CN111689889A - Aromatic amine compound and use thereof - Google Patents

Aromatic amine compound and use thereof Download PDF

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CN111689889A
CN111689889A CN202010704032.5A CN202010704032A CN111689889A CN 111689889 A CN111689889 A CN 111689889A CN 202010704032 A CN202010704032 A CN 202010704032A CN 111689889 A CN111689889 A CN 111689889A
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aromatic amine
unsubstituted
amine compound
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CN111689889B (en
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范洪涛
王湘成
向传义
何为
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention discloses an aromatic amine compound and application thereof,belongs to the technical field of organic electroluminescence. The aromatic amine compound has a general structure shown by the following formula:
Figure DDA0002594015080000011
x is selected from O, S or-NR-, and R1、R2、R3、R4And R is independently selected from hydrogen, deuterium, substituted or unsubstituted aryl group having a carbon number of 6 to 30, substituted or unsubstituted heteroaryl group having a carbon number of 5 to 30, substituted or unsubstituted alkyl group having a carbon number of 1 to 30, substituted or unsubstituted fluoroalkyl group having a carbon number of 1 to 30, substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 30, and substituted or unsubstituted aralkyl group having a carbon number of 7 to 30, respectively, as a hole transporting material in the organic electroluminescent device. Due to the addition of the naphthalene heterocyclic ring structure, the aromatic amine compound can effectively improve the hole transport capability of the OLED device, thereby improving the light efficiency and prolonging the service life of the device.

Description

Aromatic amine compound and use thereof
Technical Field
The invention belongs to the field of organic electroluminescence, and particularly relates to an aromatic amine compound and application thereof in an organic electroluminescent device and display.
Background
The OLED can emit light in a solid state and is widely used in the fields of display, illumination and the like, and an OLED device is composed of an anode, a cathode and an organic material therebetween, holes are injected from the anode and are transported to a light emitting layer, electrons are injected from the cathode and are transported to the light emitting layer, and in order to achieve the best light emitting performance, the amounts of the holes and the electrons entering the light emitting layer are often balanced. While suitable hole transport materials have a great influence on the light emitting performance of OLEDs, common amine-containing hole transport materials have poor hole injection capability and a small hole injection amount, resulting in high device voltage and low efficiency, and aromatic amine compounds are widely used as hole transport materials, but the hole transport capability still needs to be improved.
Disclosure of Invention
In order to overcome the above defects of the prior art, the present invention provides an aromatic amine compound having a naphtho-heterocycle, which is used as a hole transport material of an OLED device to effectively improve the hole transport ability of the OLED device, thereby improving the device performance, and the aromatic amine compound has a chemical structure shown in formula (i):
Figure BDA0002594015060000011
wherein X is selected from O, S or-NR-;
R1、R2、R3、R4and R is independently selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms in a ring, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in a ring, substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms in a ring, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms in a ring, and substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms in a ring.
According to some embodiments of the invention, the aromatic amine compound is selected from the group consisting of the chemical structures shown as any one of C1 to C36:
Figure BDA0002594015060000021
Figure BDA0002594015060000031
the invention provides application of any one of the aromatic amine compounds as a hole transport material in an organic electroluminescent device.
According to some embodiments of the present invention, the organic electroluminescent device is a top emission structure, and sequentially includes a first electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, a second electrode, and a cap layer; wherein the content of the first and second substances,
any of the aromatic amine compounds having a chemical structure represented by the general formula (I) is used as the first hole transport layer and/or the second hole transport layer.
The invention also provides a display panel comprising any one of the organic electroluminescent devices.
The invention also provides a display device comprising any one of the display panels.
The display panel or the display device comprising the organic electroluminescent device has the following advantages: high luminous efficiency, low driving voltage and long service life.
Compared with the prior art, the aromatic amine compound used as the hole transport material can effectively improve the hole transport capability of the OLED device due to the addition of the naphthalene heterocyclic structure, so that the light efficiency and the service life of the device are improved.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device.
