CN103201273A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Novel compounds for organic electronic material and organic electroluminescent device using the same Download PDF

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CN103201273A
CN103201273A CN2011800499936A CN201180049993A CN103201273A CN 103201273 A CN103201273 A CN 103201273A CN 2011800499936 A CN2011800499936 A CN 2011800499936A CN 201180049993 A CN201180049993 A CN 201180049993A CN 103201273 A CN103201273 A CN 103201273A
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alkyl
organic
aryl
compound
arylsilyl
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黄守振
安熙春
李美爱
尹石根
金奉玉
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

Provided are novel compounds for organic electronic material and an organic electroluminescent device using the same. Because the compounds for organic electronic material according to the present invention are highly efficient at transporting electrons, crystallization is prevented when manufacturing a device and current properties of the device are improved due to favorably formed layers. Accordingly, OLED devices having improved power efficiency as well as reduced operating voltage can be manufactured. Chemical formula 1.

Description

Novel compound for organic electronic material and organic electroluminescent device using the same
Technical Field
The present invention relates to a novel compound for an organic electronic material and an organic electroluminescent device using the same.
Technical Field
Among display devices, Electroluminescent (EL) devices are preferable because they provide a wide viewing angle, excellent contrast, and a fast response rate as a self-emissive display device. Issman Kodak (Eastman Kodak) first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer in 1987 [ appl. Phys. Lett.51,913,1987 ].
In the organic EL device, when electric charges are applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), electrons and holes are paired and excitons are generated. Light is emitted by utilizing electroluminescence (phosphorescence or fluorescence) in a state where excitons are deactivated. The organic EL device is operated at a voltage of about 10V and a voltage of about 100 to 10,000cd/m2To emit polarized light. The organic EL device is characterized by emitting light in a spectral range of blue to red by a simple selection of fluorescent materials. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate (e.g., plastic), can operate at a lower voltage (10V or less) than a plasma display panel or an inorganic EL display, consumes less power, and provides excellent color.
In an organic EL device, the most important factor determining its performance (including luminous efficiency and operating life) is an electroluminescent material. Some requirements for electroluminescent materials include high solid-state electroluminescent quantum yield, high electron and hole transport, resistance to decomposition during vacuum deposition, ability to form uniform thin films, and stability.
Organic electroluminescent materials are generally classified into high molecular materials and low molecular materials. From the aspect of molecular structure, the low molecular material includes a metal complex and a metal-free completely organic electroluminescent material. Such electroluminescent materials include chelated complexes such as tris (8-hydroxyquinoline) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis (styrylarylene) derivatives and oxadiazole derivatives. According to these materials, it is reported that light emission in the visible light range from blue to red is obtained.
Three electroluminescent materials (red, green and blue) are employed to realize a full-color Organic Light Emitting Diode (OLED) display. An important problem is to develop red, green and blue electroluminescent materials having high efficiency and long life, thereby improving the overall characteristics of organic Electroluminescent (EL) devices. From the functional aspect, EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be manufactured by doping an EL layer prepared by doping a dopant in a host. Currently, the development of organic EL devices having high efficiency and long life is an urgent target, and in view of the EL performance required for medium to large sized OLED display panels, it is particularly urgent to develop materials having much better EL performance than conventional EL materials.
From this point of view, the development of matrix materials is one of the most important issues to be solved. The properties required for the matrix material (to act as a solvent and energy transporter for the solid state) are high purity and suitable molecular weight to enable vacuum vapor deposition. In addition, the glass transition temperature and the thermal decomposition temperature should be sufficiently high to ensure thermal stability. In addition, the matrix material should have high electrochemical stability to provide long lifetime. Amorphous films are easily formed, which have high adhesion to other adjacent materials, but no interlayer migration.
When an organic EL device is manufactured using a doping technique, energy transfer from host molecules to a dopant in an excited state at a rate of 100% cannot be achieved, and both the host material and the dopant emit light. In particular, in the case of a red light emitting device, since the host material emits light in a wavelength range that is visible higher than the dopant, color purity is deteriorated due to dim light emission of the host material. If this technique is actually used, it is required to increase the light emission life and improve the durability.
