KR20170060836A - Compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents
Compound for organic electroluminescent device and organic electroluminescent device comprising the same Download PDFInfo
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Abstract
The present invention provides a compound for an organic electroluminescent device and an organic electroluminescent device including the same. As a result, it is possible to provide a compound for an organic electroluminescent device which can be used as a host of a light emitting layer capable of improving the color purity and luminous efficiency of a phosphorescent material, and an organic electroluminescent device containing the same.
Description
BACKGROUND OF THE
The organic electroluminescent device has a simpler structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP) and a field emission display (FED) And has a high response speed and a low driving voltage, so that it is being actively developed to be used as a light source for a flat panel display such as a wall-mounted TV or a backlight of a display, a lighting, and a billboard.
In general, when a direct current voltage is applied to an organic electroluminescent device, holes injected from the anode recombine with electrons injected from the cathode to form an electron-hole pair exciton, and the exciton returns to a stable ground state, It is converted into light by transmission to the material.
In order to improve the efficiency and stability of the organic electroluminescent device, a laminated organic thin film is formed between two opposing electrodes by CW Tang et al. Of Eastman Kodak Company, and a low voltage driven organic electroluminescent device is reported (CW Tang, SA Vanslyke, Applied Physics Letters, vol. 51, p. 913, 1987), studies on organic materials for multilayer thin film structure organic electroluminescent devices have been actively conducted. The efficiency and lifetime of such a stacked organic electroluminescent device are closely related to the molecular structure of the material constituting the thin film. For example, the quantum efficiency is greatly influenced by the structures of the light emitting material, the hole transporting layer material, and the electron transporting layer material among the materials constituting the thin film, and when the thermal stability is deteriorated, the crystallization of the material occurs at a high temperature or a driving temperature, Is shortened.
Particularly, among the thin film constituting materials of the organic electroluminescent device, a light emitting material which can be largely divided into a host material and a light emitting material (dopant) is distinguished by fluorescence and phosphorescence depending on the light emitting mechanism. A phosphorescent host material capable of satisfying higher efficiency, color purity, and long life is required.
The present invention provides an organic electroluminescent compound having excellent electrical stability, high efficiency, high color purity and long life, emits purple light and can be used in a phosphorescent light emitting layer as a host, and an organic electroluminescent device including the compound have.
According to one aspect of the present invention, a compound for an organic electroluminescence device represented by the following
[Structural formula 1]
In
m is an integer of 1 to 4,
Each R is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 To C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 1 to R 4 are the same or different from each other, and R 1 to R 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
Preferably, the compound represented by the
[Structural formula 2]
[Structural Formula 3]
In Structural Formulas 2 and 3,
R 1 to R 4 are the same or different from one another and each of R 1 to R 4 is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 5 to R 8 are the same or different from each other and each of R 5 to R 8 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 9 to R 12 are the same or different from each other and each of R 9 to R 12 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
More preferably, R 1 to R 4 are the same or different from each other, and R 1 to R 4 are each independently
R 13 to R 26 are the same or different from each other and each of R 13 to R 26 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
More preferably, R 9 represents a hydrogen atom, a small or medium-sized atom,
Y 1 is a sulfur atom or an oxygen atom,
R 27 to R 31 are the same or different from each other and each of R 27 to R 31 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
The organic electroluminescent device compound may be any one selected from
According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound for an organic electroluminescent device.
According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, The organic electroluminescent device may further include at least one organic compound layer including the organic electroluminescent compound.
The singular or plural organic layers may include a light emitting layer.
The plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer.
The light emitting layer may include a host and a dopant.
The present invention relates to a compound for an organic electroluminescent device which is excellent in stability, can greatly improve the color purity, luminous efficiency and lifetime of a phosphorescent material, and can be used for a luminescent layer exhibiting purple emission as a host, and an organic electroluminescent device Can be provided.
1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating an organic electroluminescent device according to another embodiment of the present invention.
The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.
Furthermore, terms including an ordinal number such as first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.
Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >
The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
As used herein, "atomic bond" means a single bond, a double bond or a triple bond, unless otherwise defined.
The term "substituted" as used herein means that at least one hydrogen atom is replaced by a substituent selected from the group consisting of deuterium, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, C2 to C30 heterocycloalkyl groups, C1 to C30 halogenated alkyl groups, C6 to C30 aryl groups, C1 to C30 heteroaryl groups, C1 to C30 alkoxy groups, C2 to C30 alkenyl groups, C2 to C30 alkynyl group, C6 to C30 aryloxy group, a silyloxy (-OSiH 3), -OSiR 1 H 2 (
Further, two adjacent substituents among the substituents may be fused to form a saturated or unsaturated ring.
The carbon number range of the alkyl group or aryl group in the above "substituted or unsubstituted C1 to C30 alkyl group" or "substituted or unsubstituted C6 to C30 aryl group" Quot; means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is considered to be " substituted ". For example, a phenyl group substituted with a butyl group at the para position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.
In addition, the carbon number range of the fused aryl group in the "substituted or unsubstituted C6 to C30 fused aryl group" or the like is fused when it is considered that the substituent is not substituted without considering the substituted portion, Quot; means the total number of carbon atoms constituting the aryl moiety.
As used herein, unless otherwise defined, it is meant that one functional group contains 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, and the remainder is carbon.
In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.
As used herein, "hydrogen" means monohydrogen, double hydrogen, or tritium, unless otherwise defined.
As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group.
The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.
The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond.
"Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.
The alkyl group may be a C1 to C30 alkyl group. More specifically, a C1 to C20 alkyl group, a C1 to C10 alkyl group, or a C1 to C6 alkyl group.
For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.
Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.
An "amine group" includes an amino group, an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group, and may be represented by -NRR ', wherein R and R' , A C1 to C30 alkyl group, and a C6 to C30 aryl group.
"Cycloalkyl group" includes monocyclic or fused-ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.
"Heterocycloalkyl group" means that the cycloalkyl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the remainder is carbon. When the heterocycloalkyl group is a fused ring, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.
"An aromatic group" means a functional group in which all elements of a functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.
An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.
"Heteroaryl group" means that the aryl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.
In the aryl group and the heteroaryl group, the number of atoms in the ring is the sum of carbon number and non-carbon atom number.
When used in combination, such as "alkylaryl" or "arylalkyl group ", the terms alkyl and aryl of each of the above have the meanings and contents indicated above.
The term "arylalkyl group " means an aryl substituted alkyl radical, such as benzyl, and is included in the alkyl group.
The term "alkylaryl group " means an alkyl substituted aryl radical and is included in the aryl group.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. Referring to the accompanying drawings, the same or corresponding components are denoted by the same reference numerals, .
According to one aspect of the present invention, a compound for an organic electroluminescence device represented by the following
[Structural formula 1]
In
m is an integer of 1 to 4,
Each R is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 To C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 1 to R 4 are the same or different from each other, and R 1 to R 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
Preferably, the compound represented by the
[Structural formula 2]
[Structural Formula 3]
In Structural Formulas 2 and 3,
R 1 to R 4 are the same or different from one another and each of R 1 to R 4 is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 5 to R 8 are the same or different from each other and each of R 5 to R 8 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 9 to R 12 are the same or different from each other and each of R 9 to R 12 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
More preferably, R 1 to R 4 are the same or different from each other, and R 1 to R 4 are each independently
R 13 to R 26 are the same or different from each other and each of R 13 to R 26 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
More preferably, R 9 represents a hydrogen atom, a small or medium-sized atom,
Y 1 is a sulfur atom or an oxygen atom,
R 27 to R 31 are the same or different from each other and each of R 27 to R 31 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
Examples of the substituted or unsubstituted C2 to C30 heteroaryl group include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiophenyl group , A substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo [1,2-a] pyridinyl group, a substituted or unsubstituted A substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzoyl group, Substituted or unsubstituted imidazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted tetrazolyl groups, substituted or unsubstituted oxadiazolyl groups, substituted or unsubstituted oxatriazolyl groups, However, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, Or a substituted or unsubstituted phenanthrolinyl group, preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted aryidinyl group, a substituted or unsubstituted pyrazolinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzothiazolyl group, , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.
