CN114106056A - Metal organic light-emitting material and application thereof in OLED device - Google Patents
Metal organic light-emitting material and application thereof in OLED device Download PDFInfo
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- CN114106056A CN114106056A CN202111457834.1A CN202111457834A CN114106056A CN 114106056 A CN114106056 A CN 114106056A CN 202111457834 A CN202111457834 A CN 202111457834A CN 114106056 A CN114106056 A CN 114106056A
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- YOLNUNVVUJULQZ-UHFFFAOYSA-J iridium;tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ir] YOLNUNVVUJULQZ-UHFFFAOYSA-J 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical class C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
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Abstract
The invention relates to the technical field of organic electroluminescent display, and particularly discloses a metal organic luminescent material, wherein the metal complex is remarkably improved in the aspects of the luminescent life and the luminescent efficiency of a device, and the application of the metal complex in an organic electroluminescent device is also disclosed. The metal organic light emitting material of the present invention has the following structure. The electroluminescent device prepared by the metal organic luminescent material has the advantages of high purity, high brightness and high efficiency.
Description
The invention relates to the technical field of organic electroluminescent display, and particularly discloses a metal organic luminescent material, wherein the metal complex is remarkably improved in the aspects of the luminescent life and the luminescent efficiency of a device, and the application of the metal complex in an organic electroluminescent device is also disclosed.
Background
In 1987, Tang et al from Ishmann Kodak company in USA reported for the first time a green electroluminescent device made of a double-layer organic film, the device uses Indium Tin Oxide (ITO) as an anode, an amorphous non-pinhole aromatic diamine film with a thickness of 75nm is evaporated on the anode for hole transport, then an 8-hydroxyquinoline aluminum film with a thickness of 60nm is further coated on the aromatic diamine film for an electron transport layer and a light emitting layer, and a magnesium-silver alloy is used as a cathode, the double-layer film structure successfully reduces the starting voltage to 5.5V, and high-radiation luminescence is realized (high-radiation luminescence)>1000 cd.m-2), the wavelength is 550nm, the external quantum efficiency reaches 1.0 percent, and the method has great practical significance. In 1994, Kido et al from Japan produced white light-emitting organic electroluminescent devices for the first time. The fluorescent dyes with 3 colors of blue, green and orange are doped in a poly (N-vinyl carbazole) (PVK) film to be used as a hole transport layer and an emission layer, 1,2, 4-triazole derivative (TAZ) is used as a hole blocking layer, 8-hydroxyquinoline aluminum (Alq3) is used as an electron transport layer, and the device is composed of a glass substrate/ITO/PVK/TAZ/Alq 3/Mg: Ag in a multilayer structure, and under the drive voltage of 14V, the device has the advantages that the visible light region coverage is wide, and the brightness is as high as 3400 cd.m-2The high brightness white emission is realized by doping fluorescent compounds of multiple colors in a polymer film to form a single light emitting layer. The discovery of Kido et al adds a strong color of thick ink to the application of organic electroluminescence, opens the door of the organic light-emitting device in the field of illumination, and promotes the further development of the organic light-emitting device.
Light emitted from the organic electroluminescent device is also classified into fluorescence and phosphorescence, and light emitted by energy of singlet excitons is fluorescence, while light emitted by energy of singlet and triplet excitons is phosphorescence. Since the number of singlet and triplet states formed by excitons has a fixed value ratio of 1: 3, the internal quantum efficiency of a fluorescent device which uses only singlet excitons alone is theoretically only 25% at the highest, whereas the internal quantum efficiency when phosphorescence is emitted can reach 100%.
At present, organometallic complexes having phosphorescent emission and organic electroluminescent devices are reported, and various organometallic complex phosphorescent materials are also disclosed in the patent. For example, EP 3825320 a1 discloses a class of Ir complexes containing dibenzofuran ligands, which have hindered the possibility of commercialization due to serious problems of low phosphorescence efficiency, poor stability and lifetime. Therefore, the structural improvement of the compound is carried out, a deuterated benzene structure is introduced at the substituted position of dibenzofuran, a novel phosphorescent material with better performance is developed, and the commercial application is promoted, which has important significance.
Disclosure of Invention
The invention aims to develop a novel organic electrophosphorescent luminescent material containing a metal iridium complex, which is applied to an organic electroluminescent device, and the prepared electroluminescent device shows excellent performances of high purity, high brightness and high efficiency.