Currently, CBP is known to be the most widely used host material for phosphorescent materials. High efficiency OLEDs using hole blocking layers comprising BCP, BAlq, etc. have been reported. Pioneer corporation (japan) and others have reported high performance OLEDs using BAlq derivatives as the matrix.
Figure DEST_PATH_GDA00003186253600021
Although these materials provide good electroluminescent properties, they have some drawbacks, such as degradation during vacuum high temperature deposition processing, due to their low glass transition temperature and poor thermal stability. Since the power efficiency of the OLED is determined by (pi/voltage) × current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce the power consumption of the OLED. In fact, OLEDs using phosphorescent materials provide much better current efficiency (cd/a) than OLEDs using fluorescent materials. However, when existing materials such as BAlq, CBP, etc. are used as a host of a phosphorescent material, there is no significant advantage in power efficiency (lm/W) compared to an OLED using a fluorescent material because of a high driving voltage. In addition, OLED devices do not have a satisfactory operational lifetime. Therefore, development of more stable, higher performance matrix materials is desired.
Disclosure of Invention
Technical problem
Accordingly, an object of the present invention is to provide a compound for an organic electronic material having an excellent backbone (backbone) with improved luminous efficiency and device operating life compared to the existing materials and having appropriate color coordinates, to solve the above problems. It is another object of the present invention to provide a high-efficiency organic electroluminescent device having a long operating life, which uses a compound for organic electro-electronic materials as an electroluminescent material.
Technical scheme
Provided are a compound for an organic electronic material represented by the following chemical formula 1 and an organic electroluminescent device using the same. Since the compound for an organic electronic material of the present invention has superior light emitting efficiency and excellent life property, it can be used to manufacture an OLED device having very superior operation life and low power consumption due to improved power efficiency.
Chemical formula 1
Figure DEST_PATH_GDA00003186253600031
Wherein:
L1and L2Independently represent a single bond, (C3-C30) cycloalkylene, (C6-C30) arylene, or (C3-C30) heteroarylene;
X1and X2Independently represent CR6Or N, other than X1And X2Are all CR6The case (1);
R1to R6Independently represent hydrogen, deuterium,(C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro or hydroxy; and
L1and L2Cycloalkylene, arylene and heteroarylene radicals of (A), and R1To R6The alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl groups of (a) may also be further independently substituted with one or more substituents selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro and hydroxy;
the heteroarylene, heterocycloalkyl and heteroaryl groups comprise one or more heteroatoms selected from B, N, O, S, P (= O), Si and P;
except that1-R1Is the case with hydrogen.
In the present invention, "alkyl", "alkoxy" and other substituents containing an "alkyl" moiety include both straight chain and branched chain types. In the present invention, "cycloalkyl" includes polycyclic hydrocarbon rings such as adamantyl with or without substituents or (C7-C30) bicycloalkyl with or without substituents and monocyclic hydrocarbon rings. In the present invention, "aryl group" means an organic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and may include 4-to 7-membered, specifically 5-or 6-membered, monocyclic or condensed rings, including a plurality of aryl groups connected by single bonds. Specific examples thereof include, but are not limited to, phenyl, naphthyl, biphenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9,10] phenanthryl (triphenylenyl), pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. The naphthyl group includes 1-naphthyl group and 2-naphthyl group, the anthracenyl group includes 1-anthracenyl group, 2-anthracenyl group and 9-anthracenyl group, and the fluorenyl group includes 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group and 9-fluorenyl group. In the present invention, "heteroaryl" refers to an aryl group containing 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring main chain atoms with the remaining aromatic ring main chain atoms being carbon atoms, such as 5-or 6-membered monocyclic heteroaryl and polycyclic heteroaryl groups condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl group includes more than one heteroaryl group connected by a single bond. Heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary ammonium salt. Specific examples thereof include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl (furazanyl), pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like; polycyclic heteroaryl groups such as benzofuranyl (benzofuranyl), benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl (cinnolinyl), quinazolinyl, quinoxalinyl (quinoxalinyl), carbazolyl, phenanthridinyl (phenanthridinyl), benzodioxolyl (benzodioxolyl), and the like; and N-oxides thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.); and quaternary ammonium salts thereof, but not limited thereto.
