CN112830900A - Phosphorescent compound, method of preparing the same, and organic electroluminescent device comprising the same - Google Patents
Phosphorescent compound, method of preparing the same, and organic electroluminescent device comprising the same Download PDFInfo
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Abstract
The invention discloses a phosphorescent compound, a preparation method thereof and an organic electroluminescent device comprising the same, belonging to the technical field of chemistry and organic luminescent materials, wherein the phosphorescent compound has a general structural formula as follows:
Description
Technical Field
The invention relates to the technical field of chemistry and organic luminescent materials, in particular to a phosphorescent compound, a preparation method thereof and an organic electroluminescent device containing the phosphorescent compound.
Background
The Organic electronic device is typically represented by an Organic Light Emitting device, and a typical example of the Organic Light Emitting device is an Organic Light Emitting Diode (OLED). The organic light emitting diode is a current-driven light emitting device using an organic material as an active material, and particularly means that the advantages of the technology OL ED display technology of light emission caused by carrier injection and recombination of an organic semiconductor material and an organic light emitting material under the drive of an electric field are very obvious, such as thin device thickness, simple structure, no need of a backlight source, active light emission, low power consumption, wide viewing angle, high response speed and the like, and the organic light emitting diode is regarded as a powerful competitor of the next generation display technology.
The OLED emission is divided into two modes of fluorescence emission and phosphorescence emission, and it is theoretically assumed that the ratio of a singlet excited state to a triplet excited state due to charge binding is 1:3, and therefore, when a small molecular fluorescent material is used, only 25% of the total energy is available for emission, and the remaining 75% of the energy is lost due to a non-emission mechanism of the triplet excited state, so that the internal quantum efficiency limit of the fluorescent material is considered to be 25%. In phosphorescence emission, singlet and triplet excitons are utilized, and only singlet excitons are utilized as opposed to fluorescent materials, and efficient utilization of triplet excitons in proportions up to 75% enables a phosphorescent-material-based PhOLED to theoretically achieve 100% internal quantum efficiency. In recent three years, phosphorescent materials gradually replace traditional fluorescent materials, and become hot spots for research on OLED luminescent materials.
A light emitting material may be prepared by combining a host material with a dopant to improve color purity, light emitting efficiency, and stability. The host material greatly affects the efficiency and performance of the EL device, and it is important to develop a novel host material that meets the practical requirements. However, since the synthesis process of the phosphorescent material is complicated, takes a long time, and has a short lifetime, further development of the phosphorescent material is urgently needed.
Disclosure of Invention
It is an object of an embodiment of the present invention to provide a phosphorescent compound to solve the problems set forth in the above background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a phosphorescent compound having the general structural formula I:
in the formula, the ring A can be connected with any two adjacent positions on the benzene ring to form a ring; ring A independently represents at least one of substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 3-to 18-membered heteroaryl, substituted or unsubstituted C3-C12 cycloalkyl; and ring a is monocyclic or polycyclic;
l is at least one of a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 3-to 18-membered heteroaryl; l is monocyclic or polycyclic and L is not anthracene;
n is selected as a natural number from 0 to 10;
b is at least one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 24-membered heteroaryl, substituted or unsubstituted cycloalkyl of C3-C10, substituted or unsubstituted C10-C24 fused ring, substituted or unsubstituted C5-C30 spiro ring, a (C3-C30) aliphatic ring or a (C6-C30) aromatic ring which are linked to adjacent substituents to form a single ring or multiple rings;
R1is at least one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C15 alkoxy, substituted or unsubstituted C6-C15 aryloxy, substituted or unsubstituted C1-C15 alkylthio, substituted or unsubstituted C6-C15 arylthio, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C24 fused ring, substituted or unsubstituted C10-C30 spiro ring, a (C3-C30) aliphatic ring or (C6-C30) aromatic ring linked to an adjacent substituent to form a single or multiple ring.
Preferably, the carbon atom in the (C3-C30) aliphatic ring or (C6-C30) aromatic ring, which is linked to an adjacent substituent to form a mono-or polycyclic ring, is replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, silicon.
Preferably, ring a is one of phenyl, biphenyl, naphthyl, methylbenzene and adamantane.
