CN111217739A - Organic compound, organic electroluminescent device comprising organic compound and display device comprising organic compound - Google Patents

Organic compound, organic electroluminescent device comprising organic compound and display device comprising organic compound Download PDF

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CN111217739A
CN111217739A CN202010102635.8A CN202010102635A CN111217739A CN 111217739 A CN111217739 A CN 111217739A CN 202010102635 A CN202010102635 A CN 202010102635A CN 111217739 A CN111217739 A CN 111217739A
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organic compound
carbon atoms
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陈跃
丰佩川
邢其锋
胡灵峰
孙志武
陈义丽
孙伟
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The embodiment of the invention provides an organic compound with the following formula (I), an organic electroluminescent device comprising the organic compound and a display device comprising the organic compound. The organic compound provided by the embodiment of the invention has higher refractive index and lower evaporation temperature; the material can be used as a light extraction layer material to improve the light extraction efficiency of the organic electroluminescent device and prolong the service life of the device; meanwhile, the difficulty of the evaporation process can be reduced due to the lower evaporation temperature.
Figure DDA0002387381950000011

Description

Organic compound, organic electroluminescent device comprising organic compound and display device comprising organic compound
Technical Field
The invention relates to the technical field of material chemistry, in particular to an organic compound, an organic electroluminescent device comprising the organic compound and a display device comprising the organic compound.
Background
An organic electroluminescent device is a self-luminous device having a multi-layered organic thin film structure in which a light-emitting layer is disposed between a cathode and an anode. After the electricity is applied, the light emitted by the light-emitting layer is transmitted from the transparent electrode side, and only a part of the light can be transmitted because the light can generate waveguide effects such as total reflection among all the film layers. A light extraction layer with high refractive index is added on the transparent electrode, so that the light extraction efficiency can be greatly improved.
The material forming the light extraction layer may be an inorganic compound or an organic compound. The inorganic compound has the characteristics of high refractive index and is beneficial to improving the light extraction efficiency, but the coating temperature is very high (more than 1000 ℃), and the organic electroluminescent device can be damaged. The organic compound film has low vapor deposition temperature and has great advantages in process compared with inorganic matters. However, the refractive index of organic compounds is relatively low compared to inorganic compounds, and excellent light extraction layer materials generally require a refractive index of greater than 1.8. In view of the above, it is an urgent technical problem to develop a light extraction layer material of an organic compound having a high refractive index and a low evaporation temperature.
Disclosure of Invention
An object of the present invention is to provide an organic compound that has advantages of high refractive index and low evaporation temperature when used as a light extraction layer material.
Another object of the present invention is to provide an organic electroluminescent device and a display device including the organic compound.
The invention firstly provides an organic compound which has a structure shown in the following formula (I):
Figure BDA0002387381930000021
wherein n is 2 or 3;
x is selected from NRaO, S or C (R)b)(Rc)，R1～R23And Ra、Rb、RcIndependently selected from hydrogen, deuterium, halogen, C1-10 linear or branched alkyl, C1-10 alkoxy, C1-10 amido, C3-10 cycloalkyl, C6-14 aryl or C5-14 heteroaryl; or RbAnd RcAn aryl group having 6 to 14 carbon atoms or a heteroaryl group having 5 to 14 carbon atoms is formed with the carbon atom to which the aryl group is bonded;
said alkyl, alkoxy, amino, cycloalkyl, aryl and heteroaryl groups being optionally substituted by at least one R24Substitution;
each R24Independently selected from hydrogen, hydroxyl, amino, carboxyl, cyano, nitro, halogen, straight chain or branched chain alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, amido with 1-10 carbon atoms, naphthenic base with 3-10 carbon atoms, aryl with 6-14 carbon atoms or heteroaryl with 5-14 carbon atoms.
In some embodiments of the invention, R1～R23Each independently selected from hydrogen or deuterium.
