CN112480089A - Novel compound and organic light emitting device comprising the same - Google Patents

Novel compound and organic light emitting device comprising the same Download PDF

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CN112480089A
CN112480089A CN202011398980.7A CN202011398980A CN112480089A CN 112480089 A CN112480089 A CN 112480089A CN 202011398980 A CN202011398980 A CN 202011398980A CN 112480089 A CN112480089 A CN 112480089A
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nitrile
nitro
amino
halogen
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咸昊完
金奉记
金成勋
安贤哲
金熙宙
金东骏
李萤振
林东焕
安慈恩
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Dongjin Semichem Co Ltd
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Priority claimed from CN201580071738.XA external-priority patent/CN107108585B/en
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Abstract

The novel compound of the present invention can be suitably used for a light emitting layer, an electron injection layer, an electron transport layer or a hole blocking layer of an organic light emitting device, and the novel compound of the present invention and a carbazole derivative are used together as a host of the organic light emitting device, so that the wavelength of the exciplex can be appropriately adjusted, and the efficiency and lifetime of the organic light emitting device can be maximized.

Description

Novel compound and organic light emitting device comprising the same
This application is a divisional application of chinese patent application having an application date of 2015, 12/29, No. of "201580071738. X", the name of the invention of "novel compound and organic light emitting device comprising the same", and the original application is a chinese national phase application of international application PCT/KR 2015/014444.
Technical Field
The present invention relates to a novel compound and an organic light emitting device comprising the same. The present invention also relates to an organic light-emitting device which can suitably adjust the wavelength of the exciplex and maximize the efficiency and lifetime by using the novel compound and a carbazole derivative as a host.
Background
Recently, organic light emitting devices capable of low-voltage driving by self-light emission type have excellent viewing angle, contrast ratio, and the like, compared to Liquid Crystal Displays (LCDs) which are the mainstream of flat panel display devices, do not require a backlight, can be reduced in weight and thickness, are advantageous in power consumption, and have a wide color reproduction range, and thus have attracted attention as next-generation display devices.
In the organic light emitting device, materials used as the organic layer are broadly classified into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like, according to functions.
The light-emitting material may be classified into a high-molecular material and a low-molecular material according to molecular weight, a fluorescent material in a singlet excited state derived from electrons and a phosphorescent material in a triplet excited state derived from electrons according to a light-emitting mechanism, and blue, green and red light-emitting materials and yellow and orange light-emitting materials required for exhibiting a better natural color may be classified according to light-emitting colors. Further, in order to increase color purity and increase light emission efficiency by energy transfer, a host/dopant species may be used as the light-emitting substance. The principle is that when a small amount of dopant having a smaller energy band gap and superior light emission efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant, and light with high efficiency is emitted. At this time, the wavelength of the host is shifted to the wavelength range of the dopant, and thus light of a desired wavelength can be obtained according to the kind of the dopant and the host used.
As is well known, there are many compounds as substances used in such organic light emitting devices, but in the case of organic light emitting devices using substances well known so far, it is difficult to put them into practical use because of high driving voltage, low efficiency and short lifetime.
Therefore, efforts are continuously made to develop an organic light emitting device having low voltage driving, high luminance, and long life span using a substance having excellent characteristics.
Disclosure of Invention
Technical problem
In order to solve the above problems, an object of the present invention is to provide a compound which can be used as a light emitting host or an electron injecting material, an electron transporting material or a hole blocking material of an organic light emitting device, and which can ensure a long life, high efficiency, low voltage, high Tg, and thin film stability when applied to an organic light emitting device, and in particular, can maximize the efficiency and life of the organic light emitting device by exciplex formation and energy transfer to a dopant.
It is another object of the present invention to provide an organic light emitting device including the above compound, which has a long lifetime, high efficiency, low voltage, high Tg, and thin film stability, and in particular, which has maximized efficiency and lifetime through exciplex formation and energy transfer to a dopant.
Means for solving the problems
In order to achieve the above object, the present invention provides a compound represented by the following chemical formula 1:
chemical formula 1
Figure BDA0002816385260000031
In the above chemical formula 1, X represents N or CR independently of each other0At least 2 of X are N, wherein R0Represents hydrogen; heavy hydrogen; by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
y is O, and Y is O,
R1and R2And R3Each independently represents hydrogen; heavy hydrogen; halogen; an amino group; nitrile group and nitro group; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); substituted or not by deuterium, halogen, amino, nitrile, nitroSubstituted C6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
m and n independently represent an integer of 0 or 2.
Also, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1.
ADVANTAGEOUS EFFECTS OF INVENTION
The compound of the present invention and the organic light-emitting device to which the above compound is applied have the following characteristics.
1. The triphenylene structure introduced into the compound has excellent durability against electrons and holes, thereby ensuring a long life of the organic light-emitting device.
2. By maintaining triplet energy suitable as green phosphorescence, high efficiency of the organic light emitting device is ensured.
3. Introduction of a heteroaryl group into the compound facilitates electron injection and transport, thereby ensuring low-voltage driving and high efficiency of the organic light-emitting device.
4. High Tg can be formed by Fused rings (Fused rings) within the compound, improving film stability when driving an organic light emitting device.
5. When applied to an organic light-emitting device, the novel compound (light-emitting host 1) and the carbazole derivative (light-emitting host 2) of the present invention facilitate electron injection and transport, and can realize low-voltage driving and high efficiency.
6. When applied to an organic light-emitting device, the novel compound (light-emitting host 1) of the present invention and the carbazole derivative (light-emitting host 2) are used to form an exciplex and transfer energy to a dopant to maximize efficiency, thereby realizing high efficiency and long lifetime.