Detailed Description
The present invention is further illustrated by the following examples and comparative examples, which are intended to be illustrative only and are not to be construed as limiting the invention. The technical scheme of the invention is to be modified or replaced equivalently without departing from the scope of the technical scheme of the invention, and the technical scheme of the invention is covered by the protection scope of the invention.
The aromatic amine compound provided by the invention has a chemical structure shown as a general formula (I):
Figure BDA0002594015060000041
wherein X is selected from O, S or-NR-;
R1、R2、R3、R4and R are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having a carbon number of 6 to 30 in the ring, a substituted or unsubstituted heteroaryl group having a carbon number of 5 to 30 in the ring, a substituted or unsubstituted alkyl group having a carbon number of 1 to 30 in the ring, a substituted or unsubstituted fluoroalkyl group having a carbon number of 1 to 30 in the ring, a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 30 in the ring, or a substituted or unsubstituted aralkyl group having a carbon number of 7 to 30, the above aromatic amine compound may in some embodiments have a chemical structure as shown in any one of C1 to C36:
Figure BDA0002594015060000051
Figure BDA0002594015060000061
Figure BDA0002594015060000071
the invention also provides the application of the aromatic amine compound as a hole transport material in the organic electroluminescent device; in some embodiments, the organic electroluminescent device may be a top emission structure and sequentially include a first electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, a second electrode, and a cap layer; wherein an aromatic amine compound having a chemical structure represented by the above general formula (I) is used as the first hole transporting layer and/or the second hole transporting layer.
The invention also provides a display panel comprising the organic electroluminescent device.
The invention also provides a display device comprising the display panel.
The following synthetic examples 1 to 5 exemplarily describe the synthesis of the above-mentioned compounds C1, C2, C7, C19 and C28, wherein the starting materials for the preparation methods are not indicated as commercially available ones.
Synthesis example 1
This example synthesizes compound C1(1-1), the synthetic route is shown below:
Figure BDA0002594015060000072
the preparation method comprises the following specific steps:
m-1 was synthesized by charging M-1A (100g,553.6mmol), M-1B (102g,553.6mmol) and 1, 4-dioxane (1.00L) in this order into a three-necked flask, displacing nitrogen gas three times, dropwise adding concentrated sulfuric acid (33.8mL,609mmol) into the three-necked flask while stirring, after completion of heating, setting the external temperature at 100 ℃ and refluxing for 10hrs, cooling the reaction liquid, pouring into water (2.00L), extracting with toluene (1.00L × 2), washing the organic phase with a saturated aqueous NaCl solution (1.00L × 3) and purifying by column chromatography to obtain M-1(155.2g, 85%), MS (70eV, EI+):m/z:329.10。
Synthesis of M-2: m-1(100g, 303.2mmol), toluene (1.00L) and DDQ (77.1g, 333.5mmol) were added to a three-necked flask in this order, and nitrogen was replaced three times with a nitrogen gas, and the flask was openedStirring and heating, setting external temperature at 120 deg.C, refluxing for 5hrs, adding saturated NaOH aqueous solution (200mL), reacting for 1hr, cooling, filtering, washing the filtrate with saturated NaCl aqueous solution (300mL × 3), and purifying with column to obtain M-2(79.5g, 80%), MS (70eV, EI)+):m/z:327.08。