The organic electroluminescent device compound may be any one selected from
Referring to FIGS. 1 and 2, an
According to another embodiment of the present invention, the organic electroluminescent device includes a
Here, the single or plural
The plurality of
The
The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.
As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO 2 and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.
As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO 2 , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm.
In order to increase the luminous efficiency of the organic EL device, at least one electrode preferably has a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.
When the compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, Or may be used in combination with the organic electroluminescent device compound of the present invention selectively.
N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'- (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N'N'N'N'- Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like, aromatic tertiary (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as nonmetal phthalocyanine and copper phthalocyanine, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.
The diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) as an electron transport material .
In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.
Examples of the light emitting material include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, a carbazole compound, a phosphine oxide compound, a carbazole-based phosphine oxide compound, bis (3,5-difluoro-4-cyanophenyl) pyridine, iridium picolinate (FCNIrpic), tris (8-hydroxyquinoline) aluminum Alq 3 ), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1,4- Bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6- Liquid scintillation scintillators such as 3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzanthracene There may be mentioned a colorant, a xanthene colorant, a carbostyryl colorant, a perylene colorant, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.
Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.
The compound for an organic electroluminescence device according to the present invention can be formed by a vacuum deposition method, so that it is advantageous that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.
[Example]
Hereinafter, the compound for an organic electroluminescent device according to the present invention and the method for manufacturing the organic electroluminescent device including the same will be described in more detail with reference to the following examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.
Manufacturing example 1: Intermediate (1) 1,2- Bis (4,4,5,5- Tetramethyl -1,3,2- Dioxabororanyl ) Synthesis of benzene
To a 1000 ml round-bottomed three-necked flask under a nitrogen atmosphere were added 20.0 g of 1,2-dibromobenzene, 47.4 g of bis (pinacolato) diboron, 25.0 g of potassium acetate, 1,1'-bis (diphenylphosphino) Ferrocene] dichloropalladium (II), and 320 ml of dimethylsulfoxide were placed, and the mixture was stirred for 20 hours while keeping the temperature at 95 ° C. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. Column chromatography was performed with a mixed solvent of ethyl acetate and n-hexane to concentrate the solution to obtain 10.5 g of intermediate (1). (Yield: 38%)
MS (ESI): [M + H] < + > 330
Example 1: Synthesis of Compound (1)
