CN109890815B - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
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Abstract
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compounds according to the present disclosure can provide an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long life characteristics.
Description
Technical Field
The present disclosure relates to organic electroluminescent compounds useful in the field of organic electroluminescence (OLED) and organic electroluminescent devices comprising the same.
Background
An electroluminescent device (EL device) is a self-luminous display device which is advantageous in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 by using a small aromatic diamine molecule and an aluminum complex as materials for forming a light emitting layer (see appl. Phys. Lett.51,913, 1987).
An organic EL device (OLED) converts electric energy into light by applying the electric energy to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layers of the organic EL device may include a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron blocking layer, a light emitting layer (containing a host and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like, if necessary. Materials used in the organic layer may be classified into a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, and the like, depending on their functions. In the organic EL device, holes from an anode and electrons from a cathode are injected into a light emitting layer by applying a voltage, and excitons having high energy are generated by recombination of the holes and the electrons. When the organic light emitting compound returns from the excited state to the ground state, the organic light emitting compound enters the excited state by energy and emits light with the energy.
The electron buffer layer is provided to improve the problem of reduction in light emission luminance, which may occur due to variation in current characteristics in the device when the device is exposed to high temperature in the process of manufacturing the panel. Therefore, the properties of the compound contained in the electron buffer layer are important. In addition, the compound used in the electron buffer layer desirably plays a role of controlling electron injection by electron withdrawing characteristics and an electron affinity LUMO (lowest unoccupied molecular orbital) level, and thus may play a role of improving the efficiency and lifetime of the organic electroluminescent device.
Chinese patent publication No. 105237519 (hereinafter referred to as patent document 1) discloses a compound having the following structure as an organic electroluminescent compound.
Korean patent application publication No. 2010-0062973 (hereinafter, referred to as patent document 2) discloses a compound having the following structure as an organic electroluminescent compound.
However, the compounds disclosed in the above documents have a low glass transition temperature (Tg) and a low decomposition temperature (Td), thereby decreasing thermal stability. In addition, OLED devices comprising such compounds still need to be improved in terms of luminous efficiency.
Disclosure of Invention
Problems to be solved
It is an object of the present disclosure to provide an organic electroluminescent compound capable of firstly preparing an organic electroluminescent device having a low driving voltage and/or a high luminous efficiency and/or a long life, and secondly providing an organic electroluminescent device comprising the organic electroluminescent compound.
Solution to the problem
As a result of intensive studies to solve the above-mentioned technical problems, the present inventors have found that a compound containing a fused imidazolphenanthrene nucleus of the present disclosure can provide an organic electroluminescent device having characteristics of low driving voltage and/or high luminous efficiency, and thus have completed the present invention. This is believed to be due to the compounds of the present disclosure having a positional chemical structure that reduces internal steric hindrance compared to compounds disclosed in prior art documents. For example, the compound of the present disclosure has a main core closer to a plane than the structure of the above-described compound disclosed in patent document 2. The above structure of patent document 2 has a large deformation to the core due to steric hindrance between internal hydrogens, so that the distorted shape of such core molecules may interfere with pi-pi stacking in the vacuum deposition layer; and may result in a low glass transition temperature (Tg), a low decomposition temperature (Td), and ultimately reduced thermal stability. That is, the present disclosure may increase thermal stability and electron transport capacity by reducing deformation of the inner primary core.
More specifically, the above object can be achieved by an organic electroluminescent compound represented by the following formula 1.
Ar 1 To Ar 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 、-SiR 13 R 14 R 15 、-SR 16 、-OR 17 Cyano, nitro or hydroxy; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30) mono-or polycyclic, alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be substituted with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
R 11 to R 17 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30) mono-or polycyclic, alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be substituted with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
a and b each independently represent an integer of 1 to 5, c and d each independently represent an integer of 1 to 4, and when a to d each independently represent an integer of 2 or more, ar 1 To Ar 4 Each of which may be the same or different, an
Heteroaryl and heterocycloalkyl each independently contain at least one heteroatom selected from B, N, O, S, si and P.