In some embodiments of the invention, RaSelected from aryl with 6-14 carbon atoms;
Rband RcAnd an aryl group having 6 to 14 carbon atoms is formed with the carbon atom to which it is bonded.
In some embodiments of the invention, X is NRa，RaIs phenyl.
In some embodiments of the invention, the organic compound is selected from any one of the compounds shown below:
Figure BDA0002387381930000031
the present invention also provides an organic electroluminescent device comprising:
an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode electrode;
a light extraction layer is arranged on the light-emitting side electrode, and the light extraction layer contains the organic compound in any one of the technical schemes; the light-emitting side electrode is a transparent or semitransparent electrode.
In some embodiments of the present invention, the thickness of the light extraction layer is 30nm to 120nm, preferably 60nm to 90 nm.
In some embodiments of the present invention, the light extraction layer is formed on the light exit-side electrode by evaporation.
The invention also provides a display device which comprises the organic electroluminescent device.
The terms used in the present application are generally terms commonly used by those skilled in the art, and if they are not consistent with the commonly used terms, the terms in the present application shall control.
In the invention, the evaporation rate refers to the variation of the thickness increase of a film formed by an organic material in the evaporation process along with time, and the evaporation rate of the material of the light extraction layer is
Figure BDA0002387381930000042
In the present invention, the vapor deposition temperature means a temperature at which the organic material is deposited at a rate of
Figure BDA0002387381930000043
The temperature of the corresponding organic material is heated to the second sublimation temperature, and the arithmetic mean value of the temperatures is measured by two thermocouples arranged above and below the crucible in which the organic material is positioned.
The organic compound provided by the embodiment of the invention has higher refractive index and lower evaporation temperature; the material can be used as a light extraction layer material to improve the light extraction efficiency of the organic electroluminescent device and prolong the service life of the device; meanwhile, the difficulty of the evaporation process can be reduced due to the lower evaporation temperature.
Drawings
Fig. 1 is a schematic view of the structure of an organic electroluminescent device produced in device example 1.
Detailed Description
Organic compounds
The invention provides an organic compound which has a structure shown in a formula (I):
Figure BDA0002387381930000041
Figure BDA0002387381930000051
wherein n is 2 or 3;
x is selected from NRaO, S or C (R)b)(Rc)，R1～R23And Ra、Rb、RcIndependently selected from hydrogen, deuterium, halogen, C1-10 linear or branched alkyl, C1-10 alkoxy, C1-10 amido, C3-10 cycloalkyl, C6-14 aryl or C5-14 heteroaryl; or RbAnd RcAn aryl group having 6 to 14 carbon atoms or a heteroaryl group having 5 to 14 carbon atoms is formed with the carbon atom to which the aryl group is bonded;
said alkyl, alkoxy, amino, cycloalkyl, aryl and heteroaryl groups being optionally substituted by at least one R24Substitution;
each R24Independently selected from hydrogen, hydroxyl, amino, carboxyl, cyano, nitro, halogen, C1-10 straight chain or branched chain alkyl, C1-10 alkoxy, C1-10 amido, C3-10 cycloalkyl, C6-14 aryl or C6-14 alkylA heteroaryl group having 5 to 14 atoms.
The linear or branched alkyl group of the present invention has 1 to 10, preferably 1 to 6, and more preferably 1 to 4 carbon atoms. Examples thereof may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, etc., but are not limited thereto.
The inventor of the present invention finds that the organic compound having a linear structure shown in formula (i) has advantages of high refractive index and low evaporation temperature, and when the organic compound is used for forming a light extraction layer of an organic electroluminescent device, the light extraction efficiency of the organic electroluminescent device can be improved, and the service life of the device can be prolonged.
In some embodiments of the invention, R1～R23May each be independently selected from hydrogen or deuterium.
In some embodiments of the invention, RaCan be selected from aryl with 6-14 carbon atoms;
Rband RcAnd an aryl group having 6 to 14 carbon atoms is formed with the carbon atom to which it is bonded.