7.0 g of the intermediate (1) prepared in Preparation Example 1, 11.4 g of 2-chloro-4,6-diphenyl-1,3,5-triazine and 17.6 g of potassium carbonate were placed in a 500 ml three- 1.2 g of tetrakistriphenylphosphine palladium (0), 300 ml of tetrahydrofuran and 75 ml of water were added and the mixture was stirred and refluxed at 60 ° C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the concentrated solution was recrystallized from dichloromethane and cyclohexane to obtain 4.8 g of compound (1). (Yield: 42%)
MS (ESI): [M + H] < + > 541
1 H NMR (600MHz, DMSO) : δ 8.34 (d, 8H), 8.26 (q, 2H), 7.87 (q, 2H), 7.58 (t, 4H), 7.42 (t, 8H)
Manufacturing example 2: Intermediate (2) 9- (4,6- Dichloro -1,3,5- Triazinyl ) -9H- Carbazole synthesis
20.0 g of carbazole and 130 ml of anhydrous tetrahydrofuran were placed in a 500 ml round-bottomed three-necked flask under a nitrogen atmosphere and dissolved by stirring. After dropping the temperature of the reaction solution to 0 占 폚, 47.8 ml of n-butyllithium (2.5M) was slowly added dropwise. After the dropwise addition, the reaction solution was warmed to room temperature and stirred for 30 minutes. 21.0 g of cyanuric chloride and 130 ml of anhydrous tetrahydrofuran were placed in a 500 ml round-bottomed three-necked flask under a nitrogen atmosphere and dissolved by stirring. The carbazole reaction liquid was slowly added dropwise to the cyanuric chloride reaction solution and stirred at room temperature for 1 hour or longer. After distilled water was poured into the reaction solution and stirred for 30 minutes or more, the reaction solution was filtered. The filtered solid was washed with acetone to obtain 24.3 g of intermediate (2). (Yield: 68%)
MS (ESI): [M + H] < + > 315
Manufacturing example 3: Intermediate (3) 9- (4- Chloro -6-phenyl-1,3,5- Triazinyl ) -9H- Carbazole synthesis
20.0 g of the intermediate (2) prepared in Preparation Example 2, 26.3 g of potassium carbonate, 3.7 g of tetrakistriphenylphosphine palladium (0), 300 ml of tetrahydrofuran and 115 ml of water were placed in a 1000 ml round-bottomed three-necked flask under nitrogen atmosphere And the temperature was raised to 60 캜 with stirring. Phenylboronic acid were dissolved in 160 ml of tetrahydrofuran, and the mixture was stirred for 4 hours and refluxed. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution, which was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, was concentrated, and the concentrated solution was recrystallized from toluene and methanol to obtain 7.8 g of intermediate (3). (Yield: 34%)
MS (ESI): [M + H] < + > 357
Example 2: Synthesis of compound (2)
3.5 g of Intermediate (1) prepared in Preparation Example 1, 7.6 g of Intermediate (3) prepared in Preparation Example 3, 8.8 g of potassium carbonate, 0.1 g of tetrakistriphenylphosphine palladium (0) ), 200 ml of tetrahydrofuran and 50 ml of water, and the mixture was stirred and refluxed at 60 DEG C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution, which had been subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, was concentrated, and the concentrated solution was recrystallized from dichloromethane and cyclohexane to obtain 3.0 g of the compound (2). (Yield: 39%)
MS (ESI): [M + H] < + > 719
1 H NMR (600MHz, DMSO) : δ 8.61 (d, 4H), 8.36 (q, 2H), 8.32 (d, 4H), 8.06 (d, 4H), 7.97 (q, 2H), 7.60 (t, 2H ), 7.47 (t, 4H), 7.24-7.23 (m, 8H)
Manufacturing example 4: Intermediate (4) 1,3- Bis (4,4,5,5- Tetramethyl -1,3,2- Dioxabororanyl ) Synthesis of benzene
To a 1000 ml round-bottomed three-necked flask under a nitrogen atmosphere were added 10.0 g of 1,3-dibromobenzene, 23.7 g of bis (pinacolato) diboron, 20.8 g of potassium acetate, 1,1'-bis (diphenylphosphino) Ferrocene] dichloropalladium (II), and 500 ml of dimethylsulfoxide were placed, and the mixture was stirred for 20 hours while maintaining the temperature at 95 ° C. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resultant solution was subjected to column chromatography using a mixed solvent of ethyl acetate and n-hexane to obtain 7.0 g of intermediate (4). (Yield 50%)
