CN112680218A - Composition and organic electroluminescent element comprising same - Google Patents

Composition and organic electroluminescent element comprising same Download PDF

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CN112680218A
CN112680218A CN202011571797.2A CN202011571797A CN112680218A CN 112680218 A CN112680218 A CN 112680218A CN 202011571797 A CN202011571797 A CN 202011571797A CN 112680218 A CN112680218 A CN 112680218A
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王子兴
陈清泉
吕伯彦
吴空物
赵晓宇
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

The invention belongs to the field of organic photoelectricity, and particularly relates to a composition containing an iridium metal complex and an organic compound and an organic electroluminescent element containing the composition, in particular to an organic electroluminescent diode, wherein the iridium metal complex has a structure shown in a formula (I), and the organic compound has a structural formula (II) or (III):
Figure DDA0002862935420000011
in the iridium metal complex formula (I), (L ^ Z) is selected from a formula (IV),

Description

Composition and organic electroluminescent element comprising same
Technical Field
The invention belongs to the field of organic electroluminescence, and particularly relates to a composition of an iridium metal complex and an organic compound, and an organic electroluminescent element containing the composition.
Background
As a novel display technology, the organic electroluminescent element has the unique advantages of self luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide application temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, can be applied to flat panel displays and new generation illumination, and can also be used as a backlight source of an LCD.
Since the invention of the 20 th century and the 80 th century, organic electroluminescent devices have been used in industry, such as display screens of mobile phones, but the current OLED devices have limited their wider application, especially large screen displays, due to low efficiency and short service life. And the most important factor restricting the wide application thereof is the performance of the organic electroluminescent material. Meanwhile, when an OLED device is operated by applying a voltage, joule heat is generated, so that organic materials are easily crystallized, and the lifetime and efficiency of the device are affected.
Since the ratio of the singlet excited state to the triplet excited state due to charge binding is theoretically estimated to be 1:3, the use of a small molecular fluorescent material is considered to be only 25% of the total energy available for light emission, and the remaining 75% of the energy is lost due to the non-light-emitting mechanism of the triplet excited state, so that the internal quantum efficiency limit of the fluorescent material is considered to be 25%. Professor Baldo and Forrest in 1998 discovered that triplet phosphorescence can be utilized at room temperature, and the upper limit of the original internal quantum efficiency is raised to 100%, and triplet phosphors are complex compounds composed of heavy metal atoms, and by utilizing the heavy atom effect, the strong spin-orbit coupling effect causes the energy levels of singlet excited states and triplet excited states to be mixed with each other, so that the originally forbidden triplet energy is relieved to emit light in the form of phosphorescence, and the quantum efficiency is greatly improved.
At present, almost all light emitting layers in an organic OLED module use a host-guest light emitting system mechanism, that is, a guest light emitting material is doped in a host material, and generally, the energy system of the organic host material is larger than that of the guest material, that is, the energy is transferred from the host to the guest, so that the guest material is excited to emit light. A commonly used phosphorescent organic host material such as CBP (4, 4' -bis (9-carbazolyl) -biphenyl) has a high efficiency and a high triplet energy level, and when it is used as an organic material, the triplet energy can be efficiently transferred from a light emitting organic material to a guest phosphorescent light emitting material. A commonly used organic guest material is an iridium metal complex.
The invention discovers that the combination of a specific organic compound and an iridium metal compound can be used as a light-emitting layer of an organic electroluminescent element to remarkably improve the current efficiency of the organic electroluminescent element, reduce the operating voltage of the element and prolong the service life of the element.
Disclosure of Invention
The invention aims to provide a composition of an iridium metal complex and an organic compound and an organic electroluminescent element comprising the composition.
