阅读说明：本技术 化合物及利用其的有机发光元件 (Compound and organic light-emitting element using same ) 是由 韩美连 许瀞午 洪性佶 李东勋 尹喜敬 于 2019-05-27 设计创作，主要内容包括：本发明提供新型化合物及利用其的有机发光元件,所述新型化合物由化学式1、化学式2或化学式3表示,在化学式1、化学式2和化学式3中,X为O或S,M为碱金属或碱土金属,Z为O或S,Y为CH或N,L为O、S、CO、SO<Sub>2</Sub>、<Image he="263" wi="700" file="DDA0002073287540000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>或<Image he="253" wi="247" file="DDA0002073287540000012.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>A为苯、萘或吡啶,B为苯或吡啶,R全部为氢,或者R中的两个一起形成单键且其余为氢,并且化合物<Image he="301" wi="700" file="DDA0002073287540000013.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>从所述化学式1中排除。<Image he="272" wi="700" file="DDA0002073287540000014.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The present invention provides a novel compound represented by chemical formula 1, chemical formula 2 or chemical formula 3, wherein in chemical formula 1, chemical formula 2 and chemical formula 3, X is O or S, M is an alkali metal or an alkaline earth metal, Z is O or S, Y is CH or N, L is O, S, CO, SO 2 , or a is benzene, naphthalene or pyridine, B is benzene or pyridine, R is all hydrogen, or two of R together form a single bond and the rest are hydrogen, and compound is excluded from chemical formula 1, or 3)

1. A compound represented by the following chemical formula 1, chemical formula 2 or chemical formula 3:

Chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

x is O or S, and X is O or S,

M is an alkali metal or an alkaline earth metal,

Y is a group of CH or N,

L is O, S, CO, SO₂、A is benzene, naphthalene or pyridine,

B is benzene or pyridine, and the content of the benzene or pyridine,

R are all hydrogen, or two of R together form a single bond and the remainder are hydrogen,

Wherein the following compounds are excluded from the chemical formula 1,

Chemical formula 2

In the chemical formula 2, the first and second organic solvents,

X is O or S, and X is O or S,

M is an alkali metal or an alkaline earth metal,

Z is O or S, and the compound is,

chemical formula 3

In the chemical formula 3, the first and second organic solvents,

X is O or S, and X is O or S,

M is an alkali metal or an alkaline earth metal,

Y is CH or N.

2. the compound according to claim 1, wherein the chemical formula 1 is any one selected from the following chemical formulas:

in the chemical formula, the compound represented by the formula,

X, M and Y are as defined in claim 1.

3. The compound of claim 1, wherein M is Li.

4. The compound according to claim 1, wherein the compound represented by the chemical formula 1, chemical formula 2 or chemical formula 3 is any one selected from the group consisting of:

5. An organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer including the compound according to any one of claims 1 to 4.

Technical Field

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

Background

In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.

An organic light emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.

as for organic materials used for the organic light emitting element as described above, development of new materials is continuously demanded.

disclosure of Invention

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

The present invention provides a compound represented by the following chemical formula 1, chemical formula 2 or chemical formula 3:

[ chemical formula 1]

In the chemical formula 1 described above,

X is O or S, and X is O or S,

M is an alkali metal or an alkaline earth metal,

y is a group of CH or N,

L is O, S, CO, SO₂、

A is benzene, naphthalene or pyridine,

B is benzene or pyridine, and the content of the benzene or pyridine,

R are all hydrogen, or 2 of R together form a single bond and the remainder are hydrogen,

Wherein the following compounds are excluded from the above chemical formula 1,

[ chemical formula 2]

In the chemical formula 2 described above, the,

X is O or S, and X is O or S,

M is an alkali metal or an alkaline earth metal,

Z is O or S, and the compound is,

[ chemical formula 3]

In the chemical formula 3 above, the first and second,

X is O or S, and X is O or S,

M is an alkali metal or an alkaline earth metal,

y is CH or N.

In addition, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer, and the electron injection layer includes a compound represented by chemical formula 1, chemical formula 2, or chemical formula 3.