Specifically, in a first aspect, the present invention provides a metal organic light emitting material having a structure represented by general formula (i):
in formula (I), n is 1,2 or 3; m is 0, 1,2, 3 or 4; p is 0 or 1; q is 1 or 2;
in formula (I), Y is selected from O, S or Se;
in formula (I), A is selected from one of the following formulas A1, A2 or A3:
in the formula (I), X1、X2、X3、X4、X5、X6、X7And X8Each independently selected from C, CR or N;
R、R1independently selected from any one of hydrogen, deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryloxy, C1-C20 alkylsilyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 deuterated chain alkyl, C3-C20 deuterated cycloalkyl, C1-C20 deuterated alkoxy, C6-C60 deuterated aryloxy, C1-C20 deuterated alkylsilyl, C6-C60 deuterated aryl, C3-C60 deuterated heteroaryl, fluorinated C1-C20 chain alkyl, fluorinated C3-C20 cycloalkyl, fluorinated C1-C20 alkoxy, fluorinated C6-C60 aryloxy, fluorinated C1-C20 alkyl, fluorinated C6-C60 arylyl and fluorinated C2C 60 8C 3 heteroaryl;
when R is1When there are plural, two adjacent R1The connection between the two rings is annular or not;
in the formula (I), L is a monovalent bidentate anion, wherein the bonding atoms M, N are independently selected from nitrogen atoms and carbon atoms.
As a preferred embodiment of the present invention, L is a monovalent bidentate anionic ligand, preferably L is a substituted or unsubstituted phenylpyridyl group, and when L has a substituent group, the substituent group is selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, chain alkyl of C1 to C30, alkoxy of C1 to C30, cycloalkyl of C3 to C20, heterocycloalkyl of C3 to C20, aryl of C6 to C60, and heteroaryl of C3 to C60.
Further, the metal organic luminescent material of the invention has a structure shown as a general formula (I-1):
in the formula (I-1), Y is O, S or Se; n is 1 or 2; m, p, q are as defined in formula (I);
A、R1、X3、X4、X5、X6、X7and X8Are as defined in formula (I).
Further preferably, in the above formula (i) and formula (i-1), L is represented by the following formula L:
in the formula L, R2～R9Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted deuterated aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 0 to 20 carbon atoms, substituted or unsubstituted alkyl substituted with carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atoms, and substituted or unsubstituted aryl substituted with carbon atoms, One of substituted or unsubstituted arylalkylsilyl groups having 6 to 20 carbon atoms, R2～R9Adjacent two of them may form a parallel ring structure by bridging;
r is as defined above2～R9When each of the substituted or unsubstituted groups in (1) has a substituent group, the substituent group is one or a combination of two selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C60, and heteroaryl of C3-C60.
As a more preferred embodiment of the present invention, L is selected from one of the following groups:
as a preferred embodiment of the present invention, the metal organic light emitting material of the present invention has a junction represented by the general formula (I-2):
in the formula (I-2), n is 1 or 2; r1、m、X3、X4、X5、X6、X7And X8Are as defined in formula (I);
in the formula (I-2), R2～R9Independently selected from deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryloxy, C1-C20 alkylsilyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 deuterated chain alkyl, C20-C20 deuterated cycloalkyl, C20-C20 deuterated alkoxy, C20-C20 deuterated aryloxy, C20-C20 deuterated alkylsilyl, C20-C20 deuterated aryl, C20-C20 deuterated heteroaryl, fluorinated C20-C20 chain alkyl, fluorinated C20-C20 cycloalkyl, fluorinated C20-C20 alkoxy, fluorinated C20-C20 aryloxy, fluorinated C20-C20 alkylsilyl, fluorinated C20-C20 aryl, and fluorinated C20 heteroaryl, and any one of 20R, wherein the R is selected from deuterium, halogen, C1-C202～R9May form a fused ring structure by bridging between adjacent two.
As a further preferred embodiment of the present invention, in the formula (I-2), R is as described above2～R9Independently and optionally selected from one of hydrogen, deuterium, fluorine atom, trifluoromethyl, methyl, silicon methyl, trimethylsilyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isobutyl, deuterated tert-butyl, phenyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl.
As a further preferred embodiment of the present invention, there are mentioned the above-mentioned compounds of the formula (I), the formula (I-1) and the formula (I-2)R, R1Each independently selected from one of hydrogen, deuterium, halogen, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 4-isopropyl cyclopentyl, deuterated methyl, deuterated ethyl, deuterated propyl, phenyl, biphenyl, benzo, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl.
In the present specification, the expression of Ca to Cb represents that the group has carbon atoms a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified. In the present invention, unless otherwise specified, the expressions of chemical elements generally include the concept of chemically identical isotopes, for example, the expression of "hydrogen" also includes the concept of chemically identical "deuterium" and "tritium", and carbon (C) includes 12C and 13C, and the description thereof is omitted.
