CN117209482A - Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device - Google Patents
Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- CN117209482A CN117209482A CN202310221763.8A CN202310221763A CN117209482A CN 117209482 A CN117209482 A CN 117209482A CN 202310221763 A CN202310221763 A CN 202310221763A CN 117209482 A CN117209482 A CN 117209482A
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- light
- auxiliary material
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 101100391182 Dictyostelium discoideum forI gene Proteins 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention discloses a luminescent auxiliary material and a preparation method thereof, belonging to the field of organic light electroluminescent materials. Compared with the existing organic electroluminescent device, the device can improve the service life of the device and remarkably improve the luminous efficiency under the condition of maintaining the driving voltage basically unchanged. Compared with the prior art, the organic electroluminescent device has the technical effects of improving the service life of the device and remarkably improving the luminous efficiency under the condition of keeping the driving voltage basically unchanged.
Description
Technical Field
The invention relates to the field of organic light-emitting materials, in particular to a light-emitting auxiliary material, a preparation method thereof and an organic light-emitting device.
Background
Organic electroluminescence (OLED) is a type of self-luminous display element, and a display has advantages of high brightness, high resolution, wide viewing angle, low power consumption, and high response speed. In general, organic electroluminescence refers to a phenomenon in which an organic substance converts electric energy into light energy. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emitting layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
In order to solve the lifetime and efficiency problems, a light-emitting auxiliary layer (multi-layer hole transport layer) is generally added between the hole transport layer and the light-emitting layer. The light-emitting auxiliary layer mainly functions as an auxiliary hole transport layer, and is therefore sometimes also referred to as a second hole transport layer. The light-emitting auxiliary layer can enable holes transferred from the anode to smoothly move to the light-emitting layer, and can block electrons transferred from the cathode so as to limit the electrons in the light-emitting layer, reduce potential barriers between the hole-transporting layer and the light-emitting layer, reduce driving voltage of the organic electroluminescent device, further increase utilization rate of the holes, and improve luminous efficiency and service life of the device.
But there are few materials that can form a light emitting auxiliary layer and have excellent device performance. In particular, the service life and luminous efficiency of the OLED are not obviously improved, so it is important to develop higher-performance organic functional materials to meet the requirements of panel manufacturing enterprises.
Therefore, how to provide a luminescent auxiliary material with long service life and high luminous efficiency, a preparation method thereof and an organic electroluminescent device are technical problems to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the invention provides a luminescent auxiliary material and a preparation method thereof, and the blue light luminescent auxiliary material provided by the invention is based on benzonaphthofuran, wherein a triarylamine group is connected to naphthalene, and 9-phenyl-9H-carbazole is connected to benzene at the other side. Compared with the existing organic electroluminescent device, the device has the advantages that the service life of the device can be improved and the luminous efficiency can be obviously improved under the condition that the driving voltage is kept unchanged basically.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a luminous auxiliary material has a structural general formula shown in formula I:
wherein,
ar is condensed with an adjacent benzene ring;
ar is independently selected from substituted or unsubstituted C6-C30 aryl;
Ar 1 -Ar 2 independently selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl;
further, ar 1 -Ar 2 Independently selected from substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 3-to 24-membered heteroaryl;
further, ar 1 ，Ar 2 Selected from substituted or unsubstituted C3-C18 cycloalkyl,preferred are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylcyclopentyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, 2, 3-dimethylcyclopentyl, bicyclo [3.1.1 ]]Heptyl and adamantyl;
further, ar 1 ，Ar 2 When selected from substituted or unsubstituted C6-C18 aryl, it is preferably phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, indenyl, triphenylenyl, pyrenyl, perylenyl, droyl, naphthacene, fluoranthryl, spirobifluorenyl, azulenyl, methylphenyl, ethylphenyl, methoxyphenyl, cyanophenyl;
further, ar 1 ，Ar 2 When selected from substituted or unsubstituted 3-to 24-membered heteroaryl groups, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzoxadiazazinyl, and dihydropentanyl are preferred.