MS (ESI): [M + H] < + > 330
Example 3: Synthesis of compound (6)
3.0 g of the intermediate (4) prepared in Preparation Example 4, 7.5 g of the intermediate (3) prepared in Preparation Example 3, 7.5 g of potassium carbonate, 0.1 g of tetrakistriphenylphosphine palladium (0) ), 160 ml of tetrahydrofuran, and 40 ml of water, and the mixture was stirred and refluxed at 60 ° C for 4 hours. After cooling the reaction solution, the reaction solution was filtered. The precipitated solid was washed with distilled water, high-temperature dichloromethane and chloroform, and recrystallized with chloroform to obtain 3.2 g of compound (6). (Yield: 49%)
MS (ESI): [M + H] < + > 719
1 H NMR (600MHz, CDCl 3 ): δ 10.2 (s, 1H), 9.24 (d, 2H), 9.18 (d, 1H), 9.14 (d, 2H), 9.05 (t, 2H), δ 8.84 (t (M, 3H),? 8.14-8.07 (m, 5H),? 7.68 (d, 1H),? 7.63 (t, 2H),? 7.59-7.54 [delta] 7.45-7.42 (m, 4H), [delta] 7.39 (t, IH)
Manufacturing example 5: Intermediate (5) 9- (4 - ([1,1'-biphenyl]) -6- Chloro -1,3,5- Triazinyl ) -9H-carbazole < / RTI >
20.0 g of the intermediate (2) prepared in Preparation Example 2, 26.3 g of potassium carbonate, 3.7 g of tetrakistriphenylphosphine palladium (0), 300 ml of tetrahydrofuran and 125 ml of water were placed in a 1000 ml round-bottomed three-necked flask under a nitrogen atmosphere And the temperature was raised to 60 캜 with stirring. [1,1'-biphenyl] -boronic acid (12.6 g) was dissolved in 200 ml of tetrahydrofuran, and the mixture was stirred for 4 hours and refluxed. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the concentrated solution was recrystallized from toluene and methanol to obtain 6.7 g of intermediate (5). (Yield: 24%)
MS (ESI): [M + H] < + > 433
Manufacturing example 6: Intermediate (6) 9- (4 - ([1,1'-biphenyl) -6- (3- (4,4,5,5- Tetramethyl -1,3,2-dioxabororanyl) phenyl) -1,3,5-triazinyl) -9H-carbazole Synthesis of
5.0 g of Intermediate (4) prepared in Preparation Example 4, 6.6 g of Intermediate (5) prepared in Preparation Example 5, 12.6 g of potassium carbonate, 0.67 g of tetrakistriphenylphosphine palladium (0) ), 150 ml of tetrahydrofuran and 40 ml of water, and the mixture was stirred and refluxed at 60 ° C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the concentrated solution was recrystallized from dichloromethane and hexane to obtain 4.2 g of intermediate (6). (Yield: 46%)
MS (ESI): [M + H] < + > 601
Example 4: Synthesis of compound (9)
In a 250 ml round-bottomed three-necked flask under nitrogen atmosphere, 4.6 g of the intermediate (6) prepared in Preparation Example 6, 2.7 g of the intermediate (3) prepared in Preparation Example 3, 6.4 g of potassium carbonate, ), 90 ml of tetrahydrofuran and 20 ml of water were added, and the mixture was stirred and refluxed at 60 ° C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the concentrated solution was recrystallized with toluene to obtain 3.4 g of Compound (9). (Yield: 56%)
MS (ESI): [M + H] < + > 795
1 H NMR (600MHz, CDCl 3 ): δ 9.87 (s, 1H), 9.32 (d, 2H), 9.25 (d, 1H), 9.23 (d, 2H), 9.17 (t, 2H), δ 9.03 (t , 7.38 (m, 3H), 7.89-7.54 (m, 9H), 7.48 (t, 2H)
Manufacturing example 7: Intermediate (7) 2,6- Dichloro Synthesis of -1,1'-biphenyl