Effects of the invention
By including the organic electroluminescent compounds according to the present disclosure, an organic electroluminescent device having a low driving voltage and/or high luminous efficiency and/or a long life can be manufactured.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.
The term "organic electroluminescent compound" in the present disclosure refers to a compound that can be used in an organic electroluminescent device, and can be contained in any layer constituting the organic electroluminescent device, if necessary. The term "organic electroluminescent material" in the present disclosure refers to a material that may be used in an organic electroluminescent device, and may include at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, or the like.
The compound represented by formula 1 will be described in more detail as follows.
In formula 1, ar 1 To Ar 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 、-SiR 13 R 14 R 15 、-SR 16 、-OR 17 Cyano, nitro or hydroxy; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30) mono-or polycyclic, alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur, preferably hydrogen, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-to 25-membered) heteroaryl, -NR 11 R 12 、-SiR 13 R 14 R 15 、-SR 16 、-OR 17 Cyano, nitro or hydroxy; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C25) mono-or polycyclic, alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur, more preferably hydrogen, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-to 18-membered) heteroaryl, or-NR 11 R 12 (ii) a Or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C18) monocyclic ringOr a polycyclic aromatic ring. For example, ar 1 To Ar 4 May represent hydrogen, a substituted or unsubstituted phenyl group, an unsubstituted pyridyl group, a substituted pyrimidyl group, a substituted triazinyl group, a substituted or unsubstituted carbazolyl group, or-NR 11 R 12 (ii) a Or may be linked to an adjacent substituent to form an unsubstituted benzene ring; the substituent of the substituted phenyl group may be a triazine substituted with a diphenyl group; the substituents of the substituted pyrimidinyl, triazinyl and carbazolyl groups may be one or more phenyl groups.
In formula 1, R 11 To R 17 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30) mono-or polycyclic, alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur, preferably a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5-to 25-membered) heteroaryl group, a substituted or unsubstituted (3-to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C3-C25) cycloalkyl group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C25) mono-or polycyclic, alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be substituted with at least one heteroatom selected from nitrogen, oxygen and sulfur, more preferably a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 18-membered) heteroaryl group, for example, may be an unsubstituted phenyl group.
In formula 1, a and b each independently represent an integer of 1 to 5, c and d each independently represent an integer of 1 to 4, preferably, a to d may be an integer of 1 or 2, and when a to d each independently represent an integer of 2 or more, ar 1 To Ar 4 Each of which may be the same or different.
In formula 1, the heteroaryl and heterocycloalkyl each independently contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S, more preferably at least one nitrogen.
Herein, "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, constituting a chain, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. "(C2-C30) alkenyl" means a straight or branched chain alkenyl group having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, constituting the chain, and includes ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. "(C2-C30) alkynyl" is a straight or branched alkynyl group having 2 to 30 carbon atoms, preferably 2 to 20, more preferably 2 to 10, constituting a chain, and includes ethynyl, 1- (propynyl), 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. "(C3-C30) cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. "(3-to 7-membered) heterocycloalkyl" is a cycloalkyl group having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from B, N, O, S, si and P, preferably O, S and N, and includes tetrahydrofuran, pyrrolidine, thiacyclopentane, tetrahydropyran and the like. "(C6-C30) aryl" is a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, wherein the number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, perylene, etc,
Mesityl, tetracenyl, fluoranthenyl, spirobifluorenyl and the like. "(5-to 30-membered) heteroaryl" is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from B, N, O, S, si and P and 5 to 30 ring backbone atoms, and is a single ring, or a fused ring fused to at least one benzene ring; may be partially saturated; may be a group formed by connecting at least one heteroaryl group or an aryl group to a heteroaryl group by a single bond; may contain a group having a spiro structure; and include monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furoyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused heteroaryl groups including benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzisothiazole, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl and the like. "halogen" includes F, cl, br and I.
