CN111072677A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN111072677A
CN111072677A CN201911375375.5A CN201911375375A CN111072677A CN 111072677 A CN111072677 A CN 111072677A CN 201911375375 A CN201911375375 A CN 201911375375A CN 111072677 A CN111072677 A CN 111072677A
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reaction
compound
organic compound
organic
toluene
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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 invention provides a compound with a condensed structure, wherein the large conjugated condensed ring structure of the compound has very high transmission rate of charges, can reduce the voltage of the material, has very good transmission effect on electrons when being connected with an electro-absorption segment, and a carbazole derived segment has very good effect on hole transmission, and the synergistic effect of the carbazole derived segment and the hole transmission is favorable for the balance of charges. 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 BDA0002340806190000021
wherein R is1、R2、R3、R4Each independently is hydrogen, C1-C10Alkyl radical, C1-C10Alkenyl, cyano, amino, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C20A heteroaryl group;
x is O, S, NR, CR' or R ";
r is C6-C30Arylene radicals or C3-C20A heteroarylene group;
r 'and R' are each independently C1-C6Alkyl radical, C6-C30Aryl or C3-C20A heteroaryl group;
m, n, o and p are integers of 0-4.
Further, the organic compound has the following structural formula:
Figure BDA0002340806190000022
further, the above organic compound has the following structural formula:
Figure BDA0002340806190000031
further, R1、R2、R3、R4Each independently hydrogen, methyl, ethyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, pyrenyl, perylenyl, triphenylenyl, fluoranthenyl, triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, quinoxalinyl, or amino.
Further, R', R "are each independently methyl, ethyl, propyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;
r is phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, pyrenyl, perylenyl, triphenylenyl, fluoranthenyl, triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl or quinoxalinyl.
Further, R1、R2、R3Or R4The aromatic rings adjacent thereto are fused to form a ring.
Further, the organic compound has the following structural formula:
Figure BDA0002340806190000041
Figure BDA0002340806190000051
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 invention provides a compound with a condensed structure, wherein the large conjugated condensed ring structure of the compound has very high transmission rate of charges, can reduce the voltage of the material, has very good transmission effect on electrons when being connected with an electro-absorption segment, and a carbazole derived segment has very good effect on hole transmission, and the synergistic effect of the carbazole derived segment and the hole transmission is favorable for the balance of charges, so that the compound can be used as a bipolar main body material for a light-emitting layer of an organic electroluminescent device, and realizes very high luminous 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 BDA0002340806190000061
the synthesis method comprises the following steps:
(1) in a reaction flask, 20g (100mmol) of o-bromoiodobenzene and 5, 7-indolino [2,3-b ] are added]Carbazole 25.6g (100mmol), Pd2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; 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) m126 g (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 DMF200 mL, 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 M326 g (50mmol), 2-chloro-4, 6-diphenyl triazine 22g (110mmol), DMF500mL and potassium carbonate 40g (300mmol) into a reaction flask, and stirring at normal temperature for reacting for 8 h; stopping the reaction after the reaction is finished; after cooling to room temperature, water was added to precipitate a solid, which was filtered and the resulting solid was purified by recrystallization from toluene to give 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 A6, the reaction equation is as follows:
Figure BDA0002340806190000081
the synthesis method comprises the following steps:
(1) adding 5-phenyl-2-bromofluorobenzene (100mmol), 5, 7-indolino [2,3-b ] carbazole 25.6g (100mmol), potassium carbonate 40g and DMF 1000mL into a reaction bottle, and reacting at 120 ℃ 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) m126 g (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 DMF200 mL, 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 M326 g (50mmol), 5-chloro-2-cyanopyrimidine (110mmol), DMF500mL and potassium carbonate 40g (300mmol) into a reaction bottle, and stirring at normal temperature for reacting for 8 h; stopping the reaction after the reaction is finished; after cooling to room temperature, water was added to precipitate a solid, which was filtered and the resulting solid was purified by recrystallization from toluene to give yellow powder a 6.