Further, ar 1 ，Ar 2 Each independently selected from the group consisting of phenyl, naphthyl, phenanthryl, methylphenyl, ethylphenyl, cyanophenyl, methoxyphenyl, phenylpyridyl, phenylpyrimidinyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl,carbazolyl, 9-phenyl-9H-carbazolyl, diphenylfluorenyl, dimethylfluorenyl, cyclopentyl, cyclohexyl;
further, formula I includes the following structure:
in the above-mentioned technical scheme, the method comprises the steps of,
"substituted or unsubstituted" means substituted with one, two or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron base; C1-C30 alkyl; cycloalkyl of C3-C30; an alkoxy group; aryl of C6-C30; heteroaryl groups of 3-to 30-membered, or substituted with a substituent to which two or more of the substituents shown above are attached, or not having a substituent.
Cycloalkyl refers to monocyclic, polycyclic and spiroalkyl groups;
aryl refers to monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems, polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings being "fused");
heteroaryl groups include monocyclic aromatic groups and polycyclic aromatic ring systems of at least one heteroatom including, but not limited to O, S, N, P, B, si and Se;
further, the above formula I includes the following structure:
the preparation method of the luminescent auxiliary material comprises the following steps:
the synthetic route is as follows:
wherein Hal is 1 ，Hal 2 Selected from Cl, br, I; r' is
Ar 1 -Ar 2 Ar is the same as the above range;
the preparation method comprises the following steps:
(1)N 2 under the protection, the reactants A-I (1.0 eq), the reactants B-I (1.0-1.4 eq), the palladium catalyst (0.01-0.1 eq) and the alkali (2.0-4.0 eq) are respectively added into a mixed solvent of toluene, ethanol and water, the temperature is raised to 80-100 ℃, the reaction is carried out for 8-14h, diatomite is used for carrying out suction filtration while the heat is used for removing salt and catalyst, after the filtrate is cooled to room temperature, a rotary evaporator is used for removing the solvent, and the obtained solid is dried and then passes through a silica gel funnel to obtain dichloromethane: petroleum ether with the volume ratio of 1:2-6 is used as a developing agent, filtrate is removed by a rotary evaporator, and obtained solid is dried to obtain an intermediate C-I.
(2) After adding intermediate C-I (1.0 eq) and reactant D-I (1.0-1.5 eq) to a reaction vessel and dissolving in xylene, adding palladium catalyst (0.01-0.1 eq), phosphorus ligand (0.01-1.0 eq) and alkali (2.0 eq-3.0 eq) under the protection of nitrogen; after the addition, the reaction temperature is slowly increased to 120-140 ℃, and the mixture is stirred for 8-14h; the remaining material was purified by column chromatography to give formula I.
Or,
the synthetic route is as follows:
wherein Hal is 1 ，Hal 2 Selected from Cl, br, I; r' is
Ar 1 -Ar 2 Ar is the same as the above range;
the preparation method comprises the following steps:
(1) After adding reactants A-I (1.0 eq) and reactants B-I (1.0-1.5 eq) into a reaction vessel and dissolving in toluene, adding a palladium catalyst (0.01-0.1 eq), a phosphorus ligand (0.01-1.0 eq) and a base (2.0-3.0 eq) under the protection of nitrogen; after the addition, the reaction temperature was slowly raised to 85-95℃and the mixture was stirred for 6-14h, and the remaining material was purified by column chromatography to obtain intermediate C-I.
(2)N 2 Under the protection, the intermediate C-I (1.0 eq), the reactant D-I (1.0-1.5 eq), the palladium catalyst (0.01-0.1 eq), the phosphorus ligand (0.01-1.0 eq) and the alkali (2.0-3.0 eq) are respectively added into a mixed solvent of toluene, ethanol and water, the temperature is raised to 80-90 ℃, the reaction is carried out for 6-12 hours, the residual substances are purified by using a column chromatography, the solvent is removed from filtrate by using a rotary evaporator, and the obtained solid is dried to obtain the compound I.
Wherein,
the palladium catalyst may be: pd (Pd) 2 (dba) 3 ，Pd(PPh 3 ) 4 ，PdCl 2 ，PdCl 2 (dppf)，Pd(OAc) 2 ，Pd(PPh 3 ) 2 Cl 2 ，NiCl 2 (dppf)；
The phosphine ligand may be: p (t-Bu) 3 ，X-phos，PET 3 ，PMe 3 ，PPh 3 ，KPPh 2 ，P(t-Bu) 2 Cl；
The base may be: k (K) 2 CO 3 ，K 3 PO 4 ，Na 2 CO 3 ，CsF，Cs 2 CO 3 ，t-BuONa。
It is still another object of the present invention to provide an organic electroluminescent device that may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting auxiliary layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and may include a smaller or larger number of organic layers.
