Patent Application
20240130216
The present invention relates to the technical field of organic electroluminescence, in particular to a technology of an organic luminescent material applicable to organic electroluminescent devices, and specially relates to an iridium complex and application thereof in an organic electroluminescent device.
At present, as a new-generation display technology, an organic electroluminescent device (OLED) has attracted more and more attention in display and lighting technologies, thus having a wide application prospect. However, compared with market application requirements, properties, such as luminous efficiency, driving voltage, and service life of OLED devices still need to be strengthened and improved.
In generally, the OLED devices include various organic functional material films with different functions sandwiched between metal electrodes as basic structures, which are similar to sandwich structures. Under the driving of a current, holes and electrons are injected from a cathode and an anode, respectively. After moving a certain distance, the holes and the electrons are compounded in a light-emitting layer, and then released in the form of light or heat to achieve luminescence of the OLED. However, organic functional materials are core components of the OLED devices, and the thermal stability, photochemical stability, electrochemical stability, quantum yield, film forming stability, crystallinity, and color saturation of the materials are main factors affecting properties of the devices.
In general, the organic functional materials include fluorescent materials and phosphorescent materials. The fluorescent materials are usually organic small-molecule materials, which can only use 25% of singlet luminescence, thus having low luminous efficiency. Meanwhile, due to a spin-orbit coupling effect caused by a heavy atom effect, the phosphorescent materials can use 25% of singlet excitons, and can also use 75% of energy of triplet excitons, so that the luminous efficiency can be improved. However, compared with the fluorescent materials, the phosphorescent materials are developed later, and the thermal stability, service life, color saturation and the like of the materials need to be improved. Thus, the phosphorescent materials are a challenging topic. Various organic metal compounds have been developed to serve as the phosphorescent materials. For example, according to an invention patent document CN107973823, a quinoline iridium compound is disclosed. However, the color saturation and device properties, especially luminous efficiency and device service life, of the compound need to be improved. According to an invention patent document CN106459114, an iridium compound coordinated with a β-dione coordination group is disclosed. However, the compound has high sublimation temperature and low color saturation. In particular, the device performance is unsatisfactory, which needs to be further improved. According to an invention patent CN109721628, a compound with a fluorenyl thiophenpyrimidine structure and an organic electroluminescent device and compound including the compound are disclosed. According to invention patents CN111377969A and CN111620910A, a complex with a dibenzofuran-isoquinoline structure and an organic electroluminescent device and compound including the complex are disclosed.
However, a novel material capable of further improving properties of organic electroluminescent devices is still expected to be developed.
In order to solve the above defects, the present invention provides an organic electroluminescent device having high properties and a novel material capable of realizing the organic electroluminescent device.
In order to achieve the above purposes, the inventor has conducted in-depth studies repeatedly and found that an organic electroluminescent device having high properties can be obtained by using an iridium complex having a structure as shown in the following formula (1) as a ligand.
One of the purposes of the present invention is to provide an iridium complex. The iridium complex has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, and long device service life, and can be used in organic electroluminescent devices. In particular, the iridium complex has the potential for application in the OLED industry as a red light-emitting dopant.
In order to achieve the above purposes, the following technical solutions are adopted in the present invention.
An iridium complex has a structure of Ir(La)(Lb)(Lc),
The Lb has a structure as shown in a formula (2):
The Ra, the Rb, and the Rc are the same as the Re, the Rf, and the Rg, respectively.
The Ra, the Rb, the Rc, the Re, the Rf, and the Rg are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl containing 1-10 carbon atoms on a main chain, and substituted or unsubstituted cycloalkyl containing 3-20 ring forming carbon atoms, or any two of the Ra, the Rb, and the Rc are connected to each other to form an aliphatic ring structure, and any two of the Rc, the Rf, and the Rg are connected to each other to form an aliphatic ring structure; and the “substituted” refers to substitution with deuterium, F, Cl, Br, C1-C4 alkyl, or C3-C6 cycloalkyl.
Rd is selected from hydrogen, deuterium, halogen, and substituted or unsubstituted alkyl containing 1-10 carbon atoms on a main chain.
As a preferred iridium complex, the Lc has any one structure as shown in a formula (3) to a formula (5):
R0 and the Ra are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxyl, substituted or unsubstituted C6-C30 aryloxyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amino, cyano, nitrile, isonitrile, and phosphino, or two adjacent substituents may be optionally connected to form a ring or a fused structure;
As a preferred iridium complex, at least two of the Ra are not hydrogen.
As a preferred iridium complex, at least one of the Z1-Z6 is CR0.
As a preferred iridium complex, the Ra is substituted or unsubstituted C1-C8 alkyl, the R0 is selected from substituted or unsubstituted C1-C8 alkyl and substituted or unsubstituted C3-C6 cycloalkyl, and the “substituted” refers to substitution with deuterium, F, Cl, Br, or C1-C4 alkyl.
As a preferred iridium complex, the R6 is substituted or unsubstituted C1-C4 alkyl, or substituted or unsubstituted C3-C6 cycloalkyl.
As a preferred iridium complex, the F is not positioned at the R5.