Drawings
Fig. 1 schematically shows a cross-section of an Organic Light Emitting Diode (OLED) according to an embodiment of the present invention.
Description of reference numerals
10: substrate 11: anode
12: hole injection layer 13: hole transport layer
14: light-emitting layer 15: electron transport layer
16: cathode electrode
Detailed Description
The compound of the present invention is represented by the following chemical formula 1.
Chemical formula 1
Figure BDA0002816385260000051
In the above chemical formula 1, X represents N or CR independently of each other0At least 2 of X are N, wherein R0Represents hydrogen; heavy hydrogen; by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
y is O, and Y is O,
R1and R2And R3Each independently represents hydrogen; heavy hydrogen; halogen; an amino group; nitrile group and nitro group; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
y is O, and Y is O,
R1and R2And R3Each independently represents hydrogen; heavy hydrogen; halogen; an amino group; nitrile group and nitro group; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro、C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
m and n each independently represent an integer of 0 or 2, and specifically, m and n are 1.
In the present invention, the compound represented by the above chemical formula 1 may be one of the compounds represented by the following chemical formulas 1-1 to 1-6.
Chemical formula 1-1
Figure BDA0002816385260000071
Chemical formula 1-2
Figure BDA0002816385260000072
Chemical formulas 1 to 3
Figure BDA0002816385260000073
Chemical formulas 1 to 4
Figure BDA0002816385260000074
Chemical formulas 1 to 5
Figure BDA0002816385260000075
Chemical formulas 1 to 6
Figure BDA0002816385260000076
In the above chemical formula, X, Y is as defined in chemical formula 1.
In the present invention, specific examples of the compound represented by the above chemical formula 1 are as follows:
Figure BDA0002816385260000081
Figure BDA0002816385260000091
Figure BDA0002816385260000101
Figure BDA0002816385260000111
the compound of chemical formula 1 of the present invention has excellent hole and electron transport properties, excellent light emitting efficiency, high color purity, high efficiency, and long lifetime, and can exhibit excellent device properties when applied to an organic light emitting device. Also, the compound of chemical formula 1 has a LUMO level where electron injection is easy, has excellent electron transport characteristics, and can have excellent low voltage, high efficiency, stability due to high Tg, and long life when applied to an electron injection layer or an electron transport layer of an organic light emitting device.
Also, the compound of the present invention may be prepared by a reaction formula represented by one of the following reaction formulae 1 to 3:
reaction scheme 1
Figure BDA0002816385260000121
Reaction formula 2
Figure BDA0002816385260000122
Reaction formula 3
Figure BDA0002816385260000123
In the above reaction formula, X and Y are as defined in chemical formula 1.
Also, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1 in an organic layer. At this time, the compound of the present invention is specifically used as a light emitting host, an electron injecting material, an electron transporting material, or a hole blocking substance alone, or may be used together with a known compound. More specifically, the compound of the present invention is used as a light-emitting host, and at this time, it is preferable that a light-emitting compound represented by the following chemical formula 2 (light-emitting host 2) is used as a light-emitting host together with a compound represented by the chemical formula 1 of the present invention (light-emitting host 1).
Chemical formula 2
Figure BDA0002816385260000131
In the above chemical formula 2, r1To r8Each independently represents hydrogen; heavy hydrogen; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
ar is composed of heavy hydrogen, halogen, amino, nitrile, nitro and C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
m is an integer of 1 to 4,
when m is 2 to 4, Ar and r1～r8Can be connected.
Specifically, the compound of the above chemical formula 2 is preferably one of the compounds represented by the following chemical formulas 2-1 to 2-7.
Chemical formula 2-1
Figure BDA0002816385260000141
Chemical formula 2-2
Figure BDA0002816385260000142
Chemical formula 2-3
Figure BDA0002816385260000143
Chemical formula 2-4
Figure BDA0002816385260000151
Chemical formula 2-5
Figure BDA0002816385260000152
Chemical formula 2-6
Figure BDA0002816385260000153
Chemical formula 2-7
Figure BDA0002816385260000154
In the above formula, Ar1、Ar2、Ar3、Ar4、Ar5Each independently as defined above for Ar of formula 2,
R1、R2、R3、R4r of the above chemical formula 21To r8The definition of the content of the compound is as follows,
a. b independently represents an integer of 0 to 3.
More specifically, the compound of chemical formula 2 is preferably a compound represented by chemical formula 2-3, in which case the carbazole-containing phenyl moiety included in the chemical formula includes a substituted structure therebetween, whereby the highest occupied molecular orbital is larger, hole injection is easier, and the driving voltage can be reduced.
When the organic light emitting device of the present invention uses the compound of chemical formula 2 as described above as a light emitting host, the mixing ratio of chemical formula 1 and chemical formula 2 is preferably 9:1 to 2:8 by weight. When falling within the above range, the organic light emitting device may have a low driving voltage and may have high efficiency and a long life span, but when exceeding the above range and the compound represented by chemical formula 2 is excessive, hole injection and transport are excessive, thereby reducing efficiency and life span.
Specific compounds of chemical formula 2 are as follows.
Figure BDA0002816385260000161
Figure BDA0002816385260000171
Figure BDA0002816385260000181
Figure BDA0002816385260000191
Figure BDA0002816385260000201
In the present invention, the wavelength of the exciplex formed by the above-mentioned luminescent hosts 1 and 2 can be formed to 400-650nm, the wavelength of the exciplex formed by selecting the luminescent hosts 1 and 2 to form 450-500nm can be used for the green organic luminescent device, and the wavelength of the exciplex formed by 500-630nm can be used for the red organic luminescent device.