1H NMR(CDCl3,400MHz)δ9.25(s,2H),8.61-8.42(m,3H),8.10(d,J＝8.0Hz,4H),7.75(s,1H),7.62-7.49(m,4H),7.40(d,J＝7.6Hz,4H),7.19(d,J＝10.0Hz,4H)。
Example 3
Synthesis of Compound A13, the reaction equation is as follows:
Figure BDA0002340806190000091
the synthesis method comprises the following steps:
(1) in a reaction flask, 20g (100mmol) of o-bromoiodobenzene and 5, 7-indolino [2,3-b ] are added]Carbazole 25.6g (100mmol), Pd2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; 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 1-bromo-2-nitronaphthalene (100mmol), diboron pinacol ester (100mmol) and Pd in a reaction bottle2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, and concentrating the organic phase to obtain yellow powder M2;
(3) to a reaction flask, M126 g (50mmol), M2(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 M3;
(4) adding M3(100mmol), stannous chloride (200mmol), ethyl acetate 500mL and ethanol 500mL into a reaction bottle, and heating and refluxing for reaction for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, adding sodium hydroxide aqueous solution to adjust to neutrality, and concentrating the organic phase to obtain yellow powder M4;
(5) adding M4(50mmol) and tetrahydrofuran (150mmol) into a reaction bottle, stirring for dissolving, dropwise adding 50ml of sodium nitrite (50mmol) aqueous solution at 0 ℃, and reacting for 12 hours after dropwise adding; 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) m5(50mmol), iodobenzene (55mmol) and Pd were added to a reaction flask2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; stopping the reaction after the reaction is finished; after cooling to room temperature, water was added and a solid precipitated, which was filtered and the resulting solid was purified by recrystallization from toluene to give a yellow powder a 13.
1H NMR(CDCl3,400MHz)δ8.57(d,J＝10.4Hz,2H),8.42-8.19(m,3H),8.10-7.99(m,3H),7.72(s,1H),7.60(t,J＝10.0Hz,4H),7.55–7.47(m,4H),7.39(d,J＝8.0Hz,3H),7.19(d,J＝10.0Hz,4H)。
Example 4
Synthesis of Compound A14, the reaction equation is as follows:
Figure BDA0002340806190000101
the synthesis method comprises the following steps:
(1) 2-dibenzofuran boronic acid (50mmol), o-bromonitrobenzene (55mmol), 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), triphenylphosphine (100mmol) and 500mL of o-dichlorobenzene in a reaction bottle, and reacting for 12h at 150 ℃; stopping the reaction after the reaction is finished; purifying by column chromatography to obtain M2;
(3) 20g (100mmol) of o-bromoiodobenzene, M2(100mmol) and Pd were added to a reaction flask2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; 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), 2-chlorobenzeneboronic acid (55mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314 mmol)/water 1000mL were added to a reaction flask and reacted at 80 ℃ 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) into a reaction flask, M4(50mmol), Pd (OAc) were added2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200 mL, 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 A14.
1H NMR(CDCl3,400MHz)δ8.64-8.42(m,3H),8.14(d,J＝12.0Hz,2H),7.98-7.72(m,6H),7.54(s,1H),7.39(d,J＝8.0Hz,3H),7.19(d,J＝10.0Hz,2H)。
Example 5
Synthesis of Compound A16, the reaction equation is as follows:
Figure BDA0002340806190000121
the synthesis method comprises the following steps:
(1) adding 2-dibenzofuran boric acid (50mmol) and 300mL of dichloromethane into a reaction bottle, dropwise adding bromine (55mmol), stirring at normal temperature for 30min, and concentrating the reaction solution after the reaction is finished to obtain an intermediate M1;
(2) m1(50mmol), o-bromonitrobenzene (55mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314mmol) per 1000mL of water were added to a reaction flask and reacted at 80 ℃ 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 M2;
(3) adding M2(50mmol), triphenylphosphine (100mmol) and 500mL of o-dichlorobenzene in a reaction bottle, and reacting for 12h at 150 ℃; stopping the reaction after the reaction is finished; purifying by column chromatography to obtain M3;
(4) 20g (100mmol) of o-bromoiodobenzene, M3(100mmol) and Pd were added to a reaction flask2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; 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 M4;
(5) m4(50mmol), 2-chlorobenzeneboronic acid (55mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314 mmol)/water 1000mL were added to a reaction flask and reacted at 80 ℃ 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 M5;
(6) into a reaction flask, M5(50mmol), Pd (OAc) were added2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200 mL, 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 M6;
(7) in a reaction flask, M6(100mmol), pinacol diboron (100mmol) and Pd were added2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; 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 M7;
(8) in a reaction flask, M7(50mmol), 2-chloro-4-phenylquinazoline (55mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314 mmol)/water 1000mL were added, and reaction was carried out at 80 ℃ for 8 h; 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 16.