In the present invention, "(C1-C30) alkyl" includes (C1-C20) alkyl, more specifically (C1-C10) alkyl, and "(C6-C30) aryl" includes (C6-C20) aryl, more specifically (C6-C12) aryl. Likewise, "(C3-C30) heteroaryl" includes (C3-C20) heteroaryl, more specifically (C3-C12) heteroaryl, and "(C3-C30) cycloalkyl" includes (C3-C20) cycloalkyl, more specifically (C3-C7) cycloalkyl. Likewise, "(C2-C30) alkenyl or alkynyl" includes (C2-C20) alkenyl or alkynyl, more specifically (C2-C10) alkenyl or alkynyl.
In addition, the compound for an organic electronic material of the present invention may be represented by the following chemical formula 2 or 3.
Chemical formula 2
Figure DEST_PATH_GDA00003186253600051
Chemical formula 3
Figure DEST_PATH_GDA00003186253600061
Wherein,
L1and L2Independently represent a single bond, (C3-C30) cycloalkylene, (C6-C30) arylene, or (C3-C30) heteroarylene; r1Is (C6-C30) aryl or (C3-C30) heteroaryl; r2To R6Is as defined in chemical formula 1; l is1And L2Cycloalkylene, arylene and heteroarylene radicals of (A), and R1The aryl and heteroaryl groups of (a) may also be further substituted independently by one or more substituents selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono-or di (C1-C30) alkylamino, mono-or di (C6-C30)Arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro and hydroxyl.
R1The heteroaryl group of (a) may be selected from the following structures:
Figure DEST_PATH_GDA00003186253600062
wherein,
y is NR13O or S; z is NR13、CR14R15O or S; r11To R15Independently hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C39 1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C8678) arylsilyl, hydroxy or nitro (30); a is a monocyclic or polycyclic aromatic ring or a monocyclic or polycyclic heteroaromatic ring.
Specifically, R 1 Selected from the following structures:
Figure DEST_PATH_GDA00003186253600071
R2、R3、R4、R5and R6Independently is hydrogen;
L1is a single bond or is selected from the following structures:
Figure DEST_PATH_GDA00003186253600072
(ii) a And
L2is a single bond, phenylene or cyclohexylene.
More specifically, the compounds for organic electronic materials of the present invention may be exemplified by, but are not limited to, the following compounds:
Figure DEST_PATH_GDA00003186253600081
Figure DEST_PATH_GDA00003186253600101
the compound for an organic electronic material of the present invention is prepared by the following scheme 1, but is not limited thereto, and can be prepared using adjacent well-known organic synthesis.
Scheme 1
Wherein,
l of chemical formula 11、L2、X1、X2And R1To R5As defined in formula 1, and X is halogen.
An organic electroluminescent device is provided, which comprises a first electrode; a second electrode; and one or more organic layers interposed between the first and second electrodes, wherein the organic layers include one or more compounds for an organic electronic material represented by chemical formula 1. The organic layer includes an electroluminescent layer in which a compound for the organic electronic material of chemical formula 1 is used as a host material.
When the compound for an organic electronic material of chemical formula 1 is used as a host in an electroluminescent layer, one or more phosphorescent dopants are included. The phosphorescent dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from compounds represented by chemical formula 4:
chemical formula 4
M1L101L102L103
Wherein,
M1is a metal selected from groups 7, 8, 9,10, 11, 13, 14, 15 and 16 of the periodic Table of the elements, a ligand L101、L102And L103Independently selected from the following structures:
Figure DEST_PATH_GDA00003186253600111
wherein R is201To R203Independently represent hydrogen, deuterium, a halogen substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkyl substituted or unsubstituted (C6-C30) aryl or halogen;
R204to R219Independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted mono- (C1-C30) alkylamino group or a substituted or unsubstituted mono- (C1-C30) alkylamino groupUnsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted mono- (C6-C30) arylamino or substituted or unsubstituted di- (C6-C30) arylamino, SF5, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R220to R223Independently represent hydrogen, deuterium, a halogen substituted or unsubstituted (C1-C30) alkyl group or (C1-C30) an alkyl substituted or unsubstituted (C6-C30) aryl group;
R224and R225Independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R224And R225An alicyclic ring or a monocyclic or polycyclic aromatic ring by (C3-C12) alkylene group with or without a condensed ring or (C3-C12) alkenylene group with or without a condensed ring;
R226represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R227to R229Independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen; and
q is
Figure DEST_PATH_GDA00003186253600121
Or
Figure DEST_PATH_GDA00003186253600122
Wherein R is231To R242Independently represent hydrogen, deuterium, (C1-C30) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C5-C30) cycloalkyl, or each of them may beThe spiro ring or fused ring may be formed by linking to adjacent substituents through an alkylene or alkenylene group, or may be linked to R through an alkylene or alkenylene group207Or R208Forming saturated or unsaturated fused rings.