Specifically, the wavelength of the exciplex formed by the combination of the light-emitting hosts is preferably shorter than the light-emitting wavelength of the guest molecule dopant in the light-emitting layer. In this way, the phosphorescent dopant absorbs the exciplex composed of the luminescent host combination to emit light, and thus, energy transfer is efficiently performed, so that efficiency can be maximized, and high efficiency and long lifetime can be achieved.
Further, the organic light emitting device of the present invention may be manufactured using a known method for manufacturing an organic light emitting device, in addition to 1 or more organic layers including the compound represented by the above chemical formula 1, and the method for manufacturing an organic light emitting device is described as follows as an example.
The organic light emitting device may include 1 or more organic layers such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL) between an anode (anode) and a cathode (cathode).
First, an anode electrode substance having a high work function is deposited on the substrate to form an anode. In this case, the substrate used in a conventional organic light-emitting device can be used, and in particular, a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance is preferably used. As the anode electrode material, transparent and highly conductive Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or tin oxide (SnO) can be used2) Zinc oxide (ZnO), and the like. The substance for an anode electrode can be deposited by a conventional anode formation method, specifically, by a deposition method or a sputtering method.
Next, a hole injection layer can be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett). As the hole injection layer material, a known hole injection layer material can be used, and as an example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4356429, or a starburst amine derivative TCTA (4,4',4 ″ -tris (N-carbazolyl) triphenylamine), m-MTDATA (4,4',4 ″ -tris (3-toluidino) triphenylamine), m-MTDAPB (4,4',4 ″ -tris (3-toluidino) phenoxybenzene), HI-406(N1, N1' - (biphenyl-4, 4' -diyl) bis (N1- (naphthalene-1-yl) -N4, N4-diphenylbenzene-1, 4-diamine), or the like can be used.
Next, a hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, casting, or LB.
The hole transport layer material can be used by mixing a known hole transport layer material. Specifically, as the known hole transporting layer substance, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, or a conventional amine derivative having an aromatic condensed ring such as N, N ' -bis (3-methylphenyl) -N, N ' -bisphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD) or N, N ' -bis (naphthalene-1-yl) -N, N ' -bisphenylbenzidine (α -NPD) can be used.
Then, a light-emitting layer material can be formed on the hole-transporting layer by a method such as vacuum deposition, spin coating, casting, or LB. When the light-emitting layer is formed by the vacuum deposition method, the deposition conditions are generally selected within the range of conditions almost the same as those for forming the hole injection layer, depending on the compound used.
Further, the above-mentioned light-emitting layer material may use a known host or dopant, and it is preferable to use a compound represented by chemical formula 1 of the present invention as a host, specifically, it is preferable to use a compound represented by chemical formula 1 of the present invention (light-emitting host 1) and a compound represented by chemical formula 2 (light-emitting host 2) at the same time, and more specifically, it is preferable to use a compound represented by chemical formula 1 of the present invention (light-emitting host 1) and compounds represented by chemical formulae 2 to 3 (light-emitting hosts 2) at the same time. As the light-emitting host, a dopant substance is preferably selected and used so that an exciplex wavelength formed by combining the compound represented by chemical formula 1 (light-emitting host 1) and the compound represented by chemical formula 2 (light-emitting host 2) of the present invention can be formed at a wavelength shorter than the light-emitting wavelength of the dopant of the light-emitting layer.
The fluorescent dopant that can be used may be IDE102 or IDE105, or BD142 (N) available from Nippon light-emitting company (Idemitsu corporation)6,N12-bis (3, 4-dimethylphenyl) -N6,N12-two pod bases
Figure BDA0002816385260000221
6, 12-diamine) as phosphorescent dopant, green phosphorescent dopant Ir (ppy) can be co-vacuum evaporated (doped)3(tris (2-phenylpyridine) iridium), a blue phosphorescent dopant F2Irpic (iridium (III), bis [4, 6-difluorophenyl) -phenylpyridine-N, C2']Picolinate), UDC corporation red phosphorescent dopant RD61, and the like.
Further, a light-emitting auxiliary layer may be provided between the hole transport layer and the light-emitting layer, and a known material may be used as a material of the light-emitting auxiliary layer.
Further, in order to prevent diffusion of triplet excitons or holes into the electron transport layer, a hole blocking material (HBL) may be laminated on the light emitting layer by a vacuum evaporation method or a spin coating method. The hole-blocking substance that can be used at this time is not particularly limited, but any known substance that is used as a hole-blocking material can be selected and used. Examples of the known materials include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and the hole-blocking materials described in jp 11-329734 a1 a, and typical examples thereof include Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenoxide) and phenanthroline (phenanthroline) compounds (e.g., BCP (bathocuproine) from UDC).
In the case where the electron transport layer is formed on the light emitting layer formed as described above, the electron transport layer may be formed by a method such as vacuum evaporation, spin coating, or casting.
The electron transport layer material may be a compound represented by the above chemical formula 1 or a known material, and as an example of the known material, a quinoline derivative, particularly tris (8-quinolinato) aluminum (Alq), may be used3) Or ET4(6,6'- (3, 4-dioxido-1, 1-dimethyl-1H-silole-2, 5-diyl) di-2, 2' -bipyridine).
An Electron Injection Layer (EIL) which is a substance having a function of easily injecting electrons from the cathode may be stacked on the electron transport layer, and the compound represented by the above chemical formula 1, LiF, NaCl, CsF, Li, or the like may be used as the electron injection layer material2O, BaO, etc.
