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CN106220645B - 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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CN106220645B
CN106220645B CN201610259300.0A CN201610259300A CN106220645B CN 106220645 B CN106220645 B CN 106220645B CN 201610259300 A CN201610259300 A CN 201610259300A CN 106220645 B CN106220645 B CN 106220645B
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fluorenone
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molar ratio
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CN106220645A (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 and its application based on monosubstituted base -9-Fluorenone
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of compound containing monosubstituted base -9-Fluorenone, with And its application as emitting layer material on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED：Organic Light Emission Diodes) device technology both can be used for make New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is very extensive.
OLED luminescent devices like the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various different function materials are overlapped mutually according to purposes collectively constitutes OLED luminescent devices together. As current device, when the two end electrodes to OLED luminescent devices apply voltage, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, that is, generates OLED electroluminescent.
Organic Light Emitting Diode (OLEDs) large-area flat-plate show and illumination in terms of application cause industrial quarters and The extensive concern of art circle.However, traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, device The internal quantum efficiency of part is relatively low (up to 25%).External quantum efficiency is generally less than 5%, also has with the efficiency of phosphorescent devices very big Gap.Although phosphor material can efficiently use electricity since the strong SO coupling in heavy atom center enhances intersystem crossing The singlet exciton formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material exists Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits its application in OLEDs.Hot activation is prolonged Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.It should Class material generally has small poor (the Δ E of singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing It shines at singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior Quantum efficiency can reach 100%.Meanwhile material structure is controllable, property is stablized, cheap to be not necessarily to precious metal, in OLEDs Field has a extensive future.
Although theoretically 100% exciton utilization rate may be implemented in TADF materials, following problem there are in fact：(1) T1 the and S1 states for designing molecule have strong CT features, very small S1-T1 states energy gap, although can be realized by TADF processes High T1→S1State exciton conversion ratio, but low S1 state radiation transistion rates are also resulted in, consequently it is difficult to have both (or realizing simultaneously) High exciton utilization rate and high fluorescent radiation efficiency；(2) even if having used doping device to mitigate T exciton concentration quenching effects, greatly Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls Afterwards in the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Invention content
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of change based on monosubstituted base -9-Fluorenone Close object and its application.The present invention is based on the monosubstituted base of TADF mechanism -9-Fluorenone class compounds to be applied to as emitting layer material On Organic Light Emitting Diode, there are good photoelectric properties using the OLED device of the compounds of this invention, disclosure satisfy that panel system Make the requirement of enterprise.
Technical scheme is as follows：
A kind of compound based on monosubstituted base -9-Fluorenone, shown in the structural formula general formula such as general formula (1) of the compound：
In general formula (1), R uses-Ar-R1Or-R1It indicates；Wherein, Ar is expressed as phenyl, C1-10Linear or branched alkyl group takes Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl or the benzo phenanthryl in generation；
R1It is indicated using general formula (2)：
In general formula (2), X1For oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution One kind in the amido of substituted alkylidene, alkyl or aryl substitution；
R2、R3Structure shown in selection hydrogen independently, general formula (3) or general formula (4)：
In general formula (3), a isX2、X3Be expressed as oxygen atom, sulphur atom, selenium atom, C1-10One kind in the amido that the alkylidene of linear or branched alkyl group substitution, the alkylidene of aryl substitution, aryl replace；
General formula (3), general formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL, 2Key, CL‘2-CL, 3Key or CL‘3-CL, 4Key connection.
R in the compound based on monosubstituted base -9-Fluorenone1It is expressed as group：
Any one of.
The concrete structure formula of the compound based on monosubstituted base -9-Fluorenone is：
Any one of.
A method of the compound being prepared, reaction equation is：
Reaction process is：9-Fluorenone bromine compounds and amine compound are weighed, is dissolved with toluene；Add Pd (dppf) Cl2, sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95~100 DEG C of reaction temperature, reaction 10~ 24 hours, cooling, filtering reacting solution, filtrate revolving crossed silicagel column, obtains target product；The 9-Fluorenone bromine compounds with The molar ratio of amine compound is 1: 1.0~1.5；Pd(dppf)Cl2With the molar ratio of 9-Fluorenone bromine compounds be 0.003~ 0.01: 1, the molar ratio of sodium tert-butoxide and 9-Fluorenone bromine compounds is 1.0~3.0: 1.
A method of the compound being prepared, reaction equation is：
Reaction process is：9-Fluorenone boronic acid compounds and R1-Ar-Br are weighed, the toluene ethyl alcohol for being 2: 1 with volume ratio mixes Solvent dissolves；Add Na2CO3Aqueous solution, Pd (PPh3)4；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in anti- 95~100 DEG C of temperature is answered, is reacted 10~24 hours, cooling, filtering reacting solution, filtrate revolving crosses silicagel column, obtains target production Object；The molar ratio of the 9-Fluorenone boronic acid compounds and R1-Ar-Br are 1: 1.0~1.5；Pd(PPh3)4With 9-Fluorenone boration The molar ratio for closing object is 0.003~0.01: 1, Na2CO3Molar ratio with 9-Fluorenone boronic acid compounds is 1.0~3.0: 1.