According to one embodiment of the present specification, the compound of formula I prepared according to the present invention is used as a light-emitting auxiliary layer material.
In the case of producing an organic light-emitting device, the compound represented by the formula I may be formed by vacuum vapor deposition or solution coating. The solution coating method is, but not limited to, spin coating, dip coating, blade coating, ink jet printing, screen printing, spray coating, roll coating, and the like.
The organic light emitting element of the present invention may be of a top emission type, a bottom emission type or a bi-directional emission type, depending on the materials used.
The device of the present invention may be used in organic light emitting devices including, but not limited to, flat panel displays, computer monitors, a medical monitor, a television, billboards, a light for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, a laser printer, a telephone, a cell phone, a tablet, a photo album, a Personal Digital Assistant (PDA), a wearable device, a notebook, a digital camera, a video camera, a viewfinder, a micro-display, a three-dimensional display, a virtual reality or augmented reality display, a vehicle, a video wall comprising a plurality of displays tiled together, theatre or venue screens, phototherapy devices, and signs.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); a combination of metal such as ZnO A1 or SnO2 and oxide such as Sb; and conductive polymers such as polypyrrole and polyaniline.
The hole injection layer is preferably a p-doped hole injection layer, by which is meant a hole injection layer doped with a p-dopant. A p-dopant is a material capable of imparting p-type semiconductor characteristics. The p-type semiconductor property means a property of injecting holes or transporting holes at the HOMO level, that is, a property of a material having high hole conductivity.
The hole transporting material is a material capable of receiving holes from the anode or the hole injecting layer and transporting the holes to the light emitting layer, and has high hole mobility. The hole transporting material may be selected from arylamine derivatives, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
A light-emitting auxiliary layer (multilayer hole-transporting layer) is interposed between the hole-transporting layer and the light-emitting layer. The light-emitting auxiliary layer mainly functions as an auxiliary hole transport layer, and is therefore sometimes also referred to as a second hole transport layer. The light emitting auxiliary layer enables holes transferred from the anode to smoothly move to the light emitting layer, and can block electrons transferred from the cathode to confine electrons in the light emitting layer, reduce potential barrier between the hole transporting layer and the light emitting layer, reduce driving voltage of the organic electroluminescent device, further increase utilization ratio of holes, thereby improving luminous efficiency and lifetime of the device.
The light-emitting substance of the light-emitting layer is a substance capable of receiving and binding holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence.
The light emitting layer may include a host material and a dopant material.
The mass ratio of the host material to the doping material is 90-99.5:0.5-10.
The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, pyrimidine derivatives, and the like.
The dopant materials of the present invention include fluorescent doping and phosphorescent doping. May be selected from aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
The electron transport layer may function to facilitate electron transport. The electron transporting material is a material that advantageously receives electrons from the cathode and transports the electrons to the light emitting layer, preferably a material having high electron mobility. The electron transport layer may include at least one of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and preferably at least one of an electron transport layer and an electron injection layer.
The electron injection layer may function to promote electron injection. Has an ability to transport electrons, and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The material of the electron injection layer includes, but is not limited to, metal such as oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylmethane, anthrone, their derivatives, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, ytterbium, or their alloys, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like.
The cathode is generally preferably of a material having a small work function so that electrons are smoothly injected into the organic material layer, which layer preferably has a layer thickness of between 0.5 and 5 nm. The cathode material is generally preferably a material having a small work function in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof: liF/A1, liO2/A1, mg/Ag and other multilayer structural materials.
There are no particular restrictions on other layer materials in an OLED device, except that the light-emitting auxiliary layers disclosed herein comprise formula I. Existing hole injection materials, hole transport auxiliary materials, dopant materials, hole blocking layer materials, electron transport layer materials, and electron injection materials may be used.
The principle involved in the invention is as follows:
the invention carries out a series of palladium catalytic coupling reactions, on one hand, utilizes the difference that the activity of Br is larger than that of Cl, on the other hand, controls the reaction sites by controlling the reaction conditions, and uses column chromatography or silica gel funnel purification reaction to remove byproducts, thus obtaining the target compound. The following are referred to in the common general knowledge:
transition metal organic chemistry (original sixth edition), robert H-crabtree (Robert H.Crabtree), press: publication time of Shanghai Shandong university Press: 2017-09-00, ISBN:978-7-5628-5111-0, page 388.