Bromo-1,3-dichlorobenzene, 10.8 g of phenylboronic acid, 36.7 g of potassium carbonate, 5.1 g of tetrakis (triphenylphosphine) palladium (0) and 0.1 g of tetra 580 ml of hydrofuran and 140 ml of water were added, and the mixture was stirred and refluxed at 60 ° C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution was subjected to column chromatography with a n-hexane solvent and then concentrated to obtain 16.4 g of intermediate (7). (Yield: 83%)
MS (ESI): [M + H] < + > 223
Manufacturing example 8: Intermediate (8) 2- (6- Chloro - [1,1'-biphenyl) -4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaboroline
In a 1000 ml round-bottomed three-necked flask under a nitrogen atmosphere, 16.0 g of the intermediate (7) synthesized in Production Example 7, 21.9 g of bis (pinacolato) diboron, 14.1 g of potassium acetate, 0.1 g of bis (dibenzylideneacetone) palladium , 3.0 g of tricyclohexylphosphine and 650 ml of 1,4-dioxane, and the mixture was stirred for 20 hours while keeping the temperature at 95 占 폚. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resulting solution was subjected to column chromatography using a mixed solvent of ethyl acetate and n-hexane to obtain 10.8 g of intermediate (8). (Yield: 48%)
MS (ESI): [M + H] < + > 315
Manufacturing example 9: Intermediate (9) 9- (4- (6- Chloro - [1,1'-biphenyl) -6-phenyl-1,3,5- Triazinyl ) -9H-carbazole < / RTI >
10.0 g of Intermediate (8) synthesized in Preparation Example 8, 11.3 g of Intermediate (3) synthesized in Preparation Example 3, 13.1 g of potassium carbonate, 0.1 g of tetrakistriphenylphosphine palladium (0) ), 290 ml of tetrahydrofuran and 70 ml of water, and the mixture was stirred and refluxed at 60 ° C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resultant solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 11.2 g of intermediate (9). (Yield 69%)
MS (ESI): [M + H] < + > 509
Manufacturing example 10: Intermediate (10) 9- (4-Phenyl-6- (6- (4,4,5,5- Tetramethyl -1,3,2- Dioxabororanyl ) - [1,1'-biphenyl]) - 1,3,5-triazinyl) -9H-carbazole
11.2 g of Intermediate (9) synthesized in Production Example 9, 15.3 g of bis (pinacolato) diboron, 9.9 g of potassium acetate, 0.1 g of bis (dibenzylideneacetone) palladium (0) , 2.1 g of tricyclohexylphosphine and 450 ml of 1,4-dioxane, and the mixture was stirred for 20 hours while maintaining the temperature at 95 占 폚. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The resulting solution was subjected to column chromatography using a mixed solvent of ethyl acetate and n-hexane to obtain 9.7 g of intermediate (10). (Yield 32%)
MS (ESI): [M + H] < + > 601
Example 5: Synthesis of compound (12)
9.7 g of Intermediate (10) synthesized in Preparation Example 10, 5.8 g of Intermediate (3) synthesized in Preparation Example 3, 6.7 g of potassium carbonate, 0.67 g of tetrakistriphenylphosphine palladium (0) ), 180 ml of tetrahydrofuran and 45 ml of water, and the mixture was stirred and refluxed at 60 DEG C for 4 hours. The reaction solution was cooled, extracted with dichloromethane and water, and the extracted solution was concentrated. The solution, which had been subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, was concentrated, and the concentrated solution was recrystallized with toluene to obtain 7.1 g of the compound (12). (Yield: 55%)
MS (ESI): [M + H] < + > 795
1 H NMR (600MHz, CDCl 3 ): δ 9.41 (d, 2H), 9.29 (d, 1H), 9.22 (d, 2H), 9.15 (t, 2H), δ 9.10 (t, 2H), δ 8.44- (M, 4H), 8 7.76-7.70 (m, 10H), 8 7.42-7.36 (m, 2H) 3H)
Device Example 1: Compound ( 1) to Include as host Organic electroluminescent device Produce
A glass substrate coated with ITO (Indium Tin Oxide) thin film having a thickness of 150 nm was ultrasonically cleaned with isopropyl alcohol solvent, dried and transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and the substrate was vacuum- Respectively.