Preferably, L is one of benzene, deuterated benzene, biphenyl, naphthalene, phenanthrene, spiro and fluorene.
Preferably, B is one of phenanthrene, adamantane, dimethylfluorenyl and spiro.
Preferably, n is 1 or 2.
Preferably, the chemical structural formula of the phosphorescent compound is any one of formula 1 to formula 72:
it is noted that, in the above technical solutions, the term "substituted or unsubstituted" means substituted with one, two or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted alkylamino; substituted or unsubstituted heterocyclylamino; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; and a substituted or unsubstituted heterocyclic group, or a substituent in which two or more substituents among the above-shown substituents are connected, or no substituent. For example, "a substituent in which two or more substituents are linked" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
Another object of the embodiments of the present invention is to provide a method for preparing the phosphorescent compound, which comprises the following steps:
under the protective atmosphere, placing the reactant A, the reactant B, the tetratriphenylphosphine palladium and the potassium carbonate in a solvent for reaction, and purifying to obtain an intermediate C;
under the protective atmosphere, placing the intermediate C, the reactant D, cesium carbonate and 2-dicyclohexyl phosphorus-2, 4, 6-triisopropyl biphenyl in a solvent for reaction, and purifying to obtain the phosphorescent compound;
the structural formula of the reactant A is shown as the formula A, the structural formula of the reactant B is shown as the formula B, the structural formula of the intermediate C is shown as the formula C, and the structural formula of the reactant D is shown as the formula D:
specifically, the solvent is a mixed solution of toluene/ethanol/water.
The synthetic route of the preparation method is as follows:
the method specifically comprises the following steps:
(1) under the protection of nitrogen, a three-neck flask is charged with a reactant A (1.0eq), a reactant B (1.0eq), anhydrous potassium carbonate (2.0eq) and toluene/ethanol/water (volume ratio 2:1:1), heated to 60 ℃, stirred for 20min, and added with tetratriphenylphosphine palladium (Pd (PPh)3)40.01eq), the temperature is raised to 82 ℃ and the reaction is carried out for 4 h. And after TLC detection reaction is finished, separating liquid, collecting an organic phase, removing the solvent from the organic phase by a rotary evaporator to obtain a solid organic matter, recrystallizing the solid organic matter by using toluene/ethanol, filtering, leaching a filter cake by using petroleum ether, and drying the filter cake in an oven to obtain an intermediate C.
(2) Under the protection of nitrogen, the intermediate C (1.0eq), the reactant D (1.1eq), cesium carbonate (2.0eq), and toluene/ethanol/water (volume ratio 2:1:1) were charged into a three-necked flask, heated to 60 ℃, stirred for 30min, added with X-PHOS (2-dicyclohexyl-2, 4, 6-triisopropyl-biphenyl, 0.01eq), heated to 85 ℃, and reacted for 6 h. And after TLC detection reaction is finished, separating liquid, collecting an organic phase, removing a solvent from the organic phase by a rotary evaporator to obtain a solid organic matter, dissolving the organic matter by dichloromethane, slowly dropwise adding the dissolved organic matter into 1L of petroleum ether under stirring, separating out a solid, performing suction filtration, drying a filter cake, adding toluene for recrystallization, filtering, leaching the filter cake by using petroleum ether, and drying the filter cake in an oven to obtain the phosphorescent compound shown in the formula I.
Another object of the embodiments of the present invention is to provide a use of the above phosphorescent compound in the preparation of an organic electroluminescent device.
It is another object of an embodiment of the present invention to provide an organic electroluminescent device, which includes an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the phosphorescent compound described above.
Specifically, at least one or more layers including a hole injection layer, a light emitting layer, a hole transport layer, a light emitting auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer may be further disposed between the anode and the cathode.
Among them, the anode preferably contains a material having a high work function. Such as Indium Tin Oxide (ITO) or indium zinc oxide (izo). Since the lifetime of the device of the invention is shortened in the presence of water and/or air, the device is suitably (depending on the application) structured, provided with contacts and finally sealed.
The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and has high hole mobility. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.
The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a material known in the art, for example, an arylamine-based organic material, may be used.
The material of the light emitting layer is a material capable of emitting visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons.
