CN113929585A - Organic compound and organic electroluminescent device - Google Patents

Organic compound and organic electroluminescent device Download PDF

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CN113929585A
CN113929585A CN202010674829.5A CN202010674829A CN113929585A CN 113929585 A CN113929585 A CN 113929585A CN 202010674829 A CN202010674829 A CN 202010674829A CN 113929585 A CN113929585 A CN 113929585A
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organic compound
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黄鑫鑫
王志鹏
曾礼昌
高文正
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Beijing Eternal Material Technology Co Ltd
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Abstract

An organic compound having a structure represented by (1):
Figure DDA0002583675400000011
wherein L is1、L2And L are each independently a single bond, substituted or unsubstituted C6‑C30Arylene group of (A) or substituted or unsubstituted C3‑C30The heteroarylene group of (a); ar (Ar)1And Ar2Each independently is substituted or unsubstituted C6‑C60Aryl, substituted or unsubstituted C9‑C60With condensed ring aryl, substituted or unsubstituted C3‑C60Or substituted or unsubstituted C3‑C60The fused ring heteroaryl of (a); r1‑R4The same or different, each independently is H, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1‑C30Alkyl, substituted or unsubstituted C1‑C30Alkoxy, substituted or unsubstituted C3‑C30Cycloalkyl, substituted or unsubstituted C3‑C12With heterocycloalkyl radical, substituted or unsubstituted C6‑C30Aryl, substituted or unsubstituted C9‑C30With condensed ring aryl, substituted or unsubstituted C3‑C30Or substituted or unsubstituted C3‑C30The fused ring heteroaryl of (a); wherein R is3And R4Can be connected with each other to form a ring; m and n are respectively and independently selected from 1 to the maximum desirable integer.

Description

Organic compound and organic electroluminescent device
Technical Field
The present invention relates to a novel organic compound, and more particularly, to an organic compound for an organic electroluminescent device and an application thereof in an organic electroluminescent device.
Background
The organic light-emitting diode (OLED) is a phenomenon that an organic functional material is excited by current and voltage to emit light under the action of an electric field, and is a process for directly converting electric energy into light energy. In 1979, Duncong cloud doctor of "father of OLED" discovered the electroluminescent property of organic thin film devices accidentally in the laboratory, thereby opening the research introduction of OLED devices and making a great contribution to the practical application of OLED technology. The OLED device is an all-solid-state self-luminous device and has the characteristics of high response speed, wide visual angle and wide working temperature range. The organic light-emitting material can be structurally designed and improved according to the use requirement, and theoretically, full-color output can be realized. Compared with the liquid crystal display technology, the OLED device has a simpler structure, can realize ultrathin large-area flat panel display, has the characteristics of lightness, flexibility and foldability, and has a wider application range.
In the current era of rapid development of information technology, the use of 4G network technology and the coming 5G ultra-high speed network communication technology, any information needing to be acquired comes almost instantaneously, and the display technology plays an important role in acquiring knowledge, understanding information and entertaining. Therefore, the requirements of people for display devices are higher and higher, and the aspects of high resolution, high response speed, wide viewing angle, portability, low power consumption, full color and the like become the development direction of the future flat panel display.
Organic electroluminescent diodes using organic semiconductors as functional materials are rapidly developed as a new generation of all-solid-state flat panel display technology. Compared with other display technologies, the OLED technology has the advantages of wide viewing angle, high response speed, low starting voltage, wide adaptable display temperature range, capability of realizing full-color display from blue light to red light spectrum region and the like. The device process is relatively simple, and the OLED is most attractive by using a flexible substrate to realize a rollable flexible display.
In the organic light emitting device, materials used as an organic layer are broadly classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and the like according to functions. According to the light emission mechanism, the fluorescent material can be classified into a fluorescent material emitting light by a singlet excited state of electrons and a phosphorescent material emitting light by a triplet excited state of electrons. In order to effectively alleviate aggregation of a light emitting material and triplet excitons and avoid concentration quenching, a host-guest doping system in which a light emitting material is doped in a host material is generally adopted, and excitons generated by the host are transferred to a dopant, thereby emitting light with high efficiency.