Further, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is substituted with another atom or another functional group, i.e., a substituent. Substituted alkyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aralkyl, and substituted mono-or polycyclic, alicyclic, or aromatic ring substituents, or combinations thereof, at Ar 1 To Ar 4 And R 11 To R 17 Each independently selected from at least one of the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl, (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl, (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (C6-C30) aryl;(C6-C30) aryl substituted or unsubstituted (5-to 30-membered) heteroaryl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; a di (C1-C30) alkyl (C6-C30) arylsilyl group; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di (C6-C30) arylborono carbonyl; di (C1-C30) alkylborono; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl, preferably, at least one selected from the group consisting of: (C1-C20) alkyl, (C6-C25) aryl and (C6-C25) aryl substituted or unsubstituted (5-to 25-membered) heteroaryl, more preferably (C6-C18) aryl and (C6-C18) aryl substituted or unsubstituted (5-to 18-membered) heteroaryl, for example phenyl, or triazine substituted with one or more phenyl groups.
The compound represented by formula 1 may be illustrated by, but is not limited to, the following compounds:
the compounds of formula 1 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, for example, as shown in the following reaction scheme 1.
[ reaction scheme 1]
In reaction scheme 1, ar 1 To Ar 4 As defined in formula 1, X and Y each independently may represent H, cl, br, I OR B (OR) 2 But are not limited thereto; r may be hydrogen, but is not limited thereto.
The organic electroluminescent compound of formula 1 of the present disclosure may be contained in a Hole Transport Layer (HTL), an emission layer (EML), an electron buffer layer (a compound deposited between the electron transport layer and the emission layer), and an Electron Transport Layer (ETL), and preferably may be contained in the electron buffer layer.
In addition, the present disclosure may provide an organic electroluminescent material including the organic electroluminescent compound of formula 1 and an organic electroluminescent device including the organic electroluminescent material.
The organic electroluminescent material may be composed of only the organic electroluminescent compound of the present disclosure, and may further include conventional materials included in the organic electroluminescent material.
According to one embodiment of the present disclosure, there is provided an electron buffer material including a compound represented by formula 1. An electron buffer material means a material that controls the flow characteristics of electric charges. The electron buffering material may be, for example, a material that traps electrons, blocks electrons, or lowers an energy barrier between an electron transport band and the light emitting layer. Specifically, the electron buffer material may be an electron buffer material of an organic electroluminescent device. The electron buffer material may be used in the electron buffer layer, or may be incorporated into another region in the organic electroluminescent device, such as an electron injection layer, an electron transport layer, or a light emitting layer. The electronic buffer material may be a mixture or a composition further comprising common materials used in the preparation of organic electroluminescent devices.
An organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic layer may include at least one organic electroluminescent compound represented by formula 1.
One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic layer includes a light emitting layer, and may include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. Here, the hole assist layer or the light emission assist layer is provided between the hole transport layer and the light emitting layer; and controls the transport speed of holes. The hole assist layer or the light-emitting assist layer provides an effect of improving the efficiency and lifetime of the organic electroluminescent device.
The organic electroluminescent device of the present disclosure includes the organic electroluminescent compound of formula 1, and at the same time, may include at least one compound selected from the group consisting of an aromatic amine-based compound and a styryl aromatic amine-based compound.
Further, in the organic electroluminescent device of the present disclosure, the organic layer may further include at least one metal selected from the group consisting of: group 1 metals, group 2 metals, period 4 transition metals, period 5 transition metals, lanthanides, and organometallic compounds of d-block transition elements of the periodic table of the elements, or at least one complex comprising such metals. In addition, the organic layer may include a light emitting layer and a charge generation layer.
Further, the organic electroluminescent device of the present disclosure includes at least one light-emitting layer including a blue, red or green light-emitting compound known in the art, in addition to the compound of the present disclosure, so that it can emit white light. Further, it may further include a yellow or orange light emitting layer, if necessary.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be disposed on the inner surface of one or both electrodes. Specifically, a layer of a silicon or aluminum chalcogenide (including oxide) is preferably disposed on the anode surface of the electroluminescent media layer, and a layer of a metal halide or metal oxide is preferably disposed on the cathode surface of the electroluminescent media layer. The operational stability of the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide comprises SiO X (1≤X≤2)、AlO X (X is more than or equal to 1 and less than or equal to 1.5), siON, siAlON and the like; the metal halide includes LiF, mgF 2 、CaF 2 Rare earth metal fluorides, etc.; the metal oxide comprises Cs 2 O、Li 2 O, mgO, srO, baO, caO, etc.