A kind of luminescent device including the compound, the compound is as emitting layer material, for making OLED devices Part.
The present invention is beneficial to be had technical effect that：
The compounds of this invention is connected with aromatic heterocycle group using monosubstituted base -9-Fluorenone as parent nucleus, to destroy molecule Crystallinity avoids intermolecular aggtegation, the film forming having had；It is mostly rigid radical in molecule, improves the heat of material Stability；With good photoelectric characteristic, suitable HOMO and lumo energy, the compounds of this invention HOMO and lumo energy electronics Cloud efficiently separates the S1-T1 state energy gaps, it can be achieved that smaller, can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduces Efficiency roll-off under high current density reduces device voltage, improves device performance.
Compound of the present invention can be applied to the making of OLED luminescent devices, and can obtain good device performance, The compound as OLED luminescent devices emitting layer material in use, device current efficiency, power efficiency and outer quantum Efficiency is greatly improved；Compound of the present invention has good application effect in OLED luminescent devices, has good Good industrialization prospect.
Description of the drawings
Fig. 1 is the OLED structure schematic diagram using the compounds of this invention.
In figure：1, it is transparent substrate layer；2, it is ito anode layer；3, it is hole injection layer；4, be hole transport electronics resistance Barrier；5, it is luminescent layer；6, it is hole barrier/electron transfer layer；7, it is electron injecting layer；8, it is cathode reflection electrode layer.
Specific implementation mode
With reference to the accompanying drawings and examples, the present invention is specifically described.
1 compound 26 of embodiment
The bromo- 9-Fluorenones of 0.01mol (2.59g) 1- are added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml, 0.015mol (5.23g) compounds M1,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g)Pd(dppf)Cl2, 180ml toluene is heated to reflux 10 hours, samples contact plate, the reaction was complete；Natural cooling, filtering, filtrate revolving carry out filtrate Column chromatography obtains target product, purity 99.2%, yield 82%；
Elemental analysis structure (molecular formula C37H22N2O2)：Theoretical value C, 84.39；H, 4.21；N, 5.32；O, 6.08；It surveys Examination 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.
2 compound 44 of embodiment
The preparation method is the same as that of Example 1 for compound 44, the difference is that replacing M1 using raw material M2；
Elemental 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.
3 compound 56 of embodiment
The preparation method is the same as that of Example 1 for compound 56, the difference is that replacing M1 using raw material M3；
Elemental analysis structure (molecular formula C31H17NO3)：Theoretical value C, 82.47；H, 3.80；N, 3.10；O, 10.63；It surveys Examination 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.
4 compound 58 of embodiment
The bromo- 9-Fluorenones of 0.01mol (2.59g) 2- are added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml, 0.015mol (6.59g) compounds M4,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g)Pd(dppf)Cl2, 180ml toluene is heated to reflux 9 hours, samples contact plate, the reaction was complete；Filtrate is carried out column by natural cooling, filtering, filtrate revolving Chromatography, obtains target product, purity 98.9%, yield 78%；
Elemental analysis structure (molecular formula C43H27N3O2)：Theoretical value C, 83.61；H, 4.41；N, 6.80；O, 5.18；It surveys Examination 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.
5 compound 63 of embodiment
The bromo- 9-Fluorenones of 0.01mo1 (2.59g) 3- are added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml, 0.015mol (6.09g) compounds M5,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g)Pd(dppf)Cl2, 180ml toluene is heated to reflux 12 hours, samples contact plate, the reaction was complete；Natural cooling, filtering, filtrate revolving carry out filtrate Column chromatography obtains target product, purity 99.4%, yield 77%；
Elemental 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.
6 compound 67 of embodiment
The preparation method of compound 67 is with embodiment 5, the difference is that replacing M5 using raw material M6；
Elemental 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.
7 compound 82 of embodiment
The preparation method is the same as that of Example 1 for compound 82, the difference is that replacing M1 using raw material M7；
Elemental 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.
8 compound 86 of embodiment
The preparation method is the same as that of Example 1 for compound 86, the difference is that replacing M1 using raw material M8；
Elemental 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.
9 compound 89 of embodiment
The preparation method is the same as that of Example 1 for compound 89, the difference is that replacing M1 using raw material M9；
Elemental analysis structure (molecular formula C49H29N3O3)：Theoretical value C, 83.15；H, 4.13；N, 5.94；O, 6.78；It surveys Examination 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.
