KR101828669B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents
Hetero-cyclic compound and organic light emitting device comprising the same Download PDFInfo
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Abstract
TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.
Description
This application claims the benefit of Korean Patent Application No. 10-2015-0033832, filed on March 11, 2015, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.
In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.
Development of new materials for such organic light emitting devices has been continuously required.
The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.
The present invention provides a heterocyclic compound represented by the following general formula (1).
[Chemical Formula 1]
In Formula 1,
X 1 to X 4 are the same or different and each independently N or CH,
R 1 to R 14 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or substituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a heterocyclic compound represented by the general formula (1).
The heterocyclic compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device and by using it, it is possible to improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting device.
1 shows an organic
2 shows an organic
Hereinafter, the present invention will be described in more detail.
The present invention provides a heterocyclic compound represented by the above formula (1).
In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.
In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
Examples of substituents in the present specification are described below, but are not limited thereto.
The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
As used herein, the term "substituted or unsubstituted" A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
In the present specification,
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the amide group may be mono- or di-substituted with nitrogen of the amide group with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
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 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is 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 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
In this specification, the amine group is -NH 2 ; An alkylamine group; An aralkylamine group; An arylamine group; And a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, a triphenylenyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the fluorenyl group is substituted,
In this specification, the heteroaryl group in the present specification includes one or more non-carbon atoms and hetero atoms, and specifically, the hetero atom may be an atom selected from the group consisting of O, N, Se and S, . The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a thiazolyl group, an isoxazolyl group, A thiadiazolyl group, a benzothiazolyl group, a thienothiophene group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.
The heteroaryl group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring.
In the present specification, the heterocyclic ring may be an aliphatic ring or an aromatic ring, meaning that at least one carbon atom of the aliphatic or aromatic ring is substituted with N, O, Se or S atoms, and may be monocyclic or polycyclic.
According to one embodiment of the present invention, in Formula 1, at least one of X 1 to X 4 is N and the others are CH.
According to one embodiment of the present invention, in the general formula (1), X 1 to X 4 are N.
According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be represented by Formula 2 below.
(2)
In Formula 2,
The definitions of R 1 to R 14 are the same as those in the above formula (1).
According to one embodiment of the present invention, in Formula 1, R 1 to R 14 are the same or different and each independently hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to one embodiment of the present invention, R 1 to R 14 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
According to one embodiment of the present invention, R 1 to R 14 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 16 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms.
According to one embodiment of the present invention, R 1 to R 14 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted crecenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; And a substituted or unsubstituted dibenzothiophene group.
According to one embodiment of the present invention, R 1 to R 14 are the same or different from each other, and each independently hydrogen; Diphenylamine group; A phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; Pyrenyl; A crycenyl group; A triphenylrenyl group; A fluoranthenyl group; Anthracenyl group substituted or unsubstituted with an aryl group; A carbazolyl group substituted or unsubstituted with an aryl group; A dibenzofuranyl group; And dibenzothiophene groups.
According to one embodiment of the present invention, R 1 to R 14 are the same or different from each other, and each independently hydrogen; Diphenylamine group; A phenyl group substituted with a naphthyl group; A phenyl group substituted with a carbazolyl group; Pyrenyl; A crycenyl group; A triphenylrenyl group; A fluoranthenyl group; Anthracenyl group substituted or unsubstituted with a phenyl group; A carbazolyl group; A carbazolyl group substituted with a phenyl group; A dibenzofuranyl group; And dibenzothiophene groups.
According to one embodiment of the present invention, in Formula 1, R 1 and R 8 are the same or different and each independently hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to one embodiment of the present disclosure, R 1 and R 8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
According to one embodiment of the present disclosure, R 1 and R 8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 16 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms.
According to one embodiment of the present disclosure, R 1 and R 8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted crecenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; And a substituted or unsubstituted dibenzothiophene group.
According to one embodiment of the present disclosure, R 1 and R 8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted diphenylamine group; A phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; Pyrenyl; A crycenyl group; A triphenylrenyl group; A fluoranthenyl group; Anthracenyl group substituted or unsubstituted with an aryl group; A carbazolyl group substituted or unsubstituted with an aryl group; A dibenzofuranyl group; And dibenzothiophene groups.
