CN106220645A - Compound based on monosubstituted-9-fluorenone and application thereof - Google Patents

Compound based on monosubstituted-9-fluorenone and application thereof Download PDF

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CN106220645A
CN106220645A CN201610259300.0A CN201610259300A CN106220645A CN 106220645 A CN106220645 A CN 106220645A CN 201610259300 A CN201610259300 A CN 201610259300A CN 106220645 A CN106220645 A CN 106220645A
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fluorenone
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CN106220645B (en
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巨成良
石宇
张学衡
刘英瑞
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Jiangsu Sunera Technology Co Ltd
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Valiant Co Ltd
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Abstract

The invention discloses a compound based on monosubstituted-9-fluorenone and application thereof, wherein the compound takes the monosubstituted-9-fluorenone as a parent nucleus, and an aromatic heterocyclic group is connected to one side of the parent nucleus, so that the crystallinity of molecules is damaged, the aggregation among the molecules is avoided, and the compound has good film forming property. The compound of the invention is used as a luminescent layer material to be applied to an organic light-emitting diode, and has good photoelectric property.

Description

A kind of compound based on monosubstituted base-9-Fluorenone and application thereof
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of compound containing monosubstituted base-9-Fluorenone, And it is as emitting layer material application on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to Manufacture novel display product, it is also possible to be used for making novel illumination product, be expected to substitute existing liquid crystal display And fluorescent lighting, application prospect is quite varied.
OLED luminescent device, just as the structure of sandwich, including electrode material film layer, and is clipped in Different electrodes Organic functional material between film layer, various difference in functionality materials are overlapped mutually common group together according to purposes Become OLED luminescent device.As current device, when the two end electrodes applying voltage to OLED luminescent device, And by the positive and negative charge in electric field action organic layer functional material film layer, positive and negative charge is further at luminescent layer In compound, i.e. produce OLED electroluminescent.
Organic Light Emitting Diode (OLEDs) shows and application in terms of illumination causes industry at large-area flat-plate Boundary and the extensive concern of academia.But, tradition organic fluorescence materials is only with being electrically excited the 25% of formation Singlet exciton is luminous, and the internal quantum efficiency of device is relatively low (being up to 25%).External quantum efficiency is generally less than 5%, also there is a big difference with the efficiency of phosphorescent devices.Although phosphor material due to the strong spin in heavy atom center- Orbit coupling enhances intersystem crossing, can effectively utilize and be electrically excited the singlet exciton of formation and triplet state swashs Son is luminous, makes the internal quantum efficiency of device reach 100%.But phosphor material exists expensive, stability of material Poor, device efficiency tumbles the problem such as serious and limits its application at OLEDs.Hot activation delayed fluorescence (TADF) material is the third generation organic light emission material of development after organic fluorescence materials and organic phosphorescent material Material.Such material typically has poor (the △ E of little singletstate-tripletST), triplet excitons can be led to Cross anti-intersystem crossing and be transformed into singlet exciton luminescence.This can make full use of the singletstate being electrically excited lower formation Exciton and triplet excitons, the internal quantum efficiency of device can reach 100%.Meanwhile, material structure is controlled, Stable in properties, low price is without precious metal, having a extensive future of OLEDs field.
Although TADF material can realize the exciton utilization rate of 100% in theory, but there are in fact and ask as follows Topic: T1 and the S1 state of (1) design molecule has a strong CT feature, the least S1-T1 state energy gap, although High T can be realized by TADF process1→S1State exciton conversion ratio, but also result in low S1 state radiation Transfer rate, consequently it is difficult to have (or realizing) high exciton utilization rate and high fluorescent radiation efficiency concurrently simultaneously；(2) i.e. Making to have used doping device to alleviate T exciton concentration quenching effect, the device of most of TADF materials is at height Under electric current density, efficiency roll-off is serious.
For the actual demand of current OLED display Lighting Industry, the development of current OLED material is the most far away Not, lag behind the requirement of panel manufacturing enterprise, as the organic functions material of material enterprise development higher performance Material is particularly important.
Summary of the invention
The problems referred to above existed for prior art, the applicant provides a kind of based on monosubstituted base-9-Fluorenone Compound and application thereof.The present invention monosubstituted base-9-Fluorenone compounds based on TADF mechanism is as luminescence Layer material is applied on Organic Light Emitting Diode, and the OLED of application the compounds of this invention has good Photoelectric properties, it is possible to meet the requirement of panel manufacturing enterprise.