In some embodiments of the invention, X is NRa，RaIs phenyl.
In some embodiments of the invention, the organic compound of formula (i) is selected from any one of the compounds shown in table 1 below:
TABLE 1
Figure BDA0002387381930000052
Figure BDA0002387381930000061
Figure BDA0002387381930000071
Organic electroluminescent device and display device
The present invention also provides an organic electroluminescent device comprising: an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode electrode;
a light extraction layer is arranged on the light-extraction-side electrode, and the light extraction layer contains the organic compound shown in the formula (I); the light-emitting side electrode is a transparent or semitransparent electrode.
By providing a light extraction layer comprising the organic compound represented by the formula (i) on the light-extraction-side electrode, the light extraction efficiency of the device can be improved, and the lifetime of the device can be prolonged.
The organic electroluminescent device of the present invention may be a light-emitting device having a top emission structure, and may include a structure comprising an anode, a hole transport layer, a light-emitting layer, an electron transport layer, a transparent or translucent cathode, and a light extraction layer in this order on a substrate.
The organic electroluminescent element of the present invention may be a light-emitting element having a bottom emission structure, and may include a light-extraction layer, a transparent or translucent anode, a hole-transport layer, a light-emitting layer, an electron-transport layer, and a cathode structure in this order on a substrate.
The organic electroluminescent element of the present invention may be a light-emitting element having a double-sided light-emitting structure, and may include a light-extracting layer, a transparent or translucent anode, a hole-transporting layer, a light-emitting layer, an electron-transporting layer, a transparent or translucent cathode structure, and a light-extracting layer, which are sequentially provided on a substrate.
In addition, a hole injection layer may be provided between the anode electrode and the hole transport layer. An electron blocking layer is provided between the hole transport layer and the light emitting layer. A hole blocking layer is provided between the light emitting layer and the electron transport layer. An electron injection layer is provided between the electron transport layer and the cathode electrode. However, the structure of the organic electroluminescent device of the present invention is not limited to the above-described specific structure, and the above-described layers may be omitted or simultaneously provided, if necessary. For example, the organic electroluminescent device may include an anode made of metal, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, a transparent or semi-transparent cathode, and a light extraction layer structure in this order on a substrate, with the electron injection layer omitted.
In the organic electroluminescent device of the present invention, any material as used in the prior art for the layer may be used for the other layers except that the light extraction layer contains the organic compound represented by formula (i).
Among them, a material having a large work function, for example, a metal such as vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; combinations of metals and oxides, and the like, but is not limited thereto.
A transparent or translucent cathode electrode, and a material having a small work function, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, or an alloy thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al, etc., but are not limited thereto.
As the hole injection layer, metalloporphyrin, oligothiophene, arylamine-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, polythiophene-based conductive polymer, or the like can be used. For example, the following compound 13 can be used, but is not limited thereto.
Figure BDA0002387381930000091
The hole injection material may be used as a host material to form a hole injection layer together with another dopant, for example, the following compound 14.
Figure BDA0002387381930000092
As the hole transport layer, for example, compound 13, an arylamine organic compound, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, or the like can be used, but the present invention is not limited thereto.
The electron blocking layer may be a compound having an electron blocking effect, specifically, a compound having a triarylamine structure, for example, compound 15, but is not limited thereto.
Figure BDA0002387381930000093
The light-emitting material used in the light-emitting layer may include a host material and a dopant, but is not limited thereto. The host material may include various metal complexes, anthracene derivatives, distyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, thiazole derivatives, benzoxazole derivatives, imidazole derivatives, and the like. The dopant may include quinacridone, coumarin, rubrene, perylene, derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyrene derivatives, and metal complexes such as iridium and platinum. For example, the red light emitting layer may be formed with a host material compound 16 and a dopant compound 17.