The organic hole material plays an important role in transferring holes injected from the anode to the light emitting layer, and the hole transport material with excellent hole mobility is beneficial to the injection balance of carriers in the device, so that the starting voltage of the device is reduced. On the other hand, in order to prevent excitons generated in the light-emitting layer from diffusing into the hole transport layer, which causes color cast and reduction of light-emitting efficiency, the hole transport layer is also required to be capable of blocking the excitons from diffusing out, preventing efficiency roll-off and improving the stability of the device.
Disclosure of Invention
Problems to be solved by the invention
However, the currently used OLED materials and device structures are increasingly unable to meet the current efficiency, starting voltage, cost, and other needs of human OLED devices. Therefore, it is desirable to develop a novel compound that can be applied to OLED devices and improve device performance.
The invention aims to provide an organic compound which can be used as an organic thin layer material in an organic electroluminescent device, so that the device has high luminous efficiency and long service life.
Means for solving the problems
As a result of intensive studies to solve the above-mentioned problems in the prior art, the inventors of the present invention have found that, when one aryl group of triarylamine is a terphenyl group and a specific alkylfluorene group is bonded to the ortho-position of arylamine N on the benzene ring directly bonded to arylamine N in the terphenyl group, the obtained compound has significantly improved lifetime and luminous efficiency of an organic electroluminescent device obtained when it is used as an electron blocking layer material, as compared with the compounds in the prior art, and have completed the present invention.
Specifically, one of the objects of the present invention is to provide an organic compound having a structure represented by (1):
Figure BDA0002583675390000021
wherein L is1、L2And L are each independently a single bond, substituted or unsubstituted C6-C30Arylene group of (A) or substituted or unsubstituted C3-C30The heteroarylene group of (a); ar (Ar)1And Ar2Each independently is substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C9-C60With condensed ring aryl, substituted or unsubstituted C3-C60Or substituted or unsubstituted C3-C60The fused ring heteroaryl of (a); r1-R4The same or different, each independently is H, deuterium, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C1-C30Alkoxy, substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C3-C12With heterocycloalkyl radical, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C9-C30With condensed ring aryl, substituted or unsubstituted C3-C30Or substituted or unsubstituted C3-C30The fused ring heteroaryl of (a); wherein R is3And R4Can be connected with each other to form a ring; m and n are respectively and independently selected from 1 to the maximum desirable integer;
when the above-mentioned substituted or unsubstituted group has a substituent, the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, and C1-C12Alkyl of (C)1-C12Alkoxy group of (C)3-C12Cycloalkyl of, C3-C12Heterocycloalkyl of (A), C6-C30Aryl of (C)9-C30Condensed ring aryl of (C)3-C30Heteroaryl of (A), C3-C30One or a combination of two or more of the fused ring heteroaryls of (a).
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent or with a plurality of substituents, and when a plurality of substituents are present, they may be selected from different substituents or may be all or part of the same. When the same expression mode is involved in the invention, the same meanings are provided, and the selection ranges of the substituents are shown above and are not repeated.
The OLED device prepared by the organic compound has longer service life and higher efficiency, and can meet the requirements of current panel manufacturing enterprises on high-performance materials. The specific reason why the above organic compound is excellent in performance when used as an electron blocking layer material in an organic electroluminescent device is not clear, and is presumed as follows.
In the compound, the terphenyl group and the arylamine N are directly connected on the benzene ring, and the ortho position of the arylamine N is directly connected or connected with substituted or unsubstituted fluorenyl through arylene/heteroarylene, so that the compound has good planarity and aromaticity. Under the synergistic effect of the terphenylamine structure and the substituted or unsubstituted fluorenyl, the mobility of charges is further improved, and hole injection and migration are well balanced, so that the current efficiency of an organic electroluminescent device using the compound as an electron blocking layer material is improved. Meanwhile, due to the molecular structure, the terphenylamine with the substituted or unsubstituted fluorenyl group connected to the ortho position of the arylamine N is easy to form an amorphous film, so that the space structure of the device can be more compact, and the service life of the device can be further prolonged.