In addition, in the organic electroluminescent device of the present disclosure, a mixed region of the electron transport compound and the reductive dopant or a mixed region of the hole transport compound and the oxidative dopant may be preferably placed on at least one surface of the pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it is easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole-transporting compound is oxidized to cations, and thus holes are more easily injected and transported from the mixed region to the electroluminescent medium. Preferably, the oxidizing dopants include various Lewis acids and acceptor compounds, and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light emitting layers and emitting white light.
The formation of each layer of the organic electroluminescent device of the present disclosure may use one of a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., and a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc., but is not limited thereto. When the film is formed with the dopant compound and the host compound of the present disclosure, they may be processed by co-deposition or hybrid deposition, but are not limited thereto.
When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like. The solvent may be any solvent in which the material forming each layer can be dissolved or diffused, and there is no problem in film-forming ability.
Co-deposition is a hybrid deposition method that puts two or more kinds of isomer materials into respective crucible sources while applying electric current to two cells to evaporate the materials and perform hybrid deposition; hybrid deposition is a hybrid deposition method that mixes two or more isomer materials in a crucible source prior to deposition and then applies current to a cell to evaporate the materials.
In addition, the organic electroluminescent device of the present disclosure may be used to manufacture a display device such as a smart phone, a tablet computer, a notebook computer, a personal computer, a television, or a vehicle, or a lighting device such as outdoor or indoor lighting.
Hereinafter, in order to understand the present disclosure in more detail, the preparation method of the organic electroluminescent compound according to the present disclosure and the properties thereof will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited by the following examples.
Example 1: preparation of Compound H-14
Preparation of Compound 1-1
Phenylacetylene (17.3g, 170mmol), 1-bromo-2-iodobenzene (40g, 141mmol), palladium (II) chloride (0.2g, 1mmol) and pyrrolidine (50g, 707mmol) were dissolved in 180mL of H in a flask 2 O, and stirred at 50 ℃ for 24 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 29g of compound 1-1 (yield: 80%).
Preparation of Compounds 1-2
Compound 1-1 (28g, 109mmol), palladium (II) acetate (2.4g, 11mmol) and copper bromide (2.4g, 11mmol) were dissolved in 440mL of dimethyl sulfoxide (DMSO) in a flask and refluxed for 20 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 16.3g of compound 1-2 (yield: 52%).
Preparation of Compounds 1-3
In a flask, compounds 1-2 (16.3g, 56mmol), 2-chlorophenylboronic acid (10.5g, 68mmol), tetrakis (triphenylphosphine) palladium (0) (3.2g, 3mmol) and 2M potassium carbonate (19.5g, 141mmol) were dissolved in 280mL of toluene and 70mL of ethanol and refluxed for 5 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 14.7g of the compounds 1 to 3 (yield: 81%).
Preparation of Compounds 1-4
In a flask, compound 1-3 (13.7g, 43mmol), 4-chlorobenzaldehyde (6 g, 43mmol) and ammonium acetate (19.7g, 256mmol) were dissolved in 215mL of acetic acid and refluxed for 24 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate to obtain 20g of compounds 1 to 4.
Preparation of Compounds 1-5
In a flask, compounds 1-4 (20g, 45mmol), copper powder (2.8g, 45mmol) and cesium carbonate (59g, 181mmol) were dissolved in 300mL of 1, 2-dichlorobenzene and refluxed for 17 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 14.2g of compounds 1 to 5 (yield: 77%).
Preparation of Compounds 1-6
In a flask, compounds 1-5 (6g, 15mmol), bis-pinacolato diboron (4.5g, 18mmol), tris (dibenzylideneacetone) dipalladium (0.6 g, 0.7mmol), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (0.6 g, 1mmol) and potassium acetate (3.6 g, 37mmol) were dissolved in 75mL of 1, 4-dioxane and refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 6.8g of compounds 1 to 6 (yield: 92%).