Heteroaryl in this specification refers to an aromatic cyclic group containing a heteroatom, typically selected from N, O, S, P, Si and Se, preferably N, O, S.
In the present specification, the aryl group having 6 to 60 carbon atoms and the heteroaryl group having 3 to 60 carbon atoms are aromatic groups satisfying pi conjugated system unless otherwise specified, and include both monocyclic rings and condensed rings. The monocyclic ring means that at least one phenyl group is contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the condensed ring means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are condensed with each other, illustratively, naphthyl, anthryl, phenanthryl, etc.; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl groups, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like
In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, and exemplary preferred is an aryl group in the group consisting of a phenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a celtyl group, a perylenyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a trimeric indenyl group, an isotridecyl group, a spirotrimeric indenyl group, and a spiroisotridemic indenyl group. The aryl group having C6 to C60 in the present invention may be a group in which the above groups are bonded by a single bond or/and condensed.
In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, and may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like. Preferred examples of the heterocyclic ring in the present invention include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole. The heteroaryl group having C3-C60 in the present invention may be a group in which the above groups are bonded by a single bond or/and condensed.
In the present specification, alkyl is not particularly specified, and includes straight-chain alkyl and branched-chain alkyl as well as the concept of cycloalkyl. Examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl and the like.
In the present specification, cycloalkyl groups include monocycloalkyl groups and polycycloalkyl groups, and there may be mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
In the present specification, examples of the C1 to C20 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
In the present specification, examples of the aryloxy group having C6 to C60 include groups in which each group listed in the above substituted or unsubstituted aryl group having C6 to C60 is linked to oxygen, and specific examples thereof are given by reference to the above examples and are not described herein again.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
As a preferred embodiment of the present invention, the metal organic light emitting material is selected from compounds represented by the following structural formula:
the invention provides a novel metal organic luminescent material containing metal iridium, which can be used as a phosphorescent luminescent material. The phosphorescent material provided by the invention can effectively solve the problems of the conventional phosphorescent material in the aspects of color purity, luminous efficiency, service life and the like, and an organic electroluminescent device prepared by using the phosphorescent material provided by the invention has excellent performances of high purity, high brightness and high efficiency.
Specifically, the deuterated benzene-containing iridium metal complex material provided by the invention has the following advantages:
the material of the invention introduces deuterated aromatic groups into the molecular structure, particularly preferably deuterated phenyl, deuterated naphthyl and the like, improves the stability of the material, improves the phosphorescent quantum efficiency and electroluminescent efficiency of the material, and improves the stability of OLED devices using the material, thereby obtaining the good effect of prolonging the service life of the OLED devices. The good effect is obtained because the heavy atom effect of the deuterated benzene is introduced, the spin-orbit coupling effect of the luminescent molecule is enhanced, and the electronic gap crossing capability in the molecule is increased, so that the production of phosphorescence is facilitated, the quantum efficiency of the molecule is enhanced, and finally the excellent performance is shown in the device.
In a second aspect, the invention provides the application of the metal organic luminescent material in the preparation of an organic electroluminescent device. Specifically, the application is applicable to organic electronic devices including organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper. Most preferably as an organic electroluminescent device.
Further preferably, the metal organic luminescent material is used as a dye material of a host material in an organic electroluminescent device. The material of the invention is used as a dye doped in an organic electroluminescent device to emit light, and the electroluminescent device prepared by utilizing the phosphorescent material of the invention has the superior performances of high purity, high brightness and high efficiency.
In a third aspect, the present invention provides an organic electroluminescent device comprising a light-emitting layer comprising the above-mentioned metal organic light-emitting material as a light-emitting dye, wherein the organic electroluminescent device exhibits superior properties of high purity, high brightness and high efficiency.
Furthermore, the organic electroluminescent device provided by the invention comprises a substrate, and an anode layer, a plurality of light-emitting unit layers and a cathode layer which are sequentially formed on the substrate; the light-emitting unit layer comprises a light-emitting layer and further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer and the like, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a plurality of light-emitting layers are arranged between the hole transport layer and the electron transport layer. Preferably, the luminescent dye in the luminescent layer is the luminescent material of the present invention.
Further preferably, the doping concentration of the metal organic light emitting material in the host material is 3-12%, more preferably 4-8%, and more preferably 5-7%. When the doping concentration of the metal organic light-emitting material in the host material is about 5%, the performance of the device is best. The doping concentration is mass percentage concentration.
In a fourth aspect, the invention further provides a display device comprising the organic electroluminescent device.
In a fifth aspect, the invention further provides a lighting device comprising the organic electroluminescent device.