The compound represented by chemical formula 1, chemical formula 2, or chemical formula 3 described above may be used as a material of an organic layer of an organic light emitting element in which improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics can be achieved. In particular, the above-described compound represented by chemical formula 1, chemical formula 2, or chemical formula 3 may be used as an electron injecting material.

Drawings

Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

Fig. 2 shows an example of an organic light-emitting element composed of 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, an electron injection layer 9, and a cathode 4.

Description of the symbols

1: substrate 2: anode

3: light-emitting layer 4: cathode electrode

5: hole injection layer 6: hole transport layer

7: light-emitting layer 8: electron transport layer

9: electron injection layer

Detailed Description

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

in the context of the present specification,OrRepresents a bond to other substituents.

In the present specification, the term "substituted or unsubstituted" means,is selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group(s) ((S))alkyl thio), arylthio(s) ((R) Aryl thio), alkylsulfonyl(s) ((s)Alkyl sulfoxy), arylsulfonyl (C)Aryl sufoxy), silyl, boryl, alkyl, cycloalkyl, alkenyl, Aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, or a heterocyclic group containing N, O and one or more of S atoms, or a substituent formed by connecting 2 or more substituents among the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.

In the ester group, in the present specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.

in the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group includes specifically 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 is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadiene, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the 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 number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may beAnd the like. But 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 is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl group,Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinylAzolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoylOxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group can be applied to the above description of the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description about the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.

Preferably, the above chemical formula 1 is any one selected from the following chemical formulas:

in the above formula, X, M and Y are the same as defined above.

Preferably, M is Li.

Representative examples of the compound represented by the above chemical formula 1, chemical formula 2 or chemical formula 3 are as follows:

In addition, as an example, when M is Li, the present invention provides a method for producing the compounds represented by the following chemical formulas 1 'and 2' as the following reaction formulas 1 and 2, and the remaining compounds can be produced by a similar method, but is not limited to this method.

[ reaction formula 1]

[ reaction formula 2]

In the above reaction formulae 1 and 2, the definition of each substituent is the same as that described above.

The above reaction formulas 1 and 2 are reactions in which a starting material is reacted with an organolithium compound (organolithium agent). The organolithium compound that can be used in the above reaction can be appropriately selected according to the compound to be produced, and tert-butyllithium can be used as an example. The above-described manufacturing method can be further embodied in the manufacturing examples described later.

In addition, the present invention provides an organic light emitting element including the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3. As an example, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron injection layer, and the electron injection layer includes a compound represented by chemical formula 1, chemical formula 2, or chemical formula 3.

the organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.

In addition, the organic light emitting element according to the present invention may be an organic light emitting element having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting element according to the present invention may be an inverted (inverted) type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure example of an organic light emitting element 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 element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

Fig. 2 shows an example of an organic light-emitting element composed of 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, an electron injection layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3 may be included in the above electron injection layer.

the organic light emitting element according to the present invention may be manufactured by materials and methods well known in the art, except that the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3 is included in the above electron injection layer. In addition, when the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

For example, the organic light emitting element according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.

In addition, when the compound represented by chemical formula 1, chemical formula 2, or chemical formula 3 is used to manufacture an organic light-emitting device, the organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

The anode material is preferably a material having a large work function so that holes can be smoothly injected into the organic layer. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SnO₂a combination of a metal such as Sb and an oxide; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; such as LiF/Al or LiO₂and a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; a poly (p-phenylene vinyl) (PPV) polymer; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds: ( ) And pyrimidine derivatives, but are not limited thereto.

As the dopant material, there are an aromatic amine derivative, a styrene amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,Diindenopyrene and the like, as the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons from the cathode well and transfer the electrons to the light emitting layer, and a substance having a high electron mobility is preferable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in which case they are accompanied by an aluminum or silver layer.

The organic light emitting element according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the material used.

In addition, the compound represented by the above chemical formula 1, chemical formula 2, or chemical formula 3 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.

The production of the compound represented by the above chemical formula 1, chemical formula 2 or chemical formula 3 and the organic light emitting element comprising the same is specifically described in the following examples. However, the following examples are illustrative of the present invention, and the scope of the present invention is not limited thereto.