10 compound 92 of embodiment
The bromo- 9-Fluorenones of 0.01mol (2.59g) 4- are added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml, 0.015mol (7.72g) compounds M10,0.03mol (2.88g) sodium tert-butoxide, 10-4mol(0.073g)Pd(dppf)C12, 180ml toluene is heated to reflux 14 hours, samples contact plate, the reaction was complete；Natural cooling, filtering, filtrate revolving carry out filtrate Column chromatography obtains target product, purity 98.5%, yield 73%；
Elemental 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.
11 compound 95 of embodiment
The preparation method is the same as that of Example 1 for compound 95, the difference is that replacing M1 using raw material M11；
Elemental 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.
12 compound 96 of embodiment
The preparation method is the same as that of Example 1 for compound 96, the difference is that replacing M1 using raw material M12；
Elemental 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.
13 compound 99 of embodiment
The preparation method is the same as that of Example 10 for compound 99, the difference is that replacing M10 using raw material M13；
Elemental 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.
14 compound 128 of embodiment
The preparation method is the same as that of Example 1 for compound 128, the difference is that replacing M1 using raw material M14；
Elemental 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.
15 compound 143 of embodiment
The preparation method of compound 143 is with embodiment 4, the difference is that replacing M4 using raw material M15；
Elemental analysis structure (molecular formula C44H30N2O2)：Theoretical value C, 85.41；H, 4.89；N, 4.53；O, 5.17；It surveys Examination 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.
16 compound 148 of embodiment
0.01mol (2.68g) 1- boric acid -9-Fluorenone is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250mL, 0.015mol (7.45g) compound M16 dissolves (180ml toluene, 90ml ethyl alcohol) with mixed solvent, 0.03mol is then added Na2CO3Aqueous solution (2M), leads to nitrogen gas stirring 1 hour, and 0.0001mol Pd (PPh are then added3)4, it is small to be heated to reflux 10-24 When, contact plate is sampled, the reaction was complete.Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, HPLC purity 98.5%, yield 66.00%.
Elemental 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 be used as emitting layer material, be carried out to the compounds of this invention 118, current material CBP Hot property, luminescent spectrum and HOMO energy levels are tested, and testing result is as shown in table 1.
Table 1
Compound Tg(℃) Td(℃) λPL(nm) Φf HOMO energy levels (ev)
Compound 118 132 385 503 61.2 -5.79
Material C BP 113 353 369 26.1 -5.9
Note：Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi companies DSC204F1 differential scanning calorimetries Instrument) it measures, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in Japanese Shimadzu public affairs It is measured on the TGA-50H thermogravimetric analyzers of department, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, General health SR-3 spectroradiometers are opened up using Japan to measure；Φ f are that solid powder fluorescence quantum efficiency (utilizes U.S.'s marine optics Maya2000Pro fiber spectrometers, Lan Fei companies of the U.S. C-701 integrating spheres and marine optics LLS-LED light sources composition Solid fluorescence quantum efficiency test system, reference literature Adv.Mater.1997 are tested, 9,230-232 method is measured)； Highest occupied molecular orbital HOMO energy levels are measured by photoelectron emissions spectrometer (AC-2 type PESA), are tested as atmospheric environment.
By upper table data it is found that the compounds of this invention has suitable HOMO energy levels and higher thermal stability, it is suitble to Material of main part as luminescent layer；Meanwhile the compounds of this invention has suitable luminescent spectrum, higher Φ f so that application is originally Invention compound gets a promotion as the OLED device efficiency of dopant material and service life.
Below by way of device embodiments 1~16 and device comparative example 1 compound that the present invention will be described in detail synthesizes in device The middle application effect as emitting layer material.Device embodiments 2~16, device comparative example 1 and device embodiments 1 of the present invention Manufacture craft compared to the device is identical, and uses identical baseplate material and electrode material, electrode material Film thickness be also consistent, except that in device luminous layer main body and dopant material convert.Obtained device knot Structure composition is as shown in table 2；The test result of obtained device is shown in Table 3.
Device embodiments 1
2/ hole injection layer of ito anode layer, 3 (thickness：10nm；Material：Molybdenum trioxide MoO3)/hole transport/electronic blocking 4 (thickness of layer：140nm；Material：NPB)/5 (thickness of luminescent layer：30nm；Material：Compound 26 and DCJTB are according to 100：3 weight Amount proportioning blending is constituted)/6 (thickness of hole barrier/electron transfer layer：40nm；Material：TPBI)/LiF/A1
Specific preparation process is as follows：
Ito anode layer 2 (film thickness 150nm) is washed, i.e., carry out successively neutralizing treatment, pure water, it is dry after again Ultraviolet-ozone washing is carried out to remove the organic residue on the transparent surfaces ITO.