Detailed Description
The technical solution of the present invention will be described in detail by specific examples. The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
The synthetic routes for the structural formulae of the present invention are shown below, and it will be understood by those skilled in the art that similar routes can also be used for the synthesis of other routes.
Synthesis of ligand M1
The synthesis route is as follows:
the specific synthesis preparation method comprises the following steps:
1. synthesis of Compound M1-1:
(1) 2-bromopyridine (15.8g,0.1mol), phenylboronic acid (12.2g, 0.1mol), potassium carbonate (27g, 0.2mol), tetrakis (triphenylphosphine) palladium (1.1 g), tetrahydrofuran (400 mL) and water (100 mL) were sequentially added to a 1L three-necked flask equipped with a mechanical stirrer, reflux condenser and nitrogen protector, and the mixture was heated under reflux for 12 hours. After the reaction is finished, separating an organic phase, extracting, drying, carrying out column chromatography, and spin-drying the solvent to obtain 12.7g of a product with the yield of 82%.
2. Synthesis of Compound M1-2:
m1-1(15.5g,0.1mol), iridium trichloride hydrate (8.8g,0.25mol), 450mL of ethylene glycol monoethyl ether, and 150mL of distilled water were sequentially added to a 1L three-necked flask equipped with a mechanical stirring, reflux condenser, and nitrogen gas protector. Heated to 130 ℃ and refluxed for 24 hours. After natural cooling, 100mL of distilled water is added, and the mixture is shaken, filtered, washed with water and washed with ethanol. Drying in vacuo afforded 22.8g of the product as a yellow solid in 85% yield.
3. Synthesis of compound M1:
m1-2(26.8g,0.1mol) and 300ml of dichloromethane were added in this order to a 1L three-necked flask equipped with a nitrogen blanket, followed by stirring thoroughly, then 300ml of a methanol solution of silver trifluoromethanesulfonate (51.2g, 0.2mol) was added, and the mixture was stirred at room temperature for 24 hours, filtered through celite, and the filtrate was dried by rotary evaporation to give 49.9g of a yellowish solid with a yield of 35%.
Synthesis of ligand M2
Referring to the synthesis method of the ligand M1, deuterated phenylboronic acid is used for replacing phenylboronic acid, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand M1, so that the ligand M2 is obtained.
Synthesis of ligand M3
Referring to the synthesis method of the ligand M1, deuterated phenylboronic acid is used for replacing phenylboronic acid, 2-bromo-5-methylpyridine is used for replacing 2-bromopyridine, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand M1, so that the ligand M3 is obtained.
Synthesis of ligand M4
Referring to the synthesis method of the ligand M1, 2-bromo-5-methylpyridine is used to replace 2-bromopyridine, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand M1, so that the ligand M4 is obtained.
Synthesis of ligand M5
Referring to the synthesis method of the ligand M1, 4-methylphenylboronic acid is used for replacing phenylboronic acid, 2-bromo-5-methylpyridine is used for replacing 2-bromopyridine, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand M1, so that the ligand M5 is obtained.
Synthesis of ligand M6
Referring to the synthesis method of the ligand M1, 2-bromo-5-deuterated methylpyridine is used for replacing 2-bromopyridine, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand M1, so that the ligand M6 is obtained.
Synthesis of ligand H1
The synthesis route is as follows:
the specific synthesis preparation method comprises the following steps:
1. synthesis of Compound H1-1:
2-bromo-6-chlorophenol (20.7g, 0.1mol), 2-fluoro-4-methylphenylboronic acid (15.4g, 0.1mol), toluene 500mL, ethanol 300mL, water 300mL potassium carbonate (27.6g, 0.2mol) were added to a 2L three-necked flask equipped with mechanical stirring, stirring was turned on, tetrakis (triphenylphosphine) palladium (1.15g, 0.001mol) was added under nitrogen, reflux reaction was carried out for 24h, after the reaction was completed, the organic phase was separated, extracted, dried, column-chromatographed, and the solvent was spin-dried to give 17.7g of a solid in a yield of 75%.
2. Synthesis of Compound H1-2:
in a 1L three-necked flask equipped with mechanical stirring, H1-1(23.6g, 0.1mol) and potassium carbonate (11.6g, 0.1mol) were added, 200mL of DMF was added, reaction was carried out at 120 ℃ for 5 hours, and after completion of the reaction, the organic phase was separated, extracted, dried, subjected to column chromatography, and the solvent was dried by spinning to obtain 18.3g of a solid with a yield of 85%.