The invention provides a composition of an iridium metal complex and an organic compound, wherein the iridium metal complex has a structure shown in a formula (I), and the organic compound has a structural formula (II) or (III):
Figure BDA0002862935400000021
preferably, in formula (I), X is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; y is selected from N or C-R1;
(L ^ Z) is selected from structural formulas represented by the formula (IV),
Figure BDA0002862935400000022
R1-R8, R11 are independently selected from hydrogen, deuterium, cyano, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroarylether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted aryloxysilyl group, or substituted or unsubstituted aryloxysilyl group,Any one of substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl, and substituted or unsubstituted phosphinyl; r9, R10 is selected from any one of cyano, C1-C18 alkyl, C1-C18 alkoxy, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted aryl acyl, substituted or unsubstituted heteroaryl acyl, and substituted or unsubstituted phosphinyl; all groups may be partially deuterated or fully deuterated. m is taken from 1 or 2, and m + n is 3; heteroaryl means containing B, N, O, S, P (═ O), Si, P at least one heteroatom;
in formula (II) and formula (III), X1 to X6 are CR or N; y1 to Y8 are CR or N, and at least 2 are N; l is absent or selected from single bond, O, S, CRR, SiRR, NR; a and B are each independently selected from C6-C30 aryl, C2-C30 heteroaryl; r is independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, aryl or heteroaryl substituted amine; n is an integer of 0 to 6; adjacent X or Y may form a ring; all groups may be partially deuterated or fully deuterated.
Preferably, R1 to R11 in the iridium metal complex of the present invention are selected from one of the following representative structural formulae, but do not represent and are not limited thereto:
Figure BDA0002862935400000031
preferably, the iridium metal complex of the present invention is selected from one of the following structures, but does not represent a limitation thereto:
Figure BDA0002862935400000041
Figure BDA0002862935400000051
Figure BDA0002862935400000061
Figure BDA0002862935400000071
Figure BDA0002862935400000081
Figure BDA0002862935400000091
Figure BDA0002862935400000101
Figure BDA0002862935400000111
Figure BDA0002862935400000121
Figure BDA0002862935400000131
Figure BDA0002862935400000141
Figure BDA0002862935400000151
Figure BDA0002862935400000161
Figure BDA0002862935400000171
Figure BDA0002862935400000181
Figure BDA0002862935400000191
Figure BDA0002862935400000201
Figure BDA0002862935400000211
the present invention provides compositions wherein the organic compound is preferably selected from the group consisting of compounds described in formula (II) -1 to II-7, but not limited thereto, when the structure of the organic compound is formula (II):
Figure BDA0002862935400000221
wherein X1 to X6, L, A, B, R, n are the same as described above.
Preferably, a and B are selected from the group described by the following structures, but do not represent a limitation thereto:
Figure BDA0002862935400000222
wherein X1 to X6, Y1 to Y8, L, R, n are the same as described above.
Preferably, one organic compound represented by formula (II) or formula (III) is selected from at least one of the following representative structures, but does not represent a limitation thereto:
Figure BDA0002862935400000231
Figure BDA0002862935400000241
Figure BDA0002862935400000251
Figure BDA0002862935400000261
Figure BDA0002862935400000271
Figure BDA0002862935400000281
Figure BDA0002862935400000291
Figure BDA0002862935400000301
Figure BDA0002862935400000311
Figure BDA0002862935400000321
Figure BDA0002862935400000331
Figure BDA0002862935400000341
Figure BDA0002862935400000351
Figure BDA0002862935400000361
Figure BDA0002862935400000371
Figure BDA0002862935400000381
Figure BDA0002862935400000391
Figure BDA0002862935400000401
Figure BDA0002862935400000411
Figure BDA0002862935400000421
Figure BDA0002862935400000431
Figure BDA0002862935400000441
Figure BDA0002862935400000451
Figure BDA0002862935400000461
Figure BDA0002862935400000471
Figure BDA0002862935400000481
Figure BDA0002862935400000491
Figure BDA0002862935400000501
Figure BDA0002862935400000511
Figure BDA0002862935400000521
Figure BDA0002862935400000531
Figure BDA0002862935400000541
Figure BDA0002862935400000551
Figure BDA0002862935400000561
Figure BDA0002862935400000571
Figure BDA0002862935400000581
Figure BDA0002862935400000591
Figure BDA0002862935400000601
Figure BDA0002862935400000611
Figure BDA0002862935400000621
Figure BDA0002862935400000631
Figure BDA0002862935400000641
Figure BDA0002862935400000651
Figure BDA0002862935400000661
Figure BDA0002862935400000671
Figure BDA0002862935400000681
Figure BDA0002862935400000691
Figure BDA0002862935400000701
Figure BDA0002862935400000711
Figure BDA0002862935400000721
Figure BDA0002862935400000731
Figure BDA0002862935400000741
Figure BDA0002862935400000751
Figure BDA0002862935400000761
Figure BDA0002862935400000771
Figure BDA0002862935400000781
Figure BDA0002862935400000791
Figure BDA0002862935400000801
the solvent used in the present invention is not particularly limited, and examples thereof include unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decahydronaphthalene, bicyclohexyl, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., ether solvents such as tetrahydrofuran, tetrahydropyran, etc., ester solvents such as alkyl benzoate, etc., which are well known to those skilled in the art.
