CN112687819B - Composition and organic electroluminescent element comprising same - Google Patents

Composition and organic electroluminescent element comprising same Download PDF

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CN112687819B
CN112687819B CN202011571796.8A CN202011571796A CN112687819B CN 112687819 B CN112687819 B CN 112687819B CN 202011571796 A CN202011571796 A CN 202011571796A CN 112687819 B CN112687819 B CN 112687819B
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CN112687819A (en
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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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Abstract

The invention belongs to the field of organic mattersThe photoelectric field, in particular to a composition containing an iridium metal complex and an organic compound and an organic electroluminescent element containing the composition, especially 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 DDA0002862935070000011
in the iridium metal complex formula (I), (L ^ Z) is selected from a formula (IV),
Figure DDA0002862935070000012
the organic compounds of formula (II) or (III) and the organic photovoltaic element can be understood by reference to the specific description provided herein. The composition is applied to a light-emitting layer of an organic light-emitting diode, so that the current efficiency of a light-emitting element is improved, the driving voltage is obviously reduced, the service life is prolonged, and the composition has good commercialization prospect.

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 BDA0002862935050000021
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 formula (IV)
Figure BDA0002862935050000022
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 and R10 are 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 a single bond, O, S, CRR, SiRR, NR; a and B are each independently selected from the group consisting of 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, the iridium metal complex of the present invention is selected from one of the following structures, but does not represent a limitation thereto:
Figure BDA0002862935050000031
wherein X, Y, R1 to R11 are the same as described above.
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 BDA0002862935050000032
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 BDA0002862935050000041
Figure BDA0002862935050000051
Figure BDA0002862935050000061
Figure BDA0002862935050000071
Figure BDA0002862935050000081
Figure BDA0002862935050000091
Figure BDA0002862935050000101
Figure BDA0002862935050000111
Figure BDA0002862935050000121
Figure BDA0002862935050000131
Figure BDA0002862935050000141
Figure BDA0002862935050000151
Figure BDA0002862935050000161
Figure BDA0002862935050000171
Figure BDA0002862935050000181
Figure BDA0002862935050000191
Figure BDA0002862935050000201
Figure BDA0002862935050000211
Figure BDA0002862935050000221
Figure BDA0002862935050000231
Figure BDA0002862935050000241
Figure BDA0002862935050000251
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 BDA0002862935050000261
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 BDA0002862935050000262
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 BDA0002862935050000271
Figure BDA0002862935050000281
Figure BDA0002862935050000291
Figure BDA0002862935050000301
Figure BDA0002862935050000311
Figure BDA0002862935050000321
Figure BDA0002862935050000331
Figure BDA0002862935050000341
Figure BDA0002862935050000351
Figure BDA0002862935050000361
Figure BDA0002862935050000371
Figure BDA0002862935050000381
Figure BDA0002862935050000391
Figure BDA0002862935050000401
Figure BDA0002862935050000411
Figure BDA0002862935050000421
Figure BDA0002862935050000431
Figure BDA0002862935050000441
Figure BDA0002862935050000451
Figure BDA0002862935050000461
Figure BDA0002862935050000471
Figure BDA0002862935050000481
Figure BDA0002862935050000491
Figure BDA0002862935050000501
Figure BDA0002862935050000511
Figure BDA0002862935050000521
Figure BDA0002862935050000531
Figure BDA0002862935050000541
Figure BDA0002862935050000551
Figure BDA0002862935050000561
Figure BDA0002862935050000571
Figure BDA0002862935050000581
Figure BDA0002862935050000591
Figure BDA0002862935050000601
Figure BDA0002862935050000611
Figure BDA0002862935050000621
Figure BDA0002862935050000631
Figure BDA0002862935050000641
Figure BDA0002862935050000651
Figure BDA0002862935050000661
Figure BDA0002862935050000671
Figure BDA0002862935050000681
Figure BDA0002862935050000691
Figure BDA0002862935050000701
Figure BDA0002862935050000711
Figure BDA0002862935050000721
Figure BDA0002862935050000731
Figure BDA0002862935050000741
Figure BDA0002862935050000751
Figure BDA0002862935050000761
Figure BDA0002862935050000771
Figure BDA0002862935050000781
Figure BDA0002862935050000791
Figure BDA0002862935050000801
Figure BDA0002862935050000811
Figure BDA0002862935050000821
Figure BDA0002862935050000831
Figure BDA0002862935050000841
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, in which the OLED device according to the invention comprises a hole transport layer, the hole transport material may preferably be selected from known or unknown materials, particularly preferably from, but not limiting the invention to, the following structures:
Figure BDA0002862935050000861
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 BDA0002862935050000862
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 BDA0002862935050000871
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 BDA0002862935050000872
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 ℃) formed by a ligand L ^ Z (2.4mmol) and butyllithium, slowly heating to room temperature, heating under reflux 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 successively 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 BDA0002862935050000881
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate as lithium reagent, the final product was obtained in 76% yield. Mass spectrum m/z, theoretical 1161.54; found M + H: 1162.5.