1H NMR(CDCl3,400MHz)δ8.94-8.70(m,3H),8.23–8.08(m,5H),7.99(d,J＝7.6Hz,2H),7.80(d,J＝9.6Hz,4H),7.72(s,1H),7.65-7.54(m,3H),7.39(d,J＝8.0Hz,3H),7.19(d,J＝10.0Hz,4H)。
Example 6
Synthesis of Compound A21, the reaction equation is as follows:
Figure BDA0002340806190000141
the synthesis method comprises the following steps:
(1) 9-bromobenzocarbazole (50mmol), 2-nitrophenylboronic acid (22 g, 110mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL, and potassium carbonate 43.3g (314 mmol)/water 1000mL were added to a reaction flask and reacted at 80 ℃ 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 M1;
(2) adding M1(50mmol), triphenylphosphine (100mmol) and 500mL of o-dichlorobenzene in a reaction bottle, and reacting for 12h at 150 ℃; stopping the reaction after the reaction is finished; purifying by column chromatography to obtain M2;
(3) 20g (100mmol) of o-bromoiodobenzene, M2(100mmol) and Pd were added to a reaction flask2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; 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), 2-chlorobenzeneboronic acid (55mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314 mmol)/water 1000mL were added to a reaction flask and reacted at 80 ℃ 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) into a reaction flask, M4(50mmol), Pd (OAc) were added2(1％)、Pcy3(2%) and potassium carbonate 21g (150mmol) in DMF200 mL, 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) adding M5(50mmol), 3-bromobiphenyl (55mmol) and Pd into a reaction bottle2(dba)3(1％)、P(t-Bu)3(2 percent), 40g of sodium tert-butoxide and 1000mL of toluene, and reacting for 8 hours at 100 ℃; stopping the reaction after the reaction is finished; after cooling to room temperature, water was added and a solid precipitated, which was filtered and the resulting solid was purified by recrystallization from toluene to give a yellow powder a 21.
1H NMR(CDCl3,400MHz)δ9.01(s,1H),8.54-8.42(m,3H),8.29–8.09(m,4H),8.08(s,1H),7.73(d,J＝15.0Hz,3H),7.61(d,J＝8.0Hz,2H),7.57(dd,J＝10.4,8.0Hz,4H),7.58–7.32(m,8H),7.24–7.04(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. First electricityWhen the cathode is a metal, a metal alloy, or any combination thereof, such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).
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 BDA0002340806190000161
Figure BDA0002340806190000171
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 BDA0002340806190000181
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 BDA0002340806190000182
Figure BDA0002340806190000191
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 BDA0002340806190000201
Figure BDA0002340806190000211
Figure BDA0002340806190000221
The device may further comprise an electron injection layer between the electron transport layer and the cathode, and the electron injection layer comprises, but is 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 BDA0002340806190000222
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: a6 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: a14 was used as the host material instead of a 1.
Application example 5
The same as in application example 1, except that: a16 was used as the host material instead of a 1.
Application example 6
The same as in application example 1, except that: a21 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 BDA0002340806190000241
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 (9)

1. An organic compound is characterized in that the structural formula is as follows:
Figure FDA0002340806180000011
wherein R is1、R2、R3、R4Each of which isIndependently of one another is hydrogen, C1-C10Alkyl radical, C1-C10Alkenyl, cyano, amino, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C20A heteroaryl group;
x is O, S, NR, CR' or R ";
r is C6-C30Arylene radicals or C3-C20A heteroarylene group;
r 'and R' are each independently C1-C6Alkyl radical, C6-C30Aryl or C3-C20A heteroaryl group;
m, n, o and p are integers of 0-4.
2. An organic compound according to claim 1, having the formula:
Figure FDA0002340806180000012
3. an organic compound according to claim 2, having the formula:
Figure FDA0002340806180000021
4. the organic compound of any one of claims 1-3, wherein R is1、R2、R3、R4Each independently hydrogen, methyl, ethyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, pyrenyl, perylenyl, triphenylenyl, fluoranthenyl, triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, quinoxalinyl, or amino.
5. The organic compound of any one of claims 1-3, wherein R', R "are each independently methyl, ethyl, propyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;
r is phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, pyrenyl, perylenyl, triphenylenyl, fluoranthenyl, triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl or quinoxalinyl.
6. The organic compound of any one of claims 1-3, wherein R is1、R2、R3Or R4The aromatic rings adjacent thereto are fused to form a ring.
7. The organic compound according to any one of claims 1 to 3, having the formula:
Figure FDA0002340806180000031
Figure FDA0002340806180000041
8. use of an organic compound according to any one of claims 1 to 7 in an organic electroluminescent device.
9. 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 7.
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