In this specification, C representsa～CbThe expression (b) represents that the group has the number of carbon atoms of a to b, and generally the number of carbon atoms does not include the number of carbon atoms of the substituent unless otherwise specified. In the present invention, unless otherwise specified, the expressions of chemical elements generally include the concept of chemically identical isotopes, such as the expression "hydrogen", and also include the concept of chemically identical "deuterium" and "tritium".
In the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include only a single ring.
In the present specification, substituted or unsubstituted C6～C60Aryl of (A) is preferably substituted or unsubstituted C6～C30Aryl, more preferably C6～C20Aryl, more preferably phenyl, biphenyl, terphenyl, or quaterphenyl. In particular, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl.
In the present specification, a fused ring aryl group means a group containing at least two aromatic rings in a molecule, and the aromatic rings are not independent of each other but are fused to each other with two adjacent carbon atoms in common. In the present invention, substituted or unsubstituted C9-C60The condensed ring aryl of (A) is preferably C9-C30The condensed ring aryl group of (b) is more preferably a group selected from the group consisting of naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, perylenyl, anthryl, tetracenyl, pentacenyl, benzopyrenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl. Specifically, the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
The hetero atom in the present invention generally refers to an atom or group of atoms selected from N, O, S, P, Si and Se, preferably N, O, S.
In the present specification, a fused ring heteroaryl group means a group which has at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in a molecule, and which is not independent of each other but shares two adjacent atoms fused to each other. In the present invention, substituted or notSubstituted C3～C60Heteroaryl of (A) is preferably substituted or unsubstituted C3～C30Heteroaryl, more preferably C4～C20The heteroaryl group is more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc., and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, pyrazolyl, imidazolyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl.
In the present specification, substituted or unsubstituted C3～C60The fused ring heteroaryl group of (A) is preferably substituted or unsubstituted C3～C30Fused ring heteroaryl, more preferably C4～C20Fused ring heteroaryl groups, more preferably nitrogen-containing fused ring heteroaryl groups, oxygen-containing fused ring heteroaryl groups, sulfur-containing fused ring heteroaryl groups, and the like, and specific examples thereof include: benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, indazolyl, benzimidazolyl, naphthoimidazolyl, phenanthrimidazolyl, pyridoimidazolyl, pyrazinimidazolyl, quinoxalimidazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, benzopyrazinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazoanthrenyl, 2, 7-diazepanyl, 2, 3-diazapyranyl, 1, 6-diazapyranyl, 1, 8-diazepanyl, 4,5,9, 10-tetraazaperyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, or the like, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole。
In the present specification, C1～C30Examples of the alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl and the like.
In the present specification, C3～C30Cycloalkyl includes monocycloalkyl and polycycloalkyl radicals, and may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, cycloheptyl, cyclooctyl, and the like.
In the present specification, C3～C12Heterocycloalkyl includes monocyclic and polycyclic heteroalkyl groups, and may be, for example, piperidinyl, tetrahydropyrrolyl, 1, 4-dioxane, and the like.
In the present specification, the term "C" means C1～C30Examples of alkoxy groups are: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, etc., preferably fluorine.
In the compound of the above general formula of the present invention, the substituted or unsubstituted fluorenyl group is preferably a 9, 9-dimethylfluorenyl group, 9, 9-diphenylfluorenyl group or spirofluorenyl group. The three belong to the category of alkyl fluorene group. When the compound of the invention and the terphenylamine structure have synergistic effect on 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl or spirofluorenyl, the current efficiency of the organic electroluminescent device using the compound as the electron blocking layer material is further improved.
Preferred compounds of the above formula of the present invention are R1Is H, R2Is H.
The compound of the above general formula of the present invention preferably has one of the structures represented by (2-1) to (2-4):
Figure BDA0002583675390000051
the ranges of the groups in the formula are the same as in the formula (1).