The present invention also relates to an organic opto-electronic device comprising: a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the light-emitting layer comprises the composition.
The mass percentage of the iridium metal complex in the formula (I) in the light-emitting layer of the organic electroluminescent device is 0.1-50%.
In the present invention, the organic electroluminescent element is an anode which can be formed by depositing metal, an oxide having conductivity, or an alloy thereof on a substrate by a sputtering method, electron beam evaporation, vacuum deposition, or the like; and sequentially evaporating a hole injection layer, a hole transport layer, a luminescent layer, a hole blocking layer and an electron transport layer on the surface of the prepared anode, and then evaporating a cathode. The organic electroluminescent device is prepared by vapor deposition of the cathode, the organic layer and the anode on the substrate except the above method. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer. In the invention, the organic layer is prepared by adopting a high polymer material according to a solvent engineering (spin-coating), tape-casting (tape-casting), doctor-blading (sector-Printing), Screen-Printing (Screen-Printing), ink-jet Printing or Thermal-Imaging (Thermal-Imaging) method instead of an evaporation method, so that the number of the device layers can be reduced.
The materials used for the organic electroluminescent element according to the present invention may be classified into top emission, bottom emission, or double-sided emission. The compounds of the organic electroluminescent device according to the embodiment of the present invention can be applied to the aspects of the organic electroluminescent element such as an organic light emitting cell, an illuminating OLED, a flexible OLED, an organic photoreceptor, an organic thin film transistor and the like in a similar principle to the organic light emitting device.
The invention has the beneficial effects that:
the invention relates to a novel iridium metal complex and an organic compound composition, which have better thermal stability, the organic compound can balance the transport of holes and electrons, and the energy transmission between the organic compound and the iridium metal complex in the composition is more efficient.
Drawings
FIG. 1 is a structural diagram of an organic electroluminescent diode device according to the present invention.
Where 110 denotes a substrate, 120 denotes an anode, 130 denotes a hole injection layer, 140 denotes a hole transport layer, 150 denotes a light emitting layer, 160 denotes a hole blocking layer, 170 denotes an electron transport layer, 180 denotes an electron injection layer, and 190 denotes a cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In a preferred embodiment of the present invention, the OLED device according to the invention comprises a hole transport layer, which may preferably be selected from known or unknown materials, particularly preferably from the following structures, without representing the present invention being limited to the following structures:
Figure BDA0002862935400000821
in a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants. Preferred p-type dopants of the present invention are, but do not represent a limitation of the present invention to:
Figure BDA0002862935400000822
in a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the compounds ET-1 to ET-13, but does not represent that the present invention is limited to the following structures:
Figure BDA0002862935400000831
the organic compounds referred to in the present invention are obtained by known synthetic methods.
The general synthesis steps of the iridium metal complex related to the formula (I) are as follows:
Figure BDA0002862935400000832
the general procedure is as follows,
(1) ligand 1(0.10 mol), IrCl are added under the protection of argon3.3H2Heating and refluxing a mixed solution of O (0.045 mol), 2-ethoxyethanol (300 ml) and water (100 ml) for 16-20 hours until a supernatant is obtained, detecting the content of the ligand 1 by using high performance liquid chromatography to be less than 5%, stopping heating, cooling to room temperature, performing suction filtration by using a Buchner funnel, leaching a filter cake by using a mixed solution of water and 2-ethoxyethanol, and drying to obtain a bridging dimer 2 or 3 of yellow powder, wherein the yield is 81-89%.