Figure BDA0002387381930000101
As the hole-blocking layer, a compound having a hole-blocking effect, such as a phenanthroline derivative, a metal complex of a hydroxyquinoline derivative, various rare earth complexes, a triazole derivative, a triazine derivative, or an oxadiazole derivative, can be used, but the hole-blocking layer is not limited thereto. For example, a compound of compound 18 can be used to form a hole blocking layer.
Figure BDA0002387381930000102
For the electron transport layer, metal complexes of hydroxyquinoline derivatives such as tris (8-hydroxyquinoline) aluminum (Alq3) and bis (8-hydroxy-2-methylquinoline) - (4-phenylphenoxy) aluminum (BAlq), triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, pyridoindole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, imidazole derivatives, and the like can be used, but not limited thereto. The electron transport layer can be formed using, for example, compound 19.
Figure BDA0002387381930000111
The electron transport layer may also be formed using the above-described materials as host materials together with dopants, and for example, the electron transport layer may be formed using the compound 20 as a dopant together with a host material.
Figure BDA0002387381930000112
As the electron injection layer, an alkali metal salt such as lithium fluoride or cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, a metal oxide such as alumina, or the like can be used, but the electron injection layer is not limited thereto.
The thin film can be formed by a known method such as vapor deposition, spin coating, or ink jet. The thickness of each layer is not limited, and the thickness conventional in the art may be used.
In some embodiments of the present invention, the thickness of the light extraction layer may be 30nm to 120 nm; preferably 60nm to 90 nm. In this case, good light emission efficiency can be obtained.
In some embodiments of the present invention, the light extraction layer may be formed on the cathode electrode by evaporation. The deposition method is not particularly limited, and may be performed by a method known in the art.
The invention also provides a display device which comprises the organic electroluminescent device.
By using the organic electroluminescent device of the present invention, the display device of the present invention has high luminous efficiency and longer life.
Detection of refractive index
The measuring instrument is a Version-1.0.1.4 spectrum ellipsometer of a Radiation technology company; the size of the glass substrate is 200mm multiplied by 200mm, and the thickness of the material film is 80 nm. The refractive index of the compound at 620nm was measured.
Performance detection of organic electroluminescent device
Specifically, the BJV test system was used to test the current efficiency and CIE color coordinates of the organic electroluminescent device. The T95 lifetime of the organic electroluminescent device was tested using an BJV lifetime test system. The environment tested was atmospheric with room temperature, where T95 lifetime represents the time for the luminance to decay to 95% of the initial luminance.
Synthesis of Compounds
Synthesis example 1
Figure BDA0002387381930000121
Preparation of (Compound 1)
The synthesis method comprises the following steps:
Figure BDA0002387381930000122
(1) adding N-phenylcarbazole-2-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M1 a;
(2) under the protection of nitrogen, adding 500ml of intermediate M1(100mmol) and tetrahydrofuran into a reaction bottle, cooling the reaction solution to-78 ℃, dropwise adding n-butyllithium (110mmol), keeping the temperature for reaction for 1h after dropwise adding, dropwise adding triisopropyl borate (110mmol), naturally heating after dropwise adding, and reacting for 12 h. Adding water into the reaction solution, extracting with ethyl acetate, and concentrating the organic phase to obtain an intermediate M2 a;
(3) into a reaction flask, M2a (100mmol), M1a (100mmol), 0.9g (0.785mmol, 0.5%) of tetrakistriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water, and 40g of potassium carbonate (300mmol) were added, followed by reaction at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating out solid, filtering, and recrystallizing the obtained solid with xylene to obtain the final product.
Nuclear magnetic analysis:1H NMR(CDCl3,400MHz)δ7.80(d,J＝13.2Hz,4H),7.62(s,2H),7.51(d,J＝10.0Hz,6H),7.41(d,J＝10.0Hz,6H),7.38-7.25(m,8H),7.23–7.14(m,6H)。
the relative refractive index of compound 1 is shown in table 2.