The phosphorescent dopant compound of chemical formula 4 is exemplified by the following compounds, but is not limited thereto.
Figure DEST_PATH_GDA00003186253600131
Figure DEST_PATH_GDA00003186253600141
In the organic electronic device of the present invention, the organic layer may simultaneously include one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds, in addition to the compound for the organic electronic material represented by chemical formula 1. Examples of the arylamine compound or styryl arylamine compound are described in korean patent application nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
Further, in the organic electroluminescent device according to the present invention, the organic layer may further include one or more metals or complex compounds selected from the group consisting of organometallic of group 1 and group 2 of the periodic table, transition metal of fourth and fifth periods, lanthanide series metal and d-transition element, in addition to the compound for organic electronic material represented by chemical formula 1. The organic layer may include an electroluminescent layer and a charge generation layer.
In addition, the organic layer may simultaneously include one or more organic electroluminescent layers emitting blue, green, or red light in addition to the compound for an organic electronic material represented by chemical formula 1 to realize an organic electroluminescent device emitting white light. Examples of the blue, green, or red light-emitting compound may be, but are not limited to, the compounds described in korean patent application nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428.
In the organic electroluminescent device of the present invention, a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer") may be provided on the inner surface of one or both of the pair of electrodes. More specifically, a layer of a metal chalcogenide (including oxide) of silicon or aluminum may be disposed on the anode surface of the electroluminescent medium layer, and a layer of a metal halide or a metal oxide may be disposed on the cathode surface of the electroluminescent medium layer. Thereby obtaining operational stability. For example, the chalcogenide may be SiOx(1≤x≤2)、AlOx(x is more than or equal to 1 and less than or equal to 1.5), SiON, SiAlON and the like. For example, the metal halide may be LiF, MgF2、CaF2Rare earth metal fluorides, and the like. For example, the metal oxide may be Cs2O、Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device of the present invention, it is also preferable to provide a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant on at least one surface of the prepared electrode pair. In this case, the injection and transport of electrons from the mixing region to the electroluminescent medium is promoted as the electron-transporting compound is reduced to an anion. In addition, the hole transport compound is oxidized to form cations, thereby facilitating the injection and transport of holes from the mixing region to the electroluminescent medium. Preferred oxidative dopants include various lewis acids and acceptor compounds. Preferred reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white light-emitting electroluminescent device having two or more electroluminescent layers may be prepared using a reductive dopant layer as a charge generation layer.
Advantageous effects of the invention
Since the compound used in the organic electronic material of the present invention has good luminous efficiency and excellent life property, it can be used to manufacture an OLED device having very excellent operation life.
Modes for carrying out the invention
The invention further describes compounds for use in the organic electronic materials of the invention, methods of making the compounds, and light emitting properties of devices using the compounds. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
[ PREPARATION EXAMPLE 1] preparation of Compound 4
Figure DEST_PATH_GDA00003186253600161
Preparation of Compound 1-1
10g (49.5mmol) of 1-bromo-2-nitrobenzene, 10.2g (59.3mmol) of 1-naphthaleneboronic acid, 200mL of toluene, 50mL of ethanol and 50mL of water were mixed, followed by 2.9g (2.5mmol) of Pd (PPh)3)4And 20.5g (148.3mmol) of potassium carbonate. The mixture was stirred at 120 ℃ for 5 hours, then cooled to room temperature, after which the reaction was quenched with 40mL of aqueous ammonium chloride. The resulting mixture was extracted with 500mL of EA, then washed with 100mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, reduced pressure treatment to remove the organic solvent, and then purification using silica gel column chromatography, thereby obtaining compound 1-1(10g, 81%).