The X is an O atom.
As a preferred iridium complex, one of the R1-R5 is F, another one is substituted or unsubstituted alkyl containing no more than 4 carbon atoms on a main chain, or substituted or unsubstituted cycloalkyl containing no more than δ ring forming carbon atoms, and the other three are hydrogen.
As a preferred iridium complex, when one of the R1-R5 is F, another one is branched C1-C4 alkyl substituted with C1-C4 alkyl.
As a preferred iridium complex, the La is independently selected from one of the following structural formulas, or corresponding parts or complete deuterides or fluorides thereof:
As a preferred iridium complex, the Lb is independently selected from one of the following structural formulas, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof:
As a preferred iridium complex, the Lc is independently selected from any one of La001-La182, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof, and the La and the Lc do not have the same numbered structure simultaneously.
As a preferred iridium complex, the Lc is independently selected from the following structural formulas, or corresponding parts or complete deuterides or fluorides thereof:
Another invention purpose of the present invention is to provide an electroluminescent device. The electroluminescent device includes a cathode, an anode, and organic layers arranged between the cathode and the anode. At least one of the organic layers includes the iridium complex.
Another invention purpose of the present invention is to provide an electroluminescent device, where the organic layers include a light-emitting layer, and the iridium complex is used a red light-emitting doping material for the light-emitting layer; or the organic layers include a hole injection layer, and the iridium complex is used as a hole injection material in the hole injection layer.
The material of the present invention has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, and long device service life. As a phosphorescent material, the material of the present invention can convert a triplet excited state into light, so that the luminous efficiency of an organic electroluminescent device can be improved, and the energy consumption is reduced.
An iridium complex of the present invention has a structure of Ir(La)(Lb)(Lc),
R6 is substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, or substituted or unsubstituted C3-C20 heterocycloalkyl;
The Lb has a structure as shown in a formula (2):
The Ra , the Rb, and the Rc are the same as the Re, the Rf, and the Rg, respectively.
The Ra-Rg are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl containing 1-10 carbon atoms on a main chain, and substituted or unsubstituted cycloalkyl containing 3-20 ring forming carbon atoms, or any two of the Ra , the Rb, and the Rc are connected to each other to form an aliphatic ring structure, and any two of the Re, the Rf, and the Rg are connected to each other to form an aliphatic ring structure; and the “substituted” refers to substitution with deuterium, F, Cl, Br, C1-C4 alkyl, or C3-C6 cycloalkyl.
Rd is selected from hydrogen, deuterium, halogen, and substituted or unsubstituted alkyl containing 1-10 carbon atoms on a main chain.
As a preferred iridium complex, the Lc has any one structure as shown in a formula (3) to a formula (5):
As a preferred iridium complex, at least two of the Ra are not hydrogen.
As a preferred iridium complex, at least one of the Z1-Z6 is CR0.
As a preferred iridium complex, the Ra is substituted or unsubstituted C1-C8 alkyl, the R0 is selected from substituted or unsubstituted C1-C8 alkyl and substituted or unsubstituted C3-C6 cycloalkyl, and the “substituted” refers to substitution with deuterium, F, Cl, Br, or C1-C4 alkyl.
As a preferred iridium complex, the R6 is substituted or unsubstituted C1-C4 alkyl, or substituted or unsubstituted C3-C6 cycloalkyl.
As a preferred iridium complex, the F is not positioned at the R5.
The X is an O atom.
As a preferred iridium complex, one of the R1-R5 is F, another one is substituted or unsubstituted alkyl containing no more than 4 carbon atoms on a main chain, or substituted or unsubstituted cycloalkyl containing no more than 6 ring forming carbon atoms, and the other three are hydrogen.
As a preferred iridium complex, when one of the R1-R5 is F, another one is branched C1-C4 alkyl substituted with C1-C4 alkyl.
Examples of various groups of the compound as shown in the formula (1) to the formula (5) are described below.
It should be noted that in the specification, “Ca-Cb” in the term “substituted or unsubstituted Ca-Cb X group” refers to the number of carbons when the X group is unsubstituted, excluding the number of carbons of a substituent when the X group is substituted.
As a linear or branched alkyl, the C1-C10 alkyl specifically includes methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-octyl and isomers thereof, n-nonyl and isomers thereof, and n-decyl and isomers thereof, preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl, and more preferably propyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.
The C3-C20 cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl, preferably cyclopentyl and cyclohexyl.
The C2-C10 alkenyl may include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, and 3-hexatrienyl, preferably propeny and allyl.
As a linear or branched alkyl or cycloalkyl consisting of atoms other than carbon and hydrogen, the C1-C10 heteroalkyl may include mercaptomethyl methyl, methoxymethyl, ethoxymethyl, tert-butoxyl methyl, N,N-dimethyl methyl, epoxy butyl, epoxy pentyl, and epoxy hexyl, preferably methoxymethyl and epoxy pentyl.