(2) Under the protection of argon, dropwise adding a tetrahydrofuran solution of a dichloro crosslinked dimer complex (2.2mmol) into a lithium salt solution (-78 ℃), which is formed by a ligand L ^ Z (2.4mmol) and butyllithium, slowly heating to room temperature, heating for reflux reaction for 6 hours, stopping heating, cooling to room temperature, adding a proper amount of distilled water, and filtering to obtain a solid. The solid was dissolved in dichloromethane and passed through a short column of silica gel. Removing the solvent under reduced pressure, and washing the solid obtained by concentration with methanol and petroleum ether in sequence to obtain the final target product. Ligand 1 was obtained by custom synthesis. These are merely examples illustrating embodiments of the present invention and the scope of the present invention is not limited thereto.
Example 1: synthesis of Compound 1
Figure BDA0002862935400000841
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate as lithium reagent gave a yield of 74% of the final product. Mass spectrum m/z, theoretical 1125.6; found M + H: 1126.6.
example 2: synthesis of Compound 2
Figure BDA0002862935400000842
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 72% yield of the final product. Mass spectrum m/z, theoretical 1013.43; found M + H: 1014.4.
example 3: synthesis of Compound 3
Figure BDA0002862935400000843
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 75% yield of the final product. Mass spectrum m/z, theoretical 1125.55; found M + H: 1126.5.
example 4: synthesis of Compound 4
Figure BDA0002862935400000851
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate as lithium reagent gave a yield of 79% of the final product. Mass spectrum m/z, theoretical 1141.57; found M + H: 1142.6.
example 5: synthesis of Compound 5
Figure BDA0002862935400000852
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 73% yield of the final product. Mass spectrum m/z, theoretical 1189.57; found M + H: 1190.6.
example 6: synthesis of Compound 6
Figure BDA0002862935400000853
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 71% yield of the final product. Mass spectrum m/z, theoretical 1125.55; found M + H: 1126.6.
example 7: synthesis of Compound 7
Figure BDA0002862935400000854
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 76% yield of the final product. Mass spectrum m/z, theoretical 1102.56; found M + H: 1103.6.
example 8: synthesis of Compound 8
Figure BDA0002862935400000861
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 81% yield of the final product. Mass spectrum m/z, theoretical 1073.42; found M + H: 1074.4.
example 9: synthesis of Compound 9
Figure BDA0002862935400000862
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 82% yield of the final product. Mass spectrum m/z, theoretical 1277.57; found M + H: 1278.5.
example 10: synthesis of Compound 10
Figure BDA0002862935400000863
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 83% yield of the final product. Mass spectrum m/z, theoretical 1106.47; found M + H: 1107.4.
example 11: synthesis of Compound 11
Figure BDA0002862935400000864
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 71% yield of the final product. Mass spectrum m/z, theoretical 1185.54; found M + H: 1186.6.
example 12: synthesis of Compound 12
Figure BDA0002862935400000871
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 69% yield of the final product. Mass spectrum m/z, theoretical 1099.52; found M + H: 1100.5.
example 13: synthesis of Compound 13
Figure BDA0002862935400000872
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 76% yield of the final product. Mass spectrum m/z, theoretical 1163.53; found M + H: 1164.5.
example 14: synthesis of Compound 14
Figure BDA0002862935400000873
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 74% yield of the final product. Mass spectrum m/z, theoretical 1048.49; found M + H: 1049.5.
example 15: synthesis of Compound 15
Figure BDA0002862935400000874
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 72% yield of the final product. Mass spectrum m/z, theoretical 1099.32; found M + H: 1100.3.
example 16: synthesis of Compound 16
Figure BDA0002862935400000881
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 71% yield of the final product. Mass spectrum m/z, theoretical 1073.44; found M + H: 1074.4.
example 17: synthesis of Compound 17
Figure BDA0002862935400000882
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 76% yield of the final product. Mass spectrum m/z, theoretical 1137.45; found M + H: 1138.4.
example 18: synthesis of Compound 18
Figure BDA0002862935400000883
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 77% yield of the final product. Mass spectrum m/z, theoretical 1022.40; found M + H: 1023.4.
example 19: synthesis of Compound 19
Figure BDA0002862935400000884
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 79% yield of the final product. Mass spectrum m/z, theoretical 1073.46; found M + H: 1074.5.