Finally, a metal for forming a cathode is formed on the electron transport layer or the electron injection layer by a method such as vacuum deposition or sputtering, and is used as a cathode. Among them, as the metal for forming the cathode, a metal having a low work function, an alloy, a conductive compound, and a mixture thereof can be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. In addition, a transmissive cathode using ITO or IZO may be used to obtain a top-emitting device.
The organic light-emitting device not only can realize the organic light-emitting device with an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode structure, but also can realize the structure of the organic light-emitting device with various structures, and can form 1 layer or 2 layers of intermediate layers according to the requirement.
As described above, the thickness of each organic layer formed according to the present invention can be adjusted according to the desired degree, specifically 10 to 1000nm, more specifically 20 to 150nm is preferable.
In the present invention, the organic layer including the compound represented by chemical formula 1 has an advantage of uniform surface and excellent morphological stability since the thickness of the organic layer can be adjusted on a molecular basis.
The organic light emitting device of the present invention has excellent durability against electrons and holes, ensures long life, low voltage driving, high efficiency, and excellent thin film stability, and the novel compound (light emitting host 1) and carbazole derivative (light emitting host 2) of the present invention facilitate electron injection and transport, realize low voltage driving, high efficiency, maximize efficiency by exciplex formation and energy transfer to a dopant, and realize high efficiency and long life.
Hereinafter, specific examples are set forth to aid in understanding the present invention, but the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples.
Synthesis of chemical formula 1
Synthesis of intermediate I1
Figure BDA0002816385260000241
Synthesis of I1-1
In a round-bottomed flask, 8.4g of triphenylen-2-yl-2-boronic acid (triphenylen-2-ylboronic acid) and 2,8-dibromodibenzo [ b, d ]]Furan (2, 8-dibromoibenzo [ b, d ]]furan)10.0g was dissolved in 280ml of toluene, and K was added2CO3(2M)46ml and Pd (PPh)3)4After 1.1g, stirring was carried out under reflux. The reaction was confirmed by Thin Layer Chromatography (TLC), and water was added to complete the reaction. Extracting the organic layer with MC and carrying outAfter filtration under reduced pressure, 8.1g (yield 56%) of intermediate I1-1 was obtained.
Synthesis of I1
The intermediate I1-18.1 g, bis (pinacolato) diboron 5.6g, Pd (dppf) Cl20.06g and KOAc 5.04g were dissolved in 200ml of 1,4-Dioxane (1,4-Dioxane), followed by stirring under reflux. The reaction was confirmed by TLC, and the organic layer was MC extracted and column purified to obtain 7.0g (yield 79%) of intermediate I1.
Synthesis of intermediate I2
Figure BDA0002816385260000251
Intermediate I2 was synthesized in the same manner as in the synthesis of intermediates I1-1 and I1, using 4,6-dibromodibenzo [ b, d ] furan (4,6-dibromodibenzo [ b, d ] furan) in place of 2,8-dibromodibenzo [ b, d ] furan (2,8-dibromodibenzo [ b, d ] furan). (yield 50%)
Synthesis of intermediate I3
Figure BDA0002816385260000252
Synthesis of I3-1
In a round-bottomed flask, 15.0g of 2-bromotriphenylene (2-bromotriphenylene) and dibenzo [ b, d ]]Furan-4-ylboronic acid (dibenzo [ b, d ]]furan-4-ylboronic acid)10.5g were dissolved in 380ml of toluene, and K was added2CO3(2M)75ml and Pd (PPh)3)4After 1.7g, stirring was carried out under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. The organic layer was extracted with MC, filtered under reduced pressure and then recrystallized to obtain 15.2g (yield 66%) of Compound I3-1.
Synthesis of I3-2
After 3-115.0 g of the intermediate I was dissolved in 150ml of Dimethylformamide (DMF), a solution in which 7.5g of N-Bromosuccinimide (N-Bromosuccinimide) was dissolved was slowly dropped into 70ml of DMF, and the mixture was stirred for 16 hours. The reaction was confirmed by TLC, precipitated with distilled water and recrystallized to obtain 13.5g (yield 75%) of intermediate I3-2.
Synthesis of I3
The intermediate I1-113.5 g, bis (pinacolato) diboron 9.4g, Pd (dppf) Cl20.1g of KOAc (8.4 g) was dissolved in 350ml of 1,4-Dioxane (1,4-Dioxane), followed by stirring under reflux. The reaction was confirmed by TLC, and the organic layer was MC extracted and column purified to obtain 10.8g (73% yield) of intermediate I3.
Synthesis of intermediate I4
Figure BDA0002816385260000261
Intermediate I4 was synthesized in the same manner as in the synthesis of intermediates I3-1 and I3, using 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-bromotriphenylene (2-bromotriphenylene). (yield 47%)
Synthesis of chemical formula 1
Compound 1-1
Figure BDA0002816385260000262
In a round-bottomed flask, intermediate I15.0g and 2.8g of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine) were dissolved in 120ml of toluene, and K was added2CO3(2M)15ml and Pd (PPh)3)4After 0.33g, stirring was carried out under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. The organic layer was extracted with MC, filtered under reduced pressure, and then recrystallized to obtain 4.0g (yield: 67%) of Compound 1-1.
m/z：625.22(100.0％)、626.22(49.0％)、627.22(12.3％)、628.23(1.8％)、626.21(1.1％)
Compound 1-2
Figure BDA0002816385260000271
Compound 1-2 was synthesized by the same method as that of Compound 1-1 described above, using 4-chloro-2, 6-diphenylpyrimide instead of 2-chloro-4, 6-diphenylyl-1, 3, 5-triazine.