3. Synthesis of Compound H1-3:
in a 1L three-necked flask equipped with mechanical stirring, H1-2(21.6g,0.1mol), pinacol diborate (25.4g, 0.1mol), DPPF palladium dichloride (0.7g, 0.001mol), potassium acetate (19.6g, 0.2mol), 300mL DMF were added and reacted at 90 ℃ under nitrogen for 10 hours, after the reaction was completed, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried to obtain 22g of a solid with a yield of 72%.
4. Synthesis of Compound H1-4:
in a 1L three-necked flask equipped with mechanical stirring, H1-3(30.8g, 0.1mol), 2-bromopyridine (15.8g,0.1mol), potassium acetate (19.6g, 0.2mol), DPPF palladium dichloride (0.7g, 0.001mol), 400mL tetrahydrofuran and 100mL water were added, warmed to reflux reaction for 12 hours, cooled to room temperature, water was added, extraction was performed with ethyl acetate, the organic layer was separated, washed with brine, the organic phase was separated, extracted, dried, column-chromatographed, and the solvent was spin-dried to give 20.7g of a solid with a yield of 80%.
5. Synthesis of Compound H1-5:
adding H1-4(25.9g, 0.1mol) and 300mL tetrahydrofuran into a 1L three-necked bottle with mechanical stirring, starting stirring under the protection of nitrogen, cooling to-78 ℃, dropwise adding LDA150mL, keeping the temperature and stirring for 2 hours, adding iodine (25.3g, 0.1mol), naturally heating to room temperature for reaction for 14 hours, separating an organic phase after the reaction is finished, extracting, drying, performing column chromatography, and spin-drying a solvent to obtain 27.3g of solid with the yield of 71%.
6. Synthesis of compound H1:
in a 1L three-necked flask equipped with a mechanical stirrer, H1-5(38.5g, 0.1mol), deuterated phenylboronic acid (12.7g, 0.1mol), 500mL of toluene and 100mL of water were added, and the mixture was refluxed for 12 hours, after the reaction was completed, the organic phase was separated, extracted and the solvent was dried by spinning to obtain 23.8g of a solid with a yield of 70%.
Elemental analysis (C24H12D5 NO): theoretical value C, 84.67; h, 6.51; n, 4.11; o, 4.70; found C, 84.66, H, 6.48, N, 4.13.
Synthesis of ligand H2
Referring to the synthesis method of the ligand H1, 2, 4-difluorophenylboronic acid is used for replacing 2-fluoro-4-methylphenylboronic acid, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand H1, so that the ligand H2 is obtained.
Elemental analysis (C23H9D5 FNO): theoretical value C, 80.21; h, 5.56; f, 5.52; n, 4.07; o, 4.65; found C, 80.22, H, 5.51, N, 4.03.
Synthesis of ligand H3
Referring to the synthesis method of ligand H1, 2, 4-difluorophenylboronic acid is used for replacing 2-fluoro-4-methylphenylboronic acid, 2-bromo-5-methylpyridine is used for replacing 2-bromopyridine, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of ligand H1, so that ligand H2 is obtained.
Elemental analysis (C24H11D5 FNO): theoretical value C, 80.42; h, 5.90; f, 5.30; n, 3.91; o, 4.46; found C,80.42, H, 5.91, N, 4.00.
Synthesis of ligand H4
Referring to the synthesis method of the ligand H1, 2-fluoro-4-deuterated methyl phenylboronic acid is used for replacing 2-fluoro-4-methylbenzeneboronic acid, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand H1, so that the ligand H4 is obtained.
Elemental analysis (C24H9D8 NO): theoretical value C, 83.93; h, 7.33; n, 4.08; o, 4.66; found C, 83.92, H, 7.31, N, 4.05.
Synthesis of ligand H5
Referring to the synthesis method of the ligand H1, 2, 4-difluorophenylboronic acid is used for replacing 2-fluoro-4-methylphenylboronic acid, 2-bromo-4-deuterated phenylpyridine is used for replacing 2-bromopyridine, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand H1, so that the ligand H5 is obtained.
Elemental analysis (C29H8D10 FNO): theoretical value C, 81.86; h, 6.63; f, 4.46; n, 3.29; o, 3.76; found C, 81.82, H, 6.61, N, 3.25.
Synthesis of ligand H6
Referring to the synthesis method of the ligand H1, 2, 4-difluorophenylboronic acid is used for replacing 2-fluoro-4-methylphenylboronic acid, 1-deuterated naphthylboronic acid is used for replacing deuterated phenylboronic acid, and a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the ligand H1, so that the ligand H6 is obtained.
Elemental analysis (C27H9D7 FNO): theoretical value C, 81.80; h, 5.84; f, 4.79; n, 3.53; o, 4.04; found C, 81.82, H, 5.81, N, 3.55.