In the compounds of the above general formula of the present invention, L1、L2And L is preferably selected from a single bond, a substituted or unsubstituted one of the following groups:
Figure BDA0002583675390000052
the compounds of the above formula of the present invention are preferably: ar (Ar)1And Ar2Each independently is substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C9-C30With condensed ring aryl, substituted or unsubstituted C3-C30Or substituted or unsubstituted C3-C30The fused ring heteroaryl of (1).
In the compounds of the above general formula of the present invention, Ar1、Ar2More preferably selected from one of the following substituted or unsubstituted groups:
Figure BDA0002583675390000061
in the compounds of the above general formula of the present invention, Ar1、Ar2More preferably selected from one of the following substituted or unsubstituted groups:
Figure BDA0002583675390000062
the compounds of the above general formula of the present invention preferably have the structure shown by P1-P277:
Figure BDA0002583675390000071
Figure BDA0002583675390000081
Figure BDA0002583675390000091
Figure BDA0002583675390000101
Figure BDA0002583675390000111
Figure BDA0002583675390000121
Figure BDA0002583675390000131
Figure BDA0002583675390000141
Figure BDA0002583675390000151
Figure BDA0002583675390000161
another object of the present invention is to provide an application of the compound of the above general formula in an organic electronic device, which is suitable for use as an electron blocking layer material, and the application field is not limited to organic electroluminescent materials, but can be applied in the technical fields of large-area sensors such as optical sensors, solar cells, lighting devices, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, and electronic paper.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the above-mentioned organic compounds.
Specifically, one embodiment of the present invention provides an organic electroluminescent device, an anode layer, a plurality of light emitting functional layers, and a cathode layer; the plurality of light-emitting functional layers comprise at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and an electron transport layer which are sequentially formed, wherein the hole injection layer is formed on the anode layer, and the cathode layer is formed on the electron transport layer; wherein the hole transport layer and/or the electron blocking layer contain an organic compound represented by the general formula.
Effects of the invention
The compound of the invention can form an amorphous film, so that the space structure of the device becomes more compact, the service life of the device is further prolonged, the mobility of charges is also improved, and hole injection and migration are better balanced, so that the efficiency of the device is further improved. Compared with the compounds in the prior art, the compound provided by the invention has the advantages that the service life and the luminous efficiency of the obtained organic electroluminescent device are obviously improved when the compound is used as an electron barrier material. In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The basic chemical materials of various chemicals used in the present invention, such as tetrahydrofuran and potassium carbonate, are commercially available from Shanghai Tantake technology Co., Ltd and Xiong chemical Co., Ltd. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
The synthesis of the compounds of the present invention is briefly described below.
Figure BDA0002583675390000171
It is to be noted that the method and route for obtaining the compound are not limited to those used in the present invention, and those skilled in the art can select other methods or routes to obtain the novel compound proposed in the present invention.
Synthesis of intermediate M1:
Figure BDA0002583675390000181
synthesis of intermediate M1-1:
a1000 mL three-necked flask equipped with magnetic stirring was charged with THF 500mL, 4-amino-P-terphenyl (20.00g, 81.52mmol), cooled to-10 deg.C, NBS (N-bromosuccinimide) (14.51g, 81.52mmol) was slowly added several times at this temperature, after the addition was complete, the temperature was maintained and stirring was continued for 30min, the reaction was monitored for completion, and ice water was added to stop the reaction. Extracting with ethyl acetate, collecting supernatant, mixing concentrated organic phases, and separating by column chromatography to obtain intermediate M1-120.59. Calculated molecular weight: 322, found M/Z: 324.
synthesis of intermediate M1:
under a nitrogen atmosphere, intermediate M1-1(20.59g, 63.51mmol), 9, 9-dimethylfluorene-2-boronic acid (15.12g, 63.51mmol), tetrakistriphenylphosphine palladium (Pd (PPh)3)4，1.47g，1.27mmol), potassium carbonate (K)2CO317.55g, 127.01mmol), 300ml of 1, 4-dioxane and 100ml of distilled water are put into a 1L reaction vessel and reacted at 100 ℃ for 12 hours under reflux. Cooling to room temperature, extracting with ethyl acetate, collecting supernatant, and mixing the concentrated organic phases. Separation by column chromatography gave M120.7g of intermediate. Calculated molecular weight: 437, found M/Z: 438.