DNTPD was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a hole injection layer having a thickness of 60 nm. Subsequently, NPB was deposited as a first hole transporting layer to form a first hole transporting layer having a thickness of 10 nm. Then, mCP was deposited as a second hole transporting layer to form a second hole transporting layer having a thickness of 20 nm. Subsequently, the compound (1) was used as a host to deposit a deposition rate of 0.1 nm / sec, a deposition rate of FIr6 at 0.01 nm / sec, doping FIr6 such that the deposition rate ratio was 10%, and the light- . TSPO1 was deposited thereon as an exciton blocking layer to form an exciton blocking layer having a thickness of 15 nm. TmPyPB was deposited thereon to form an electron transport layer having a thickness of 15 nm. On the electron transport layer, 2 nm of LiQ and 50 nm of aluminum To form an anode. Thus, an organic electroluminescent device was fabricated.
The deposition rate of each material was 0.1 nm / sec for organic materials DNTPD, NPB, mCP, TSPO1, and TmPyPB, 0.02 nm / sec for LiQ, and 0.2 nm / sec for aluminum.
Device Example 2: Compound ( 2) Include as host Organic electroluminescent device Produce
An organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound (2) was used instead of the compound (1) as the host of the light emitting layer.
Device Example 3: Compound ( 6) Include as host Organic electroluminescent device Produce
An organic electroluminescent device was produced in the same manner as in the device example 1, except that the compound (6) was used instead of the compound (1) as the host of the light emitting layer.
Device Example 4: Compound ( 9) Include as host Organic electroluminescent device Produce
An organic electroluminescent device was produced in the same manner as in the device example 1 except that the compound (9) was used in place of the compound (1) as the host of the light emitting layer.
Device Example 5: Compound ( 12) Include as host Organic electroluminescent device Produce
An organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound (12) was used instead of the compound (1) as the host of the light emitting layer.
Device comparison example One: CzSi Include as host Organic electroluminescent device Produce
An organic electroluminescent device was manufactured in the same manner as in the device example 1, except that CzSi was used instead of the compound (1) as the light emitting layer and the exciton blocking layer in the device example 1.
The structural formulas of DNTPD, NPB, mCP, TSPO1, TmPyPB and CzSi used in the device and device comparative examples are as follows.
The organic electroluminescent device Character analysis
Hereinafter, characteristics of the organic EL devices manufactured according to the
The driving voltage (V)
(cd / A)
The external quantum efficiency was obtained by measuring the luminance at that time using a luminance meter (Minolta CS-2000) while increasing the voltage from 0 V to 15 V, and dividing the measured luminance value by the current density value.
According to the above Table 1, as a result of using the compound (2), (6), (9), or (12) according to the present invention in an organic electroluminescent device comprising a host as a light emitting layer, It was confirmed that the efficiency was improved and the driving voltage was reduced and the performance was excellent.
Claims (10)
[Structural formula 1]
In formula 1,
m is an integer of 1 to 4,
Each R is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 To C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 1 to R 4 are the same or different from each other, and R 1 to R 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group.
The compound represented by the structural formula 1 is represented by any one of the following structural formulas 2 and 3,
[Structural formula 2]
[Structural Formula 3]
In Structural Formulas 2 and 3,
R 1 to R 4 are the same or different from one another and each of R 1 to R 4 is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 5 to R 8 are the same or different from each other and each of R 5 to R 8 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R 9 to R 12 are the same or different from each other and each of R 9 to R 12 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
R 1 to R 4 are the same or different from each other, and R 1 to R 4 are each independently
R 13 to R 26 are the same or different from each other and each of R 13 to R 26 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
R 9 represents a hydrogen atom, a small or medium-sized atom,
Y 1 is a sulfur atom or an oxygen atom,
R 27 to R 31 are the same or different from each other and each of R 27 to R 31 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
Wherein the compound for an organic electroluminescence device is any one selected from compounds 1 to 13 represented by the following formulas.
The organic electroluminescent device according to claim 1, wherein the at least one organic layer selected from the group consisting of the single or plural organic layers includes the compound for an organic electroluminescent device according to claim 1.
Wherein the single or plural organic layers include a light emitting layer.
Wherein the plurality of organic layers include a light emitting layer and the plurality of organic layers further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer and a hole injecting layer Organic electroluminescent device.
Wherein the light emitting layer comprises a host and a dopant.
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