Example 1: synthesis of Compound I-1
The synthesis route is as follows:
in a 500mL three-necked flask equipped with mechanical stirring, a reflux condenser and a nitrogen blanket, M1(14.2g, 0.01mol) and H1(3.4g,0.01mol) were sequentially added, 200mL of ethanol was then added, the mixture was heated under reflux for 24 hours, the reaction was cooled to room temperature, the resulting yellow solid was filtered, dissolved in dichloromethane, and subjected to column chromatography to give 4.36 g of a bright yellow solid with a yield of 52%.
Elemental analysis (C46H27D5IrN 3O): theoretical value C, 65.77; h, 4.44; ir, 22.88; n, 5.00; o, 1.90; found C,65.71, H,4.38, N, 5.02.
Example 2: synthesis of Compound I-19
The synthesis route is as follows:
the H1 was replaced by H4, the appropriate material ratio was chosen, and the other raw materials and procedures were the same as in example 1, to give 5.45g of product I-19 with a yield of 61%.
Elemental analysis (C49H30D13IrN 3O): theoretical value C, 65.74; h, 6.30; ir, 21.47; n, 4.69; o, 1.79; found C,65.77, H,6.32, N, 4.66.
Example 3: synthesis of Compound I-21
The synthesis route is as follows:
m2 was used instead of M1, H2 was used instead of H1, and the other raw materials and procedures were the same as in example 1, by selecting an appropriate material ratio, 4.88g of product I-21 was obtained with a yield of 55%.
Elemental analysis (C48H27D13FIrN 3O): theoretical value C, 64.12; h, 5.94; f, 2.11; ir, 21.38; n, 4.67; o, 1.78; found C,64.11, H,5.92, N, 4.66.
Example 4: synthesis of Compound I-25
The synthesis route is as follows:
m4 was used instead of M1, H2 was used instead of H1, and the other raw materials and procedures were the same as in example 1, by selecting an appropriate material ratio, 3.89g of product I-25 was obtained with a yield of 53%.
Elemental analysis (C37H25D5FIrN 2O): theoretical value C, 60.47; h, 4.80; f, 2.59; ir, 26.16; n, 3.81; o, 2.18; found C,60.46, H,4.82, N, 3.84.
Example 5: synthesis of Compound I-46
The synthesis route is as follows:
m2 was used instead of M1, H3 was used instead of H1, and the other raw materials and procedures were the same as in example 1, except that the appropriate material ratio was selected, whereby 4.65g of product I-46 was obtained with a yield of 51%.
Elemental analysis (C49H29D13FIrN 3O): theoretical value C, 64.45; h, 6.07; f, 2.08; ir, 21.05; n, 4.60; o, 1.75; found C,64.44, H,6.03, N, 4.61.
Example 6: synthesis of Compound I-29
The synthesis route is as follows:
m6 was used instead of M1, H4 was used instead of H1, and the other raw materials and procedures were the same as in example 1, by selecting an appropriate material ratio, 5.26g of product I-29 was obtained with a yield of 57%.
Elemental analysis (C51H33D14IrN 3O): theoretical value C, 66.28; h, 6.65; ir, 20.80; n, 4.55; o, 1.73; found C,66.25, H,6.66, N, 4.52.
Example 7: synthesis of Compound I-26
The synthesis route is as follows:
m6 was used instead of M1, H5 was used instead of H1, and the other raw materials and procedures were the same as in example 1, by selecting an appropriate material ratio, 4.93g of product I-26 was obtained with a yield of 49%.
Elemental analysis (C56H32D16FIrN 3O): theoretical value C, 66.84; h, 6.41; f, 1.89; ir, 19.10; n, 4.18; o, 1.59; found C,66.83, H,6.43, N, 4.16.
Example 8: synthesis of Compound I-53
The synthesis route is as follows:
m5 was used instead of M1, H6 was used instead of H1, and the other raw materials and procedures were the same as in example 1, by selecting an appropriate material ratio, 5.99g of product I-53 was obtained with a yield of 61%.
Elemental analysis (C55H39D7FIrN 3O): theoretical value C, 67.19; h, 5.43; f, 1.93; ir, 19.55; n, 4.27; o, 1.63; found C,67.15, H,5.44, N, 4.25.
Example 9: stability verification experiment
As is known, 5g of each of the control compound A and the compound I-1 obtained according to the invention are placed in a high vacuum sublimation apparatus at 6.0 x 10-4Sublimation was carried out at 310 ℃ under a vacuum of pascal for 20 hours, and the sublimation results are shown in table 1.
