CN111018855A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN111018855A
CN111018855A CN201911375345.4A CN201911375345A CN111018855A CN 111018855 A CN111018855 A CN 111018855A CN 201911375345 A CN201911375345 A CN 201911375345A CN 111018855 A CN111018855 A CN 111018855A
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compound
organic compound
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邢其锋
丰佩川
陈跃
胡灵峰
陈义丽
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an organic compound and application thereof. The carbazole-fused quinoxaline structure provided by the invention has a high charge transmission rate due to a large conjugated condensed ring structure, can reduce the voltage of the material, has a good electron transmission effect due to the quinoxaline structure, has a good hole transmission effect due to a carbazole derivative fragment, and is beneficial to charge balance due to the synergistic effect of the carbazole derivative fragment and the hole transmission fragment, so that the carbazole-fused quinoxaline structure can be used as a bipolar main body material for a light-emitting layer of an organic electroluminescent device, and realizes high light-emitting efficiency. In addition, the coplanar large conjugated condensed ring structure can enable molecules to be arranged in parallel, increase acting force among the molecules, improve crystallization performance, improve the thermodynamic stability of the compound, have good material stability and can realize long-life luminescence. 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.

Description

Organic compound and application thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an organic compound and application thereof.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage direct current drive, full curing, wide viewing angle, light weight, simple composition and process and the like, compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, has the response speed which can reach 1000 times of that of the liquid crystal display, and has lower manufacturing cost than the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research of efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The phosphorescent host materials used at present have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts. The single carrier transport ability causes mismatching of electrons and holes in the light emitting layer, resulting in severe roll-off of efficiency and shortened lifetime. Therefore, in the use process of the phosphorescent host, a bipolar material or a double-host material matching mode is adopted to solve the problem of carrier imbalance of the single-host material.
The bipolar material is a compound which realizes the common transmission of electrons and holes, generally has a complex molecular structure and needs more consideration, and a good bipolar material can be obtained by simply connecting a fragment for conducting holes and a fragment for conducting electrons. Therefore, bipolar materials have many difficulties while having great potential for development. It is desired to develop a bipolar material which can be used for producing an organic electroluminescent device having high luminous efficiency, low pull-off and drop-off voltage, and a long lifetime.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides an organic compound and application thereof.
The technical scheme for solving the technical problems is as follows: an organic compound having the following structural formula:
Figure BDA0002340807040000021
wherein m and n are 0 or 1 and are not 0 or 1 simultaneously;
R1、R2、R3、R4each independently is hydrogen, C1-C10Alkyl radical, C1-C10Alkenyl, cyano, C6-C30Aryl or C3-C20A heteroaryl group;
x, Z are each independently O, S, CR5R6Or NR7；
Y1、Y2、Y3、Y4Each independently is C or N, and at least two are N;
R5、R6each independently is C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C20A heteroaryl group;
R7is C1-C10Alkyl, substituted or unsubstituted C6-C30Arylene or substituted or unsubstituted C3-C20A heteroarylene group.
Further, R1、R2、R3、R4Each independently is hydrogen, methyl, ethyl, isopropyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, or carbazolyl.
Further, R5、R6、R7Each independently is methyl, ethyl, phenyl, naphthyl, biphenyl, terphenyl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, or carbazolyl.
Further, R1、R2、R3Or R4Benzene adjacent thereto is fused to be linked.
Further, the organic compound has a structural formula:
Figure BDA0002340807040000031
Figure BDA0002340807040000041
Figure BDA0002340807040000051
Figure BDA0002340807040000061
the second object of the present invention is to provide the use of the above organic compounds in organic electroluminescent devices.
An organic electroluminescent device comprises a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer contains the organic compound.