example 20: synthesis of Compound 20
Figure BDA0002862935400000891
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate as lithium reagent gave a yield of 74% of the final product. Mass spectrum m/z, theoretical 1023.3; found M + H: 1024.3.
example 21: synthesis of Compound 21
Figure BDA0002862935400000892
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 81% yield of the final product. Mass spectrum m/z, theoretical 1051.33; found M + H: 1052.3.
example 22: synthesis of Compound 22
Figure BDA0002862935400000893
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 80% yield of the final product. Mass spectrum m/z, theoretical 1227.47; found M + H: 1228.5.
example 23: synthesis of Compound 23
Figure BDA0002862935400000894
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 81% yield of the final product. Mass spectrum m/z, theoretical 1111.42; found M + H: 1112.4.
example 24: synthesis of Compound 24
Figure BDA0002862935400000901
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 78% yield of the final product. Mass spectrum m/z, theoretical 1157.62; found M + H: 1158.6.
example 25: synthesis of Compound 25
Figure BDA0002862935400000902
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 80% yield of the final product. Mass spectrum m/z, theoretical 1135.53; found M + H: 1136.5.
example 26: synthesis of Compound 26
Figure BDA0002862935400000903
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 83% yield of the final product. Mass spectrum m/z, theoretical 1135.53; found M + H: 1136.5.
manufacturing of OLED device:
a P-doped material P-1 to P-5 is evaporated on the surface or anode of ITO/Ag/ITO glass with the size of 2mm multiplied by 2mm in light emitting area or the P-doped material is co-evaporated with the compound in the table with the concentration of 1% to 50% to form a Hole Injection Layer (HIL) with the thickness of 5 nm to 100nm and a Hole Transport Layer (HTL) with the thickness of 5 nm to 200nm, then a light emitting layer (EML) (which can contain the compound) with the thickness of 10 nm to 100nm is formed on the hole transport layer, finally an Electron Transport Layer (ETL) with the thickness of 20 nm to 200nm and a cathode with the thickness of 50 nm to 200nm are formed by the compound in sequence, if necessary, an Electron Blocking Layer (EBL) is added between the HTL and the EML layer, and an Electron Injection Layer (EIL) is added between the ETL and the cathode. The OLEDs were tested by standard methods, as listed in table 1.
To better illustrate the practical gain effects of the present invention, comparative organic electroluminescent elements were prepared using the following commonly used iridium metal complex RD-1 and the iridium metal complexes of the present invention and organic compounds H-1 to H-14 as the main components to illustrate the superiority of the composition of the present invention.
Figure BDA0002862935400000911
In the specific embodiment, the structure of the top-emitting OLED device is on ITO/Ag/ITO-containing glass, HIL is HT-1: P-3(97:3 v/v%), and the thickness is 10 nanometers; HTL is HT-1, and the thickness is 100 nanometers; EBL is HT-8, thickness is 10 nm, EML is the composition of the invention, concretely, (H-1-H-14): (RD-1-RD-6) (97:3 v/v%), thickness is 35 nm, ETL is ET-13: LiQ (50:50 v/v%) with a thickness of 35 nm, then evaporating a cathode Yb of 1 nm, an Ag of 14 nm and an evaporated CPL layer of 70 nm. The characteristics of efficiency, operating voltage, life, etc. according to the above examples and comparative examples are shown in table 1 below.