example 2: synthesis of Compound 2
Figure BDA0002862935050000882
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in a yield of 70% of the final product. Mass spectrum m/z, theoretical 1189.57; found M + H: 1190.5.
example 3: synthesis of Compound 3
Figure BDA0002862935050000883
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate as lithium reagent, the final product was obtained in 77% yield. Mass spectrum m/z, theoretical 1189.57; found M + H: 1190.5.
example 4: synthesis of Compound 4
Figure BDA0002862935050000891
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 1159.62; found M + H: 1160.6.
synthesis of Compound 5
Figure BDA0002862935050000892
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 1193.48; found M + H: 1194.5.
example 6: synthesis of Compound 6
Figure BDA0002862935050000893
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate as lithium reagent, the final product was obtained in 64% yield. Mass spectrum m/z, theoretical 1213.57; found M + H: 1214.5.
example 7: synthesis of Compound 7
Figure BDA0002862935050000894
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 1107.49; found M + H: 1108.5.
example 8: synthesis of Compound 8
Figure BDA0002862935050000901
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 1221.52; found M + H: 1222.5.
example 9: synthesis of Compound 9
Figure BDA0002862935050000902
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 78% yield of the final product. Mass spectrum m/z, theoretical 1079.42; found M + H: 1080.42.
example 10: synthesis of Compound 10
Figure BDA0002862935050000903
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 1107.45; found M + H: 1108.5.
example 11: synthesis of Compound 11
Figure BDA0002862935050000911
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate as lithium reagent gave a yield of 81% of the final product. Mass spectrum m/z, theoretical 1163.53; found M + H: 1164.5.
example 12: synthesis of Compound 12
Figure BDA0002862935050000912
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 78% yield of the final product. Mass spectrum m/z, theoretical 1163.52; found M + H: 1164.52.
example 13: synthesis of Compound 13
Figure BDA0002862935050000913
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate as lithium reagent, the final product was obtained in 77% yield. Mass spectrum m/z, theoretical 1109.42; found M + H: 1110.42.
example 14: synthesis of Compound 14
Figure BDA0002862935050000914
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: 1138.5.
example 15: synthesis of Compound 15
Figure BDA0002862935050000921
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate as lithium reagent, the yield of the final product was 79%. Mass spectrum m/z, theoretical 1296.66; found M + H: 1297.6.
example 16: synthesis of Compound 16
Figure BDA0002862935050000922
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in a yield of 70% of the final product. Mass spectrum m/z, theoretical 1137.46; found M + H: 1136.5.
example 17: synthesis of Compound 17
Figure BDA0002862935050000923
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 1141.38; found M + H: 1140.4.
example 18: synthesis of Compound 18
Figure BDA0002862935050000924
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 77% yield of the final product. Mass spectrum m/z, theoretical 1169.41; found M + H: 1170.4.
example 19: synthesis of Compound 19
Figure BDA0002862935050000931
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 1169.43; found M + H: 1170.4.
example 20: synthesis of Compound 20
Figure BDA0002862935050000932
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 78% yield of the final product. Mass spectrum m/z, theoretical 1083.42; found M + H: 1084.4.