The C3-C10 heterocycloalkyl may include oxacyclopropyl, thiocyclobutyl, azacyclopentyl, oxacyclopentyl, oxacyclohexyl, dioxacyclohexyl and the like, preferably oxacyclopentyl and oxacyclohexyl. Specific examples of the aryl include phenyl, naphthyl, anthracyl, phenanthryl, tetracenyl, pyrenyl, chrysenyl, benzo [c]phenanthryl, benzo [g]chrysenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, triphenyl, tetraphenyl, and fluoranthracyl, preferably phenyl and naphthyl.
Specific examples of the heteroaryl may include pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, dibenzothienyl, azodibenzofuryl, azodibenzothienyl, diazodibenzofuryl, diazodibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furzanyl, thienyl, benzothienyl, dihydroacridinyl, azocarbazolyl, diazocarbazolyl, and quinazolinyl, preferably pyridyl, pyrimidinyl, triazinyl, dibenzofuryl, dibenzothienyl, azodibenzofuryl, azodibenzothienyl, diazodibenzofuryl, diazodibenzothienyl, carbazolyl, azocarbazolyl, and diazocarbazolyl.
The following embodiments are merely described to facilitate the understanding of the technical invention, and should not be considered as specific limitations of the present invention.
All raw materials, solvents and the like involved in the synthesis of compounds in the present invention are purchased from Alfa, Acros, and other suppliers known to persons skilled in the art.
A compound 1 (45.00 g, 172.75 mmol, 1.0 eq), a compound 2 (22.78 g, 259.13 mmol, 1.5 eq), dichloroldi-tert-butyl-(4-dimethylaminophenyl)phosphinol palladium (II) (6.12 g, 8.64 mmol, 0.05 eq), anhydrous potassium phosphate (91.67 g, 431.88 mmol, 2.5 eq), and toluene (675 ml) were added into a 1 L three-mouth flask, vacuumization was conducted for the replacement of nitrogen for 3 times, and the above compounds were stirred for a reaction at 100° C. for 4 hours under the protection of nitrogen. According to monitoring by TLC, the compound 1 was completely reacted. After cooling was conducted to room temperature, concentration was conducted under reduced pressure to remove an organic solvent, dichloromethane (337 ml) and deionized water (160 ml) were added for extraction, spin drying was conducted, and separation was conducted by column chromatography (with a mixture of ethyl acetate and n-hexane at a ratio of 1:100 as an eluting agent). Then, concentration was conducted to obtain 23.32 g of a light yellow sugar solid, namely compound 3, with a yield of 60.35%. The mass spectrum was: 224.67 (M+H).
The compound 3 (22.00 g, 98.36 mmol, 1.0 eq), a compound 4 (24.46 g, 108.19 mmol, 1.1 eq), dichloroldi-tert-butyl-(4-dimethylaminophenyl)phosphinol palladium (II) (3.48 g, 4.92 mmol, 0.05 eq), potassium carbonate (27.19 g, 196.71 mmol, 2.00 eq), toluene (330 ml), ethanol (110 ml), and deionized water (110 ml) were added into a 1 mL three-mouth flask, vacuumization was conducted for the replacement of nitrogen for 3 times, and the above compounds were stirred for a reaction at 70° C. for 1.5 hour under the protection of nitrogen. According to monitoring by TLC, the compound 3 was completely reacted. After cooling was conducted to room temperature, concentration was conducted under reduced pressure to remove an organic solvent, dichloromethane (420 ml) and deionized water (180 ml) were added for extraction, spin drying was conducted, and separation was conducted by column chromatography (with a mixture of ethyl acetate and n-hexane at a ratio of 1.5:100 as an eluting agent). Then, concentration was conducted to obtain 23.88 g of a white solid, namely compound La001, with a yield of 65.71%. The mass spectrum was: 370.43 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc002 was obtained. The mass spectrum was 276.39 (M+H).
The compound La001 (21.5 g, 58.20 mmol, 3.5 eq) and IrCl3.3H2O (5.86 g, 16.63 mmol, 1.0 eq) were placed into a 1 L round-bottomed one-mouth flask, ethylene glycol ethyl ether (322 ml) and deionized water (107 ml) were added, vacuumization was conducted for replacement for 3 times, and a resulting mixture was stirred at 110° C. for 24 hours under the protection of N2. After cooling was conducted to room temperature, concentration was conducted to remove a solvent, DCM (450 ml) was added for dissolution, filtration was conducted with silica gel, and a filtrate was washed with deionized water. Then, an organic phase was concentrated to obtain 14.65 g of a dark red oily substance, namely compound Ir(La001)-1, with a yield of 91.34%. The obtained compound was directly used in the next step without further purification.
The dimer Ir(La001)-1 (13.55 g, 14.05 mmol, 1.0 eq) and dichloromethane (1.1 L) were added into a 3 L three-mouth flask, and stirred for dissolution. Silver trifluoromethanesulfonate (7.22 g, 28.10 mmol, 2.0 eq) was dissolved in methanol (720 ml) and then added into an original solution in the reaction flask, vacuumization was conducted for replacement for 3 times, and a resulting mixture was stirred at room temperature for 16 hours under the protection of N2. Then, a resulting reaction solution was filtered by diatomite, a filtrate residue was washed with dichloromethane (300 ml), and a filtrate was spin-dried to obtain 11.65 g of a compound Ir(La001)-2 with a yield of 72.65%. The obtained compound was directly used in the next step without purification.