Technical scheme is as follows:
A kind of compound based on monosubstituted base-9-Fluorenone, structural formula formula such as formula (1) institute of this compound Show:
In formula (1), R employing-Ar-R1Or-R1Represent；Wherein, Ar is expressed as phenyl, C1-10Straight chain or The substituted phenyl of branched alkyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl or benzo phenanthryl；
R1Formula (2) is used to represent:
In formula (2), X1For oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl is substituted One in the substituted alkylidene of alkylidene, aryl, the substituted amido of alkyl or aryl；
R2、R3Independently choose structure shown in hydrogen, formula (3) or formula (4):
In formula (3), a isX2、X3Be expressed as oxygen atom, sulphur atom, Selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, the substituted alkylidene of aryl, aryl are substituted One in amido；
Formula (3), formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Bonded.
R in described compound based on monosubstituted base-9-Fluorenone1It is expressed as group:
In Any one.
The concrete structure formula of described compound based on monosubstituted base-9-Fluorenone is:
In any one.
A kind of method preparing described compound, reaction equation is:
Course of reaction is: weighs 9-Fluorenone bromine compounds and amine compound, dissolves with toluene；Add Pd (dppf)Cl2, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in reaction temperature 95～100 DEG C, reacting 10～24 hours, cooling, filtering reacting solution, filtrate rotation is steamed, and crosses silicagel column, To target product；Described 9-Fluorenone bromine compounds is 1:1.0～1.5 with the mol ratio of amine compound；Pd(dppf) Cl2It is 0.003～0.01:1 with the mol ratio of 9-Fluorenone bromine compounds, sodium tert-butoxide and 9-Fluorenone bromine compounds Mol ratio is 1.0～3.0:1.
A kind of method preparing described compound, reaction equation is:
Course of reaction is: weigh 9-Fluorenone boronic acid compounds and R1-Ar-Br, by the toluene second that volume ratio is 2:1 Alcohol mixed solvent dissolves；Add Na2CO3Aqueous solution, Pd (PPh3)4；Under an inert atmosphere, by above-mentioned instead Answer the mixed solution of thing in reaction temperature 95～100 DEG C, react 10～24 hours, cooling, filtering reacting solution, Filtrate rotation is steamed, and crosses silicagel column, obtains target product；Described 9-Fluorenone boronic acid compounds rubs with R1-Ar-Br's That ratio is 1:1.0～1.5；Pd(PPh3)4It is 0.003～0.01:1 with the mol ratio of 9-Fluorenone boronic acid compounds, Na2CO3It is 1.0～3.0:1 with the mol ratio of 9-Fluorenone boronic acid compounds.
A kind of luminescent device comprising described compound, described compound, as emitting layer material, is used for making OLED.
Useful the having the technical effect that of the present invention
The compounds of this invention, with monosubstituted base-9-Fluorenone as parent nucleus, connects and has aromatic heterocycle group, thus destroys and divide The crystallinity of son, it is to avoid intermolecular aggregation, the film property that had；Molecule mostly is rigidity base Group, improves the heat stability of material；There is good photoelectric characteristic, suitable HOMO and LUMO energy Level, the compounds of this invention HOMO and lumo energy electron cloud efficiently separate, and can realize less S1-T1 State energy gap, can be effectively improved exciton utilization rate and high fluorescent radiation efficiency, reduces the efficiency under high current density Roll-off, reduce device voltage, improve device performance.
Compound of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device Performance, when described compound uses as the emitting layer material of OLED luminescent device, the current efficiency of device, Power efficiency and external quantum efficiency are all greatly improved；Compound of the present invention is at OLED luminescent device In there is good application effect, there is good industrialization prospect.
Accompanying drawing explanation
Fig. 1 is the OLED structure schematic diagram using the compounds of this invention.
In figure: 1, for transparent substrate layer；2, for ito anode layer；3, for hole injection layer；4, for hole Transmission electronic barrier layer；5, for luminescent layer；6, for hole barrier/electron transfer layer；7, inject for electronics Layer；8, for negative electrode reflection electrode layer.
Detailed description of the invention
Below in conjunction with the accompanying drawings and embodiment, the present invention is specifically described.