TABLE 1
Examples EML Driving voltage (volt) Current efficiency (cd/A) LT95 (hours)
Comparison device 1 RD-1:H-1 4.0 40.3 126
Comparison device 2 RD-1:H-4 4.0 40.6 136
Comparison device 3 RD-1:H-5 3.9 42.3 188
Comparison device 4 RD-1:H-9 4.0 41.0 160
Comparison device 5 RD-1:H-14 3.8 42.6 190
Device example 1 Compound 1:H-1 3.8 55.3 142
Device example 2 Compound 5:H-1 3.8 58.3 165
Device example 3 Compound 8:H-1 3.7 59.0 149
Device example 4 Compound 17:H-1 3.7 57.8 156
Device example 5 Compound 18:H-1 3.7 59.7 179
Device example 6 Compound 19:H-1 3.9 57.2 166
Device example 7 Compound 1:H-5 3.7 58.4 240
Device example 8 Compound 5:H-5 3.0 60.8 254
Device example 9 Compound 8:H-5 3.7 63.2 258
Device example 10 Compound 17:H-5 3.7 60.3 230
Device example 11 Compound 18:H-5 3.7 63.9 267
Device example 12 Compound 19:H-5 3.7 59.7 254
Device example 13 Compound 1:H-14 3.6 57.9 230
Device example 14 Compound 5:H-14 3.6 60.2 245
Device example 15 Compound 8:H-14 3.6 62.0 213
Device example 16 Compound 17:H-14 3.6 58.9 260
Device example 17 Compound 18:H-14 3.6 62.6 263
Device example 18 Compound 19:H-14 3.6 59.0 246
As can be seen from Table 1, the planar system, devices 1 to 18 and comparative devices 1 to 5 are incorporated on the ligand structure, and the composition provided by the invention can obviously improve the current efficiency of the OLED device and reduce the driving voltage under the same conditions. Specifically, comparing the device 1 with the device examples 1-6, the combination provided by the invention has obvious advantages. If a new combination is adopted, namely the device examples 7 to 18, the operating voltage is obviously lower than that of the comparison devices 3 to 5, the luminous efficiency is higher, and the service life is prolonged. The composition provided by the invention has remarkable advantages and commercial application value.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (11)

1. A composition is characterized by comprising an iridium metal complex and an organic compound, wherein the structural formula of the iridium metal complex is shown as a formula (I); the structural formula (II) or (III) of the organic compound
Figure FDA0002862935390000011
In formula (I), X is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; y is selected from N or C-R1;
(L ^ Z) is selected from structural formulas represented by the formula (IV),
Figure FDA0002862935390000012
R1-R8, R11 are independently selected from any one of hydrogen, deuterium, cyano, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroarylether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilicon group, substituted or unsubstituted heteroarylsilicon group, substituted or unsubstituted aryloxyside group, substituted or unsubstituted arylacyl group, substituted or unsubstituted heteroarylacyl group, substituted or unsubstituted phosphinyl group; r9, R10 is selected from any one of cyano, C1-C18 alkyl, C1-C18 alkoxy, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted aryl acyl, substituted or unsubstituted heteroaryl acyl, and substituted or unsubstituted phosphinyl; all groups may be partially deuterated or fully deuterated. m is taken from 1 or 2, and m + n is 3; heteroaryl means containing B, N, O, S, P (═ O), Si, P at least one heteroatom;
in formula (II) and formula (III), X1 to X6 are CR or N; y1 to Y8 are CR or N, and at least 2 are N; l is absent or selected from single bond, O, S, CRR, SiRR, NR; a and B are each independently selected from C6-C30 aryl, C2-C30 heteroaryl; r is independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, aryl or heteroaryl substituted amine; n is an integer of 0 to 6; adjacent X or Y may form a ring; all groups may be partially deuterated or fully deuterated.
2. The composition as claimed in claim 1, wherein R1 to R11 in the iridium metal complex of formula (I) are selected from one of the following representative structural formulae:
Figure FDA0002862935390000021
3. the composition as claimed in any one of claims 1 to 2, wherein the iridium metal complex of formula (I) is selected from one of the following representative structures:
Figure FDA0002862935390000031
Figure FDA0002862935390000041
Figure FDA0002862935390000051
Figure FDA0002862935390000061
Figure FDA0002862935390000071
Figure FDA0002862935390000081
Figure FDA0002862935390000091
Figure FDA0002862935390000101
Figure FDA0002862935390000111
Figure FDA0002862935390000121
Figure FDA0002862935390000131
Figure FDA0002862935390000141
Figure FDA0002862935390000151
Figure FDA0002862935390000161
Figure FDA0002862935390000171
Figure FDA0002862935390000181
Figure FDA0002862935390000191
Figure FDA0002862935390000201
4. the composition of claim 1, wherein formula (II) is selected from the group consisting of compounds of formula II-1 through II-7
Figure FDA0002862935390000211
Wherein X1 to X6, L, A, B, R, n are the same as in claim 1.
5. The composition of claim 1, wherein a and B are selected from the group consisting of those described by the following structures:
Figure FDA0002862935390000212
wherein X1 to X6, Y1 to Y8, L, R, n are the same as in claim 1.