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, thereby manufacturing the organic light emitting element. 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 BDA0002862935050000933
Figure BDA0002862935050000941
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
Figure BDA0002862935050000942
Figure BDA0002862935050000951
As can be seen from Table 1, the combination of the ligand structure and the planar configuration, devices 1 to 24 and comparative devices 1 to 5, can significantly improve the current efficiency and reduce the driving voltage of the OLED device under the same conditions. Specifically, comparing the device 1 with the device examples 1-10, the combination provided by the invention has obvious advantages. If a new combination is adopted, namely the device examples 9 to 24 have lower operating voltage, higher luminous efficiency and longer service life obviously compared with the comparative devices 3 to 5. The composition provided by the invention has obvious superiority 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 comprising an iridium metal complex and an organic compound, wherein the iridium metal complex is selected from one of the following structures:
Figure FDA0003660615690000011
the structure of the organic compound is shown as a formula (II) or a formula (III):
Figure FDA0003660615690000012
wherein, 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 FDA0003660615690000013
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 and R10 are 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 or fully deuterated; m is taken from 1 or 2, 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 the group consisting of 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 said iridium metal complex are selected from one of the following representative structural formulae:
Figure FDA0003660615690000021
3. the composition of claim 1 wherein said iridium metal complex is selected from one of the following representative structures:
Figure FDA0003660615690000031
Figure FDA0003660615690000041
Figure FDA0003660615690000051
Figure FDA0003660615690000061
Figure FDA0003660615690000071
Figure FDA0003660615690000081
Figure FDA0003660615690000091
Figure FDA0003660615690000101
Figure FDA0003660615690000111
Figure FDA0003660615690000121
Figure FDA0003660615690000131
Figure FDA0003660615690000141
Figure FDA0003660615690000151
Figure FDA0003660615690000161
Figure FDA0003660615690000171
Figure FDA0003660615690000181
Figure FDA0003660615690000191
Figure FDA0003660615690000201
Figure FDA0003660615690000211
Figure FDA0003660615690000221
Figure FDA0003660615690000231
Figure FDA0003660615690000241
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 FDA0003660615690000251
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 FDA0003660615690000252
wherein X1 to X6, Y1 to Y8, L, R, n are the same as in claim 1.
6. The composition of claim 1, wherein the organic compound of formula (II) or formula (III) is selected from one of the following representative structures:
Figure FDA0003660615690000261
Figure FDA0003660615690000271
Figure FDA0003660615690000281
Figure FDA0003660615690000291
Figure FDA0003660615690000301
Figure FDA0003660615690000311
Figure FDA0003660615690000321
Figure FDA0003660615690000331
Figure FDA0003660615690000341
Figure FDA0003660615690000351
Figure FDA0003660615690000361
Figure FDA0003660615690000371
Figure FDA0003660615690000381
Figure FDA0003660615690000391
Figure FDA0003660615690000401
Figure FDA0003660615690000411
Figure FDA0003660615690000421
Figure FDA0003660615690000431
Figure FDA0003660615690000441
Figure FDA0003660615690000451
Figure FDA0003660615690000461
Figure FDA0003660615690000471
Figure FDA0003660615690000481
Figure FDA0003660615690000491
Figure FDA0003660615690000501
Figure FDA0003660615690000511
Figure FDA0003660615690000521
Figure FDA0003660615690000531
Figure FDA0003660615690000541
Figure FDA0003660615690000551
Figure FDA0003660615690000561
Figure FDA0003660615690000571
Figure FDA0003660615690000581
Figure FDA0003660615690000591
Figure FDA0003660615690000601
Figure FDA0003660615690000611
Figure FDA0003660615690000621
Figure FDA0003660615690000631
Figure FDA0003660615690000641
Figure FDA0003660615690000651
Figure FDA0003660615690000661
Figure FDA0003660615690000671
Figure FDA0003660615690000681
Figure FDA0003660615690000691
Figure FDA0003660615690000701
Figure FDA0003660615690000711
Figure FDA0003660615690000721
Figure FDA0003660615690000731
Figure FDA0003660615690000741
Figure FDA0003660615690000751
Figure FDA0003660615690000761
Figure FDA0003660615690000771
Figure FDA0003660615690000781
Figure FDA0003660615690000791
Figure FDA0003660615690000801
Figure FDA0003660615690000811
Figure FDA0003660615690000821
Figure FDA0003660615690000831
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 7, wherein the composition and solvent form a formulation in which the solvent is an unsaturated hydrocarbon solvent, a halogenated saturated hydrocarbon solvent, a halogenated unsaturated hydrocarbon solvent, an ether solvent or an ester solvent,
the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene or tert-butylbenzene;
the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane or bromocyclohexane;
the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene;
the ether solvent is tetrahydrofuran or tetrahydropyran;
the ester solvent is alkyl benzoate.
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 as claimed in any one of claims 9 to 10.
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