The compound Ir(La001)-2 (6.85 g, 6.0 mmol, 1.0 eq) and the Lc002 (4.13 g, 15.01 mmol, 2.5 eq) were added into a 250 ml three-mouth flask, ethanol (75 ml) was added, vacuumization was conducted for replacement for 3 times, and a resulting mixture was stirred for reflux for 16 hours under the protection of N2. After cooling was conducted to room temperature, filtration was conducted, a solid was collected, dissolved in dichloromethane (150 ml) and filtered by silica gel. Then, a filter cake was rinsed with dichloromethane (50 ml), and a filtrate was spin-dried, recrystallized with tetrahydrofuran/methanol (the ratio of the product to tetrahydrofuran to methanol was 1:5:10) for 2 times, and dried to obtain 3.46 g of a compound Ir(La001)2(Lc002) with a yield of 47.85%. The mass spectrum was: 1204.44 (M+H).
The compound Ir(La001)2(Lc002) (3.45 g, 2.87 mmol, 1.0 eq) and zinc chloride (19.54 g, 143.34 mmol, 50 eq) were added into a 1 L one-mouth flask, 1,2-dichloroethane (207 ml) was added, vacuumization was conducted for replacement for 3 times, and a resulting mixture was stirred for reflux for a reaction for 18 hours under the protection of N2. According to monitoring by a TLC point plate, the raw material Ir(La001)2(Lc002) was basically and completely reacted. After cooling was conducted to room temperature, deionized water (250 ml) was added for washing for 3 times. Then, a filtrate was spin-dried to obtain 2.14 g of a compound Ir(La001)2(Lc002)-1 with a yield of 85.69%. The obtained compound was directly used in the next step without purification.
The compound Ir(La001)2(Lc002)-1 (3.22 g, 3.7 mmol, 1.0 eq), Lb031 (4.37 g, 18.5 mmol, 5.0 eq), and sodium carbonate (3.92 g, 36.99 mmol, 10.0 eq) were placed in a 250 ml round-bottomed one-mouth flask, ethylene glycol ethyl ether (64 ml) was added, vacuumization was conducted for replacement for 3 times, and a resulting mixture was stirred at 50° C. for 24 hours under the protection of N2. According to monitoring by TLC, the Ir(La001)2(Lc002)-1 was completely reacted. After cooling was conducted to room temperature, 128 ml of methanol was added for beating at room temperature for 2 hours. Suction filtration was conducted, a filter cake was dissolved in dichloromethane (80 ml) and filtered by silica gel, and a filtrate was washed with deionized water (60 ml). After liquid layering was conducted, an organic phase was collected, concentrated and dried to obtain a dark red solid. Then, the dark red solid was recrystallized with tetrahydrofuran/methanol (a ratio of the product to tetrahydrofuran to methanol was 1:5:8) for 3 times to obtain 1.6 g of a red solid, namely compound Ir(La001)(Lb031)(Lc002), with a yield of 40.35%. 1.6 g of the crude product (La001)(Lb031)(Lc002) was sublimated and purified to obtain 0.91 g of sublimated pure Ir(La001)(Lb031)(Lc002) with a yield of 56.87%. The mass spectrum was: 1071.36 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.86 (d, J=15.0 Hz, 2H), 8.24(s, 1H), 7.98 (d, 1H), 7.75 (m, 2H), 7.47 (m, 4H), 7.39 (m, 2H), 7.31 (m, 2H), 6.92 (d, 2H), 4.83 (s, 1H), 2.85 (m, 4H), 2.46(m, 2H), 2.32 (s, 6H), 1.96(s, 3H), 1.92 (d, J=21.5 Hz, 6H), 1.76 (m, 4H), 1.65 (m, 8H), 1.19 (m, 12H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc003 was obtained. The mass spectrum was 290.41 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La001)2(Lc003) was obtained. The mass spectrum was 1218.47 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La001)2(Lc003)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.57 g of a dark red solid, namely compound Ir(La001)(Lb031)(Lc003), with a yield of 37.62% was obtained. 