synthesis of intermediates M2-M8:
following the procedure for the synthesis of intermediate M1, the intermediates shown in table 1 below were synthesized:
Figure BDA0002583675390000182
Figure BDA0002583675390000191
Figure BDA0002583675390000201
synthesis of target Compound
Synthesis example 1:
synthesis of Compound P8
Figure BDA0002583675390000202
Under a nitrogen atmosphere, M1(20g, 45.71mmol), 4-bromobiphenyl 10.65g, 45.71mmol) and 1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride (Pd (dppf) Cl20.34g, 0.46mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (s-phos, 0.38g, 0.91mmol), sodium tert-butoxide (t-BuONa, 8.78g, 91.41mmol) and 300ml of toluene were placed in a 1L reaction vessel and reacted at 100 ℃ under reflux for 12 hours. Cool to room temperature and combine the concentrated organic phases. Separation by column chromatography gave intermediate P8-120.74 g. Calculated molecular weight: 62Measured value M/Z: 630.
Figure BDA0002583675390000211
under a nitrogen atmosphere, P8-1(20.74g, 32.93mmol), 2-bromo-9, 9-dimethylfluorene (8.96g, 32.93mol), and tris (dibenzylideneacetone) dipalladium (Pd) were added2(dba)3) 0.30g, 0.33mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (s-phos, 0.27g, 0.66mmol), sodium tert-butoxide (t-BuONa, 6.33g, 65.86mmol) and 200ml of toluene (Tol) were placed in a 1L reaction vessel and reacted at 110 ℃ under reflux for 12 hours. Cool to room temperature and combine the concentrated organic phases. The intermediate P815.12g was isolated by column chromatography. Calculated molecular weight: 781, found value M/Z: 782.
synthesis examples 2 to 7:
the target compounds shown in table 2 below can be obtained using the corresponding starting materials shown in table 2 with reference to synthesis example 1.
Figure BDA0002583675390000212
Figure BDA0002583675390000221
Figure BDA0002583675390000231
Device embodiments
Next, the organic electroluminescent device will be explained in detail:
the OLED includes first and second electrodes, and an organic material layer between the first and second electrodes. The organic material layer may be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-51; or any combination thereof.
Figure BDA0002583675390000241
Figure BDA0002583675390000251
Figure BDA0002583675390000261
Figure BDA0002583675390000271
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
Figure BDA0002583675390000272
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
Figure BDA0002583675390000281
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, the combination of one or more of BFD-1 through BFD-24 listed below.
Figure BDA0002583675390000282
Figure BDA0002583675390000291
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light-emitting layer is selected from, but not limited to, one or more of PH-1 to PH-85.
Figure BDA0002583675390000301
Figure BDA0002583675390000311
Figure BDA0002583675390000321
Figure BDA0002583675390000331
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
Figure BDA0002583675390000332
Figure BDA0002583675390000341
Figure BDA0002583675390000351
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
Figure BDA0002583675390000352
Figure BDA0002583675390000361
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1-YPD-11 listed below.
Figure BDA0002583675390000362
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77 may also be used, but are not limited thereto.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-65 listed below.