Preparation of Compound H-14
In a flask, compounds 1-6 (4.5g, 9mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (2.6 g, 10mmol), tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4mmol) and 2M potassium carbonate (3.1g, 23mmol) were dissolved in 44mL of toluene and 11mL of ethanol, and refluxed for 2 hours. After the completion of the reaction, the resulting solid was filtered and then purified by column chromatography to obtain 3.5g of Compound H-14 (yield: 64%).
| Compound (I) | MW | UV | PL | M.P. |
| H-14 | 601.71 | 375nm | 477nm | 358℃ |
Example 2: preparation of Compound H-18
In a flask, compounds 1-6 (4.5g, 9mmol), 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (3.1g, 8mmol), tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.4mmol) and 2M potassium carbonate (3.1g, 23mmol) were dissolved in 44mL of toluene and 11mL of ethanol and refluxed for 6 hours. After the completion of the reaction, the resulting solid was filtered and then purified by column chromatography to obtain 2.8g of Compound H-18 (yield: 45%).
| Compound (I) | MW | UV | PL | M.P. |
| H-18 | 677.81 | 344nm | 441nm | 272℃ |
Example 3: preparation of Compound H-55
Preparation of Compound 4-1
In a flask, compounds 1-3 (4.5g, 14mmol), 3-bromobenzaldehyde (1.6mL, 14mmol) and ammonium acetate (6.5g, 84mmol) were dissolved in 70mL of acetic acid and refluxed for 24 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 6.4g of compound 4-1 (yield: 94%).
Preparation of Compound 4-2
Compound 4-1 (6.4 g, 13.2mmol), copper powder (0.83g, 13.2mmol) and cesium carbonate (17.2g, 52.6 mmol) were dissolved in 90mL of 1, 2-dichlorobenzene in a flask and refluxed for 17 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 5.4g of compound 4-2 (yield: 86%).
Preparation of Compound 4-3
In a flask, compound 4-2 (5.4g, 12mmol), bis-pinacolyldiboron (4g, 15.6mmol), bis (triphenylphosphine) palladium (II) dichloride (0.4g, 0.6mmol) and potassium acetate (2.4g, 24mmol) were dissolved in 60mL 1,4-dioxane and refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 2.9g of compound 4-3 (yield: 48%).
Preparation of Compound H-55
In a flask, compounds 4-3 (2.9g, 5.8mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (2.6g, 10mmol), tetrakis (triphenylphosphine) palladium (0) (0.33g, 0.29mmol) and 2M potassium carbonate (2g, 14.5mmol) were dissolved in 28mL of toluene and 7mL of ethanol, and refluxed for 4 hours. After the completion of the reaction, the resulting solid was filtered and then purified by column chromatography to obtain 2.2g of Compound H-55 (yield: 63%).
| Compound (I) | MW | UV | PL | M.P |
| H-55 | 601.71 | 341nm | 453nm | 336℃ |
Comparative example: preparation of Compound X, which is a conventional Compound
Preparation of Compound 3-1
In a flask, 2-bromobenzaldehyde (10g, 54mmol), 2-chlorophenylboronic acid (10g, 65mmol), tetrakis (triphenylphosphine) palladium (0) (3.1g, 3mmol) and 2M potassium carbonate (18.6g, 135mmol) were dissolved in 280mL of toluene and 70mL of ethanol, and refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 11.7g of compound 3-1 (yield: 99%).
Preparation of Compound 3-2
In a flask, compound 3-1 (5.1g, 24mmol), di-2-pyridylglyoxal (5 g, 24mmol) and ammonium acetate (10.9g, 141mmol) were dissolved in 120mL of acetic acid and refluxed for 20 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and then purified by column chromatography to obtain 1.4g of compound 3-2 (yield: 15%).
Preparation of Compound X
In a flask, compound 3-2 (1.2g, 3mmol), copper powder (0.18g, 3mmol) and cesium carbonate (3.8g, 12mmol) were dissolved in 20mL of 1, 2-dichlorobenzene and refluxed for 4 hours. After the completion of the reaction, the resulting solid was filtered and then purified by column chromatography to obtain 0.4g of compound X (yield: 36%).
| Compound (I) | MW | UV | PL | M.P. |
| X | 372.43 | 356nm | 429nm | 213℃ |
Hereinafter, the light emitting characteristics of the organic electroluminescent device comprising the compound of the present disclosure will be described in order to understand the present disclosure in detail.