Preferably, the light emitting layer includes a host material and a dopant material; the host material partially or completely contains the phosphorescent compound. The mass ratio of the host material to the doping material is (90-99.5) to (0.5-10).
The doping material may include fluorescent doping and phosphorescent doping.
The phosphorescent dopant material is a phosphorescent material including a metal complex of iridium, platinum, or the like. For example, Ir (ppy)3Isogreen phosphorescent materials, FIrpic, FIr6Iso-blue phosphorescent material and Btp2Red phosphorescent materials such as ir (acac).
As the hole-blocking layer material, a compound having a hole-blocking effect known in the art, for example, a phenanthroline derivative such as Bathocuproine (BCP), an oxazole derivative, a triazole derivative, a triazine derivative, or the like can be used, but the invention is not limited thereto.
The electron transport layer may function to facilitate electron transport. Compounds having an electron transporting action well known in the art, for example, Al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; hydroxyflavone-metal complexes, and the like.
The electron injection layer may function to promote electron injection. Has the ability of transporting electrons and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The electron injecting material used in the present invention includes fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like, but is not limited thereto.
The cathode, generally preferably a material having a small work function, allows electrons to be smoothly injected into the organic material layer. Such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof.
In the embodiment of the present invention, the various functional layers described above may be formed by a solution coating method and a vacuum deposition method. The solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, etc., but is not limited thereto.
In addition, the organic electroluminescent device may be applied to an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), electronic paper (e-paper), an Organic Photoreceptor (OPC), an organic thin film transistor (OTF T), or the like, according to the same principle, but is not limited thereto.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the phosphorescent compound provided by the embodiment of the invention takes pyrimidine as a parent nucleus, has intramolecular charge transmission performance, can be used as a luminescent main material in an electroluminescent device, can effectively improve the balance migration of carriers, broadens an exciton recombination area, effectively improves the light extraction efficiency, greatly improves the luminescent efficiency and the service life of the device, and can be well applied to the technical field of organic electroluminescent devices.
Detailed Description
The following examples are provided to aid the understanding of the present invention and are not intended to limit the scope of the present invention. In addition, the preparation methods of the compounds which are not specifically listed in the embodiments of the present invention are methods generally applied in the related industries, and the methods described in the embodiments can be referred to when preparing other compounds.
Example 1
This example provides a phosphorescent compound, which is prepared as follows:
(1) under the protection of nitrogen, a three-necked flask was charged with a reactant A-2(50mmol), a reactant B-2(50mmol), anhydrous potassium carbonate (100mmol) and toluene/ethanol/water (300mL:150mL:150mL), heated to 60 ℃, stirred for 20min, added with tetrakistriphenylphosphine palladium (0.5mmol), heated to 82 ℃ and reacted for 4 h. After the TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, 40mL of methylbenzene is mixed with 200mL of ethanol for recrystallization, filtration is carried out, a filter cake is rinsed with 150mL of petroleum ether, and the mixture is placed into a 65 ℃ oven for drying for 8 hours to obtain an intermediate C-2(13.0g, 82%, Ms: 316.08).
(2) Under the protection of nitrogen, intermediate C-2(35mmol), reactant D-2(38.5eq), cesium carbonate (70mmol), and toluene/ethanol/water (300mL:150mL:150mL) were charged into a three-necked flask, heated to 60 ℃, stirred for 30min, added with X-PHOS (0.35mmol), heated to 85 ℃, and reacted for 6 h. After TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, the organic matter is dissolved by 100mL of dichloromethane, 1L of petroleum ether is slowly dripped into the mixture under stirring, after solid is separated out, suction filtration is carried out, a filter cake is dried, the mixture is added into 300mL of toluene for recrystallization, filtration is carried out, the filter cake is leached by 200mL of petroleum ether and is placed into an oven at 80 ℃ for drying for 8h, and the phosphorescent compound 2(16.3g, 78%) is obtained.
The phosphorescent compound 2 obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 596.23; the test value was 596.34.