Synthesis example 2
Figure BDA0002387381930000131
Preparation of (Compound 2)
The synthesis method comprises the following steps:
Figure BDA0002387381930000141
(1) adding N-phenylcarbazole-2-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M1 a;
(2) under the protection of nitrogen, adding 500ml of intermediate M1a (100mmol) and tetrahydrofuran into a reaction bottle, cooling the reaction solution to-78 ℃, dropwise adding n-butyllithium (110mmol), keeping the temperature for reaction for 1h after dropwise adding, dropwise adding triisopropyl borate (110mmol), naturally heating after dropwise adding, and reacting for 12 h. Adding water into the reaction solution, extracting with ethyl acetate, and concentrating the organic phase to obtain an intermediate M2 a;
(3) dibenzothiophene-3-boronic acid (100mmol), 4-bromo-4-iodobiphenyl (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) are added into a reaction flask, and the mixture is reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M3;
(4) into a reaction flask, M2a (100mmol), M3(100mmol), 0.9g (0.785mmol, 0.5%) of tetrakistriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) were added, and the mixture was reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating out solid, filtering, and recrystallizing the obtained solid with xylene to obtain the final product.
Nuclear magnetic analysis:1H NMR(CDCl3,400MHz)δ8.15(d,J＝10.4Hz,4H),8.07–7.63(m,6H),7.62(s,1H),7.57(d,J＝10.0Hz,4H),7.51(d,J＝10.0Hz,4H),7.42(s,1H),7.38-7.28(m,6H),7.21-7.13(m,5H).
the relative refractive index of compound 2 is shown in table 2.
Synthesis example 3
Figure BDA0002387381930000151
Preparation of (Compound 3)
The synthesis method comprises the following steps:
Figure BDA0002387381930000161
1) adding N-phenylcarbazole-2-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M1 a;
(2) under the protection of nitrogen, adding 500ml of intermediate M1a (100mmol) and tetrahydrofuran into a reaction bottle, cooling the reaction solution to-78 ℃, dropwise adding n-butyllithium (110mmol), keeping the temperature for reaction for 1h after dropwise adding, dropwise adding triisopropyl borate (110mmol), naturally heating after dropwise adding, and reacting for 12 h. Adding water into the reaction solution, extracting with ethyl acetate, and concentrating the organic phase to obtain an intermediate M2 a;
(3) adding N-phenylcarbazole-2-boric acid (100mmol), 4-bromo-4-iodobiphenyl (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M4;
(4) into a reaction flask, M2a (100mmol), M4(100mmol), 0.9g (0.785mmol, 0.5%) of tetrakistriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) were added, and the mixture was reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating out solid, filtering, and recrystallizing the obtained solid with xylene to obtain the final product.
Nuclear magnetic analysis:1H NMR(CDCl3,400MHz)δ8.13-7.82(m,3H),7.69-7.58(m,6H),7.51(d,J＝10.0Hz,6H),7.42-7.25(m,13H),7.19-7.11(m,8H).
the relative refractive index of compound 3 is shown in table 2.
Synthesis example 4
Figure BDA0002387381930000171
Preparation of (Compound 4)
The synthesis method comprises the following steps:
Figure BDA0002387381930000181
(1) adding N-phenylcarbazole-2-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M1 a;
(2) under the protection of nitrogen, adding 500ml of intermediate M1(100mmol) and tetrahydrofuran into a reaction bottle, cooling the reaction solution to-78 ℃, dropwise adding n-butyllithium (110mmol), keeping the temperature for reaction for 1h after dropwise adding, dropwise adding triisopropyl borate (110mmol), naturally heating after dropwise adding, and reacting for 12 h. Adding water into the reaction solution, extracting with ethyl acetate, and concentrating the organic phase to obtain an intermediate M2 a;
(3) 9, 9-spirobifluorene-2-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) are added into a reaction bottle, and the mixture is reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M5;
(4) m5(100mmol), M1a (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) are added into a reaction flask, and the mixture is reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating out solid, filtering, and recrystallizing the obtained solid with xylene to obtain the final product.