Apparatus comparative example 1: manufacturing blue light emitting OLED devices not in accordance with the present disclosure
An OLED device not according to the present disclosure was manufactured. A transparent electrode Indium Tin Oxide (ITO) film (10 Ω/sq) on a glass substrate for an OLED (geomatech (geomotec co., ltd., japan) was ultrasonically cleaned with acetone and isopropanol in this order, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Introducing the compound HI-1 into a cell of a vacuum vapor deposition apparatus, and then controlling the pressure in the chamber of the apparatus at 10 deg.C -7 And (7) supporting. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 60nm on the ITO substrate. Then, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. Compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole transport layer having a thickness of 20nm on the second hole injection layerAnd (7) conveying the layer. Then, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 5nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, the light emitting layer is deposited as follows. The compound BH-1 as a host was introduced into one cell of a vacuum vapor deposition apparatus, and the compound BD-1 as a dopant was introduced into the other cell of the apparatus. The two materials were evaporated at different rates, and the dopant was deposited in a doping amount of 2wt% based on the total weight of the host and the dopant to form a light emitting layer having a thickness of 20nm on the second hole transporting layer. Next, compound X as an electron buffer material was deposited on the light emitting layer to a thickness of 5nm, and then compound ETL-1 as an electron transport material was introduced into one cell and evaporated to deposit an electron transport layer having a thickness of 30nm on the light emitting layer. After depositing the compound EIL-1 as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thereby, an OLED device was manufactured. All materials used to fabricate OLED devices are disclosed at 10 -6 Purification was performed by vacuum sublimation under torr.
Device examples 1 to 3: preparation of blue light-emitting OLED devices according to the present disclosure
In device examples 1 to 3, OLED devices were manufactured in the same manner as in comparative example 1, except that the electron buffering material shown in table 1 below was used as the electron buffering material.
Results of a driving voltage, a light emitting efficiency, and an emission spectrum (EL) at 1000 nit luminance of the organic electroluminescent devices manufactured in device comparative example 1 and device examples 1 to 3, and a lifetime after measuring a constant current at 2000 nit luminance for 10 hours are shown in table 1 below. The lifetime represents the light intensity after 10 hours, assuming that the first light intensity is 100%.
TABLE 1
As can be seen from the above-described comparative device example 1 and device examples 1 to 3, the OLED device comprising the organic electroluminescent compound of the present disclosure as an electron buffer material exhibits a lower driving voltage, higher luminous efficiency and longer life span than the OLED device using the conventional electron buffer material.
That is, when the organic electroluminescent compound according to the present disclosure is used, since the voltage for emitting light of the same luminance is low, it has an advantage in reducing power consumption. In addition, it has an advantage of increasing the battery life of the portable display device, which is currently mainly used for the OLED panel.
The compounds used in the above comparative examples and apparatus examples are shown in table 2 below.
TABLE 2
Claims (6)
1. An organic electroluminescent compound represented by the following formula 1:
Ar 1 and Ar 3 Each independently represents hydrogen, deuterium, (C6-C30) aryl substituted with (C6-C30) aryl or unsubstituted (5-to 30-membered) heteroaryl, or (5-to 30-membered) heteroaryl substituted with (C6-C30) aryl;
Ar 2 and Ar 4 Each independently represents hydrogen or deuterium;
a and b each independently represent an integer of 1 to 5, c and d each independently represent an integer of 1 to 4, and when a to d each independently represent an integer of 2 or more, ar 1 To Ar 4 Each of which may be the same or different, an
The heteroaryl group contains at least one heteroatom selected from N.
2. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
3. an organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
4. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
5. The organic electroluminescent device according to claim 4, wherein the organic electroluminescent compound is contained as an electron buffer material.
6. A display device comprising the organic electroluminescent compound according to claim 1.
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| WO2014047616A1 (en) * | 2012-09-24 | 2014-03-27 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
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| JP5509634B2 (en) * | 2009-03-16 | 2014-06-04 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE, LIGHTING DEVICE, AND ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL |
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