(yield 62%)
m/z：624.22(100.0％)、625.22(50.5％)、626.23(12.3％)、627.23(2.1％)
Compounds 1 to 3
Figure BDA0002816385260000272
Compound 1-3 was synthesized by the same method as that of Compound 1-1 described above, using 2-chloro-4,6-diphenylpyrimidine in place of 2-chloro-4, 6-diphenylyl-1, 3, 5-triazine.
(yield 65%)
m/z：624.22(100.0％)、625.22(50.5％)、626.23(12.3％)、627.23(2.1％)
Compounds 1 to 4
Figure BDA0002816385260000281
Compounds 1-4 were synthesized by the same method as described for Compound 1-1 above, using intermediate I2 instead of intermediate I1. (yield 59%)
m/z：625.22(100.0％)、626.22(49.0％)、627.22(12.3％)、628.23(1.8％)、626.21(1.1％)
Compounds 1 to 5
Figure BDA0002816385260000282
Compound 1-5 was synthesized in the same manner as Compound 1-1 described above, using intermediate I2 and 4-chloro-2, 6-diphenylpyrimide in place of intermediate I1 and 2-chloro-4, 6-diphenylyl-1, 3, 5-triazine. (yield 63%)
m/z：624.22(100.0％)、625.22(50.5％)、626.23(12.3％)、627.23(2.1％)
Synthesis of Compounds 1-6
Figure BDA0002816385260000291
Compounds 1 to 6 were synthesized in the same manner as in the above-mentioned Compound 1-1, using intermediate I2 and 2-chloro-4, 6-diphenylpyrimide in place of intermediate I1 and 2-chloro-4, 6-diphenylyl-1, 3, 5-triazine. (yield 60%)
m/z：624.22(100.0％)、625.22(50.5％)、626.23(12.3％)、627.23(2.1％)
Compounds 1 to 7
Figure BDA0002816385260000292
Compounds 1-7 were synthesized by the same method as described for Compound 1-1 above, using intermediate I3 instead of intermediate I1. (yield 64%)
m/z：625.22(100.0％)、626.22(49.0％)、627.22(12.3％)、628.23(1.8％)、626.21(1.1％)
Compounds 1 to 8
Figure BDA0002816385260000293
Compounds 1 to 8 were synthesized in the same manner as described for Compound 1-1, using intermediate I4 and 2-chloro-4,6-diphenyl-1,3, 5-triazene in place of intermediate I1 and 2-bromotriphenylene. (yield 60%)
m/z：625.22(100.0％)、626.22(49.0％)、627.22(12.3％)、628.23(1.8％)、626.21(1.1％)
Synthesis of chemical formula 2
Compound 2-1
Figure BDA0002816385260000301
In a round-bottom flask, adding 3-phenyl-9H-carbo5.0g of oxazole (3-phenyl-9H-carbazole), 3'-dibromo-1,1' -biphenyl (3,3'-dibromo-1,1' -biphenyl)3.21g, t-BuONA2.96g, Pd2(dba)3 0.75g、(t-Bu)30.5ml of P was dissolved in 100ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 8.64g (yield 66%) of compound 2-1.
m/z：636.26(100.0％)、637.26(52.3％)、638.26(13.6％)、639.27(2.2％)
Compound 2-2
Figure BDA0002816385260000302
In a round bottom flask, 9- ([1,1':3', 1' -terphenyl) was placed]-5' -yl) -3-bromo-9H-carbazole (9- ([1,1':3',1 "-terphenyl)]8.0g of (5' -yl) -3-bromo-9H-carbazole), (4- (9H-carbazol-9-yl) phenyl) boronic acid ((4- (9H-carbazol-9-yl) phenyl) boronic acid)4.85g was dissolved in 200ml of toluene, and K was added2CO3(2M)25ml and Pd (PPh)3)4After 0.6g, stirring was carried out under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. The organic layer was extracted with MC, filtered under reduced pressure, and then recrystallized to obtain 7.62g (yield: 71%) of Compound 2-2.
m/z：636.26(100.0％)、637.26(52.3％)、638.26(13.6％)、639.27(2.2％)
Compound 2-3
Figure BDA0002816385260000311
In a round-bottomed flask, 10.0g of 9H,9'H-3,3' -dicarbazole (9H,9'H-3,3' -dicarbazole), 14.1g of 3-bromo-1,1'-biphenyl (3-bromo-1,1' -biphenyl), 4.4g of t-Buona, and Pd2(dba)3 1.1g、(t-Bu)3P2.5 ml was dissolved in toluene 200ml and then stirred under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. Extracting the organic layer with MC, filtering under reduced pressure, purifying with column, recrystallizing,14.2g (yield 73%) of compound 2-3 was obtained.
m/z：636.26(100.0％)、637.26(52.3％)、638.26(13.6％)、639.27(2.2％)
Compound 2-4
Figure BDA0002816385260000312
In a round-bottomed flask, 5.0g of 9-phenyl-9H,9'H-3,3' -dicarbazole (9-phenyl-9H,9'H-3,3' -bicarbazole), 4.0g of 3-bromo-1,1'-biphenyl (3-bromo-1,1' -biphenol), 1.8g of t-BuONa, Pd2(dba)3 0.5g、(t-Bu)30.5ml of P was dissolved in 70ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 5.33g (yield 67%) of compound 2-4.