Synthesis of M-3: to a three-necked flask, toluene (800mL), M-2(79.0g, 241mmol), bromobenzene (37.9g, 241mmol), sodium tert-butoxide (57.9g, 602mmol), Pd were added in this order with stirring2dba3(2.20g, 2.41mmol) and tri-tert-butylphosphine (15.0mL, 10% toluene solution, 6.02mmol), replacing nitrogen for three times, heating, reflux-reacting at 120 deg.C for 3hrs, cooling, filtering, and purifying the filtrate by column chromatography to obtain M-3(87.6g, 90%), MS (70eV, EI)+):m/z:403.11。
1-1 Synthesis: to a three-necked flask, toluene (100mL), absolute ethanol (50mL), water (50mL), M-3(20.0g, 49.5mmol), M-3A (14.3g, 49.5mmol), and K were added with stirring2CO3(13.7g，99.0mmol)，Pd(PPh3)4(575mg, 0.49mmol), replacing nitrogen for three times, heating, setting the external temperature at 100 deg.C, refluxing for 3hrs, cooling, separating, washing the organic phase with saturated NaCl aqueous solution (100mL × 3), and purifying by column chromatography to obtain 1-1(25.8g, 85%), MS (70eV, EI)+):m/z:612.26；1H NMR(CDCl3,400Hz):8.12-8.23(m,4H),7.89(s,1H),7.37-7.62(m,15H),7.01-7.24(m,12H)。
Synthesis example 2
Compound C2(1-2) of this example was synthesized using M-3 obtained in example 1, the route being shown below:
Figure BDA0002594015060000081
the preparation method comprises the following specific steps:
1-2 Synthesis: to a three-necked flask, toluene (100mL), absolute ethanol (50mL), water (50mL), M-3(20.0g, 49.5mmol), M-3B (21.9g, 49.5mmol), and K were added with stirring2CO3(13.7g，99.0mmol)，Pd(PPh3)4(575mg，0.49mmol) under nitrogen, heating, reflux reacting at 100 deg.C for 3hrs, cooling, separating, washing with saturated NaCl aqueous solution (100mL × 3), and purifying by column chromatography to obtain 1-2(31.1g, 82%) MS (70eV, EI)+):m/z:764.32；1H NMR(CDCl3,400Hz):8.12-8.30(m,4H),7.60-7.75(m,6H),7.31-7.58(m,30H)。
Synthesis example 3
Compound C7(1-3) of this example was synthesized using M-3 obtained in example 1, the synthetic route being as follows:
Figure BDA0002594015060000091
the preparation method comprises the following specific steps:
synthesis of M-4: to a three-necked flask, toluene (100mL), absolute ethanol (50mL), water (50mL), M-3(20.0g, 49.5mmol), M-3C (7.74g, 49.5mmol), K, were added with stirring2CO3(13.7g，99.0mmol)，Pd(PPh3)4(575mg, 0.49mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, carrying out reflux reaction for 3hrs, then cooling, separating liquid, washing the organic phase with saturated NaCl aqueous solution (100mL × 3), and purifying by column chromatography to obtain M-4(19.7g, 83%), MS (70eV, EI)+):m/z:479.14。
1-3 Synthesis: to a three-necked flask, toluene (190mL), M-4(19.0g, 39.58mmol), M-4A (12.7g, 39.58mmol), sodium tert-butoxide (7.61g, 79.17mmol), Pd were added in this order with stirring2dba3(365mg, 0.40mmol) and tricyclohexylphosphine (280mg, 0.99mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 120 ℃, refluxing for 3hrs, cooling, filtering, purifying the filtrate by column chromatography to obtain 1-3(30.0g, 90%), MS (70eV, EI)+):m/z:840.35；1H NMR(CDCl3,400Hz):8.12-8.30(m,4H),7.89(s,1H)7.34-7.75(m,35H),7.25(s,4H)。
Synthesis example 4
This example synthesizes compound C19(2-1), the synthetic route is shown below:
Figure BDA0002594015060000101
the preparation method comprises the following specific steps:
m-5 Synthesis by adding acetonitrile (500mL), M-5A (50.0g, 281.5mmol), M-5B (70.7g, 281.5mmol), cesium carbonate (183.5g, 563mmol) to a three-necked flask in this order with stirring, displacing nitrogen three times, heating, setting the external temperature at 100 deg.C, refluxing for 10hrs, cooling, quenching the reaction mixture in water (500mL), extracting with ethyl acetate (200mL × 2), concentrating the organic phase, and purifying by column chromatography to obtain M-5(99.2g, 86%), MS (70eV, EI+):m/z:407.99。