Nuclear magnetic analysis:1H NMR(CDCl3,400MHz)δ8.10(d,J＝12.4Hz,3H) 8.08-8.01(m,3H), 8.09-7.84 (m,7H), 7.67-7.54 (m,9H),7.34(s,1H), 7.30-7.21 (m,9H),7.16-7.11(m,3H). The relative refractive indices of Compound 4 are shown in Table 2.
Synthesis comparative example 1
Figure BDA0002387381930000191
Preparation of (Compound 21)
The synthesis method comprises the following steps:
Figure BDA0002387381930000192
(1) adding N-phenylcarbazole-2-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M1 a;
(2) under the protection of nitrogen, adding an intermediate M1a (100mmol), adding N-phenylcarbazole-2-boric acid (100mmol), 0.9g (0.785mmol, 0.5%) of palladium tetratriphenylphosphine, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, reacting at 100 ℃ for 8 hours, cooling to room temperature, separating an organic phase, concentrating, carrying out silica gel column chromatography, and recrystallizing by xylene to obtain a final product.
Nuclear magnetic analysis:1H NMR(400MHz,Chloroform)δ8.55-8.35(m,2H),8.19-8.13(m,4H),7.81(d,J＝12.0Hz,4H),7.62(s,2H),7.51(d,J＝10.0Hz,4H),7.41(d,J＝10.0Hz,4H),7.22–7.14(m,6H)。
the relative refractive index of compound 21 is shown in table 2.
Synthesis comparative example 2
Figure BDA0002387381930000201
Preparation of (Compound 22)
Figure BDA0002387381930000202
(1) Adding N-phenylcarbazole-3-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M3 a;
(2) under the protection of nitrogen, adding 500ml of intermediate M1(100mmol) and tetrahydrofuran into a reaction bottle, cooling the reaction solution to-78 ℃, dropwise adding n-butyllithium (110mmol), keeping the temperature for reaction for 1h after dropwise adding, dropwise adding triisopropyl borate (110mmol), naturally heating after dropwise adding, and reacting for 12 h. Adding water into the reaction solution, extracting with ethyl acetate, and concentrating the organic phase to obtain an intermediate M4 a;
(3) to a reaction flask, M3a (100mmol), M4a (100mmol), 0.9g (0.785mmol, 0.5%) of tetrakistriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water, and 40g of potassium carbonate (300mmol) were added, followed by reaction at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating out solid, filtering, and recrystallizing the obtained solid with xylene to obtain the final product.
Nuclear magnetic analysis: 1H NMR (400MHz, Chloroform) δ 8.20(d, J ═ 12.4Hz,3H),7.79(d, J ═ 10.0Hz,2H),7.71(s,1H), 7.72-7.51 (m,4H),7.50-7.40(m,3H), 7.23-7.14 (m,3H).
The relative refractive index of compound 22 is shown in table 2.
Synthesis comparative example 3
Figure BDA0002387381930000211
Preparation of (Compound 23)
Figure BDA0002387381930000212
(1) Adding N-phenylcarbazole-3-boric acid (100mmol), p-bromoiodobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain white powder M3 a;
(2) under the protection of nitrogen, adding 500ml of intermediate M1(100mmol) and tetrahydrofuran into a reaction bottle, cooling the reaction solution to-78 ℃, dropwise adding n-butyllithium (110mmol), keeping the temperature for reaction for 1h after dropwise adding, dropwise adding triisopropyl borate (110mmol), naturally heating after dropwise adding, and reacting for 12 h. Adding water into the reaction solution, extracting with ethyl acetate, and concentrating the organic phase to obtain an intermediate M4 a;
(3) into a reaction flask, M1a (100mmol), M4a (100mmol), 0.9g (0.785mmol, 0.5%) of tetrakistriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water, and 40g of potassium carbonate (300mmol) were added, followed by reaction at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating out solid, filtering, and recrystallizing the obtained solid with xylene to obtain the final product.