The invention has the beneficial effects that:
the carbazole-fused quinoxaline structure provided by the invention has a high charge transmission rate due to a large conjugated condensed ring structure, can reduce the voltage of the material, has a good electron transmission effect due to the quinoxaline structure, has a good hole transmission effect due to a carbazole derivative fragment, and is beneficial to charge balance due to the synergistic effect of the carbazole derivative fragment and the hole transmission fragment, so that the carbazole-fused quinoxaline structure can be used as a bipolar main body material for a light-emitting layer of an organic electroluminescent device, and realizes high light-emitting efficiency. In addition, the coplanar large conjugated condensed ring structure can enable molecules to be arranged in parallel, increase acting force among the molecules, improve crystallization performance, improve the thermodynamic stability of the compound, have good material stability and can realize long-life luminescence. The compound of the present invention can be used as a host material of a light emitting layer to realize high light emitting efficiency. 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 principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
Synthesis of Compound A1, the reaction equation is as follows:
Figure BDA0002340807040000071
the synthesis method comprises the following steps:
(1) adding 20g (100mmol) of 2, 3-dichloroquinoxaline, 25.6g (100mmol) of 5, 7-indolino [2,3-b ] carbazole, 40g of potassium carbonate and 5000mL of DMF in a reaction bottle, and reacting at 130 ℃ for 8 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, precipitating solid, filtering, and recrystallizing the obtained solid with toluene to obtain yellow powder M1;
(2) m126g (50mmol), 22g (110mmol) of 2-chlorobenzeneboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500mL of toluene, 1000mL of ethanol and 43.3g (314mmol) of potassium carbonate/1000 mL of water are added into a reaction flask, and the mixture is reacted at 80 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M2;
(3) in a reaction flask, M218.8g (50mmol), Pd (OAc)2 (1%), Pcy3 (2%) and potassium carbonate 21g (150mmol) in DMF200mL were added, and the mixture was reacted at 150 ℃ for 12 hours; stopping the reaction after the reaction is finished; adding water into the reaction liquid, separating out white solid, and recrystallizing and purifying the obtained solid by toluene to obtain M3;
(4) in a reaction flask, M326g (50mmol), bromobenzene 22g (110mmol), Pd (dba)0.9g (0.785mmol, 0.5%) S-Phos, xylene 500mL and sodium tert-butoxide 30g (300mmol) were added, and the mixture was heated under reflux for 8 hours; stopping the reaction after the reaction is finished; cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give a yellow powder a 1.
1H NMR(CDCl3,400MHz)δ8.83(s,1H),8.42(s,2H),8.14(d,J＝12.0Hz,4H),7.80(s,2H),7.67(s,2H),7.62(s,2H),7.58(s,1H),7.50(s,2H),7.40(s,2H),7.19(d,J＝10.0Hz,4H)。
Example 2
Synthesis of Compound A9, the reaction equation is as follows:
Figure BDA0002340807040000081
the synthesis method comprises the following steps:
(1) adding 2, 3-dichlorobenzofuran pyrazine (100mmol), 5, 7-indolino [2,3-b ] carbazole 25.6g (100mmol), potassium carbonate 40g and DMF5000mL into a reaction bottle, and reacting at 130 ℃ for 8 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, precipitating solid, filtering, and recrystallizing the obtained solid with toluene to obtain yellow powder M1;
(2) m126g (50mmol), 22g (110mmol) of 2-chlorobenzeneboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500mL of toluene, 1000mL of ethanol and 43.3g (314mmol) of potassium carbonate/1000 mL of water are added into a reaction flask, and the mixture is reacted at 80 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M2;
(3) in a reaction flask, M218.8g (50mmol), Pd (OAc)2 (1%), Pcy3 (2%) and potassium carbonate 21g (150mmol) in DMF200mL were added, and the mixture was reacted at 150 ℃ for 12 hours; stopping the reaction after the reaction is finished; adding water into the reaction liquid, separating out white solid, and recrystallizing and purifying the obtained solid by toluene to obtain M3;
(4) m326g (50mmol), 22g (110mmol) of 3-bromobiphenyl, 0.9g (0.785mmol, 0.5%) of Pd (dba), S-Phos, 500mL of xylene and 30g (300mmol) of sodium tert-butoxide are added into a reaction flask and heated under reflux for 8 hours; stopping the reaction after the reaction is finished; cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give a yellow powder a 9.