According to one embodiment of the present disclosure, R 1 and R 8 are the same or different from each other, and each independently hydrogen; Diphenylamine group; A phenyl group substituted with a naphthyl group; A phenyl group substituted with a carbazolyl group; Pyrenyl; A crycenyl group; A triphenylrenyl group; A fluoranthenyl group; Anthracenyl group substituted or unsubstituted with a phenyl group; A carbazolyl group; A carbazolyl group substituted with a phenyl group; A dibenzofuranyl group; A carbazolyl group; A carbazolyl group substituted with a phenyl group; And dibenzothiophene groups.
According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following compounds 1 to 14.
According to an embodiment of the present invention, there is provided an organic light emitting device comprising the heterocyclic compound represented by Formula 1.
According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a heterocyclic compound represented by the general formula (1).
The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device in the specification may have a structure including a hole injection layer, a hole transporting layer, a light emitting layer, a hole blocking layer, an electron transporting 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 may include a smaller number of organic layers.
For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.
1 illustrates a structure of an organic
2 shows a structure in which a
According to one embodiment of the present invention, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound represented by the formula (1).
According to an embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes, wherein the hole injecting layer, the hole transporting layer, And a heterocyclic compound represented by the above formula (1).
According to an embodiment of the present invention, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound represented by the formula (1).
According to one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transporting and electron injection, and the electron transporting layer, the electron injecting layer, And a heterocyclic compound represented by the above formula (1).
According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1).
According to another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer contains a heterocyclic compound represented by Formula 1 as a fluorescent dopant.
The organic light emitting device of the present invention is manufactured by materials and methods known in the art except that one or more of the organic layers include the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above formula (1) .
When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
According to one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.
According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.
As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, and Mg / Ag, but are not limited thereto.
The hole injecting layer is a layer for injecting holes from the electrode as a hole injecting material and a hole injecting effect for injecting holes in the anode as a hole injecting material and an excellent hole injecting effect for a light emitting layer or a light emitting material , The migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also the ability to form thin films is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
The light emitting material of the light emitting layer is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be included in an organic electronic device, an organic solar cell, or an organic transistor in addition to the organic light emitting device.
Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.
According to one embodiment of the present invention, the core of the heterocyclic compound represented by Formula 2 may be prepared by the following Formulas 1 and 2, but is not limited thereto.
[Formula 1]
[Formula 2]
In the general formulas 1 and 2, X is a halogen group.
Further, by introducing various substituent groups into the above-mentioned core structure, it is possible to synthesize a compound having the intrinsic characteristics of the introduced substituent. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in the production of an organic electronic device including the organic light emitting device into the structure, Materials can be prepared. The heterocyclic compound according to one embodiment of the present invention can be applied to an organic light emitting device according to a conventional method for manufacturing an organic light emitting device.
Production Example 1. Preparation of Compound 3
[Compound A] [Compound B-1] [Compound C-1] [Compound 3]
1) Preparation of compound B-1
Compound A (10 g, 31.7 mmol) and diaminobenzene (3.4 g, 31.7 mmol) were suspended in 1,4-dioxane (200 mL) and acetic acid (AcOH) (20 mL). The resulting mixture was stirred and refluxed for about 6 hours and cooled to room temperature. The mixture was diluted with water (100 mL), and the resulting solid was filtered and washed with water and ethyl ether to give the compound B-1 (8.9 g, 57%). MS: [M + H] < + > = 490
2) Preparation of Compound C-1