m/z：649.25(100.0％)、650.26(52.3％)、651.26(13.4％)、652.26(2.4％)、650.25(1.1％)
Compounds 2 to 5
Figure BDA0002816385260000321
In a round-bottom flask, 9- ([1,1' -biphenyl)]-3-yl) -3,6-dibromo-9H-carbazole (9- ([1,1' -biphenyl)]-3-yl) -3,6-dibromo-9H-carbazole)5.0g, 9H-carbazole (9H-carbazole)3.7g, t-Buona 1.5g, Pd2(dba)3 0.4g、(t-Bu)30.9ml of P was dissolved in 70ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC, and water was added to complete the reaction. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 4.22g (yield 62%) of compound 2-5.
m/z：649.25(100.0％)、650.26(52.3％)、651.26(13.4％)、652.26(2.4％)、650.25(1.1％)
Preparation of organic light-emitting device
An organic light emitting device was prepared according to the structure shown in fig. 1. The organic light emitting device is laminated with an anode (hole injection electrode 11)/a hole injection layer 12/a hole transport layer 13/a light emitting layer 14/an electron transport layer 15/a cathode (electron injection electrode 16) in this order from bottom to top.
The following materials were used for the hole injection layer 12, the hole transport layer 13, the light-emitting layer 14, and the electron transport layer 15 in examples and comparative examples.
Figure BDA0002816385260000331
Before the organic light emitting device was fabricated, in order to observe the combination of host 1 and host 2 that efficiently transfer energy to the phosphorescent dopant by the formation of the exciplex, host 1/host 2(1:1) was vapor-deposited on a glass substrate, and the wavelength of the exciplex was measured, and the results are shown in table 1 below.
TABLE 1
Figure BDA0002816385260000332
Figure BDA0002816385260000341
As shown in Table 1, the wavelengths based on the exciplex were not observed in the combination of comparative examples 1 to 3, and the wavelengths of 510nm or more were observed in the combination of comparative example 4. From this, it is understood that energy transfer does not occur efficiently considering the absorption wavelength of the phosphorescent dopant in the green region (the rightmost region of 450nm to 500 nm).
Preparation of organic light-emitting device
Example 1
Ultrasonic cleaning with distilled water
Figure BDA0002816385260000342
A glass substrate coated with a thin film of Indium Tin Oxide (ITO). Once the distilled water cleaning is finished, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone, or methanol, drying is performed, the resultant is transferred to a plasma cleaner, and then the above-mentioned is cleaned with oxygen plasmaAfter 5 minutes, the substrate was coated with the hole injection layer HI01 by a thermal evaporation coater (thermal evaporator)
Figure BDA0002816385260000343
A hole transport layer on the ITO substrate with NPB
Figure BDA0002816385260000344
Film formation is performed. Then, as the light-emitting layer, a compound 1-1/Ir (ppy) was doped310% of, or with
Figure BDA0002816385260000351
Film formation is performed. Then, as an electron transport layer, ET01: Liq (1:1)
Figure BDA0002816385260000352
After the film formation, LiF is performed
Figure BDA0002816385260000353
Aluminum (Al)
Figure BDA0002816385260000354
The green organic light emitting device was fabricated by preparing a film and sealing (Encapsulation) the device in a glove box.
Example 2
A green organic light emitting device was fabricated by the same method except that compound 1-2 was used instead of compound 1-1 as the light emitting layer host in example 1 above.
Example 3
A green organic light emitting device was fabricated by the same method except that compound 1-4 was used instead of compound 1-1 as the light emitting layer host in example 1 above.
Example 4
A green organic light emitting device was fabricated by the same method except that the compound 1-8 was used instead of the compound 1-1 as the light emitting layer host in example 1 described above.
Example 5
Ultrasonic cleaning with distilled water
Figure BDA0002816385260000355
A glass substrate coated with a thin film of Indium Tin Oxide (ITO). After the completion of the distilled water cleaning, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, or methanol, drying, transferring to a plasma cleaner, cleaning the substrate with oxygen plasma for 5 minutes, and then applying a hole injection layer HI01 with a thermal evaporation coater (thermal evaporator)
Figure BDA0002816385260000356
A hole transport layer on the ITO substrate with NPB
Figure BDA0002816385260000357
Film formation is performed. Then, as the light-emitting layer, a mixture of 1-1 (compound 2-1) (6:4 w%)/Ir (ppy) was doped310% of, or with
Figure BDA0002816385260000358
Film formation is performed. Then, as an electron transport layer, ET01: Liq (1:1)
Figure BDA0002816385260000359
After the film formation, LiF is performed
Figure BDA00028163852600003510
Figure BDA00028163852600003511
Aluminum (Al)
Figure BDA00028163852600003512
The green organic light emitting device was fabricated by preparing a film and sealing (Encapsulation) the device in a glove box.
Examples 6 to 12
In the same manner as in example 5, a green organic light-emitting device was produced, in which a mixture of compounds 1-2 to 1-8: 2-3(6:4 w%) was used as a light-emitting layer host in place of compound 1-1: compound 2-3 to form a film.
Comparative example 1
A green organic light emitting device was fabricated by the same method except that CBP was used as the light emitting layer host of example 1 described above.
Comparative example 2
A green organic light-emitting device was produced by the same method except that the comparative compound (Ref.)1 was used as the light-emitting layer host in example 1.
Comparative example 3
A green organic light-emitting device was produced by the same method except that the comparative compound (Ref.)2 was used as the light-emitting layer host in example 1.
Comparative example 4
A green organic light-emitting device was produced by the same method except that the comparative compound (Ref.)3 was used as the light-emitting layer host in example 1.