1H NMR(CDCl3,400MHz)δ8.20(d,J＝10.0Hz,2H),8.10(s,1H),7.72(d,J＝12.0Hz,2H),7.65(s,1H),7.52–7.45(m,15H),7.40(d,J＝8.0Hz,5H),7.20(t,J＝10.0Hz,6H)。
Example 3
Synthesis of Compound A13, the reaction equation is as follows:
Figure BDA0002340807040000101
the synthesis method comprises the following steps:
(1) adding 2, 3-dichloroquinoxaline (100mmol), 5, 7-indolino [2,3-b ] carbazole 25.6g (100mmol), potassium carbonate 40g and DMF5000mL into a reaction bottle, and reacting at 130 ℃ for 8 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, precipitating solid, filtering, and recrystallizing the obtained solid with toluene to obtain yellow powder M1;
(2) adding 2-bromo-1-naphthol (100mmol) into 200mL of dichloromethane, dropwise adding trifluoromethanesulfonic anhydride (110mmol) at 0 ℃, heating to room temperature after dropwise addition, stirring at normal temperature for 3h, and evaporating the solvent to obtain an intermediate M2 after reaction;
(3) into a reaction flask, M2(100mmol), pinacol diboride (120mmol), Pd (OAc)2(1％)、Pcy3(2%) and potassium carbonate (200mmol)/DMF200mL, at 120 ℃ for 12 h; stopping the reaction after the reaction is finished; adding water into the reaction solution, separating out white solid, and purifying the obtained solid by column chromatography to obtain M3;
(4) to a reaction flask, M126g (50mmol), M3(110mmol), 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500mL of toluene, 1000mL of ethanol and 43.3g (314mmol) of potassium carbonate/1000 mL of water were added, and the mixture was reacted at 80 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M4;
(5) into a reaction flask, M418.8g (50mmol), Pd (OAc)2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200mL, at 150 ℃ for 12 h; stopping the reaction after the reaction is finished; adding water into the reaction liquid, separating out white solid, and recrystallizing and purifying the obtained solid by toluene to obtain M5;
(6) in a reaction flask, M526 g (50mmol), bromobenzene 22g (110mmol), Pd (dba)0.9g (0.785mmol, 0.5%) S-Phos, xylene 500mL and sodium tert-butoxide 30g (300mmol) were added, and the mixture was heated under reflux for 8 hours; stopping the reaction after the reaction is finished; cooled to room temperature, filtered and the resulting solid purified by toluene recrystallization to give a yellow powder a 13.
1H NMR(CDCl3,400MHz)δ8.34-8.19(m,3H),7.94-7.84(m,5H),7.67(s,1H),7.60(t,J＝10.0Hz,4H),7.55–7.47(m,7H),7.19(d,J＝10.0Hz,4H)。
Example 4
Synthesis of Compound A19, the reaction equation is as follows:
Figure BDA0002340807040000111
the synthesis method comprises the following steps:
(1) adding 20g (100mmol) of 2, 3-dichloroquinoxaline, 25.6g (100mmol) of 5, 7-indolino [2,3-b ] carbazole, 40g of potassium carbonate and 5000mL of DMF in a reaction bottle, and reacting at 130 ℃ for 8 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, precipitating solid, filtering, and recrystallizing the obtained solid with toluene to obtain yellow powder M1;
(2) m126g (50mmol), 22g (110mmol) of 2-chlorobenzeneboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500mL of toluene, 1000mL of ethanol and 43.3g (314mmol) of potassium carbonate/1000 mL of water are added into a reaction flask, and the mixture is reacted at 80 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M2;
(3) into a reaction flask, were charged M218.8g (50mmol), Pd (OAc)2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200mL, at 150 ℃ for 12 h; stopping the reaction after the reaction is finished; adding water into the reaction liquid, separating out white solid, and recrystallizing and purifying the obtained solid by toluene to obtain M3;
(4) in a reaction flask, M326g (50mmol), bromobenzene 22g (110mmol), Pd (dba)0.9g (0.785mmol, 0.5%) S-Phos, xylene 500mL and sodium tert-butoxide 30g (300mmol) were added, and the mixture was heated under reflux for 8 hours; stopping the reaction after the reaction is finished; cooled to room temperature, filtered and the resulting solid purified by toluene recrystallization to give a yellow powder a 19.
1H NMR(CDCl3,400MHz)δ8.14(d,J＝12.0Hz,4H),7.99-7.80(m,4H),7.67-7.60(m,8H),7.53(s,1H),7.45(d,J＝10.0Hz,3H),7.23–7.11(m,6H)。
Example 5
Synthesis of Compound A23, the reaction equation is as follows:
Figure BDA0002340807040000121
the synthesis method comprises the following steps:
(1) 2-dibenzothiophene boric acid (50mmol), o-bromonitrobenzene (110mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314 mmol)/water 1000mL are added into a reaction flask, and the reaction is carried out for 8h at 80 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M1;
(2) adding M1(50mmol) and triphenylphosphine (50 mmol)/o-dichlorobenzene (1000 mL) into a reaction bottle, and heating and refluxing for reaction for 12 h; stopping the reaction after the reaction is finished; the solvent was evaporated and the resulting solid was purified by column chromatography to give M2;
(3) adding 20g (100mmol) of 2, 3-dichloroquinoxaline, M2(100mmol), 40g of potassium carbonate and DMF5000mL into a reaction bottle, and reacting for 8 hours at 130 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, precipitating solid, filtering, and recrystallizing the obtained solid with toluene to obtain yellow powder M3;
(4) m3(50mmol), 22g (110mmol) of 2-chlorobenzeneboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500mL of toluene, 1000mL of ethanol and 43.3g (314mmol) of potassium carbonate/1000 mL of water are added into a reaction flask, and the mixture is reacted for 8 hours at 80 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M4;
(5) into a reaction flask, M4(50mmol), Pd (OAc) were added2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200mL, at 150 ℃ for 12 h; stopping the reaction after the reaction is finished; water was added to the reaction solution to precipitate a white solid, and the obtained solid was purified by recrystallization from toluene to obtain A23.