Figure BDA0002583675390000371
Figure BDA0002583675390000381
Figure BDA0002583675390000391
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds from ET-1 to ET-65 or one or more compounds from PH-1 to PH-46; mixtures of one or more compounds from ET-1 to ET-65 with one or more compounds from PH-1 to PH-46 may also be used, but are not limited thereto.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca，Mg。
The preparation process of the organic electroluminescent device in the embodiment is as follows:
device example 1:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 10 DEG-5Pa, vacuum evaporating and plating HI-3 with the thickness of 10nm on the anode layer film to be used as a hole injection layer; vacuum evaporating 80nm HT-21 on the hole injection layer to be used as a hole transport layer of the device; continuously performing vacuum evaporation on the hole transport layer to obtain 35nm of P8 serving as an electron barrier layer material; evaporating a compound PH-61: PH-3: GPD-12(100:100:20, w/w/w) ternary mixture with the wavelength of 40nm as a light-emitting layer on the electron blocking layer by using a multi-source co-evaporation method; vacuum evaporating and plating 10nm ET-22 on the luminescent layer as a hole blocking layer; and (3) vacuum evaporating 30nm ET-60 on the hole blocking layer by a multi-source co-evaporation method: ET-57(100:150, w/w) binary mixture as electron transport layer. LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an aluminum layer with the thickness of 150nm is used as a cathode of the device. The evaporation rate of all the organic layers and LiF is 0.1nm/s, and the evaporation rate of the metal aluminum is 1 nm/s.
Devices of examples 2 to 7 were fabricated in the same manner as in example 1 except that P8 in the EBL layer was replaced with P7, P13, P93, P125, P166, P203, and P241, respectively.
Devices comparative examples 1 to 7 were fabricated in the same manner as in device example 1 except that P8 in the EBL layer was replaced with R-1, R-2, R-3, R-4, R-5, R-6 and HT14, respectively.
Figure BDA0002583675390000401
Figure BDA0002583675390000411
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement: wherein the current efficiency is 10000cd/m at luminance2The lifetime LT97 was determined at a constant current of 40mA/cm2Next, the time when the luminance decayed to 97% of the initial luminance was recorded. The device lifetime data reported in the table are relative values to comparative example 1.
The organic electroluminescent device properties are given in the following table:
EBL material Luminance (cd/m)2) Current efficiency (Cd/A) Life LT97(h)
Comparative example 1 R-1 10000 54.1 1
Comparative example 2 R-2 10000 53.8 0.96
Comparative example 3 R-3 10000 53.4 0.9
Comparative example 4 R-4 10000 51.9 0.75
Comparative example 5 R-5 10000 50.2 0.82
Comparative example 6 R-6 10000 49.8 0.77
Comparative example 7 HT14 10000 51.0 0.69
Example 1 P8 10000 54.7 1.19
Example 2 P7 10000 55.0 1.21
Example 3 P93 10000 54.5 1.1
Example 4 P125 10000 54.8 1.08
Example 5 P166 10000 54.3 1.11
Example 6 P203 10000 54.6 1.14
Example 7 P241 10000 54.7 1.15
As can be seen from the results in the table, the novel organic material of the invention is used as an electron barrier material for an organic electroluminescent device, and compared with a device prepared by using the existing compounds R-1, R-2, R-3, R-4, R-5, R-6 and HT14 as the electron barrier material, the service life of the device can be effectively prolonged. The reason for this is not clear, but is presumed as follows. The ortho position of the compound of the invention, namely the biphenyl amine, has substituted or unsubstituted fluorenyl, and has good planarity and aromaticity, compared with a fused ring aryl structure connected with the ortho position of the biphenyl amine, the structure can form an amorphous film, so that the space structure of a device becomes more compact, and meanwhile, the increased benzene ring can also reduce the electron cloud density among C-N bonds, so that the stability of the device is improved, the mobility of charges can be further improved, and the hole injection and the mobility can be well balanced. In conclusion, under the synergistic effect of the terphenylamine structure and the substituted or unsubstituted fluorenyl, the compound provided by the invention can further improve the service life and the luminous efficiency of a device. And the existing compounds R-1 to R-3 do not have a terphenyl structure in the compound, the existing compound R-4 does not have a substituted or unsubstituted fluorenyl structure in the compound, and the synergistic effect of the specific triphenylbenzidine structure and the substituted or unsubstituted fluorenyl does not naturally exist, so that when the compounds are used as an electron blocking layer material for an organic electroluminescent device, the obtained organic electroluminescent device has low current efficiency and short service life.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.