Table 1:
as can be seen from the data in Table 1 above, the purity of compound I-1 provided by the present invention was unchanged after sublimation, whereas the purity of the control compound A was significantly reduced after sublimation. Therefore, the introduction of the deuterated benzene structure adopted by the invention can effectively improve the thermal stability of the prepared phosphorescent material.
Example 10: preparation of OLED device
The application embodiment of the OLED device of the compound provided by the invention is as follows, the embodiment provides a group of OLED green light devices, and the structure of the device is as follows: ITO/HI (10nm)/HT01(60nm)/EB (5nm)/DIC-TRZ: 5% phosphorescent light-emitting material compound of the invention (30nm)/HB (10nm)/ET01: QLi (1:1) (30nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
preparing an OLED-1:
the compound I-1 prepared by the invention is selected as a phosphorescent material, the doping concentration of the compound I-1 is 5%, and an OLED device is prepared by the following specific preparation method:
(1) the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent (volume ratio is 1:1), baking in a clean environment until water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, vacuum evaporating HI on the anode layer film to be used as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 10 nm; then, evaporating a first hole layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 60 nm; then evaporating an electron barrier layer EB with the evaporation rate of 0.1nm/s and the evaporation film thickness of 5 nm;
(3) the EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material DIC-TRZ and a dye material I-1 of the invention, the doping mass percentage concentration is 5%, an organic light emitting layer of the device is formed, the evaporation rate is 0.2nm/s, and the total evaporation film thickness is 30 nm; then evaporating 10nm HB to form a hole blocking layer, wherein the evaporation rate is 0.1 nm/s;
(4) and evaporating on the hole blocking layer according to the mass ratio of 1: the ET01: QLi of 1 is used as an electron transport material of an electron transport layer of a device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device. And packaging to obtain the OLED-1 device.
Preparing devices OLED-2 to OLED-4:
according to the preparation method of the OLED-1 device, the OLED-2, the OLED-3 and the OLED-4 devices are prepared by only changing the doping concentration of the dye material I-1 in the host material DIC-TRZ in the step (3) from 5% to 3%, 7% and 9% respectively.
The performance of the devices OLED-1 to OLED-4 prepared above was tested, and the results of testing the performance of each device are detailed in Table 2.
Table 2:
comparing the detection results of the above four light emitting devices, it can be seen that the performance of the light emitting device OLED-2 is the best, i.e. when the doping concentration is about 5%, the brightness is the highest, and the efficiency is also the highest.
Preparing devices OLED-5 to OLED-9:
according to the preparation method of the OLED-1 device, the dye material I-1 in the invention in the step (3) is respectively replaced by the compounds I-2, I-8, I-31, I-45 and I-65, and the doping concentration in the host material DIC-TRZ is 5%, so that OLED-5-OLED-9 devices are prepared.
Preparation of comparative device OLED-10:
the comparative device OLED-10 is prepared by using the compound A with a known structure as a dye material to replace the dye material I-1 in the OLED-1 device, and the doping concentration in the host material DIC-TRZ is 5%.
The performance of the devices OLED-2, the devices OLED-5-OLED-9 and the comparative device are detected, and the performance detection results of the devices are detailed in Table 3.
Table 3:
from the results, compared with the compound A, the compound provided by the invention has the advantages that the stability is improved due to the introduction of the deuterated benzene structure, the luminous efficiency of the corresponding device is improved, and meanwhile, the working voltage is also obviously reduced. Therefore, the phosphorescent material provided by the invention can effectively solve the problems of the conventional phosphorescent material in the aspects of voltage, luminous efficiency and the like, and an organic electroluminescent device prepared by using the phosphorescent material has the excellent performances of high purity, high brightness and high efficiency.
While the present invention has been described in detail hereinabove with respect to general description, specific embodiments and experiments, it will be apparent to those skilled in the art that it is not intended to limit the scope of the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A metal organic light emitting material has a structure shown as a general formula (I):
in formula (I), n is 1,2 or 3; m is 0, 1,2, 3 or 4; p is 0 or 1; q is 1 or 2;
in formula (I), Y is selected from O, S or Se;
in formula (I), A is selected from one of the following formulas A1, A2 or A3:
in the formula (I), X1、X2、X3、X4、X5、X6、X7And X8Each independently selected from C, CR or N;
in formula (I), R, R1Independently selected from any one of hydrogen, deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryloxy, C1-C20 alkylsilyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 deuterated chain alkyl, C3-C20 deuterated cycloalkyl, C1-C20 deuterated alkoxy, C6-C60 deuterated aryloxy, C1-C20 deuterated alkylsilyl, C6-C60 deuterated aryl, C3-C60 deuterated heteroaryl, fluorinated C1-C20 chain alkyl, fluorinated C3-C20 cycloalkyl, fluorinated C1-C20 alkoxy, fluorinated C6-C60 aryloxy, fluorinated C1-C20 alkyl, fluorinated C6-C60 arylyl and fluorinated C2C 60 8C 3 heteroaryl;
when R is1When there are plural, two adjacent R1The connection between the two rings is annular or not;
in formula (I), L is a monovalent bidentate anion, wherein the bonding atoms M, N are each independently selected from a nitrogen atom or a carbon atom.