Embodiment 1 compound 26
The there-necked flask of 250ml, under the atmosphere being passed through nitrogen, adds the bromo-9-Fluorenone of 0.01mol (2.59g) 1-, 0.015mol (5.23g) compound M1,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g) Pd(dppf)Cl2, 180ml toluene, it is heated to reflux 10 hours, sample point plate, reaction is completely；The coldest But, filtering, filtrate rotation is steamed, and filtrate is carried out column chromatography, obtains target product, purity 99.2%, yield 82%；
Elementary analysis structure (molecular formula C37H22N2O2): theoretical value C, 84.39；H,4.21；N,5.32；O, 6.08；Test value: C, 84.36；H,4.22；N,5.33；O,6.09；
HPLC-MS: materials theory molecular weight is 526.17, actual molecular weight 526.40.
Embodiment 2 compound 44
The preparation method of compound 44 is with embodiment 1, and difference is to use raw material M2 to replace M1；
Elementary analysis structure (molecular formula C29H17NOS): theoretical value C, 81.47；H,4.01；N,3.28；O, 3.74；S,7.50；Test value: C, 81.45；H,4.00；N,3.29；O,3.7；S,7.51；
HPLC-MS: materials theory molecular weight is 427.10, actual molecular weight 427.35.
Embodiment 3 compound 56
The preparation method of compound 56 is with embodiment 1, and difference is to use raw material M3 to replace M1；
Elementary analysis structure (molecular formula C31H17NO3): theoretical value C, 82.47；H,3.80；N,3.10；O, 10.63；Test value: C, 82.45；H,3.79；N,3.11；O,10.65；
HPLC-MS: materials theory molecular weight is 451.12, actual molecular weight 451.36.
Embodiment 4 compound 58
The there-necked flask of 250ml, under the atmosphere being passed through nitrogen, adds the bromo-9-Fluorenone of 0.01mol (2.59g) 2-, 0.015mol (6.59g) compound M4,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g) Pd(dppf)Cl2, 180ml toluene, it is heated to reflux 9 hours, sample point plate, reaction is completely；The coldest But, filtering, filtrate rotation is steamed, and filtrate is carried out column chromatography, obtains target product, purity 98.9%, yield 78%；
Elementary analysis structure (molecular formula C43H27N3O2): theoretical value C, 83.61；H,4.41；N,6.80；O, 5.18；Test value: C, 83.64；H,4.40；N,6.78；O,5.18；
HPLC-MS: materials theory molecular weight is 617.21, actual molecular weight 617.39.
Embodiment 5 compound 63
The there-necked flask of 250ml, under the atmosphere being passed through nitrogen, adds the bromo-9-Fluorenone of 0.01mol (2.59g) 3-, 0.015mol (6.09g) compound M5,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g) Pd(dppf)Cl2, 180ml toluene, it is heated to reflux 12 hours, sample point plate, reaction is completely；The coldest But, filtering, filtrate rotation is steamed, and filtrate is carried out column chromatography, obtains target product, purity 99.4%, yield 77%；
Elementary analysis structure (molecular formula C40H28N2OS): theoretical value C, 82.16；H,4.83；N,4.79；O, 2.74；S,5.48；Test value: C, 82.15；H,4.81；N,4.81；O,2.73；S,5.50；
HPLC-MS: materials theory molecular weight is 584.19, actual molecular weight 584.33.
Embodiment 6 compound 67
The preparation method of compound 67 is with embodiment 5, and difference is to use raw material M6 to replace M5；
Elementary analysis structure (molecular formula C43H27N3OS): theoretical value C, 81.49；H,4.29；N,6.63；O, 2.52；S,5.06；Test value: C, 81.47；H,4.26；N,6.64；O,2.55；S,5.07；
HPLC-MS: materials theory molecular weight is 633.19, actual molecular weight 633.36.
Embodiment 7 compound 82
The preparation method of compound 82 is with embodiment 1, and difference is to use raw material M7 to replace M1；
Elementary analysis structure (molecular formula C46H33N3O): theoretical value C, 85.82；H,5.17；N,6.53；O, 2.49；Test value: C, 85.83；H,5.15；N,6.55；O,2.49；
HPLC-MS: materials theory molecular weight is 643.26, actual molecular weight 643.59.