1.57 g of the crude product (La001)(Lb031)(Lc003) was sublimated and purified to obtain 0.86 g of sublimated pure Ir(La001)(Lb031)(Lc003) with a yield of 54.77%. The mass spectrum was: 1085.39 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=15.0 Hz, 2H), 8.26(s, 1H), 8.03 (d, 1H), 7.71 (m, 2H), 7.46 (m, 4H), 7.41 (m, 2H), 7.32 (m, 2H), 6.96 (d, 2H), 4.81 (s, 1H), 2.83(m, 4H), 2.46(m, 2H), 2.32 (s, 6H), 2.21(m, 2H), 1.96(s, 3H), 1.93 (d, J=20.3 Hz, 6H), 1.74 (m, 4H), 1.62 (m, 8H), 1.08 (m, 12H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc005 was obtained. The mass spectrum was 330.48 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La001)2(Lc005) was obtained. The mass spectrum was 1258.53 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La001)2(Lc005)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.61 g of a dark red solid, namely compound Ir(La001)(Lb031)(Lc005), with a yield of 39.22% was obtained. 1.61 g of the crude product (La001)(Lb031)(Lc005) was sublimated and purified to obtain 0.89 g of sublimated pure Ir(La001)(Lb031)(Lc005) with a yield of 55.27%. The mass spectrum was: 1125.45 (M+H). δ 8.87 (d, J=15.0 Hz, 2H), 8.25(s, 1H), 8.01 (d, 1H), 7.72 (m, 2H), 7.45 (m, 4H), 7.39 (m, 2H), 7.34 (m, 2H), 6.95 (d, 2H),4.83 (s, 1H), 2.83(m, 4H), 2.44(m, 2H), 2.34 (m, 6H), 2.12(m, 2H), 1.96(s, 3H), 1.88 (d, J=19.8 Hz, 6H) 1.74 (m, 4H), 1.62 (m, 8H), 1.52 (s, 6H), 1.08 (m, 12H).0.87 (s, 6H)
With reference to the synthesis and purification methods of the compound 3, only the corresponding raw materials were required to be changed, and a target compound 10 was obtained. The mass spectrum was 238.70 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound La027 was obtained. The mass spectrum was 384.46 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La027)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)-2, only the corresponding raw materials were required to be changed, and a target compound Ir(La027)-2 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La027)2(Lc002) was obtained. The mass spectrum was 1232.50 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La027)2(Lc002)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.49 g of a dark red solid, namely compound Ir(La027)(Lb005)(Lc002), with a yield of 37.94% was obtained. 1.49 g of the crude product (La027)(Lb005)(Lc002) was sublimated and purified to obtain 0.82 g of sublimated pure Ir(La027)(Lb005)(Lc002) with a yield of 55.03%. The mass spectrum was: 1061.37 (M+H). 1H NMR (400 MHz, CDCl3) δ8.85 (d, J=15.0 Hz, 2H), 8.26(s, 1H), 8.03 (d, 1H), 7.71 (m, 2H), 7.46 (m, 4H), 7.41 (m, 2H), 7.32 (m, 2H), 6.96 (d, 2H), 4.81 (s, 1H), 2.87 (m, 1H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.80 (m, 1H), 1.25 (m, 12H), 1.09-0.89 (m, 16H), 0.86 (d, 6H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La027)2(Lc003) was obtained. The mass spectrum was 1246.52 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La027)2(Lc003)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.71 g of a dark red solid, namely compound Ir(La027)(Lb005)(Lc003), with a yield of 42.39% was obtained. 1.71 g of the crude product (La027)(Lb005)(Lc003) was sublimated and purified to obtain 1.02 g of sublimated pure Ir(La027)(Lb005)(Lc003) with a yield of 59.64%. The mass spectrum was: 1075.39 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.87 (d, J=15.0 Hz, 2H), 8.28(s, 1H), 8.04 (d, 1H), 7.76 (m, 2H), 7.51 (m, 4H), 7.42 (m, 2H), 7.33 (m, 2H), 6.97(d, 2H), 4.82 (s, 1H), 2.88(m, 1H), 2.48 (d, 2H), 2.33 (d, J=15.0 Hz, 9H), 2.22 (d, 2H),1.80 (m, 1H), 1.27 (m, 12H), 1.09-0.89 (m, 16H), 0.88(d, 6H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La027)2(Lc005) was obtained. The mass spectrum was 1286.59 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La027)2 (Lc005)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.51 g of a dark red solid, namely compound Ir(La027)(Lb005)(Lc005), with a yield of 41.33% was obtained. 1.51 g of the crude product (La027)(Lb005)(Lc005) was sublimated and purified to obtain 0.84 g of sublimated pure Ir(La027)(Lb005)(Lc005) with a yield of 55.62%. The mass spectrum was: 1115.46 (M+H).
1H NMR (400 MHz, CDCl3) 8.87 (d, J=15.0 Hz, 2H), 8.28(s, 1H), 8.04 (d, 1H), 7.76 (m, 2H), 7.51 (m, 4H), 7.42 (m, 2H), 7.33 (m, 2H), 6.97(d, 2H), 4.82 (s, 1H), 2.88(m, 1H), 2.48 (d, 2H), 2.33 (d, J=15.0 Hz, 9H), 2.22 (m, 1H), 1.88 (m, 6H), 1.27 (m, 12H), 1.09 — 0.89 (m, 16H), 0.88(s, 6H).