6. The composition according to any one of claims 1 to 7, wherein the organic compound of formula (II) or formula (III) is selected from one of the following representative structures:
Figure FDA0002862935390000221
Figure FDA0002862935390000231
Figure FDA0002862935390000241
Figure FDA0002862935390000251
Figure FDA0002862935390000261
Figure FDA0002862935390000271
Figure FDA0002862935390000281
Figure FDA0002862935390000291
Figure FDA0002862935390000301
Figure FDA0002862935390000311
Figure FDA0002862935390000321
Figure FDA0002862935390000331
Figure FDA0002862935390000341
Figure FDA0002862935390000351
Figure FDA0002862935390000361
Figure FDA0002862935390000371
Figure FDA0002862935390000381
Figure FDA0002862935390000391
Figure FDA0002862935390000401
Figure FDA0002862935390000411
Figure FDA0002862935390000421
Figure FDA0002862935390000431
Figure FDA0002862935390000441
Figure FDA0002862935390000451
Figure FDA0002862935390000461
Figure FDA0002862935390000471
Figure FDA0002862935390000481
Figure FDA0002862935390000491
Figure FDA0002862935390000501
Figure FDA0002862935390000511
Figure FDA0002862935390000521
Figure FDA0002862935390000531
Figure FDA0002862935390000541
Figure FDA0002862935390000551
Figure FDA0002862935390000561
Figure FDA0002862935390000571
Figure FDA0002862935390000581
Figure FDA0002862935390000591
Figure FDA0002862935390000601
Figure FDA0002862935390000611
Figure FDA0002862935390000621
Figure FDA0002862935390000631
Figure FDA0002862935390000641
Figure FDA0002862935390000651
Figure FDA0002862935390000661
Figure FDA0002862935390000671
Figure FDA0002862935390000681
Figure FDA0002862935390000691
Figure FDA0002862935390000701
Figure FDA0002862935390000711
Figure FDA0002862935390000721
Figure FDA0002862935390000731
Figure FDA0002862935390000741
Figure FDA0002862935390000751
Figure FDA0002862935390000761
Figure FDA0002862935390000771
Figure FDA0002862935390000781
Figure FDA0002862935390000791
7. a formulation comprising a composition according to any one of claims 1 to 6 and at least one solvent.
8. A formulation according to claim 9, wherein the composition and the solvent are formulated in the form of a solvent, and the solvent used is not particularly limited, and a halogenated saturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane and the like, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene and the like, an ether solvent such as tetrahydrofuran, tetrahydropyran and the like, an ester solvent such as alkyl benzoate and the like, which are well known to those skilled in the art can be used.
9. An organic electroluminescent device, comprising:
a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the light-emitting layer comprises the composition of any one of claims 1 to 6.
10. The organic electroluminescent device according to claim 9, wherein the iridium metal complex and the organic compound are contained in a light-emitting layer, and wherein the iridium metal complex is present in an amount of 1 to 50% by mass.
11. A display or lighting device comprising the organic electroluminescent element according to any one of claims 9 to 10.
CN202011571797.2A 2020-12-27 2020-12-27 Composition and organic electroluminescent element comprising same Withdrawn CN112680218A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104277075A (en) * 2013-07-01 2015-01-14 环球展览公司 Ancillary ligands for organometallic complexes, device comprising the same, and formulation
CN110452271A (en) * 2019-07-26 2019-11-15 浙江华显光电科技有限公司 Red phosphorescent compound and the organic electroluminescence device for using the compound
CN111848689A (en) * 2020-08-17 2020-10-30 奥来德(上海)光电材料科技有限公司 Benzofuran-containing organic iridium complex, preparation method thereof and photoelectric device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104277075A (en) * 2013-07-01 2015-01-14 环球展览公司 Ancillary ligands for organometallic complexes, device comprising the same, and formulation
CN110452271A (en) * 2019-07-26 2019-11-15 浙江华显光电科技有限公司 Red phosphorescent compound and the organic electroluminescence device for using the compound
CN111848689A (en) * 2020-08-17 2020-10-30 奥来德(上海)光电材料科技有限公司 Benzofuran-containing organic iridium complex, preparation method thereof and photoelectric device

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