Embodiment 8 compound 86
The preparation method of compound 86 is with embodiment 1, and difference is to use raw material M8 to replace M1；
Elementary analysis structure (molecular formula C42H27NO3): theoretical value C, 84.97；H,4.58；N,2.36；O, 8.09；Test value: C, 84.99；H,4.53；N,2.37；O,8.11；
HPLC-MS: materials theory molecular weight is 593.20, actual molecular weight 593.56.
Embodiment 9 compound 89
The preparation method of compound 89 is with embodiment 1, and difference is to use raw material M9 to replace M1；
Elementary analysis structure (molecular formula C49H29N3O3): theoretical value C, 83.15；H,4.13；N,5.94；O, 6.78；Test value: C, 83.11；H,4.11；N,5.98；O,6.80；
HPLC-MS: materials theory molecular weight is 707.22, actual molecular weight 707.40.
Embodiment 10 compound 92
The there-necked flask of 250ml, under the atmosphere being passed through nitrogen, adds the bromo-9-Fluorenone of 0.01mol (2.59g) 4-, 0.015mol (7.72g) compound M10,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g) Pd(dppf)Cl2, 180ml toluene, it is heated to reflux 14 hours, sample point plate, reaction is completely；The coldest But, filtering, filtrate rotation is steamed, and filtrate is carried out column chromatography, obtains target product, purity 98.5%, yield 73%；
Elementary analysis structure (molecular formula C49H32N4O): theoretical value C, 84.95；H,4.66；N,8.09；O, 2.31；Test value: C, 86.95；H,5.09；N,5.06；O,2.90；
HPLC-MS: materials theory molecular weight is 692.26, actual molecular weight 692.35.
Embodiment 11 compound 95
The preparation method of compound 95 is with embodiment 1, and difference is to use raw material M11 to replace M1；
Elementary analysis structure (molecular formula C43H27N3O): theoretical value C, 85.83；H,4.52；N,6.98；O, 2.66；Test value: C, 85.86；H,4.50；N,6.70；O,2.64；
HPLC-MS: materials theory molecular weight is 601.22, actual molecular weight 601.49.
Embodiment 12 compound 96
The preparation method of compound 96 is with embodiment 1, and difference is to use raw material M12 to replace M1；
Elementary analysis structure (molecular formula C40H28N2O): theoretical value C, 86.93；H,5.11；N,5.07；O, 2.89；Test value: C, 86.95；H,5.09；N,5.06；O,2.90；
HPLC-MS: materials theory molecular weight is 552.22, actual molecular weight 552.19.
Embodiment 13 compound 99
The preparation method of compound 99 is with embodiment 10, and difference is to use raw material M13 to replace M10；
Elementary analysis structure (molecular formula C46H33N3O): theoretical value C, 85.82；H,5.17；N,6.53；O,2.49； Test value: C, 85.86；H,5.13；N,6.55；O,2.47；
HPLC-MS: materials theory molecular weight is 643.26, actual molecular weight 643.15.
Embodiment 14 compound 128
The preparation method of compound 128 is with embodiment 1, and difference is to use raw material M14 to replace M1；
Elementary analysis structure (molecular formula C40H25NO3): theoretical value C, 84.64；H,4.44；N,2.47；O, 8.46；Test value: C, 84.66；H,4.41；N,2.45；O,8.49；
HPLC-MS: materials theory molecular weight is 567.18, actual molecular weight 567.24.
Embodiment 15 compound 143
The preparation method of compound 143 is with embodiment 4, and difference is to use raw material M15 to replace M4；
Elementary analysis structure (molecular formula C44H30N2O2): theoretical value C, 85.41；H,4.89；N,4.53；O, 5.17；Test value: C, 85.43；H,4.91；N,4.50；O,5.16；
HPLC-MS: materials theory molecular weight is 618.23, actual molecular weight 618.35.
Embodiment 16 compound 148
The there-necked flask of 250mL, under the atmosphere being passed through nitrogen, adds 0.01mol (2.68g) 1-boric acid-9-fluorenes Ketone, 0.015mol (7.45g) compound M16, dissolve (180ml toluene, 90ml ethanol) with mixed solvent, It is subsequently adding 0.03mol Na2CO3Aqueous solution (2M), logical nitrogen gas stirring 1 hour, it is subsequently adding 0.0001mol Pd(PPh3)4, it being heated to reflux 10-24 hour, sample point plate, reaction is completely.Natural cooling, filters, filtrate Rotation is steamed, and crosses silicagel column, obtains target product, HPLC purity 98.5%, yield 66.00%.