Claims (11)

1. An organic compound having a structure represented by (1):
Figure FDA0002583675380000011
wherein L is1、L2And L are each independently a single bond, substituted or unsubstituted C6-C30Arylene group of (A) or substituted or unsubstituted C3-C30The heteroarylene group of (a);
Ar1and Ar2Each independently is substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C9-C60With condensed ring aryl, substituted or unsubstituted C3-C60Or substituted or unsubstituted C3-C60The fused ring heteroaryl of (a);
R1-R4the same or different, each independently is H, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C1-C30Alkoxy, substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C3-C12With heterocycloalkyl radical, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C9-C30With condensed ring aryl, substituted or unsubstituted C3-C30Or substituted or unsubstituted C3-C30The fused ring heteroaryl of (a); wherein R is3And R4Can be connected with each other to form a ring;
m and n are respectively and independently selected from 1 to the maximum desirable integer;
when the above-mentioned substituted or unsubstituted group has a substituent, the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, and C1-C12Alkyl of (C)1-C12Alkoxy group of (C)3-C12Cycloalkyl of, C3-C12Heterocycloalkyl of (A), C6-C30Aryl of (C)9-C30Condensed ring aryl of (C)3-C30Heteroaryl of (A), C3-C30One or a combination of two or more of the fused ring heteroaryls of (a).
2. An organic compound according to claim 1, wherein R is3And R4Methyl, phenyl or are connected with each other to form a ring to form spirofluorenyl.
3. An organic compound according to claim 1, wherein R is1Is H, R2Is H.
4. The organic compound according to claim 1, wherein the organic compound has one of the structures shown in (2-1) to (2-4):
Figure FDA0002583675380000021
5. the organic compound according to any one of claims 1 to 4, wherein L is1、L2And each L is independently selected from a single bond, a substituted or unsubstituted one of the following groups:
Figure FDA0002583675380000022
6. the organic compound according to any one of claims 1 to 4, wherein Ar is Ar1And Ar2Each independently is substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C9-C30With condensed ring aryl, substituted or unsubstituted C3-C30Or substituted or unsubstituted C3-C30The fused ring heteroaryl of (1).
7. The organic compound of claim 6, wherein Ar is Ar1、Ar2Each independently selected from one of the following substituted or unsubstituted groups:
Figure FDA0002583675380000031
8. the organic compound according to any one of claims 1 to 5, wherein Ar is Ar1、Ar2Each independently selected from one of the following substituted or unsubstituted groups:
Figure FDA0002583675380000032
9. the organic compound of claim 1, wherein the organic compound has the structure shown in P1-P277:
Figure FDA0002583675380000041
Figure FDA0002583675380000051
Figure FDA0002583675380000061
Figure FDA0002583675380000071
Figure FDA0002583675380000081
Figure FDA0002583675380000091
Figure FDA0002583675380000101
Figure FDA0002583675380000111
Figure FDA0002583675380000121
Figure FDA0002583675380000131
10. use of the organic compound according to any one of claims 1 to 9 in an organic electroluminescent device, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or an electronic paper, preferably as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device.
11. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains at least one organic compound according to any one of claims 1 to 9.
CN202010674829.5A 2020-07-14 2020-07-14 Organic compound and organic electroluminescent device Pending CN113929585A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180082124A (en) * 2017-01-10 2018-07-18 에스에프씨 주식회사 organic light-emitting diode with High efficiency
CN110317139A (en) * 2019-05-09 2019-10-11 北京鼎材科技有限公司 A kind of compound and its application and the organic electroluminescence device comprising the compound
CN110382590A (en) * 2017-03-15 2019-10-25 保土谷化学工业株式会社 High-molecular compound containing substituted triarylamine skeleton

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180082124A (en) * 2017-01-10 2018-07-18 에스에프씨 주식회사 organic light-emitting diode with High efficiency
CN110382590A (en) * 2017-03-15 2019-10-25 保土谷化学工业株式会社 High-molecular compound containing substituted triarylamine skeleton
CN110317139A (en) * 2019-05-09 2019-10-11 北京鼎材科技有限公司 A kind of compound and its application and the organic electroluminescence device comprising the compound

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