Nuclear magnetic analysis:1H NMR(400MHz,Chloroform)δ8.20(d,J＝11.2Hz,2H),8.13(s,1H),7.85(d,J＝12.0Hz,2H),7.72(s,1H),7.66(d,J＝12.0Hz,4H),7.51(d,J＝10.0Hz,8H),7.41(d,J＝10.0Hz,4H),7.23–7.10(m,10H).
the relative refractive index of compound 23 is shown in table 2.
TABLE 2
Figure BDA0002387381930000221
Figure BDA0002387381930000231
In table 2, the structural formulas of compound 24 and compound 25 are shown below:
Figure BDA0002387381930000232
as can be seen from Table 2, compounds 1 to 4 prepared in the examples of the present invention have refractive indices greater than those of compounds 21 to 23 and conventional compounds 24 to 25 prepared in the synthesis of comparative examples.
Preparation of organic electroluminescent device
Device example 1
The preparation steps of the organic electroluminescent device are as follows:
step (1): cleaning a reflective anode electrode (ITO)2 on an OLED device substrate 1 for top emission, and baking the reflective anode electrode in an infrared oven for 30 seconds at 165 ℃; transferring the mixture into a cavity of an evaporator and baking the mixture for 30 minutes at 240 ℃;
step (2): vacuum evaporating a hole injection layer 3 with the thickness of 10nm on the reflecting anode electrode 2, wherein the main material of the hole injection layer is a compound 13 which contains 3% of a p-type dopant compound 14;
and (3): a layer of hole transport material compound 13 with the thickness of 1120nm is evaporated on the hole injection layer 3 in vacuum to be used as a hole transport layer 4;
and (4): a layer of compound 15 with the thickness of 10nm is evaporated on the hole transport layer 4 in vacuum to be used as an electron blocking layer 5;
and (5): and a light-emitting layer 6 with the thickness of 20nm is vacuum-evaporated on the electron blocking layer 5, and the proportion of the compound 16 to the compound 17 in the light-emitting layer is 97: 3;
and (6): a layer of compound 18 with the thickness of 5nm is vacuum evaporated on the luminescent layer 6 to be used as a hole blocking layer 7;
and (7): vacuum evaporating 35nm of electron transport material compound 19 as electron transport layer 8 containing 50% of compound 20 on hole blocking layer 7;
and (8): vacuum evaporation of Mg: ag layer, Mg: the doping ratio of Ag is 1: 9, 18nm thick, this layer being the cathode electrode 9;
and (9): compound 1 was vacuum evaporated on the cathode electrode 9 as a light extraction layer 10 with an evaporation thickness of 50nm and an evaporation temperature and an evaporation rate as shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
The structure of the compound used in the above preparation process is as follows:
Figure BDA0002387381930000241
Figure BDA0002387381930000251
device structureExample 2
The device was the same as in device example 1 except that the light extraction layer was evaporated to a thickness of 60 nm. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Device example 3
The device was the same as in device example 1 except that the evaporation thickness of the light extraction layer was 70 nm. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Device example 4
The device was the same as in device example 1 except that the evaporation thickness of the light extraction layer was 80 nm. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Device example 5
The device was the same as in device example 1 except that the evaporation thickness of the light extraction layer was 90 nm. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Device example 6
The same as in device example 4 was performed except that compound 2 was evaporated as the light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Device example 7
The same as in device example 4 was performed except that compound 3 was evaporated as the light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Device example 8
The device was the same as in device example 4 except that compound 4 was evaporated as the light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Comparative device example 1
The device was the same as in device example 4 except that compound 21 was evaporated as the light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Comparative device example 2
The device was the same as in device example 4 except that compound 22 was evaporated as light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Comparative device example 3
The device was the same as in device example 4 except that compound 23 was evaporated as the light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Comparative device example 4
The device was the same as in device example 4 except that compound 24 was evaporated as light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
Comparative device example 5
The device was the same as in device example 4 except that compound 25 was evaporated as light extraction layer 10. The evaporation temperature and the evaporation rate are shown in table 3; the current efficiency, CIE color coordinates and lifetime of the devices are shown in table 4.