Organic chemistry and photoelectric Material Experimental Instructions, chen Runfeng, press: university of east south Press, publication time: 2019-11-00, ISBN:9787564184230, page 174.
Compared with the prior art, the invention has the following beneficial effects: the blue light luminescent auxiliary material provided by the invention is based on benzonaphthofuran, wherein a triarylamine group is connected to naphthalene, and 9-phenyl-9H-carbazole is connected to benzene at the other side. The benzonaphthofuran maintains the advantage of dibenzofuran high triplet state energy level, and on the basis, a conjugated surface is increased, the hole transmission rate is increased, the extension of the conjugated surface is avoided, and the device efficiency is improved. Compared with the existing organic electroluminescent device, the device can improve the service life of the device and remarkably improve the luminous efficiency under the condition of maintaining the driving voltage basically unchanged.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only embodiments of the present invention, and that other drawings can be obtained according to the provided drawings without inventive effort for a person skilled in the art.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of intermediate C-1;
FIG. 2 shows the nuclear magnetic resonance hydrogen spectrum of Compound 1.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1: synthesis of Compound 1
CAS: reactant a-1:2472861-95-1
CAS: reactant D-1:1189047-28-6
After adding reactant A-1 (50 mmol) and reactant B-1 (55 mmol) to toluene in a reaction vessel, pd was added under nitrogen 2 (dba) 3 (0.5mmol)、P(t-Bu) 3 (1 mmol), t-BuONa (110 mmol); after the addition, the reaction temperature was slowly raised to 90℃and the mixture was stirred for 8 hours, and the remaining material was purified by column chromatography to give intermediate C-1 (21.17 g, yield: 74%, test value MS (ESI, M/Z): [ M+H ]] + = 572.33, intermediate C-1 nuclear magnetic resonance hydrogen spectrum is shown in fig. 1).
N 2 Under protection, intermediate C-1 (30 mmol), reactant D-1 (36 mmol), palladium acetate (Pd (OAc) 2 ) (0.6 mmol) and 2-cyclohexyl-2, 4, 6-triisopropylbiphenyl (X-Phos) (1.5 mmol), cesium carbonate (Cs 2 CO 3 ) (63 mmol) was added to a mixed solvent of toluene, ethanol and water (180 mL:60 mL), the temperature was raised to 80℃and the reaction was carried out for 10 hours, and the remaining material was purified by column chromatography and filteredThe solvent was removed from the solution by a rotary evaporator, and the obtained solid was dried to obtain Compound 1 (16.36 g, yield: 70%, test value MS (ESI, M/Z): [ M+H ]]Compound 1 nuclear magnetic resonance hydrogen spectrum is shown in fig. 2 + = 779.12).
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c,89.43; h,4.92; n,3.60; o,2.05
Test value: c,89.26; h,5.04; n,3.65; o,2.10
Example 2: synthesis of Compound 40
CAS: reactant a-40:2472861-93-9
After adding reactant A-40 (50 mmol) and reactant B-40 (55 mmol) to toluene in a reaction vessel, pd was added under nitrogen 2 (dba) 3 (0.5mmol)、P(t-Bu) 3 (1 mmol), t-BuONa (110 mmol); after the addition, the reaction temperature was slowly raised to 90℃and the mixture was stirred for 8 hours, and the remaining material was purified by column chromatography to give intermediate C-40 (18.58 g, yield: 68%, test value MS (ESI, M/Z): [ M+H ]] + ＝546.36)。
N 2 Under protection, intermediate C-40 (30 mmol), reactant D-40 (36 mmol), palladium acetate (Pd (OAc) 2 ) (0.6 mmol) and 2-cyclohexyl-2, 4, 6-triisopropylbiphenyl (X-Phos) (1.5 mmol), cesium carbonate (Cs 2 CO 3 ) (63 mmol) was added to a mixture of toluene, ethanol, and water (180 mL:60 mL), the temperature was raised to 80℃and the reaction was carried out for 10 hours, the remaining material was purified by column chromatography, the solvent was removed from the filtrate by a rotary evaporator, and the obtained solid was dried to give compound 1 (16.49 g, yield: 73%, test value MS (ESI, M/Z) [ M+H ]]+＝753.17)。
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c,89.33; h,4.82; n,3.72; o,2.12
Test value: c,89.14; h,4.95; n,3.78; o,2.19
Example 3: synthesis of Compound 105
CAS: reactant a-105:2692602-69-8
N 2 Under protection, reactant A-105 (50 mmol), reactant B-105 (60 mmol), tetrakis (triphenylphosphine) palladium (0.5 mmol) and potassium carbonate (110 mmol) were added to a mixed solvent of toluene, ethanol and water (150 mL:50 mL), respectively, the temperature was raised to 95 ℃, the reaction was carried out for 10h, the salt and the catalyst were removed by suction filtration while hot using celite, the solvent was removed by a rotary evaporator after the filtrate was cooled to room temperature, and the obtained solid was dried and passed through a silica gel funnel with dichloromethane: petroleum ether was used as a developing agent in a volume ratio of 1:6, the filtrate was removed by a rotary evaporator, and the resulting solid was dried to give intermediate C-105 (16.31 g, yield: 66%, mw: 494.30).