On the ito anode layer 2 after having carried out above-mentioned washing, using vacuum deposition apparatus, vapor deposition film thickness is 10nm's Molybdenum trioxide MoO3It is used as hole injection layer 3, the NPB of 140nm thickness is and then deposited as hole transport/electronic blocking Layer 4.
After above-mentioned hole transport/electronic blocking layer material vapor deposition, the luminescent layer 5 of OLED luminescent devices is made, is used The compounds of this invention 26 is used as material of main part, and DCJTB is as dopant material, and the doping mass ratio of dopant material is 3%, luminescent layer Film thickness is 30nm.
After above-mentioned luminescent layer, it is TPBI to continue vacuum evaporation hole barrier/electron transport layer materials, the material it is true Sky vapor deposition film thickness is 40nm, this layer is hole barrier/electron transfer layer 6.
On hole barrier/electron transfer layer 6, by vacuum deposition apparatus, the lithium fluoride (LiF) that film thickness is 1nm is made Layer, this layer are electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (A1) layer that film thickness is 80nm is made, this layer is cathode Reflection electrode layer 8 uses.
After completing OLED luminescent devices as described above, anode and cathode is connected with well known driving circuit, is surveyed The I-E characteristic of the current efficiency of metering device, luminescent spectrum and device.Obtained device structure composition is as shown in table 2；Institute The test result for obtaining device is shown in Table 3.
Table 2
Table 3
Note：For device detection performance using comparative example 1 as reference, 1 device property indices of comparative example are set as 1.0.Compare The current efficiency of example 1 is 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 make using with OLED luminescent devices, and compared with Example 1 is compared, and no matter material of the present invention is as luminescent layer material of main part or dopant material, the effect of obtained OLED luminescent devices Rate and startup voltage obtain larger change than known OLED material, and the efficiency roll-off especially under device high current density obtains Improve.It is of the present invention with TADF elastomeric materials in OLED luminescent devices with good application effect, have good Industrialization prospect.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.

Claims (6)

1. a kind of compound based on monosubstituted base -9-Fluorenone, it is characterised in that the structural formula general formula such as general formula (1) of the compound It is shown：
In general formula (1), R uses-Ar-R1Or-R1It indicates；Wherein, Ar is expressed as phenyl, C1-10Linear or branched alkyl group substitution Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl or benzo phenanthryl；
R1It is indicated using general formula (2)：
In general formula (2), X1For oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of linear or branched alkyl group substitution, aryl substitution Alkylidene, alkyl or aryl substitution amido in one kind；
R2、R3Structure shown in selection hydrogen independently, general formula (3) or general formula (4)：
In general formula (3), a isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight chain Or branched alkyl substitution alkylidene, aryl substitution alkylidene, aryl substitution amido in one kind；
General formula (3), general formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4 Key connection.
2. compound according to claim 1, it is characterised in that R in the compound based on monosubstituted base -9-Fluorenone1 It is expressed as group：
Any one of.
3. compound according to claim 1, it is characterised in that the tool of the compound based on monosubstituted base -9-Fluorenone Body structural formula is：
Any one of.
4. a kind of method preparing any one of claims 1 to 3 compound, it is characterised in that reaction equation is：
Reaction process is：9-Fluorenone bromine compounds and amine compound are weighed, is dissolved with toluene；Add Pd (dppf) Cl2, uncle Sodium butoxide；Under an inert atmosphere, the mixed solution of above-mentioned reactant is reacted 10~24 hours in 95~100 DEG C of reaction temperature, Cooling, filtering reacting solution, filtrate revolving, crosses silicagel column, obtains target product；The 9-Fluorenone bromine compounds and amido chemical combination The molar ratio of object is 1:1.0~1.5；Pd(dppf)Cl2Molar ratio with 9-Fluorenone bromine compounds is 0.003~0.01:1, uncle The molar ratio of sodium butoxide and 9-Fluorenone bromine compounds is 1.0~3.0:1.
5. a kind of method preparing any one of claims 1 to 3 compound, it is characterised in that reaction equation is：
Reaction process is：9-Fluorenone boronic acid compounds and R1-Ar-Br are weighed, is 2 with volume ratio:1 toluene alcohol mixed solvent Dissolving；Add Na2CO3Aqueous solution, Pd (PPh3)4；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in reaction temperature 95~100 DEG C of degree reacts 10~24 hours, cooling, filtering reacting solution, and filtrate revolving crosses silicagel column, obtains target product； The molar ratio of the 9-Fluorenone boronic acid compounds and R1-Ar-Br are 1:1.0~1.5；Pd(PPh3)4With 9-Fluorenone boronic acid compounds Molar ratio be 0.003~0.01:1, Na2CO3Molar ratio with 9-Fluorenone boronic acid compounds is 1.0~3.0:1.
6. a kind of luminescent device including any one of the Claims 1 to 5 compound, it is characterised in that the compound conduct Emitting layer material, for making OLED device.
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