With reference to the synthesis and purification methods of the compound 3, only the corresponding raw materials were required to be changed, and a target compound 12 was obtained. The mass spectrum was 238.70 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound La037 was obtained. The mass spectrum was 384.46 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc020 was obtained. The mass spectrum was 277.38 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La037)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)-2, only the corresponding raw materials were required to be changed, and a target compound Ir(La037)-2 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc020) was obtained. The mass spectrum was 1233.48 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc020)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.63 g of a dark red solid, namely compound Ir(La037)(Lb005)(Lc020), with a yield of 38.94% was obtained. 1.63 g of the crude product (La037)(Lb005)(Lc020) was sublimated and purified to obtain 0.94 g of sublimated pure Ir(La037)(Lb005)(Lc020) with a yield of 57.66%. The mass spectrum was: 1062.35 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.81 (s, 1H), 8.45(m, 1H), 8.32(s, 1H), 8.03 (d, 2H), 7.71 (m, 2H), 7.46 (m, 4H), 7.41 (m, 2H), 7.32 (m, 2H), 4.82 (s, 1H), 2.84(m, 1H), 2.42 (d, 2H), 2.27 (d, J=15.0 Hz, 9H), 1.87 (m, 1H), 1.21 (m, 12H), 1.12 — 0.85 (m, 16H), 0.72 (m, 6H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc024 was obtained. The mass spectrum was 339.39 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc024) was obtained. The mass spectrum was 1295.50 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc024)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.63 g of a dark red solid, namely compound Ir(La037)(Lb005)(Lc024), with a yield of 38.94% was obtained. 1.63 g of the crude product (La037)(Lb005)(Lc024) was sublimated and purified to obtain 0.94 g of sublimated pure Ir(La037)(Lb005)(Lc024) with a yield of 57.66%. The mass spectrum was: 1124.37 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.79(s, 1H),8.45(m, 1H), 8.32(s, 1H), 8.03 (d, 2H), 7.71 (m, 2H), 7.46 (m, 4H), 7.41 (m, 2H), 7.32 (m, 2H), 4.82 (s, 1H), 2.88(m, 1H), 2.48 (d, 2H), 2.33 (d, J=15.0 Hz, 9H), 2.22 (m, 1H), 1.88 (m, 6H), 1.27 (m, 12H), 1.09-0.89 (m, 16H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc025 was obtained. The mass spectrum was 291.40 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc025) was obtained. The mass spectrum was 1247.51 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc025)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.52 g of a dark red solid, namely compound Ir(La037)(Lb005)(Lc025), with a yield of 36.74% was obtained. 1.52 g of the crude product (La037)(Lb005)(Lc025) was sublimated and purified to obtain 0.84 g of sublimated pure Ir(La037)(Lb005)(Lc025) with a yield of 55.26%. The mass spectrum was: 1076.38 (M+H).
1H NMR (400 MHz, CDCl3) δ 8.79(s, 1H),8.45(m, 1H), 8.32(s, 1H), 8.03 (d, 2H), 7.71 (m, 2H), 7.46 (m, 4H), 7.41 (m, 2H), 7.32 (m, 2H), 4.83 (s, 1H), 2.77(m, 1H), 2.43 (d, 2H), 2.33 (d, J=15.0 Hz, 9H), 2.22 (d, 2H),1.80 (m, 1H), 1.27 (m, 12H), 1.09-0.89 (m, 16H), 0.88(d, 6H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc026 was obtained. The mass spectrum was 303.41 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc026) was obtained. The mass spectrum was 1259.52 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La037)2(Lc026)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.46 g of a dark red solid, namely compound Ir(La037)(Lb005)(Lc026), with a yield of 35.68% was obtained. 1.46 g of the crude product (La037)(Lb005)(Lc026) was sublimated and purified to obtain 0.88 g of sublimated pure Ir(La037)(Lb005)(Lc026) with a yield of 60.27%. The mass spectrum was: 1088.39 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.79(s, 1H), 8.45(m, 1H), 8.32(s, 1H), 8.03 (d, 2H), 7.71 (m, 2H), 7.46 (m, 4H), 7.41 (m, 2H), 7.32 (m, 2H), 4.83 (s, 1H), 2.77(m, 1H), 2.43 (d, 2H), 2.33 (s, 3H), 2.30 (s, 6H), 2.22 (d, 2H),1.80 (m, 1H), 1.33 (m, 8H), 1.27 (m, 6H), 1.09-0.89 (m, 16H), 0.88(d, 6H).