Elemental analysis (unit:%):
the theoretical values are: c, 90.58; h, 4.73; n,4.69
The test values are: c, 90.57; h, 4.74; n,4.68
Example 2
This example provides a phosphorescent compound, which is prepared as follows:
(1) under the protection of nitrogen, reactant A-38(50mmol), reactant B-38(50mmol), anhydrous potassium carbonate (100mmol) and toluene/ethanol/water (300mL:150mL:150mL) were put into a three-necked flask, heated to 60 ℃, stirred for 20min, added with tetrakistriphenylphosphine palladium (0.5mmol), heated to 82 ℃ and reacted for 4 h. After the TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, 40mL of methylbenzene is mixed with 200mL of ethanol for recrystallization, filtration is carried out, a filter cake is rinsed with 150mL of petroleum ether, and the mixture is placed into a 65 ℃ oven for drying for 8 hours to obtain an intermediate C-38(15.1g, 77%, Ms: 392.56).
(2) Under the protection of nitrogen, intermediate C-38(35mmol), reactant D-38(38.5eq), cesium carbonate (70mmol), and toluene/ethanol/water (300mL:150mL:150mL) were charged into a three-necked flask, heated to 60 ℃, stirred for 30min, added with X-PHOS (0.35mmol), heated to 85 ℃, and reacted for 6 h. After the TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, the organic matter is dissolved by 100mL of dichloromethane, 1L of petroleum ether in stirring is slowly dripped, a solid is separated out, suction filtration is carried out, a filter cake is dried, the filter cake is added into 300mL of toluene for recrystallization, filtration is carried out, the filter cake is leached by 200mL of petroleum ether and is placed into an oven at 80 ℃ for drying for 8 hours, and the phosphorescent compound 38(18.0g, 84%) is obtained.
The obtained phosphorescent compound 38 was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 610.24; the test value was 610.78.
Elemental analysis (unit:%):
the theoretical values are: c, 90.46; h, 4.95; n,4.59
The test values are: c, 90.45; h, 4.95; and N, 4.57.
Example 3
This example provides a phosphorescent compound, which is prepared as follows:
(1) under the protection of nitrogen, a three-necked flask was charged with a reactant A-54(50mmol), a reactant B-54(50mmol), anhydrous potassium carbonate (100mmol) and toluene/ethanol/water (300mL:150mL:150mL), heated to 60 ℃, stirred for 20min, added with tetrakistriphenylphosphine palladium (0.5mmol), heated to 82 ℃ and reacted for 4 h. After the TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, 40mL of methylbenzene is mixed with 200mL of ethanol for recrystallization, filtration is carried out, a filter cake is rinsed with 150mL of petroleum ether, and the mixture is placed into a 65 ℃ oven for drying for 8 hours to obtain an intermediate C-54(22.0g, 83%, Ms: 529.44).
(2) Under the protection of nitrogen, intermediate C-54(35mmol), reactant D-54(38.5eq), cesium carbonate (70mmol), and toluene/ethanol/water (300mL:150mL:150mL) were charged into a three-necked flask, heated to 60 ℃, stirred for 30min, added with X-PHOS (0.35mmol), heated to 85 ℃, and reacted for 6 h. After the TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, the organic matter is dissolved by 100mL of dichloromethane, 1L of petroleum ether in stirring is slowly dripped, a solid is separated out, suction filtration is carried out, a filter cake is dried, the filter cake is added into 300mL of toluene for recrystallization, filtration is carried out, the filter cake is leached by 200mL of petroleum ether and is placed into an oven at 80 ℃ for drying for 8 hours, and the phosphorescent compound 54(19.0g, 80%) is obtained.
The obtained phosphorescent compound 54 was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 677.28; the test value was 677.89.
Elemental analysis (unit:%):
the theoretical values are: c, 88.60; h, 5.20; n,6.20
The test values are: c, 88.58; h, 5.20; and N, 6.21.
Example 4
This example provides a phosphorescent compound, which is prepared as follows:
(1) under the protection of nitrogen, reactant A-66(50mmol), reactant B-66(50mmol), anhydrous potassium carbonate (100mmol) and toluene/ethanol/water (300mL:150mL:150mL) were put into a three-necked flask, heated to 60 ℃, stirred for 20min, added with tetrakistriphenylphosphine palladium (0.5mmol), heated to 82 ℃ and reacted for 4 h. After the TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, 40mL of methylbenzene is mixed with 200mL of ethanol for recrystallization, filtration is carried out, a filter cake is rinsed with 150mL of petroleum ether, and the mixture is placed into a 65 ℃ oven for drying for 8 hours to obtain an intermediate C-66(28.1g, 81 percent, Ms: 694.76).