TABLE 3
Figure BDA0002387381930000271
As can be seen from Table 3, the vapor deposition temperature for the vapor deposition of the compounds 1 to 4 prepared in the synthesis examples of the present invention was significantly lower than that for the compounds A to E.
TABLE 4
Figure BDA0002387381930000281
As can be seen from table 4, in device examples 1 to 4, the current efficiency increased as the thickness of the light extraction layer increased.
Further, as can be seen from table 4, the organic electroluminescent devices prepared in device examples 1 to 8 according to the present invention have significantly longer lifetimes than the organic electroluminescent devices prepared in device comparative examples 1 to 5. Therefore, the organic compounds provided by the invention are used for forming the light extraction layer, so that the service life of the device can be prolonged, and the film formed by the compounds has better compactness, and can play a certain role in blocking water and oxygen. Meanwhile, the film compactness increases the refractive index of the material to a certain extent.
The above description is only for the preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall fall within the protection scope of the present invention.

Claims (9)

1. An organic compound having a structure represented by the following formula (i):
Figure FDA0002387381920000011
wherein n is 2 or 3;
x is selected from NRaO, S or C (R)b)(Rc)，R1～R23And Ra、Rb、RcIndependently selected from hydrogen, deuterium, halogen, C1-10 linear or branched alkyl, C1-10 alkoxy, C1-10 amido, C3-10 cycloalkyl, C6-14 aryl or C5-14 heteroaryl; or RbAnd RcAn aryl group having 6 to 14 carbon atoms or a heteroaryl group having 5 to 14 carbon atoms is formed with the carbon atom to which the aryl group is bonded;
said alkyl, alkoxy, amino, cycloalkyl, aryl and heteroaryl groups being optionally substituted by at least one R24Substitution;
each R24Independently selected from hydrogen, hydroxyl, amino, carboxyl, cyano, nitro, halogen, straight chain or branched chain alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, amido with 1-10 carbon atoms, naphthenic base with 3-10 carbon atoms, aryl with 6-14 carbon atoms or heteroaryl with 5-14 carbon atoms.
2. The organic compound of claim 1, wherein R1～R23Each independently selected from hydrogen or deuterium.
3. The organic compound of claim 1, wherein RaSelected from aryl with 6-14 carbon atoms;
Rband RcAnd an aryl group having 6 to 14 carbon atoms is formed with the carbon atom to which it is bonded.
4. The organic compound according to claim 1 or 2, wherein X is NRa，RaIs phenyl.
5. The organic compound according to claim 1, which is selected from any one of the following compounds:
Figure FDA0002387381920000021
6. an organic electroluminescent device, comprising:
an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode electrode;
a light extraction layer comprising the organic compound according to any one of claims 1 to 5 is provided on the light-exit side electrode; the light-emitting side electrode is a transparent or semitransparent electrode.
7. The organic electroluminescent device according to claim 6, wherein the thickness of the light extraction layer is 30nm to 120nm, preferably 60nm to 90 nm.
8. The organic electroluminescent device according to claim 6, wherein the light extraction layer is formed on the light exit-side electrode by evaporation.
9. A display device comprising the organic electroluminescent device according to any one of claims 6 to 8.
CN202010102635.8A 2020-02-19 2020-02-19 Organic compound, organic electroluminescent device comprising organic compound and display device comprising organic compound Pending CN111217739A (en)

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Application publication date: 20200602