented by chemical formula 1 may be contained in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The present application will be described in detail in the following examples. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of the present application.
Preparation example
Preparation example 1: preparation of Compound 1
1-1 preparation of intermediate A
1-2 preparation of Compound 1
Intermediate a (6.34 g,13.32 mmol) and intermediate a-1 (4.91 g,12.69 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (140 ml) was added and tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol) was added thereto, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from tetrahydrofuran (180 ml) to prepare compound 1 (6.34 g, yield: 76%).
MS：[M+H] + ＝658
Preparation example 2: preparation of Compound 2
Intermediate a (6.73 g,14.14 mmol) and intermediate a-2 (5.21 g,13.46 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, 2M aqueous potassium carbonate (140 ml) was added and tetrakis (triphenylphosphine) palladium (0.47 g,0.40 mmol) was added thereto, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (210 ml) to prepare compound 2 (4.67 g, yield: 53%).
MS：[M+H] + ＝658
Preparation example 3: preparation of Compound 3
Intermediate a (6.66 g,14.00 mmol) and intermediate a-3 (5.16 g,13.33 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, 2M aqueous potassium carbonate (140 ml) was added and tetrakis (triphenylphosphine) palladium (0.46 g,0.40 mmol) was added thereto, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (190 ml) to prepare compound 3 (5.32 g, yield: 61%).
MS：[M+H] + ＝657
Preparation example 4: preparation of Compound 4
Intermediate a (6.74 g,14.16 mmol) and intermediate a-4 (5.22 g,13.49 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (140 ml) and tetrakis (triphenylphosphine) palladium (0.46 g,0.40 mmol) was added, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (180 ml) to prepare compound 4 (6.13 g, yield: 69%).
MS：[M+H] + ＝656
Preparation example 5: preparation of Compound 5
Intermediate a (7.51 g,16.32 mmol) and intermediate a-5 (5.33 g,15.54 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, 2M aqueous potassium carbonate (140 ml) was added and tetrakis (triphenylphosphine) palladium (0.54 g,0.47 mmol) was added thereto, and the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (180 ml) to prepare compound 5 (5.97 g, yield: 60%).
MS：[M+H] + ＝658
Preparation example 6: preparation of Compound 6
6-1 preparation of intermediate B
6-2 preparation of Compound 6
Intermediate B (7.67 g,16.11 mmol) and intermediate a-6 (5.63 g,15.34 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (140 ml) and tetrakis (triphenylphosphine) palladium (0.53 g,0.46 mmol) was added, and the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to prepare compound 6 (7.69 g, yield: 74%).
MS：[M+H] + ＝682
Preparation example 7: preparation of Compound 7
Intermediate B (7.03 g,14.76 mmol) and intermediate a-1 (5.44 g,14.06 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (140 ml) was added thereto and tetrakis (triphenylphosphine) palladium (0.49 g,0.42 mmol) was added, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from tetrahydrofuran (160 ml) to prepare compound 7 (6.22 g, yield: 67%).
MS：[M+H] + ＝658
Preparation example 8: preparation of Compound 8
8-1 preparation of intermediate C
8-2 preparation of Compound 8
Intermediate C (6.83 g,14.34 mmol) and intermediate a-8 (4.89 g,13.66 mmol) were dissolved completely in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, to which was added 2M aqueous potassium carbonate (140 ml) and tetrakis (triphenylphosphine) palladium (0.47 g,0.41 mmol) was added, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to prepare compound 8 (5.16 g, yield: 56%).
MS：[M+H] + ＝672
Preparation example 9: preparation of Compound 9
Intermediate C (7.08 g,14.88 mmol) and intermediate a-9 (4.93 g,14.17 mmol) were dissolved completely in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, to which was added 2M aqueous potassium carbonate (140 ml) and tetrakis (triphenylphosphine) palladium (0.49 g,0.43 mmol) was added, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to prepare compound 9 (6.33 g, yield: 67%).
MS：[M+H] + ＝663
Preparation example 10: preparation of Compound 10
Intermediate C (5.83 g,12.24 mmol) and intermediate a-10 (4.36 g,11.66 mmol) were dissolved completely in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, to which was added 2M aqueous potassium carbonate (140 ml) and tetrakis (triphenylphosphine) palladium (0.40 g,0.35 mmol) was added, and the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (260 ml) to prepare compound 10 (5.49 g, yield: 68%).
MS：[M+H] + ＝689
Preparation example 11: preparation of Compound 11
Intermediate a (7.54 g,15.85 mmol) and intermediate a-11 (4.77 g,15.09 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen, 2M aqueous potassium carbonate (140 ml) was added and tetrakis (triphenylphosphine) palladium (0.52 g,0.45 mmol) was added thereto, and the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from ethyl acetate (210 ml) to prepare compound 11 (6.66 g, yield: 70%).
MS：[M+H] + ＝631
Preparation example 12: preparation of Compound 12
Intermediate B (8.38 g,17.60 mmol) and intermediate a-12 (7.56 g,15.30 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500ml round bottom flask under nitrogen atmosphere, to which was added 2M aqueous potassium carbonate (140 ml) and tetrakis (triphenylphosphine) palladium (0.53 g,0.46 mmol) was added, and the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to ordinary temperature, the aqueous layer was removed, and the resultant product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and recrystallized from tetrahydrofuran (160 ml) to prepare compound 12 (7.46 g, yield: 64%).
MS：[M+H] + ＝764
Examples
Example 1-1
Coated with a coating having a thickness ofThe glass substrate as a thin film was put into distilled water in which a cleaning agent was dissolved, and subjected to ultrasonic cleaning. In this case, a product manufactured by Fischer co. Was used as a cleaner, 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 repeated twice using distilled water for 10 minutes. After washing with distilled waterAfter completion, the substrate was ultrasonically cleaned with isopropanol, acetone and methanol solvents, then dried and transferred to a plasma cleaner. In addition, the substrate was cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum depositor.