With reference to the synthesis and purification methods of the compound 3, only the corresponding raw materials were required to be changed, and a target compound 19 was obtained. The mass spectrum was 252.73 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound La080 was obtained. The mass spectrum was 398.48 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc048 was obtained. The mass spectrum was 377.38 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La080)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)-2, only the corresponding raw materials were required to be changed, and a target compound Ir(La080)-2 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La080)2(Lc048) was obtained. The mass spectrum was 1261.54 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La080)2(Lc048)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.71 g of a dark red solid, namely compound Ir(La080)(Lb018)(Lc048), with a yield of 39.2% was obtained. 1.71 g of the crude product (La080)(Lb018)(Lc048) was sublimated and purified to obtain 1.06 g of sublimated pure Ir(La080)(Lb018)(Lc048) with a yield of 61.98%. The mass spectrum was: 1156.51 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.75(d, 1H), 8.40(m, 1H), 8.27(s, 1H), 8.03 (d, 2H), 7.65 (m, 2H), 7.49 (m, 4H), 7.32 (m, 4H), 4.83 (s, 1H), 2.87 (m, 1H), 2.65 (m, 2H), 2.32 (s, 3H), 2.16(s, 6H), 1.52 (m, 4H), 1.34 (m, 4H), 1.17 (m, 8H), 1.00 (m, 9H), 0.86-0.71 (m, 20H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc049 was obtained. The mass spectrum was 291.41 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La080)2(Lc049) was obtained. The mass spectrum was 1275.56 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La080)2(Lc049)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.55 g of a dark red solid, namely compound Ir(La080)(Lb018)(Lc049), with a yield of 37.98% was obtained. 1.55 g of the crude product (La080)(Lb018)(Lc049) was sublimated and purified to obtain 0.93 g of sublimated pure Ir(La080)(Lb018)(Lc049) with a yield of 60%. The mass spectrum was: 1170.54 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.74(d, 1H), 8.38(m, 1H), 8.25(s, 1H), 8.04 (d, 2H), 7.65 (m, 2H), 7.37 (m, 4H), 7.32 (m, 4H), 4.83 (s, 1H), 2.83 (m, 1H), 2.61 (m, 2H), 2.42 (d, 2H), 2.32 (s, 3H), 2.16(s, 6H), 1.52 (m, 4H), 1.34 (m, 4H), 1.14 (m, 8H), 1.02 (m, 9H), 0.86-0.71 (m, 20H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc050 was obtained. The mass spectrum was 303.41 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La080)2(Lc050) was obtained. The mass spectrum was 1287.57 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La080)2(Lc050)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.79 g of a dark red solid, namely compound Ir(La080)(Lb018)(Lc050), with a yield of 43.17% was obtained. 1.79 g of the crude product (La080)(Lb018)(Lc050) was sublimated and purified to obtain 1.12 g of sublimated pure Ir(La080)(Lb018)(Lc050) with a yield of 62.56%. The mass spectrum was: 1182.55 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.75(d, 1H), 8.32(m, 1H), 8.25(s, 1H), 8.04 (d, 2H), 7.65 (m, 2H), 7.37 (m, 4H), 7.32 (m, 4H), 4.81 (s, 1H), 2.83 (m, 1H), 2.61 (m, 2H), 2.32 (s, 3H), 2.16(s, 6H), 1.52 (m, 6H), 1.34 (m, 6H), 1.14 (m, 8H), 1.02 (m, 9H), 0.86-0.71 (m, 18H).
With reference to the synthesis and purification methods of the compound 3, only the corresponding raw materials were required to be changed, and a target compound 24 was obtained. The mass spectrum was 266.71 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound La171 was obtained. The mass spectrum was 440.52 (M+H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc054 was obtained. The mass spectrum was 291.41 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La171)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)-2, only the corresponding raw materials were required to be changed, and a target compound Ir(La171)-2 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La171)2(Lc054) was obtained. The mass spectrum was 1259.64 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La171)2(Lc054)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.59 g of a dark red solid, namely compound Ir(La171)(Lb033)(Lc054), with a yield of 38.77% was obtained. 1.59 g of the crude product (La171)(Lb033)(Lc054) was sublimated and purified to obtain 0.93 g of sublimated pure Ir(La171)(Lb033)(Lc054) with a yield of 58.49%. The mass spectrum was: 1132.44 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.75(d, 1H), 8.32(m, 1H), 8.25(s, 1H), 8.04 (d, 2H), 7.65 (m, 2H), 7.37 (m, 4H), 7.32 (m, 3H), 4.81 (s, 1H), 2.83 (m, 1H), 2.77 (m, 1H), 2.61 (m, 4H), 2.44 (s, 3H), 2.32 (d, J=15.0 Hz, 6H) , 1.49 (m, 6H), 1.27 (m, 6H), 1.15(m, 9H), 0.72-0.66 (m, 18H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc055 was obtained. The mass spectrum was 305.43 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La171)2(Lc055) was obtained. The mass spectrum was 1373.66 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La171)2(Lc055)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.66 g of a dark red solid, namely compound Ir(La171)(Lb033)(Lc055), with a yield of 41.17% was obtained. 1.66 g of the crude product (La171)(Lb033)(Lc055) was sublimated and purified to obtain 0.97 g of sublimated pure Ir(La171)(Lb033)(Lc055) with a yield of 58.43%. The mass spectrum was: 1146.47 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.76(d, 1H), 8.29(m, 1H), 8.21(s, 1H), 8.01 (d, 2H), 7.64 (m, 2H), 7.33 (m, 4H), 7.29 (m, 3H), 4.81 (s, 1H), 2.83 (m, 1H), 2.69 (m, 1H), 2.57(m, 4H), 2.47(d, 2H), 2.32(s, 3H), 2.19 (d, J=15.0 Hz, 6H) , 1.46(m, 6H), 1.28(m, 6H), 1.14(m, 9H), 0.72-0.66 (m, 18H).
With reference to the synthesis and purification methods of the compound La001, only the corresponding raw materials were required to be changed, and a target compound Lc056 was obtained. The mass spectrum was 317.44 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002), only the corresponding raw materials were required to be changed, and a target compound Ir(La171)2(Lc056) was obtained. The mass spectrum was 1385.67 (M+H).