Preparation of Compounds 1-2
10g (40.1mmol) of Compound 1-1 was dissolved in 100mL of 1, 2-dichloro-benzeneTo benzene, 100mL of triethoxyphosphine was then added. The reaction mixture was stirred at 150 ℃ for 20 hours, then cooled to room temperature and the solvents, 1, 2-dichlorobenzene and triethoxyphosphine, were removed using vacuum distillation. The remaining organic material was extracted with 300mL of EA and then washed with 40mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, reduced pressure treatment to remove the organic solvent, and then purification using silica gel column chromatography, thereby obtaining compound 1-2(7g, 80%).
Preparation of Compounds 1-3
20g (92mmol) of the compound 1-2 and 43.5g (184mmol) of 1-bromo-4-iodobenzene are dissolved in 500mL of toluene, and 8.8g (46mmol) of CuI, 6.2mL (92mmol) of diaminoethane and 58.7g (276mmol) of K are added3PO4And then refluxed for 30 hours. The reaction mixture was cooled to room temperature, after which the reaction was terminated with 50mL of 2.0M aqueous hydrochloric acid, and the resulting mixture was extracted with 1L of EA, followed by washing with 200mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, reduced pressure treatment to remove the organic solvent, followed by purification using silica gel column chromatography, thereby obtaining compounds 1-3(19g, 56%).
Preparation of Compounds 1-4
19g (51mmol) of compound 1-3 was dissolved in 250mL THF, then cooled to-78 deg.C, after which 24.5mL n-BuLi (2.5M in hexane) was added thereto at-78 deg.C. The mixture was stirred at-78 ℃ for 1 hour, 8.5mL of B (OMe) were added3After stirring for 2 hours, the reaction was terminated with 100mL of an aqueous ammonium chloride solution. Subsequently, the resulting mixture was extracted with 500mL of EA, followed by washing with 100mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, treatment under reduced pressure to remove the organic solvent, and recrystallization were carried out to obtain compounds 1 to 4(14g, 81%).
Preparation of Compound 2-1
50g (247mmol) of fluoranthene were dissolved in 1L of nitrobenzene and slowly added dropwise thereto12mL (234.7mmol) of bromine diluted with 200mL of nitrobenzene were added. After completion of dropwise addition to the solution, the reaction solution was stirred at room temperature for 20 hours. To the reaction solution was added 500mL of a saturated aqueous solution of sodium thiosulfate chloride to terminate the reaction. The resulting mixture was extracted with 3L of EA and then washed with 1L of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, treatment under reduced pressure to remove the organic solvent, filtration using silica gel, and recrystallization were performed to obtain compound 2-1(65g, 94%).
Preparation of Compound 2-2
24.5g (87.1mmol) of Compound 2-1 was dissolved in 500mL THF, cooled to-78 deg.C, and 45mL n-BuLi (2.5M in hexane) was added, followed by stirring for 1 hour. Subsequently, 15mL of B (OMe) was added to the mixture3And stirred for 2 hours, and the reaction was terminated with 250mL of an aqueous ammonium chloride solution. The resulting mixture was extracted with 1L EA, then washed with 200mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, treatment under reduced pressure to remove the organic solvent, followed by recrystallization, gave compound 2-2(14g, 65%).
Preparation of Compounds 2-3
Mixing 8.1g (40.6mmol) of 2, 4-dichloroquinazoline, 10g (40.6mmol) of the compound 2-2, 200mL of toluene, 50mL of ethanol and 50mL of water, then adding 1.9g (1.64mmol) of Pd (PPh)3)4And 12.9g (122mmol) of K2CO3. The mixture was stirred at 120 ℃ for 5 hours and cooled to room temperature, after which the reaction was quenched with 200mL of aqueous ammonium chloride. The resulting mixture was extracted with 500mL of EA, then washed with 50mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, treatment under reduced pressure to remove the organic solvent, filtration using silica gel, and recrystallization were performed to obtain compound 2-3(10g, 68%).