(2) Under the protection of nitrogen, intermediate C-66(35mmol), reactant D-66(38.5eq), cesium carbonate (70mmol) and toluene/ethanol/water (300mL:150mL:150mL) were charged into a three-necked flask, heated to 60 ℃, stirred for 30min, added with X-PHOS (0.35mmol), heated to 85 ℃, and reacted for 6 h. After TLC detection reaction is finished, liquid separation is carried out, an organic phase is collected, the organic phase is subjected to solvent removal through a rotary evaporator to obtain a solid organic matter, the organic matter is dissolved by 100mL of dichloromethane, 1L of petroleum ether in stirring is slowly dripped, solid is separated out, suction filtration is carried out, a filter cake is dried, the filter cake is added into 300mL of toluene for recrystallization, filtration is carried out, the filter cake is leached by 200mL of petroleum ether and is placed into an oven at 80 ℃ for drying for 8h, and the phosphorescent compound 66(23.1g, 79%) is obtained.
The obtained phosphorescent compound 66 was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 836.32; the test value was 836.45.
Elemental analysis (unit:%):
the theoretical values are: c, 91.84; h, 4.82; n,3.35
The test values are: c, 91.82; h, 4.84; n, 3.34.
Examples 5 to 18
The synthetic routes and principles of the preparation methods of other phosphorescent compounds having the structural general formula I in the summary of the invention are the same as those of the above-listed example 1, and only the raw materials need to be replaced with the corresponding reactants of the target products respectively, and the amounts of the reactants are adjusted according to the corresponding stoichiometric ratios, so that the synthesis of the phosphorescent compounds 5, 8, 13, 16, 20, 24, 28, 32, 36, 43, 50, 58, 62, 70 is completed with reference to the preparation methods of examples 1 to 4 in the examples of the invention, and the mass spectra, the molecular formulas and the yields are shown in table 1.
TABLE 1
In addition, other compounds of the present application can be obtained by the preparation method according to the above-mentioned examples, and therefore, they are not illustrated herein.
Device example 1
The embodiment of the device provides an organic electroluminescent device, and the specific preparation method comprises the following steps:
will have a psi/cm of 152The ITO glass substrate with sheet resistance value of (1) is cut into the size of 50mm multiplied by 0.7mm to be used as an anode; the cut substrate was ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes, respectively; and UV ozone cleaned for 30 minutes. Sending the mixture into an evaporator.
Under the vacuum degree of 650X 10-7Under the conditions of Pa and a deposition speed of 0.2nm/s, an ITO glass substrate with the thickness of 150nm is firstly evaporated to be used as an anode, CuPc with the thickness of 20nm is evaporated to be used as a hole injection layer, and then NPB with the thickness of 40nm is evaporated to be used as a hole transport layer.
Under the same vacuum deposition condition, a host material and a doping substance with the thickness of 30nm are simultaneously evaporated to be used as a light emitting layer. Wherein the phosphorescent compound 2 prepared in the above example was used as a host material, (btp)2Ir (acac) is taken as a doping material and is mixed and evaporated according to the weight ratio of 97: 3.
Under the same vacuum deposition condition, bis (2-methyl-8-hydroxyquinoline) -4- (phenylphenol) aluminum (BALq) serving as a hole blocking layer and Alq3(30nm) serving as an electron transport layer are sequentially evaporated on the upper surface of the light-emitting layer, and an electron injection layer LiF (1nm) and a cathode Al (120nm) are evaporated to prepare the organic electroluminescent device.
Wherein, the chemical structural formula of the partial raw materials is as follows:
device example 2-device example 18
With reference to the preparation method provided in device example 1 above, the phosphorescent compounds 2 used in device example 1 were respectively replaced with the phosphorescent compounds 5, 8, 13, 16, 20, 24, 28, 32, 36, 38, 43, 50, 54, 58, 62, 66, 70 provided in the above examples as host materials, and the other methods and raw materials were the same, to prepare corresponding organic electroluminescent devices.