On the ITO transparent electrode thus prepared as an anode electrode, the following compound HI1 and the following compound HI2 were used at 98:2 to have a molar specific heat of vacuum depositionThereby forming a hole injection layer. Vacuum depositing the following compound HT1 to +.>To form a hole transport layer. Vacuum depositing the following compound EB1 to +.>To form an electron blocking layer. Then, the following compound BH and the following compound BD were mixed at 50:1 to +.>To form a light emitting layer. Vacuum depositing the compound 1 prepared in the above preparation example 1 to +.>To form a hole blocking layer. Then, the following compound ET1 and the following compound LiQ were mixed at 1:1 to form a thickness +.>Is provided. Sequential deposition of lithium fluoride (LiF) and aluminum on electron transport layer to respective devicesAnd->Thereby forming a cathode.
/>
In the above process, the vapor deposition rate of the organic material is maintained atSecond to->Per second, the deposition rates of lithium fluoride and aluminum of the cathode are kept at +.>Second and->Per second, the vacuum during deposition was maintained at 2X 10 -7 To 5X 10 -6 And a support, thereby manufacturing an organic light emitting device.
Examples 1-2 to 1-5
An organic light-emitting device was manufactured in the same manner as in example 1-1, respectively, except that the compound shown in table 1 below was used instead of the compound 1 during the formation of the hole blocking layer.
Comparative examples 1-1 to 1-3
An organic light-emitting device was manufactured in the same manner as in example 1-1, except that the compound shown in table 1 below was used instead of the compound 1 during the formation of the hole blocking layer. The compounds HB2, HB3 and HB4 used in table 1 below are as follows:
by the method of preparing the compositions in examples 1-1 to 1-5 and comparative examples 1-1 to 1-3The organic light emitting device manufactured applied 20mA/cm 2 Voltage, efficiency, color coordinates, and lifetime were measured and the results are shown in table 1 below. T95 means the time required for the luminance to decrease to 95% of the initial luminance (1600 nit).
TABLE 1
As shown in table 1, the organic light emitting device manufactured by using the compound of the present application as a hole blocking layer exhibited excellent characteristics in terms of driving voltage, light emitting efficiency, and lifetime of the organic light emitting device.
In particular, the embodiments of the present application exhibit low voltage, high efficiency, and long life characteristics compared to an organic light emitting device manufactured by using HB3 and HB4 in which a triazinyl group is substituted at a position different from the embodiments of the present application as a hole blocking layer or by using HB2 substituted with a carbazolyl group as a hole blocking layer.
Examples 2-1 to 2-12
An organic light-emitting device was manufactured in the same manner as in example 1-1, respectively, except that the following compound HB1 was used instead of the compound 1 during the formation of the hole blocking layer, and the compound described in table 2 below was used instead of ET1 during the formation of the electron transport layer.
Comparative examples 2-1 to 2-4
An organic light-emitting device was manufactured in the same manner as in example 1-1, respectively, except that the above compound HB1 was used instead of the compound 1 during the formation of the hole blocking layer, and the compound described in table 2 below was used instead of ET1 during the formation of the electron transport layer. The compounds ET2, ET3, ET4 and ET5 used in table 2 below are as follows:
by applying 20mA/cm to the organic light emitting devices manufactured in examples 2-1 to 2-12 and comparative examples 2-1 to 2-4 2 Voltage, efficiency, color coordinates, and lifetime were measured and the results are shown in table 2 below. T95 means the time required for the luminance to decrease to 95% of the initial luminance (1600 nit).
TABLE 2
As shown in table 2 above, the organic light emitting device manufactured by using the compound of the present application as an electron transport layer exhibited excellent characteristics in terms of driving voltage, light emitting efficiency, and lifetime of the organic light emitting device.
Embodiments 2-1 to 2-12 of the present application exhibit low voltage, high efficiency and long life characteristics compared to an organic light emitting device manufactured by using ET3 and ET4 in which a triazinyl group is substituted at a different position from the embodiment of the present application as an electron transport layer or by using ET2 in which a carbazolyl group is substituted as an electron transport layer. In addition, the organic light emitting device of the present application exhibits excellent characteristics in terms of driving voltage, light emitting efficiency and lifetime, compared to an organic light emitting device manufactured by using ET5 having a benzimidazolyl group (which is not included as the triazinyl substituent of the present application) as an electron transporting layer.
[ description of reference numerals ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: hole blocking layer
9: electron transport layer
Claims (6)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in the chemical formula 1,
m and n are each independently 0 or 1, provided that at least one of m and n is 1,
L 1 and L 2 Each independently is a single bond, phenylene, or biphenylene,
a and B are each independently selected from the group consisting of:
wherein, in the above group,
X 1 、X 2 and X 3 Each independently CH or N, provided that X 1 、X 2 And X 3 At least one of which is N, and
Ar 1 and Ar is a group 2 Each independently is C 6-60 Aryl, or C containing at least one of O and S 2-60 Heteroaryl groups.
2. The compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl, biphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.
3. The compound according to claim 1, wherein Ar 1 Is C 6-60 Aryl groups.
4. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-3:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
Wherein, in chemical formulas 1-1 to 1-3,
L 1 and a is the same as defined in claim 1.
5. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
6. an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the compound according to any one of claims 1 to 5.
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| KR1020190074432A KR102251402B1 (en) | 2018-08-17 | 2019-06-21 | Novel compound and organic light emitting device comprising the same |
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