Preparation of Compound 4
5.0g (13.7mmol) of Compound 2-3 and 5.54g (16.4 m)mol) of the compounds 1 to 4 were mixed with 100mL of toluene, 20mL of ethanol and 20mL of water, and then 1.6g (1.4mmol) of Pd (PPh) was added thereto3)4And 5.7g (41.1mmol) of K2CO3. The mixture was stirred at 120 ℃ for 5 hours and cooled to room temperature, after which the reaction was quenched with 20mL of aqueous ammonium chloride. The resulting mixture was extracted with 250mL of EA, then washed with 30mL of distilled water. The resulting organic layer was extracted with anhydrous MgSO4Drying, treatment under reduced pressure to remove the organic solvent, filtration using silica gel, and recrystallization were performed to obtain compound 4(5.9g, 69%).
MS/FAB 621.22 (Experimental value), 621.73 (calculated value)
Example 1 fabrication of OLED device Using the Compound for organic electronic Material of the present invention
The OLED device is manufactured using the compound for organic electronic material of the present invention. First, a transparent electrode ITO film (15 Ω/□) (purchased from Samsung-Corning) for OLED made of glass was ultrasonically cleaned with trichloroethylene, acetone, ethanol, and distilled water in this order, and stored in isopropyl alcohol before use. Then, the ITO substrate was set in a substrate holder (holder) of a vacuum deposition apparatus, 4' -tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA) was placed in a cell (cell) of the vacuum deposition apparatus, and then, the inside of the cell was evacuated to a degree of vacuum of up to 10-6And (4) supporting. Next, a current was applied to the cell to evaporate 2-TNATA, thereby depositing a hole injection layer having a thickness of 60nm on the ITO substrate. Subsequently, N-di (α -naphthyl) -N, N-diphenyl-4, 4' -diamine (NPB) was added to another cell of the vacuum deposition apparatus, and NPB was evaporated by applying a current to the cell, thereby depositing a hole transport layer with a thickness of 20nm on the hole injection layer. In addition, at 10-6The inventive compound 3 purified by vacuum sublimation was charged in a chamber of a vacuum vapor deposition apparatus as a matrix material, and bis- (1-phenylisoquinolinyl) iridium (III) acetylacetonate ((piq) as an electroluminescent dopant was added2Ir (acac)) into another cell. Then, at different speedsThe two materials are evaporated so that a 30nm thick electroluminescent layer is vapor deposited on the hole transport layer with a doping of 4 to 20 wt.%. After that, tris (8-hydroxyquinoline) -aluminum (III) (Alq) as an electron transport layer was deposited on the electroluminescent layer to a thickness of 20 nm. Then, after depositing 1-2nm thick lithium quinolinate (Liq) as an electron injection layer, another vacuum deposition apparatus was used to form a 150 nm thick Al cathode to manufacture an OLED.
Each compound used in the OLED was prepared at 10 deg.C-6Purifying by vacuum sublimation under the condition of torr.
As a result, the current flow at a voltage of 6.5V was 14.0mA/cm21052cd/cm transmission2Red light of (2).
[ example 2]
An OLED device was fabricated using the same method as in example 1, except that compound 4 was used as a host material in the electroluminescent layer.
As a result, the current flow at a voltage of 7.5V was 14.0mA/cm2Transmitting 1060cd/cm2Red light of (2).
[ example 3]
An OLED device was fabricated using the same method as in example 1, except that compound 14 was used as the host material in the electroluminescent layer.
As a result, the current flow at a voltage of 6.8V was 14.1mA/cm2Transmitting 1030cd/cm2Red light of (2).
[ example 4]
An OLED device was fabricated using the same method as in example 1, except that compound 20 was used as the host material in the electroluminescent layer.
As a result, the current flow at a voltage of 6.4V was 14.2mA/cm2Emitting 1048cd/cm2Red light of (2).
Comparative example 1
An OLED device was prepared by the same method as described in example 1, except that 4,4' -bis (carbazol-9-yl) biphenyl (CBP) was used as a host material in place of the compound of the present invention in the electroluminescent layer, and bis (2-methyl-8-quinolinato) (p-phenyl-phenolato) aluminum (III) (BAlq) was used as a hole blocking layer.