Elementary analysis structure (molecular formula C43H33NO2): theoretical value C, 86.69；H,5.58；N,2.35；O, 5.37；Test value: C, 86.77；H,5.55；N,2.37；O,5.31；
HPLC-MS: materials theory molecular weight is 595.25, actual molecular weight 595.30.
The compounds of this invention can use as emitting layer material, to the compounds of this invention 118, current material CBP Carrying out hot property, luminescent spectrum and HOMO energy level to test, testing result is as shown in table 1.
Table 1
Compound Tg(℃) Td(℃) λPL(nm) Φf HOMO energy level (ev)
Compound 118 132 385 503 61.2 -5.79
Material C BP 113 353 369 26.1 -5.9
Note: vitrification point Tg is measured by differential scanning calorimetry (DSC, Nai Chi company of Germany DSC204F1 differential scanning calorimeter), heats up 10 DEG C/min of speed；Thermal weight loss temperature Td is the temperature of weightless 1% in nitrogen atmosphere, in the TGA-50H thermogravimetric analysis of Shimadzu Corporation of Japan Being measured on instrument, nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, utilizes Japan to open up general health SR-3 spectroradiometric Meter measures；Φ f be solid powder fluorescence quantum efficiency (utilize the Maya2000Pro fiber spectrometer of U.S.'s marine optics, Lan Fei company of the U.S. C-701 integrating sphere and the test solid fluorescence quantum efficiency test system of marine optics LLS-LED light source composition, reference literature Adv.Mater.1997, The method of 9,230-232 is measured)；Highest occupied molecular orbital HOMO energy level is to be measured by photoelectron emissions spectrometer (AC-2 type PESA), Test is atmospheric environment.
From upper table data, the compounds of this invention has suitable HOMO energy level and higher thermally-stabilised Property, it is suitable as the material of main part of luminescent layer；Meanwhile, the compounds of this invention has suitable luminescent spectrum, Higher Φ f so that application the compounds of this invention obtained as OLED efficiency and the life-span of dopant material Promote.
Below by way of device embodiments 1～16 and device comparative example 1 describe the compound of present invention synthesis in detail and exist As the application effect of emitting layer material in device.Device embodiments 2～16 of the present invention, device comparative example 1 compared with device embodiments 1 processing technology of described device identical, and be have employed identical substrate Material and electrode material, the thickness of electrode material also keeps consistent, except that to the luminescent layer in device Main body and dopant material convert.Obtained device structure composition is as shown in table 2；The test knot of obtained device Fruit is shown in Table 3.
Device embodiments 1
Ito anode layer 2/ hole injection layer 3 (thickness: 10nm；Material: molybdenum trioxide MoO3)/hole passes Defeated/electronic barrier layer 4 (thickness: 140nm；Material: NPB)/luminescent layer 5 (thickness: 30nm；Material: Compound 26 and DCJTB is constituted according to the weight proportion blending of 100:3)/hole barrier/electron transfer layer 6 (thickness: 40nm；Material: TPBI)/LiF/Al
Concrete preparation process is as follows:
Ito anode layer 2 (thickness is 150nm) is washed, carry out the most successively neutralizing treatment, pure water, The dried ultraviolet-ozone that carries out again washs to remove the organic residue on transparent ITO surface.
On the ito anode layer 2 having carried out after above-mentioned washing, utilizing vacuum deposition apparatus, being deposited with thickness is The molybdenum trioxide MoO of 10nm3Use as hole injection layer 3, be and then deposited with the NPB of 140nm thickness As hole transport/electronic barrier layer 4.
After above-mentioned hole transport/electronic blocking layer material evaporation terminates, make the luminescent layer 5 of OLED luminescent device, Using the compounds of this invention 26 as material of main part, DCJTB is as dopant material, the doping of dopant material Amount ratio is 3%, and luminescent layer thickness is 30nm.
After above-mentioned luminescent layer, continuing vacuum evaporation hole barrier/electron transport layer materials is TPBI, this material The vacuum evaporation thickness of material is 40nm, and this layer is hole barrier/electron transfer layer 6.
On hole barrier/electron transfer layer 6, by vacuum deposition apparatus, making thickness is the fluorination of 1nm Lithium (LiF) layer, this layer is electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminum (Al) layer that thickness is 80nm, This layer is that negative electrode reflection electrode layer 8 uses.