With reference to the synthesis and purification methods of the compound Ir(La001)2(Lc002)-1, only the corresponding raw materials were required to be changed, and a target compound Ir(La171)2(Lc056)-1 was obtained and directly used in the next step without purification.
With reference to the synthesis and purification methods of the compound Ir(La001)(Lb031)(Lc002), only the corresponding raw materials were required to be changed, and 1.72 g of a dark red solid, namely compound Ir(La171)(Lb033)(Lc056), with a yield of 40.64% was obtained. 1.72 g of the crude product (La171)(Lb033)(Lc056) was sublimated and purified to obtain 1.03 g of sublimated pure Ir(La171)(Lb033)(Lc056) with a yield of 59.88%. The mass spectrum was: 1158.48 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.75(d, 1H), 8.27(m, 1H), 8.19(s, 1H),7.96 (d, 2H), 7.61(m, 2H), 7.30 (m, 4H), 7.22 (m, 3H), 4.80 (s, 1H), 2.81 (m, 1H), 2.67 (m, 1H), 2.55(m, 4H), 2.29(s, 3H), 2.17(d, J=15.0 Hz, 6H), 1.49(m, 8H), 1.28(m, 6H), 1.14(m, 9H), 0.77-0.68 (m, 18H).
A glass substrate with a size of 50 mm*50 mm*1.0 mm including an ITO anode electrode (70 Å/1,000 Å/110 Å) was ultrasonically cleaned in ethanol for 10 minutes, dried at 150° C., and then treated with N2 plasma for 30 minutes. The washed glass substrate was installed on a substrate support of a vacuum evaporation device. First, compounds HTM1 and P-dopant (at a ratio of 97%:3%) for covering the electrode were co-evaporated on the surface of the side having an anode electrode line to form a thin film having a thickness of 100 Å. Then, a layer of HTM1 was evaporated to form a thin film having a thickness of 1,720 Å. Then, a layer of HTM2 was evaporated on the HTM1 thin film to form a thin film having a thickness of 100 Å. After that, a main material 1, a main material 2 and a doping compound (including a reference compound X or the compound of the present invention) were C0-evaporated on the HTM2 film layer at a ratio of 48.5%:48.5%:3% to form a film having a thickness of 400 Å, where the ratio of the main materials to the doping material was 90%:10%. ETL and LiQ were co-evaporated on a light-emitting layer at a ratio of 50%:50% to obtain reach a thickness of 350 Å. Then, Yb was evaporated on an electron transport layer to reach a thickness of 10 Å. Finally, a layer of metal Ag was evaporated to serve as an electrode having a thickness of 150 Å.
Evaluation: Properties of a device obtained above were tested. In various examples and comparative examples, a constant-current power supply (Keithley 2400) was used, a current at a fixed density was used for flowing through light-emitting elements, and a spectroradiometer (CS 2000) was used for testing the light-emitting spectrum. Meanwhile, the voltage value was measured, and the time (LT90) when the brightness was reduced to 90% of the initial brightness was tested. Results are as follows. The current efficiency and the device service life are calculated with the valve, of the reference rnmnniind 5 as 100%.
Through comparison of the data in the above table, it can be seen that compared with reference compounds, the compound of the present invention used as a dopant in organic electroluminescent devices with the same chromaticity coordinate has more excellent properties, such as driving voltage, luminous efficiency, and device service life.
The comparison of emission wavelengths in a dichloromethane solution is defined as follows. A corresponding compound is prepared into a 10−5 mol/L solution with dichloromethane, and the emission wavelength is tested by Hitachi (HITACH) F2700 fluorescence spectrophotometer to obtain the wavelength at a maximum emission peak. Test results are shown as follows.
Through comparison of the data in the above table, it can be seen that compared with reference compounds, the metal iridium complex of the present invention has a larger red shift, so that industrial demands for dark red light, especially the BT2020 color gamut, can be met.
Comparison of the sublimation temperature is as follows. The sublimation temperature is defined as the temperature corresponding to an evaporation rate of 1 Å/s at a vacuum degree of 10−7 Torr. Test results are shown as follows.
Through comparison of the data in the above table, it can be seen that the metal iridium complex of the present invention has low sublimation temperature, and industrial application is facilitated.
Compared with the prior art, the present invention unexpectedly provides better device luminous efficiency, improved service life, lower sublimation temperature and more saturated red luminescence through special collocation of substituents. According to the above results, it is indicated that the compound of the present invention has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, and long device service life, and can be used in organic electroluminescent devices. In particular, the metal complex has the potential for application in the OLED industry as a red light-emitting dopant, especially in displays, lighting and car tail lights.
The compound of the present invention has the advantages of high optical and electrochemical stability, high color saturation, high luminous efficiency, and long device service life, and can be used in organic electroluminescent devices. In particular, the iridium complex has the potential for application in the OLED industry as a red light-emitting dopant.
| Number | Date | Country | Kind |
|---|---|---|---|
| 202011397746.2 | Dec 2020 | CN | national |
| 202111148949.2 | Sep 2021 | CN | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/CN2021/125927 | 10/24/2021 | WO |