2. The metal-organic light emitting material according to claim 1, having a structure represented by general formula (i-1):
in the formula (I-1), Y is O, S or Se; n is 1 or 2; m, p, q are as defined in formula (I);
the A, R1、X3、X4、X5、X6、X7And X8Are as defined in formula (I).
3. The metal-organic light emitting material according to claim 1 or 2, wherein L is a monovalent bidentate anionic ligand;
preferably, L is substituted or unsubstituted phenylpyridyl, and when L has a substituent group, the substituent group is one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde group, ester group, chain alkyl of C1-C30, alkoxy of C1-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C60 and heteroaryl of C3-C60.
4. The metal-organic light emitting material according to claim 1 or 2, wherein L is a structure represented by the following formula L:
in the formula L, R2～R9Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atomsA heteroalkyl group, a substituted or unsubstituted deuterated alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted deuterated aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 0 to 20 carbon atoms, a substituted or unsubstituted arylalkylsilyl group having 6 to 20 carbon atoms, R2～R9Adjacent two of them may form a parallel ring structure by bridging;
r is as defined above2～R9When each of the substituted or unsubstituted groups in (1) has a substituent group, the substituent group is one or a combination of two selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C60, and heteroaryl of C3-C60.
5. The metal-organic light emitting material according to claim 1 or 2, wherein L is selected from one of the following groups:
6. the metal-organic light emitting material according to claim 1, having a structure represented by general formula (i-2):
in the formula (I-2), n is 1 or 2; r1、m、X3、X4、X5、X6、X7And X8Are as defined in formula (I);
formula (I)In-2), R2～R9Independently selected from deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryloxy, C1-C20 alkylsilyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 deuterated chain alkyl, C20-C20 deuterated cycloalkyl, C20-C20 deuterated alkoxy, C20-C20 deuterated aryloxy, C20-C20 deuterated alkylsilyl, C20-C20 deuterated aryl, C20-C20 deuterated heteroaryl, fluorinated C20-C20 chain alkyl, fluorinated C20-C20 cycloalkyl, fluorinated C20-C20 alkoxy, fluorinated C20-C20 aryloxy, fluorinated C20-C20 alkylsilyl, fluorinated C20-C20 aryl, and fluorinated C20 heteroaryl, and any one of 20R, wherein the R is selected from deuterium, halogen, C1-C202～R9Adjacent two of them may form a parallel ring structure by bridging;
preferably, said R is2～R9Each independently selected from one of hydrogen, deuterium, fluorine atom, trifluoromethyl, methyl, silicon methyl, trimethyl silicon base, ethyl, n-propyl, isopropyl, isobutyl, tertiary butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isobutyl, deuterated tertiary butyl, phenyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl.
7. The metal-organic light emitting material of claim 1,2 or 6, wherein R, R is the metal-organic light emitting material1Each independently selected from one of hydrogen, deuterium, halogen, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 4-isopropyl cyclopentyl, deuterated methyl, deuterated ethyl, deuterated propyl, phenyl, biphenyl, benzo, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl.
8. The metal-organic light emitting material according to claim 1, having a structure represented by:
9. use of the metal-organic light emitting material according to claim 1 as a functional material in an organic electroluminescent device;
preferably, the metal organic light emitting material is used as a light emitting dye in a light emitting layer in an organic electroluminescent device.
10. An organic electroluminescent device comprising an anode, a cathode and one or more light-emitting functional layers interposed between the anode and the cathode, wherein the light-emitting functional layers contain the metal organic light-emitting material according to any one of claims 1 to 8 therein;
preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the light-emitting layer includes a host material and a dye material, the dye material is the metal organic light-emitting material according to any one of claims 1 to 8, and the doping percentage of the metal organic light-emitting material in the host material is 3 to 12%;
preferably, the doping mass percentage of the metal organic luminescent material in the main body material is 4-8%;
more preferably, the doping content percentage of the metal organic luminescent material in the main body material is 5-7%;
most preferably, the doping percentage of the metal organic light emitting material in the host material is 5%.
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