As a result, the current flow at a voltage of 7.5V was 15.3mA/cm2Transmitting 1000cd/cm2Red light of (2).
The compound for an organic electronic material of the present invention has superior characteristics compared to conventional materials. In addition, the organic electroluminescent device using the compound of the organic electronic material with the fluoranthene substituent as the host material has excellent electroluminescent characteristics, and the driving voltage is reduced by 0.7-1.2V, so that the power efficiency is improved and the power consumption is improved.
Although the preferred embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims.
Industrial applicability
Since the compound for an organic electronic material of the present invention has good luminous efficiency and excellent life property, it can be used to manufacture an OLED device having very excellent operation life.

Claims (10)

1. A compound for an organic electronic material represented by the following chemical formula 1:
chemical formula 1
Figure DEST_PATH_FDA00003186253500011
Wherein:
L1and L2Independently represent a single bond, (C3-C30) cycloalkylene, (C6-C30) arylene, or (C3-C30) heteroarylene;
X1and X2Independently represent CR6Or N, other than X1And X2Are all CR6The case (1);
R1to R6Independently represent hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C30-C30) alkylsilyl, di (C30-C30) alkyl (C30-C30) arylsilyl, tri (C30) arylsilyl, nitro (C30) arylsilyl, or nitro; and
L1and L2Cycloalkylene, arylene and heteroarylene radicals of (A), and R1To R6The alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl groups of (a) may also be independently further substituted with one or more substituents selected from the group consisting of: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro and hydroxy;
the heteroarylene, heterocycloalkyl and heteroaryl groups comprise one or more heteroatoms selected from B, N, O, S, P (= O), Si and P;
except that1-R1Is the case with hydrogen.
2. The compound for an organic electronic material according to claim 1, wherein the compound is represented by the following chemical formula 2 or 3:
chemical formula 2
Figure DEST_PATH_FDA00003186253500021
Chemical formula 3
Wherein,
L1and L2Independently represent a single bond, (C3-C30) cycloalkylene, (C6-C30) arylene, or (C3-C30) heteroarylene; r1Is (C6-C30) aryl or (C3-C30) heteroaryl; r2To R6Is as defined in claim 1; l is1And L2Cycloalkylene, arylene and heteroarylene radicals of (A), and R1The aryl and heteroaryl groups of (a) may also be further substituted independently by one or more substituents selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono-or di (C1-C30) alkylamino, mono-or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro and hydroxy.
3. The compound for organic electronic material according to claim 1, wherein R is1Is a heteroaryl group selected from the following structures:
wherein,
y is NR13O or S; z is NR13、CR14R15O or S; r11To R15Independently hydrogen, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C39 1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C8678) arylsilyl, hydroxy or nitro (30); a is a monocyclic or polycyclic aromatic ring or a monocyclic or polycyclic heteroaromatic ring.
4. The compound for organic electronic material according to claim 1, wherein R is1Selected from the following structures:
Figure DEST_PATH_FDA00003186253500032
Figure DEST_PATH_FDA00003186253500041
R2、R3、R4、R5and R6Independently is hydrogen;
L1is a single bond or is selected from the following structures:
Figure DEST_PATH_FDA00003186253500042
(ii) a And
L2is a single bond, phenylene or cyclohexylene.
5. The compound for organic electronic material according to claim 1, wherein the compound is selected from the group consisting of:
Figure DEST_PATH_FDA00003186253500043
Figure DEST_PATH_FDA00003186253500061
6. an organic electroluminescent device comprising the compound for organic electronic materials as claimed in any one of claims 1 to 5.
7. The organic electroluminescent device of claim 6, wherein the device comprises a first electrode; a second electrode; and one or more organic layers interposed between the first and second electrodes, wherein the organic layers comprise one or more compounds for an organic electronic material and one or more phosphorescent dopants.
8. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds, or one or more metals or complex compounds selected from the group consisting of organometallics of group 1, group 2 of the periodic table of elements, transition metals of the fourth and fifth periods, lanthanoid metals, and d-transition elements.
9. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generation layer.
10. The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more organic electroluminescent layers emitting red, green or blue light to emit white light.
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