Performance evaluation of organic light-emitting device
The organic light emitting devices of examples and comparative examples were evaluated by applying a voltage using a gishley 2400 source measurement unit (kinetey 2400 source measurement unit), injecting electrons and holes, measuring the luminance at the time of light emission using a Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), and measuring the performance of the organic light emitting devices and the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in table 2.
TABLE 2
Figure BDA0002816385260000361
Figure BDA0002816385260000371
As shown in table 1, the examples of the present invention have lower driving voltages, higher efficiencies and longer lifetimes than comparative examples 1 to 4, and thus have excellent physical properties in all respects. In the examples of the present invention, it is understood that the triphenylene group has dibenzofuran as a linker and a heteroatom group, and that electron injection and transport are facilitated, as compared with comparative examples 2 and 4, and thus, the driving voltage is low, and the efficiency and the lifetime are improved. Among them, the use of the host 2 compound which is easy in hole injection and transport together was confirmed to have a long life because of its excellent durability at a high current density and a lower driving voltage. This indicates that the host 2 compound which is easy to inject and transport holes is used as the host 1 compound which is easy to inject and transport electrons, and that the driving voltage is reduced, excitons are efficiently accumulated in the light-emitting layer, the efficiency is increased, the roll-off phenomenon is suppressed at a high current density, the durability is good, and the lifetime is long.
Example 13
A green organic light-emitting device was produced by using the compound 1-1: the compound 2-3(7:3 w%) as a light-emitting layer host in the same manner as in example 5.
Example 14
A green organic light-emitting device was produced by using the compound 1-1: the compound 2-3(8:2 w%) as a light-emitting layer host in the same manner as in example 5.
Example 15
A green organic light-emitting device was produced by using the compound 1-1: the compound 2-3(4:6 w%) as a light-emitting layer host in the same manner as in example 5.
Example 16
A green organic light-emitting device was produced by using the compound 1-1: the compound 2-3(2:8 w%) as a light-emitting layer host in the same manner as in example 5.
Reference example 1
A green organic light-emitting device was produced by using the compound 1-1: the compound 2-3(1:9 w%) as a light-emitting layer host in the same manner as in example 5.
In examples 13 to 16 and reference example 1, a voltage was applied using a gievi 2400 source measurement unit (kineteley 2400 source measurement unit), electrons and holes were injected, the luminance at the time of light emission was measured using a Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), and the performance of the organic light emitting devices of examples and comparative examples and the current density and luminance with respect to the applied voltage were measured under atmospheric pressure to evaluate, and the results are shown in table 3.
TABLE 3
Figure BDA0002816385260000391
In table 1, device characteristics based on the combination ratio of chemical formula 1 and chemical formula 2 are confirmed. Finally, when the ratio of chemical formula 1 to chemical formula 2 is 1:9, the result of the reduction in efficiency and lifetime is obtained, which can be considered as a result of the excessive hole injection and transport due to chemical formula 2, as compared to comparative example 1. Specifically, the ratio of chemical formula 1 to chemical formula 2 is 9:1 to 2:8, and favorable characteristics based on the combination of luminescent hosts can be confirmed.
Industrial applicability
The compound of the present invention and the organic light-emitting device to which the above compound is applied have the following characteristics.
1. The triphenylene structure introduced into the compound has excellent durability against electrons and holes, thereby ensuring a long life of the organic light-emitting device.
2. By maintaining triplet energy suitable as green phosphorescence, high efficiency of the organic light emitting device is ensured.
3. Introduction of a heteroaryl group into the compound facilitates electron injection and transport, thereby ensuring low-voltage driving and high efficiency of the organic light-emitting device.
4. High Tg can be formed by Fused rings (Fused rings) within the compound, improving film stability when driving an organic light emitting device.
5. When applied to an organic light-emitting device, the novel compound (light-emitting host 1) and the carbazole derivative (light-emitting host 2) of the present invention facilitate electron injection and transport, and can realize low-voltage driving and high efficiency.
6. When applied to an organic light-emitting device, the novel compound (light-emitting host 1) of the present invention and the carbazole derivative (light-emitting host 2) are used to form an exciplex and transfer energy to a dopant to maximize efficiency, thereby realizing high efficiency and long lifetime.

Claims (18)

1. A compound represented by the following chemical formula 1:
chemical formula 1
Figure FDA0002816385250000011
In the above chemical formula 1, X represents N or CR independently of each other0At least 2 of X are N, wherein R0Represents hydrogen; heavy hydrogen; by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
y is O, and Y is O,
R1and R2And R3Each independently represents hydrogen; heavy hydrogen; halogen; an amino group; nitrile group and nitro group; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkyne of (2)Base, C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
m and n each independently represent an integer of 0 to 2.
2. The compound according to claim 1, wherein the above chemical formula 1 is represented by one of the following chemical formulae 1-1 to 1-6:
chemical formula 1-1
Figure FDA0002816385250000021
Chemical formula 1-2
Figure FDA0002816385250000022
Chemical formulas 1 to 3
Figure FDA0002816385250000023
Chemical formulas 1 to 4
Figure FDA0002816385250000031
Chemical formulas 1 to 5
Figure FDA0002816385250000032
Chemical formulas 1 to 6
Figure FDA0002816385250000033
In the above chemical formulae 1-1 to 1-6, X, Y is as defined in the above chemical formula 1.