1H NMR(CDCl3,400MHz)δ8.43(d,J＝12.0Hz,3H),8.14(d,J＝9.6Hz,2H),7.86-7.67(m,3H),7.56(s,1H),7.36(d,J＝11.2Hz,4H),7.19(d,J＝10.0Hz,4H)。
Example 6
Synthesis of Compound A36, the reaction equation is as follows:
Figure BDA0002340807040000141
the synthesis method comprises the following steps:
(1) 4-bromodibenzofuran (50mmol), 2-chloroaniline (60mmol), Pd (dba)0.9g (0.785mmol, 0.5%), S-Phos, xylene 500mL and sodium tert-butoxide 30g (300mmol) are added into a reaction bottle and heated under reflux for reaction for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M1;
(2) adding M1(50mmol) and dichloromethane 200ml into a reaction bottle, adding bromine (55mmol), stirring at normal temperature for 5h, and concentrating after the reaction is finished to obtain an intermediate M2;
(3) into a reaction flask, M2(50mmol), Pd (OAc) were added2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200mL, at 150 ℃ for 12 h; stopping the reaction after the reaction is finished; adding water into the reaction liquid, separating out white solid, and recrystallizing and purifying the obtained solid by toluene to obtain M3;
(4) adding M3(50mmol), diphenylamine (60mmol), Pd (dba)0.9g (0.785mmol, 0.5%) and S-Phos, xylene 500mL and sodium tert-butoxide 30g (300mmol) into a reaction bottle, and heating and refluxing for reaction for 8 h; stopping the reaction after the reaction is finished; cooling to room temperature, filtering, and purifying the obtained solid by toluene recrystallization to obtain yellow powder M4;
(5) adding 20g (100mmol) of 2, 3-dichloroquinoxaline, M4(100mmol), 40g of potassium carbonate and DMF5000mL into a reaction bottle, and reacting for 8 hours at 130 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, precipitating solid, filtering, and recrystallizing the obtained solid with toluene to obtain yellow powder M5;
(6) to a reaction flask, M5(50mmol), 22g (110mmol) of 2-chlorobenzeneboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500ml of toluene, 1000ml of ethanol, 43.3g (314mmol) of potassium carbonate/1000 ml of water were added and reacted at 80 ℃ for 8 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, filtering, and purifying the obtained solid by recrystallization from toluene to obtain yellow powder M6;
(7) into a reaction flask, M6(50mmol), Pd (OAc) were added2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200mL, at 150 ℃ for 12 h; stopping the reaction after the reaction is finished; water was added to the reaction solution to precipitate a white solid, and the obtained solid was purified by recrystallization from toluene to obtain A36.
1H NMR(CDCl3,400MHz)δ8.42(s,1H),8.20(d,J＝12.0Hz,1H),8.10(s,1H),7.83(d,J＝7.6Hz,2H),7.76(d,J＝10.0Hz,2H),7.76(d,J＝10.0Hz,2H),7.69–7.30(m,3H),7.21(dd,J＝13.2,7.2Hz,4H),7.08-7.00(m,3H)。
The other compounds of the present invention can be synthesized by selecting raw materials with suitable structures according to the above-mentioned ideas of examples 1-6, and the synthesis process is not repeated here.
Device application example
The OLED includes first and second electrodes, and an organic layer between the electrodes. The organic layer may in turn be divided into a plurality of regions. For example, the organic layer may include a hole transport region, a light emitting layer, an electron transport region, and the like.
In a specific application example, 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 layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic layer may be small organic molecules, large organic molecules, and polymers, and combinations 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 multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
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-34; or any combination thereof.
Figure BDA0002340807040000161
Figure BDA0002340807040000171
Figure BDA0002340807040000181
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-34 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
Figure BDA0002340807040000182
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.
The luminescent layer of the device can adopt the technology of phosphorescence electroluminescence. 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 BDA0002340807040000191
The OLED organic layer may also 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).