After adding intermediate C-105 (30 mmol) and reactant D-105 (33 mmol) to xylene (180 mL) in a reaction vessel, pd (OAc) was added under nitrogen blanket 2 (1.5 mmol), X-Phos (3.6 mmol), t-BuONa (63 mmol); after the addition, the reaction temperature was slowly raised to 135 ℃ and the mixture was stirred for 10h; the remaining material was purified by column chromatography to give compound 105 (18.00 g, yield: 72%, test MS (ESI, M/Z): [ M+H)] + ＝833.24)。
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c,87.96; h,4.84; n,3.36; o,3.84
Test value: c,87.81; h,4.97; n,3.40; o,3.88
Examples 4 to 31
The synthesis of the following compounds, whose molecular formulas and mass spectra are shown in table 1 below, was accomplished with reference to the synthesis methods of examples 1 to 3.
Table 1 molecular formula and mass spectrum
Further, since other compounds of the present invention can be obtained by referring to the synthetic methods of the above-described examples, they are not exemplified herein.
The invention provides an organic electroluminescent device, which comprises a hole injection layer and a hole transport layer
Application example 1 preparation of organic electroluminescent device:
a. ITO anode: washing ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing with ultrasonic waves for 30min, washing with distilled water for 2 times repeatedly, washing with ultrasonic waves for 10min, baking in a vacuum oven at 220 ℃ for 2 hours after washing, and cooling after baking. The substrate is used as an anode, a vapor deposition device process is performed by using a vapor deposition machine, and other functional layers are sequentially vapor deposited on the substrate.
b. HIL (hole injection layer): to be used forThe vacuum evaporation of the hole injection layer materials HT and P-dopant is performed, and the chemical formulas are shown below. The evaporation rate ratio of HT to P-dock is 98:2, the thickness is 10nm;
c. HTL (hole transport layer): to be used forVacuum evaporating 120nm HT as a hole transport layer on the hole injection layer;
d. prime (light-emitting auxiliary layer): to be used forVacuum evaporating 10nm of the compound of the present invention on the hole transport layer as a light-emitting auxiliary layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer toThe Host material (Host) and the Dopant material (Dopant) having a thickness of 25nm were vacuum-deposited as light-emitting layers, and the chemical formulas of Host and Dopant are shown below. Wherein the evaporation rate ratio of Host to Dopant is 97:3.
f. HB (hole blocking layer): to be used forIs used for vacuum evaporation of a hole blocking layer with a thickness of 5.0 nm.
g. ETL (electron transport layer): to be used forET and Liq having a thickness of 35nm were vacuum-deposited as electron transport layers. Wherein the evaporation rate ratio of ET to Liq is 50:50.
h. EIL (electron injection layer): to be used forThe vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used forThe vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be used forCPL with a thickness of 70nm was vacuum deposited on the cathode as a light extraction layer.
k. And packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The device structure is as follows:
ITO/Ag/ITO/HT P-pinch (10 nm, 2%)/HT (120 nm)/prime (compound of the invention) (10 nm)/Host: pinch (25 nm, 3%)/HB (5 nm)/ET: liq (35 nm, 50%)/Yb (1 nm)/Mg: ag (18 nm, 1:9)/CPL (70 nm).
Application examples 2 to 31
The organic electroluminescent devices of application examples 2 to 31 were prepared according to the above-described preparation method of the organic electroluminescent device, except that the compound 1 of application example 1 was replaced with the corresponding compound of examples 2 to 31, respectively, to form a light-emitting auxiliary layer.