3. The compound of claim 1, wherein the chemical formula 1 is represented by one of the following chemical formulas:
Figure FDA0002816385250000034
Figure FDA0002816385250000041
Figure FDA0002816385250000051
Figure FDA0002816385250000061
Figure FDA0002816385250000071
4. an organic light-emitting device, comprising:
an anode;
a cathode; and
1 or more organic layers comprising the compound of claim 1 between two electrodes.
5. The organic light-emitting device according to claim 4, wherein the organic layer is a light-emitting layer, an electron-injecting layer, an electron-transporting layer, or a hole-blocking layer.
6. The organic light-emitting device according to claim 5, wherein the light-emitting layer contains a compound represented by chemical formula 1 as a light-emitting host.
7. A mixture comprising a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2:
chemical formula 1
Figure FDA0002816385250000081
In the above-described chemical formula 1,
x independently represents N or CR0At least 2 of X are N, wherein R0Represents hydrogen; heavy hydrogen; by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
y is O, and Y is O,
R1、R2and R3Each independently represents hydrogen; heavy hydrogen; halogen; an amino group; a nitrile group; a nitro group; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); from heavy hydrogenHalogen, amino, nitrile, nitro or unsubstituted C2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
m and n each independently represent an integer of 0 to 2,
chemical formula 2
Figure FDA0002816385250000091
In the above chemical formula 2, r1To r8Each independently represents hydrogen; heavy hydrogen; c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkyl groups of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkenyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro2-30Alkynyl of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro1-30Alkoxy group of (a); c substituted or unsubstituted by deuterium, halogen, amino, nitrile, nitro6-30An aryloxy group of (a); by heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
ar is composed of heavy hydrogen, halogen, amino, nitrile, nitro and C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C6-50Aryl of (a); or heavy hydrogen, halogen, amino, nitrile, nitro, C1-30Alkyl of (C)2-30Alkenyl of, C2-30Alkynyl of (A), C1-30Alkoxy group of (C)6-30Aryloxy group of (A), C6-30Aryl of, or C2-30Heteroaryl substituted or unsubstituted C2-50The heteroaryl group of (a) is a group,
m is an integer of 1 to 4,
when m is 2 to 4, Ar and r1～r8Can be connected.
8. The mixture according to claim 7, wherein the compound represented by the above chemical formula 2 is one of the compounds represented by the following chemical formulae 2-1 to 2-7:
chemical formula 2-1
Figure FDA0002816385250000101
Chemical formula 2-2
Figure FDA0002816385250000111
Chemical formula 2-3
Figure FDA0002816385250000112
Chemical formula 2-4
Figure FDA0002816385250000113
Chemical formula 2-5
Figure FDA0002816385250000114
Chemical formula 2-6
Figure FDA0002816385250000121
Chemical formula 2-7
Figure FDA0002816385250000122
In the above formula, Ar1、Ar2、Ar3、Ar4、Ar5Each independently defined as Ar of the above chemical formula 2, R1、R2、R3、R4R of the above chemical formula 21To r8As defined, a and b each independently represent an integer of 0 to 3.
9. The mixture according to claim 8, wherein the compound represented by the above chemical formula 2 is the following chemical formula 2-3:
chemical formula 2-3
Figure FDA0002816385250000123
In the above chemical formula 2-3, Ar1、Ar2、Ar3Each independently defined as Ar of the above chemical formula 2, R1、R2R of the above chemical formula 21To r8As defined, a is an integer from 0 to 3.
10. The mixture according to claim 7, wherein the compound represented by the above chemical formula 2 is one of compounds represented by the following chemical formulae:
Figure FDA0002816385250000131
Figure FDA0002816385250000141
Figure FDA0002816385250000151
Figure FDA0002816385250000161
11. the mixture according to claim 7, wherein the above chemical formula 1 is represented by one of the following chemical formulae 1-1 to 1-6:
chemical formula 1-1
Figure FDA0002816385250000162
Chemical formula 1-2
Figure FDA0002816385250000163
Chemical formulas 1 to 3
Figure FDA0002816385250000171
Chemical formulas 1 to 4
Figure FDA0002816385250000172
Chemical formulas 1 to 5
Figure FDA0002816385250000173
Chemical formulas 1 to 6
Figure FDA0002816385250000174
In the above chemical formulae 1-1 to 1-6, X, Y is as defined in the above chemical formula 1.
12. The mixture according to claim 7, wherein the above chemical formula 1 is represented by one of the following chemical formulas:
Figure FDA0002816385250000175
Figure FDA0002816385250000181
Figure FDA0002816385250000191
Figure FDA0002816385250000201
13. an organic light-emitting device, comprising: an anode; a cathode; and a light-emitting layer comprising the mixture of claim 7 between two electrodes.
14. The organic light-emitting device according to claim 13, wherein the light-emitting layer comprises a compound represented by chemical formula 1 as a light-emitting host 1 and a compound represented by chemical formula 2 as a light-emitting host 2.
15. The organic light-emitting device as claimed in claim 14, wherein the wavelength of the exciplex formed by the light-emitting host 1 and the light-emitting host 2 is 400-650 nm.
16. The organic light-emitting device as claimed in claim 14, wherein the wavelength of the exciplex formed by the light-emitting host 1 and the light-emitting host 2 is 450-500 nm.
17. The organic light-emitting device according to claim 14, wherein the mixing ratio of the light-emitting body 1 and the light-emitting body 2 is 9:1 to 2:8 by weight.
18. The organic light-emitting device according to claim 14, wherein the wavelength of the exciplex light emitted from the light-emitting host 1 and the light-emitting host 2 is shorter than the wavelength of the light emitted from the dopant of the guest molecule serving as the light-emitting layer.
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