The electron transport layer materials include, but are not limited to, combinations of one or more of ET1-ET57 listed below.
Figure BDA0002340807040000201
Figure BDA0002340807040000211
Figure BDA0002340807040000221
The device can also comprise an electron transport layer and a cathodeAn electron injection layer between the electrodes, the electron injection layer material including but not limited to LiQ, LiF, NaCl, CsF, Li in the prior art2O、Cs2CO3One or a combination of more of materials such as BaO, Na, Li, Ca and the like.
Organic electroluminescent devices were prepared using the compounds prepared in examples 1 to 6 and R1, R2 as host materials.
Figure BDA0002340807040000222
Application example 1
The preparation process of the organic electroluminescent device in the application example of the device is as follows:
(1) ultrasonically treating the glass plate coated with the ITO transparent conducting layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent, baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
(3) evaporating HT-4 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
(4) and (2) performing vacuum evaporation on a light-emitting layer of the device on the hole transport layer, wherein the light-emitting layer comprises a main material and a dye material RPD-1, and the weight ratio of the main material to the dye material is 97: 3, adjusting the evaporation rate of the main material A1 to be 0.1nm/s, setting the evaporation rate of the dye GPD-1 according to the proportion of 3%, and setting the total film thickness of evaporation to be 30 nm;
(5) an electron transport layer of the device is vacuum evaporated on the light emitting layer, and the material ET-42 is selected, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
(6) 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 Al layer with the thickness of 150nm is used as a cathode of the device.
Application example 2
The same as in application example 1, except that: a9 was used as the host material instead of a 1.
Application example 3
The same as in application example 1, except that: a13 was used as the host material instead of a 1.
Application example 4
The same as in application example 1, except that: a19 was used as the host material instead of a 1.
Application example 5
The same as in application example 1, except that: a23 was used as the host material instead of a 1.
Application example 6
The same as in application example 1, except that: a36 was used as the host material instead of a 1.
Comparative example 1
The same as in application example 1, except that: r-1 was used as the host material instead of A1.
Comparative example 2
The same as in application example 1, except that: r-2 was used as the host material instead of A1.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the organic electroluminescent device obtained in the application example and the comparative example was measured for driving voltage, current efficiency and lifetime at the same luminance using a digital source meter and a luminance meter, specifically, for increasing the voltage at a rate of 0.1V per second, and it was measured that the luminance of the organic electroluminescent device reached 5000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours, the results are shown in table 1 below.
TABLE 1
Figure BDA0002340807040000241
As is apparent from the data of Table 1, the organic electroluminescent devices prepared using the compounds of examples 1 to 6 of the present invention as host materials have lower drop-out voltage, higher current efficiency, and longer life span than those of comparative examples 1 and 2. The results show that the novel organic material is used for the organic electroluminescent device, can effectively reduce the rise-fall voltage, improve the current efficiency and prolong the service life, and is a red light main body material with good performance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (7)

1. An organic compound is characterized in that the structural formula is as follows:
Figure FDA0002340807030000011
wherein m and n are 0 or 1 and are not 0 or 1 simultaneously;
R1、R2、R3、R4each independently is hydrogen, C1-C10Alkyl radical, C1-C10Alkenyl, cyano, C6-C30Aryl or C3-C20A heteroaryl group;
x, Z are each independently O, S, CR5R6Or NR7；
Y1、Y2、Y3、Y4Each independently is C or N, and at least two are N;
R5、R6each independently is C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C20A heteroaryl group;
R7is C1-C10Alkyl, substituted or unsubstituted C6-C30Arylene or substituted or unsubstituted C3-C20A heteroarylene group.
2. An organic compound according to claim 1, wherein R is1、R2、R3、R4Each independently is hydrogen, methyl, ethyl, isopropyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, or carbazolyl.
3. An organic compound according to claim 1, wherein R is5、R6、R7Each independently is methyl, ethyl, phenyl, naphthyl, biphenyl, terphenyl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, phenanthryl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, or carbazolyl.
4. An organic compound according to claim 1, wherein R is1、R2、R3Or R4Benzene adjacent thereto is fused to be linked.
5. An organic compound according to claim 1, having the formula:
Figure FDA0002340807030000021
Figure FDA0002340807030000031
Figure FDA0002340807030000041
Figure FDA0002340807030000051
6. use of an organic compound according to any one of claims 1 to 5 in an organic electroluminescent device.
7. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, characterized in that the organic layer contains the organic compound according to any one of claims 1 to 5.
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