Comparative example 1
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 in application example 1 was replaced with comparative compound 1, wherein the structural formula of comparative compound 1 is as follows:
comparative example 2
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 2, wherein the structural formula of comparative compound 2 is as follows:
comparative example 3
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 3, wherein the structural formula of comparative compound 3 is as follows:
comparative example 4
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 4, wherein the structural formula of comparative compound 4 is as follows:
comparative example 5
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 5, wherein the structural formula of comparative compound 5 is as follows:
comparative example 6
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 6, wherein the structural formula of comparative compound 6 is as follows:
comparative example 7
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 7, wherein the structural formula of comparative compound 7 is as follows:
the organic electroluminescent devices obtained in the above device examples 1 to 31 and device comparative examples 1 to 7 were characterized in terms of driving voltage, luminous efficiency, BI value and lifetime at a luminance of 1000 (nits), and the test results are shown in table 2 below:
TABLE 2 luminescence property test results (brightness value 1000 nits)
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It is known to those skilled in the art that the energy level of the light-emitting auxiliary layer is matched with the light-emitting layer and the hole-transporting layer, and the target value to be adjusted is different for different light-emitting layers. The difference is larger for the light emitting layers of different colors. Even with the same blue light, there is a significant difference for different host, dopant materials.
The blue light organic electroluminescent device is influenced by microcavity effect, and the luminous efficiency is greatly influenced by chromaticity, so that a BI value is introduced as the basis of the efficiency of the blue light luminescent material, and BI=luminous efficiency/CIEy. And the problems of short lifetime and low efficiency of blue light devices have been one of the problems to be solved urgently by those skilled in the art, and the improvement of BI values by 7-8% has been achieved in the art.
The blue light luminescent auxiliary material provided by the invention is based on benzonaphthofuran, wherein a triarylamine group is connected to naphthalene, and 9-phenyl-9H-carbazole is connected to benzene at the other side. As can be seen from table 2, compared with the existing organic electroluminescent devices provided in comparative examples 1 to 7, the organic electroluminescent devices prepared by using the blue light emitting auxiliary materials provided in the embodiments of the present invention have the technical effects of improving the lifetime of the device and remarkably improving the luminous efficiency while maintaining the driving voltage substantially unchanged.
Compound 20 of the present invention and comparative compound 1; compound 21 differs from comparative compound 2 in that the present invention is based on benzonaphthofuran, the comparative compound is dibenzofuran, the benzonaphthofuran retains the advantage of the dibenzofuran high triplet energy level, and on this basis, the conjugated surface is added, the hole transport rate is increased, and the extension of the conjugated surface is avoided, so that the present invention has the effect of improving the device efficiency, the BI value is improved by about 8%, and the efficiency is improved by 8%.
The main difference between the compound 6 of the invention and the comparative compound 3 is that the substitution positions of 9-phenyl-9H-carbazole and triarylamine are different, the performance of the obtained device shows that the service life of the comparative compound 3 is equivalent to that of the compound 6, but the luminous efficiency of the device is obviously improved by 8 percent, and the substitution positions of carbazole and triarylamine can possibly have different influences on the performance of the device between similar compounds, so that the substitution positions of the compounds can be regulated according to the linear energy production requirement, and I can further study based on the fact.
According to the invention, the compound 26 and the comparative compound 6 adopt different carbazole, and the benzene of the benzonaphthofuran is connected with 9-phenyl-9H-carbazole, so that on one hand, the introduced phenyl bridging structure can avoid large electron jump difficulty caused by overlarge energy gap of the compound, and the compound structure is stable.
It can be seen that the position of the ring and what kind of ring are bonded between similar substances, and the substituents on the ring all affect the triplet energy level and mobility, thus affecting the device performance in the organic electroluminescence. Although the structure of the compound is similar to that of the compound in the prior art, the compound can obviously improve the performance advantage of the luminous efficiency only when the compound which accords with the formula I is used as a blue light luminous auxiliary layer.
In the present specification, each embodiment is described in a progressive manner, and each embodiment is mainly described in a different point from other embodiments, and identical and similar parts between the embodiments are all enough to refer to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant points refer to the description of the method section.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. The luminous auxiliary material is characterized by having a structural general formula shown in formula I:
wherein,
ar is condensed with an adjacent benzene ring;
ar is independently selected from substituted or unsubstituted C6-C30 aryl;
Ar 1 and Ar is a group 2 Independently selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted 3-to 30-membered heteroaryl.