(186 mg, 2 mol%) of compound B-1 (8.9 g, 18.2 mmol), sodium-tertiary-butoxide (NaOt- Bu) (5.2 g, 54.6 mmol) and Pd [P ) Was suspended in toluene (200 mL). The resulting mixture was stirred and refluxed for about 6 hours and cooled to room temperature. The reaction solution was filtered, washed with water and ethanol, and dried to obtain the compound C-1 (7.8 g, 95%). MS: [M + H] < + > = 452
3) Preparation of Compound 3
Compound C-1 (7.8 g, 17.3 mmol) and carbazole (6.4g, 38.1mmol) and sodium-tert-butoxide (NaOt-Bu) (5.0 g , 51.9 mmol) and Pd [P (t-Bu) 3 ] 2 (186 mg, 2 mol%) was suspended in toluene (200 mL). The resulting mixture was stirred and refluxed for about 6 hours and cooled to room temperature. The reaction solution was filtered, washed with water and ethanol, refluxed with dimethylsulfoxide (DMSO) (200 ml), and filtered at room temperature. The residue was dried to give Compound 3 (10. g, 81%). MS: [M + H] < + > = 713
Production Example 2. Preparation of Compound 2
[Compound D-1] [Compound E-1] [Compound F-1] [Compound 2]
1) Preparation of compound E-1
Compound D-1 (10 g, 35.6 mmol) and diaminobenzene (3.9 g, 35.6 mmol) were suspended in 1,4-dioxane (200 mL) and acetic acid (AcOH) (20 mL). The resulting mixture was stirred and refluxed for about 25 hours and cooled to room temperature. The mixture was diluted with water (100 mL), and the resulting solid was filtered and washed with water and ethyl ether to give the above compound E-1 (6.2 g, 38%). MS: [M + H] < + > = 455
2) Preparation of compound F-1
(305 mg, 2 mol%) of compound E-1 (6.2 g, 13.6 mmol), sodium tertiary-butoxide (NaOt- Bu) (3.9 g, 40.9 mmol) and Pd [ ) Was suspended in toluene (200 mL). The resulting mixture was stirred and refluxed for about 15 hours and cooled to room temperature. The reaction solution was filtered, washed with water and ethanol, and dried to obtain the compound F-1 (4.3 g, 76%). MS: [M + H] < + > = 452
3) Preparation of Compound 2
Compound F-1 (4.3 g, 10.3 mmol) and carbazole (5.2g, 30.9mmol) and sodium-tert-butoxide (NaOt-Bu) (4.0 g , 41.2 mmol) and Pd [P (t-Bu) 3 ] 2 (105 mg, 2 mol%) was suspended in toluene (200 mL). The resulting mixture was stirred at reflux for about 39 hours and cooled to room temperature. The reaction solution was filtered, washed with water and ethanol, refluxed with xylene (200 ml), and filtered at room temperature. The residue was dried to give Compound 2 (3.2 g, 57%). MS: [M + H] < + > = 548
Experimental Example 1
A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1000 Å was placed in distilled water in which a dispersant was dissolved and ultrasonically cleaned. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
Nitrile hexahydro on the ITO electrode hexa aza triphenylene (500 Å), 4,4'- bis [N- (1- naphthyl) -N- phenylamino] biphenyl (NPB) (400 Å), Alq 3 ( 300 Å) and Compound 3 (200 Å) prepared in Preparation Example 1 were successively subjected to thermal vacuum deposition to form a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer in this order.
Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2000 Å were sequentially deposited on the electron transport layer to form a cathode. Thus, an organic light emitting device was prepared.
In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of lithium fluoride at 0.3 Å / sec for aluminum and 2 Å / sec for aluminum was maintained, and the degree of vacuum during deposition was 2 × 10 -7 to 5 x 10 < -8 > torr. When a forward electric field of 6 V was applied to the device fabricated as described above, green emission corresponding to 3200 nits was observed.
Experimental Example 2
An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 2 was used instead of the compound 3. When a forward electric field of 6 V was applied to the device fabricated as described above, green light corresponding to 3200 nits Observed
Comparative Example 1
An organic light emitting device was fabricated in the same manner as in Example 1 except that the following compound ET1 was used instead of the compound 3. When a forward electric field of 6 V was applied to the thus fabricated device, a green Luminescence was observed.
[Compound ET1]
10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron transport layer
90: electron injection layer
Claims (10)
[Chemical Formula 1]
In Formula 1,
X 1 to X 4 are the same or different and each independently N or CH,
R 1 and R 8 are the same or different and each independently hydrogen; An arylamine group; A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; And a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms,
R 2 to R 7 and R 9 to R 14 are hydrogen.
(2)
In Formula 2,
The definitions of R 1 to R 14 are the same as those in the above formula (1).
R 1 and R 8 are the same or different from each other, and each independently hydrogen; Diphenylamine group; A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a phenyl group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; Pyrenyl; A crycenyl group; A triphenylrenyl group; A fluoranthenyl group; Anthracenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A carbazolyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A dibenzofuranyl group; And a dibenzothiophene group,
Wherein R 2 to R 7 and R 9 to R 14 are hydrogen.
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