Synthesis of M-6: to a three-necked flask, toluene (200mL), M-5(20.0g, 48.82mmol), sodium t-butoxide (9.38g, 97.63mmol), Pa, were added in this order with stirring2(dba)3(447mg，0.488mmol)，P(t-Bu)3(2.0g, 10% toluene solution, 0.989mmol), nitrogen was replaced three times, heating was started, the external temperature was set at 120 deg.C, reflux reaction was carried out for 2hrs, cooling was carried out, filtration was carried out, and the filtrate was purified by column chromatography to obtain M-6(13.24g, 82.5%), MS (70eV, EI)+):m/z:328.07。
2-1 Synthesis: to a three-necked flask, toluene (40mL), absolute ethanol (20mL), water (20mL), M-6(10.0g, 30.41mmol), M-6A (8.79g, 30.41mmol), and K were added with stirring2CO3(6.31g，45.62mmol)，Pd(PPh3)4(351mg, 0.3mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, carrying out reflux reaction for 3hrs, then cooling, separating liquid, washing an organic phase with a saturated NaCl aqueous solution (50mL × 3), and purifying by column chromatography to obtain 2-1(15.53g, 95%) MS (70eV, EI)+):m/z:537.21；1H NMR(CDCl3,400Hz):8.23(d,1H),7.75-7.88(m,6H),7.37-7.55(m,10H),7.00-7.24(m,10H)。
Synthesis example 5
This example synthesizes compound C28(2-2), the synthetic route is shown below:
Figure BDA0002594015060000111
the preparation method comprises the following specific steps:
synthesis of M-7: to a three-necked flask, toluene (200mL), absolute ethanol (100mL), water (100mL), M-7A (50.0g, 194.62mmol), M-7B (60.43g, 194.62mmol), K were added with stirring2CO3(40.35g，292mmol)，Pd(PPh3)4(2.25g, 1.95mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, carrying out reflux reaction for 3hrs, then cooling, separating liquid, washing an organic phase with a saturated NaCl aqueous solution (100mL × 3), and purifying by column chromatography to obtain M-7(70.1g, 91%), MS (70eV, EI)+):m/z:393.94。
M-8 synthesis, namely adding methanesulfonic acid (350mL) and M-7(70.0g, 176.9mmol) into a three-necked flask, replacing nitrogen for three times, starting heating, setting the external temperature at 150 ℃, reacting for 12hrs, cooling, pouring the reaction solution into a mixed solution of initial water (1L) and toluene (1L), uniformly stirring, separating, washing an organic phase by a saturated NaCl aqueous solution (300mL × 3), and purifying by column chromatography to obtain M-8(59.8 g), MS (70eV, EI)+):m/z:361.92。
M-9 Synthesis by adding M-8(50.0g, 137.49mmol), toluene (500mL) and DDQ (34.33g, 151.24mmol) in sequence to a three-necked flask, displacing nitrogen three times, stirring and heating, setting the external temperature at 120 ℃, refluxing for 5hrs, adding saturated aqueous NaOH (200mL), continuing to react for 1hr, cooling, filtering, washing the filtrate with saturated aqueous NaCl solution (300mL × 3), purifying with column to obtain M-9(43.26g, 90.5%), MS (70eV, EI)+):m/z:345.92。
Synthesis of M-10: to a three-necked flask, toluene (160mL), absolute ethanol (80mL), water (80mL), M-9(40.0g, 115.06mmol), phenylboronic acid (14.03g, 115.06mmol), and K were added with stirring2CO3(23.85g，172.6mmol)，Pd(PPh3)4(1.33g, 1.15mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, carrying out reflux reaction for 3hrs, then cooling, separating liquid, washing an organic phase with a saturated NaCl aqueous solution (100mL × 3), and purifying by column chromatography to obtain M-10(37.7g, 95%), MS (70eV, EI)+):m/z:344.04。
2-2 Synthesis: to a three-necked flask, toluene (120mL), absolute ethanol (60mL), water (60mL), M-10(30.0g, 87.0 mmol) were added with stirring)，M-10A(25.15g，87.0mmol)，K2CO3(18.0g，130.4mmol)，Pd(PPh3)4(1.00g, 0.87mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, carrying out reflux reaction for 3hrs, cooling, separating liquid, washing an organic phase with a saturated NaCl aqueous solution (100mL × 3), and purifying by column chromatography to obtain M-10(43.35g, 90%), MS (70eV, EI)+):m/z:553.19；1H NMR(CDCl3,400Hz):7.99-8.23(m,5H),7.75-7.83(m,3H),7.38-7.55(m,6H),7.00-7.24(m,13H)。
The technical effects of the compounds of the invention are explained in detail below by means of device examples.