2. A light-emitting auxiliary material according to claim 1, wherein Ar 1 And Ar is a group 2 Independently selected from substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted 3-to 24-membered heteroaryl.
3. A light-emitting auxiliary material according to claim 2, wherein Ar 1 And Ar is a group 2 Independently selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylcyclopentyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, 2, 3-dimethylcyclopentyl, bicyclo [3.1.1 ]]Heptyl or adamantyl.
4. A light-emitting auxiliary material according to claim 2, wherein Ar 1 And Ar is a group 2 Independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, perylenyl, droyl, naphthacene, fluoranthryl, spirobifluorenyl, azulenyl, methylphenyl, ethylphenyl, methoxyphenyl, and cyanophenyl.
5. According to the weightsA luminescent auxiliary material as claimed in claim 2, wherein Ar is 1 And Ar is a group 2 Independently selected from the group consisting of furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxanyl, or dihydroacridinyl.
6. A light-emitting auxiliary material according to any one of claims 3 to 5, wherein Ar 1 And Ar is a group 2 Independently selected from the group consisting of phenyl, naphthyl, phenanthryl, methylphenyl, ethylphenyl, cyanophenyl, methoxyphenyl, phenylpyridyl, phenylpyrimidinyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenyl-9H-carbazolyl, diphenylfluorenyl, dimethylfluorenyl, cyclopentyl, cyclohexyl.
7. A light-emitting auxiliary material according to claim 6, wherein the formula I comprises the following structure:
8. a light-emitting auxiliary material according to claim 7, wherein the formula I specifically comprises the following structure:
9. a method for preparing the luminescent auxiliary material according to claim 1, wherein the synthetic route is as follows:
wherein Hal is 1 ，Hal 2 Selected from Cl, br, I; r' is
Ar 1 -Ar 2 Ar is as defined in claim 1 for formula I;
the preparation method comprises the following steps:
(1)N 2 under the protection, respectively adding the reactants A-I, B-I, a palladium catalyst and alkali into a mixed solvent of toluene, ethanol and water, heating to 80-100 ℃, and reacting for 8-14h to obtain an intermediate C-I;
(2) Adding an intermediate C-I and a reactant D-I into a reaction container, dissolving in dimethylbenzene, adding a palladium catalyst, a phosphorus ligand and alkali under the protection of nitrogen, slowly heating the reaction temperature to 120-140 ℃ after adding, stirring the mixture for 8-14h, and purifying the residual substances by using a column chromatography to obtain a formula I;
wherein the equivalent ratio of the reactants A-I, the reactants B-I, the palladium catalyst and the alkali is as follows: 1: (1-1.4): (0.01-0.1): (2-4);
the equivalent ratio of the intermediate C-I, the reactant D-I, the palladium catalyst, the phosphorus ligand and the alkali is as follows: 1: (1-1.5): (0.01-0.1): (0.01-1): (2-3);
or alternatively, the first and second heat exchangers may be,
the synthetic route is as follows:
wherein Hal is 1 ，Hal 2 Selected from Cl, br, I; r' is
Ar 1 -Ar 2 Ar is as defined in claim 1 for formula I;
the preparation method comprises the following steps:
(1) Adding reactants A-I and B-I into a reaction container, dissolving in toluene, adding a palladium catalyst, a phosphorus ligand and alkali under the protection of nitrogen, slowly heating the reaction temperature to 85-95 ℃ after adding, and stirring the mixture for 6-14h to obtain an intermediate C-I;
(2)N 2 under the protection, the intermediate C-I (1.0 eq), the reactant D-I (1.0-1.5 eq), the palladium catalyst (0.01-0.1 eq), the phosphorus ligand (0.01-1.0 eq) and the alkali (2.0-3.0 eq) are respectively added into toluene and ethanolHeating the mixture to 80-90 ℃ in a mixed solvent of water, and reacting for 6-12h to obtain a formula I;
wherein the equivalent ratio of the reactants A-I, the reactants B-I, the palladium catalyst, the phosphorus ligand and the alkali is as follows: 1: (1-1.5): (0.01-0.1): (0.01-1): (2-3);
the equivalent ratio of the intermediate C-I, the reactant D-I, the palladium catalyst, the phosphorus ligand and the alkali is as follows: 1: (1-1.5) (0.01-0.1): (0.01-1): (2-3).
10. An organic electroluminescent device comprising a light-emitting auxiliary layer comprising the light-emitting auxiliary material according to claim 1.
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