After OLED luminescent device accomplished as described above, with known drive circuit, anode and negative electrode are connected Come, measure the current efficiency of device, luminescent spectrum and the I-E characteristic of device.Obtained device structure Composition is as shown in table 2；The test result of obtained device is shown in Table 3.
Table 2
Table 3
Note: device detection performance is set to 1.0 using comparative example 1 as reference, comparative example 1 device property indices.Comparative example 1 Current efficiency be 2.3cd/A；CIE chromaticity coordinates is (0.64,0.37)；Driving voltage is 5.2v (@10mA/cm2)。
The result of table 3 can be seen that compound of the present invention can be applied and makes with OLED luminescent device, and Compared with comparative example 1, material the most of the present invention is as luminescent layer material of main part or dopant material, obtained OLED luminescent device efficiency and start voltage all ratio known OLED material obtain bigger change, especially It is that the efficiency roll-off under device high current density obtains improvement.Of the present invention have TADF elastomeric material and exist OLED luminescent device has good application effect, there is good industrialization prospect.
Although disclosing the present invention by embodiment and preferred implementation, it should be appreciated that the invention is not restricted to Disclosed embodiment.On the contrary, it will be understood by those skilled in the art that it is intended to various modification and class As arrange.Therefore, scope of the following claims should consistent with the widest explanation with contain all so Modification and similar arrangement.

Claims (6)

1. a compound based on monosubstituted base-9-Fluorenone, it is characterised in that the structural formula formula of this compound As shown in formula (1):
In formula (1), R employing-Ar-R1Or-R1Represent；Wherein, Ar is expressed as phenyl, C1-10Straight chain or The substituted phenyl of branched alkyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl or benzo phenanthryl；
R1Formula (2) is used to represent:
In formula (2), X1For oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl is substituted One in the substituted alkylidene of alkylidene, aryl, the substituted amido of alkyl or aryl；
R2、R3Independently choose structure shown in hydrogen, formula (3) or formula (4):
In formula (3), a isX2、X3Be expressed as oxygen atom, sulphur atom, Selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, the substituted alkylidene of aryl, aryl are substituted One in amido；
Formula (3), formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Bonded.
Compound the most according to claim 1, it is characterised in that described based on monosubstituted base-9-Fluorenone R in compound1It is expressed as group:
In any one.
Compound the most according to claim 1, it is characterised in that described based on monosubstituted base-9-Fluorenone The concrete structure formula of compound is:
In any one.
4. prepare the method for compound described in any one of claims 1 to 3 for one kind, it is characterised in that reactional equation Formula is:
Course of reaction is: weighs 9-Fluorenone bromine compounds and amine compound, dissolves with toluene；Add Pd (dppf)Cl2, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in reaction temperature 95～100 DEG C, reacting 10～24 hours, cooling, filtering reacting solution, filtrate rotation is steamed, and crosses silicagel column, To target product；Described 9-Fluorenone bromine compounds is 1:1.0～1.5 with the mol ratio of amine compound；Pd(dppf) Cl2It is 0.003～0.01:1 with the mol ratio of 9-Fluorenone bromine compounds, sodium tert-butoxide and 9-Fluorenone bromine compounds Mol ratio is 1.0～3.0:1.
5. prepare the method for compound described in any one of claims 1 to 3 for one kind, it is characterised in that reactional equation Formula is:
Course of reaction is: weigh 9-Fluorenone boronic acid compounds and R1-Ar-Br, by the toluene second that volume ratio is 2:1 Alcohol mixed solvent dissolves；Add Na2CO3Aqueous solution, Pd (PPh3)4；Under an inert atmosphere, by above-mentioned instead Answer the mixed solution of thing in reaction temperature 95～100 DEG C, react 10～24 hours, cooling, filtering reacting solution, Filtrate rotation is steamed, and crosses silicagel column, obtains target product；Described 9-Fluorenone boronic acid compounds rubs with R1-Ar-Br's That ratio is 1:1.0～1.5；Pd(PPh3)4It is 0.003～0.01:1 with the mol ratio of 9-Fluorenone boronic acid compounds, Na2CO3It is 1.0～3.0:1 with the mol ratio of 9-Fluorenone boronic acid compounds.
6. one kind comprises the luminescent device of compound described in any one of Claims 1 to 5, it is characterised in that described Compound, as emitting layer material, is used for making OLED.
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