Comparative device example 1
The device comparative example produced an organic electroluminescent device. Specifically, according to the preparation method of device example 1, the host material phosphorescent compound 2 in the light-emitting layer was replaced with the comparative compound 1, and the other methods and raw materials were the same, to prepare an organic electroluminescent device. Wherein, the structural formula of comparative compound 1 is as follows:
the anode and cathode of the resulting device were connected by a known driving circuit to measure the performance luminescence characteristics of the resulting device, which was evaluated by a KEITHLEY model 2400 source measuring unit, a CS-2000 spectroradiometer, to evaluate driving voltage, luminous efficiency and device lifetime, and the evaluation results are shown in table 2 below.
TABLE 2
As can be seen from Table 2, compared with the organic electroluminescent device prepared by using the phosphorescent compound provided by the invention as the host material, the driving voltage of the organic electroluminescent device prepared by using the phosphorescent compound provided by the invention as the host material is reduced by 1.5-2.1V, the luminous efficiency is improved by 7.9-14.8%, and the service life is improved by 115-183 h.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (10)
1. A phosphorescent compound, wherein the phosphorescent compound has a general structural formula of formula I:
in the formula, the ring A can be connected with any two adjacent positions on the benzene ring to form a ring; ring A independently represents at least one of substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 3-to 18-membered heteroaryl, substituted or unsubstituted C3-C12 cycloalkyl; and ring a is monocyclic or polycyclic;
l is at least one of a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 3-to 18-membered heteroaryl; l is monocyclic or polycyclic and L is not anthracene;
n is selected as a natural number from 0 to 10;
b is at least one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 24-membered heteroaryl, substituted or unsubstituted cycloalkyl of C3-C10, substituted or unsubstituted C10-C24 fused ring, substituted or unsubstituted C5-C30 spiro ring, a (C3-C30) aliphatic ring or a (C6-C30) aromatic ring which are linked to adjacent substituents to form a single ring or multiple rings;
R1is at least one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C15 alkoxy, substituted or unsubstituted C6-C15 aryloxy, substituted or unsubstituted C1-C15 alkylthio, substituted or unsubstituted C6-C15 arylthio, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C24 fused ring, substituted or unsubstituted C10-C30 spiro ring, a (C3-C30) aliphatic ring or (C6-C30) aromatic ring linked to an adjacent substituent to form a single or multiple ring.
2. The phosphorescent compound of claim 1, wherein a carbon atom in the (C3-C30) aliphatic ring or the (C6-C30) aromatic ring linked to an adjacent substituent to form a single ring or multiple rings is replaced with at least one hetero atom selected from nitrogen, oxygen, sulfur and silicon.
3. The phosphorescent compound of claim 1, wherein the ring a is one of phenyl, biphenyl, naphthyl, methyl benzene and adamantane.
4. The phosphorescent compound of claim 1, wherein L is one of benzene, deuterated benzene, biphenyl, naphthalene, phenanthrene, spiro, and fluorene.
5. The phosphorescent compound of claim 1, wherein B is one of phenanthrene, adamantane, dimethylfluorenyl, and spiro.
6. A phosphorescent compound according to claim 1, wherein n is 1 or 2.
7. The phosphorescent compound according to claim 1, wherein the chemical structural formula of the phosphorescent compound is any one of formula 1 to formula 72:
8. a method for preparing a phosphorescent compound according to any one of claims 1 to 7, comprising the steps of:
under the protective atmosphere, placing the reactant A, the reactant B, the tetratriphenylphosphine palladium and the potassium carbonate in a solvent for reaction, and purifying to obtain an intermediate C;
under the protective atmosphere, placing the intermediate C, the reactant D, cesium carbonate and 2-dicyclohexyl phosphorus-2, 4, 6-triisopropyl biphenyl in a solvent for reaction, and purifying to obtain the phosphorescent compound;
the structural formula of the reactant A is shown as the formula A, the structural formula of the reactant B is shown as the formula B, the structural formula of the intermediate C is shown as the formula C, and the structural formula of the reactant D is shown as the formula D:
9. an organic electroluminescent device comprising an anode, a cathode and at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises the phosphorescent compound according to any one of claims 1 to 7.
10. An organic electroluminescent device according to claim 9, wherein the organic layer comprises a light-emitting layer; the light-emitting layer comprises a host material and a doping material; the host material partially or completely contains the phosphorescent compound.
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