Comparative example 1
Comparative example 1 Using the Compound
Figure BDA0002594015060000121
As a first hole transport layer, an OLED display panel with a top emission structure was prepared according to the structure shown in fig. 1, and the specific preparation process was:
forming a reflecting anode Ag 100nm on a glass substrate, forming an ITO film layer on the Ag with a thickness of 15nm to obtain a first electrode as an anode, and then evaporating 30nm HATCN (
Figure BDA0002594015060000122
) As a hole injection layer, HTL1 was evaporated to a thickness of 100nm
Figure BDA0002594015060000123
A first hole transport layer is obtained, and then the layer with the thickness of 20nm is evaporated
Figure BDA0002594015060000124
Obtaining a second hole transport layer, and then evaporating at an evaporation rate of 95% to 5%
Figure BDA0002594015060000125
And
Figure BDA0002594015060000126
30nm, preparing a blue light emitting unit, and then evaporating to deposit 10nm
Figure BDA0002594015060000131
Forming a hole blocking layer, and then evaporating 30nm at an evaporation rate of 50% to 50%
Figure BDA0002594015060000132
And
Figure BDA0002594015060000133
the mixture is used as an electron transport layer, then magnesium silver with the thickness of 15nm is formed at the evaporation rate of 90% to 10% as a second electrode, and then 700nm is formed
Figure BDA0002594015060000134
As a capping layer.
Device examples 1 to 5
And comparative example 1 with HTL1(
Figure BDA0002594015060000135
) Examples 1 to 5 used compounds C1, C2, C7, C19 and C28 prepared in the above-described synthesis examples 1 to 5, respectively, as the first hole transport layer, differently from the first hole transport layer, and the other structures were the same.
Comparative example 2
And comparative example 1 with HTL1(
Figure BDA0002594015060000136
) Comparative example 2, which is different from the first hole transport layer, employs HTL2 (h 1)
Figure BDA0002594015060000137
) The first hole transport layer is different from the second hole transport layer, and the other structures are the same.
TABLE 1
Figure BDA0002594015060000141
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. It will be readily apparent to those skilled in the art that various modifications to these embodiments and the generic principles defined herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments. Those skilled in the art should appreciate that many modifications and variations are possible in light of the above teaching without departing from the scope of the invention.

Claims (6)

1. An aromatic amine compound having the chemical structure shown in formula (i):
Figure FDA0002594015050000011
wherein X is selected from O, S or-NR-;
R1、R2、R3、R4and R is independently selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms in a ring, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in a ring, substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms in a ring, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms in a ring, and substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms in a ring.
2. The aromatic amine compound of claim 1, wherein the aromatic amine compound has a chemical structure selected from the group consisting of C1-C36:
Figure FDA0002594015050000012
Figure FDA0002594015050000021
Figure FDA0002594015050000031
3. use of the aromatic amine compound according to claim 1 or 2 as a hole transport material in an organic electroluminescent device.
4. The use according to claim 3, wherein the organic electroluminescent device is a top-emitting structure comprising, in order, a first electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, a second electrode, and a cap layer; wherein the aromatic amine compound according to claim 1 or 2 is used as the first hole transport layer and/or the second hole transport layer.
5. A display panel comprising the organic electroluminescent device according to claim 3 or 4.
6. A display device characterized by comprising the display panel according to claim 5.
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