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CN106397398A - Organic compound and application thereof to organic electroluminescent devices - Google Patents

Organic compound and application thereof to organic electroluminescent devices Download PDF

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Publication number
CN106397398A
CN106397398A CN201610796598.9A CN201610796598A CN106397398A CN 106397398 A CN106397398 A CN 106397398A CN 201610796598 A CN201610796598 A CN 201610796598A CN 106397398 A CN106397398 A CN 106397398A
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yield
compound
synthesis
organic compound
unsubstituted
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Inventor
吕瑶
贾学艺
冯玉
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Green People's Science And Technology Ltd Co In Beijing
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Green People's Science And Technology Ltd Co In Beijing
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Priority to CN201610796598.9A priority Critical patent/CN106397398A/en
Publication of CN106397398A publication Critical patent/CN106397398A/en
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Abstract

The invention provides an organic compound. The structure of the compound is shown in formula I or II, wherein X1, X2, X3 and X4 are single bond, oxygen, sulfur, nitrogen-containing group or carbonaceous group independently; R1-R10 are hydrogen, C1-C10 alkyl group, C6-C40 aromatic base or C6-C40 heterocyclic aromatic base independently; or two of R1-R10 which are randomly adjacent and carbon atoms which are bonded to the two form a ring structure together. The invention also provides an application of the organic compound to electronic devices. The organic compound ensures good power efficiency and long lifetime, and low working voltage of OLED.

Description

A kind of organic compound and its application in organic electroluminescence device
Technical field
The present invention relates to a kind of organic compound and its application in organic electroluminescence device.
Background technology
Organo-metallic compound can be done up to four times of energy as phosphorescent emitter and power efficiency increases.So And, phosphorescent OLED still needs and improves, such as in efficiency, running voltage and the improvement in terms of the life-span.Can not be only by three lines State luminous body determines the performance of phosphorescent OLED.Particularly, the other materials of use, such as host material, hole barrier materials, electricity Sub- transmission material, hole mobile material and electronics or exciton-blocking material, equally have the meaning of particular importance herein.Therefore, The improvement of these materials equally can lead to significantly improving of OLED performance.Purpose herein particularly develops following chemical combination Thing, can be realized in for example luminous effectiveness of performance of one or more reference points, life-span or color coordinates using described compound The improvement of the property of electronic device.
Content of the invention
First purpose of the present invention is to provide a kind of organic compound.
Second object of the present invention is to provide application in organic electroluminescence device for the described organic compound.
In the first aspect, the invention provides a kind of organic compound, as shown in Formulas I or II：
Wherein, X1、X2、X3And X4Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group；R1、R2、R3、R4、R5、R6、 R7、R8、R9And R10Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、 R7、R8、R9And R10Form ring structure together with two carbon atoms being bonded with them of middle arbitrary neighborhood.
According to certain embodiments of the present invention, the structure of described organic compound such as formula III, IV, V, VI or VII institute Show：
Wherein, X1、X2、X3、X4、X5、X6And X7Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group, R1、R2、R3、 R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkane Base, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、 R16、R17、R18、R19、R20、R21And R22Form ring structure together with two carbon atoms being bonded with them of middle arbitrary neighborhood.
According to certain embodiments of the present invention, the structure of described organic compound is as shown in formula G1, G2 or G3：
Wherein, X1、X2、X3、X4、X5、X6And X7Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group；R1、R2、R3、 R4、R5、R6、R7、R8、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1-R22Formed together with two carbon atoms being bonded with them of middle arbitrary neighborhood Ring structure.
According to certain embodiments of the present invention, the structure of described organic compound for example formula G4, G5, G6, G7, G8, G9, Shown in G10, G11 or G12,
Wherein, R3Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group；R1、R2、R3、R4、R5、R6、R7、R8、R9、 R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、 R21And R22Form ring structure together with two carbon atoms being bonded with them of middle arbitrary neighborhood.
According to certain embodiments of the present invention, the structure of described compound for example formula G13, G14, G15, G16, G17, G18, Shown in G19, G20, G21 or G22：
Wherein, in formula G13, G14, G15, G16, G17 and G18, X1、X2、X3And X4Stand alone as singly-bound, N-R3Or O, R3For Hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、 R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base； Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22In any phase Two adjacent carbon atoms being bonded with them form ring structure together；
In formula G19, G20, G21 and G22, X3And X4Each stand alone as singly-bound, O, S, N-R3Or CR1R2；R1、R2、R3、R4、 R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、 R17、R18、R19、R20、R21And R22Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together；R1、R2、R3、 R4And R5It is independently selected from hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base, R4And R5Exclude following group：
According to the preferred embodiment of the present invention, the structure of described compound is as shown in formula G23, G24 or G25：
X3And X4It is independently each singly-bound, O, S, N-R3Or CR1R2；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、 R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Miscellaneous Aromatic radical；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22 Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together；R1、R2、R4And R5Independently selected from following base Group：
Wherein asterisk represents the junction point with other parts.
According to the preferred embodiment of the present invention, R19-R22It is independently selected from C1-C10Alkyl.
According to the preferred embodiment of the present invention, X1、X2、X3、X4、X5、X6And X7Stand alone as CR1R2Or NR3, wherein R1、R2 And R3It is independently selected from hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1And R2Former with their connected carbon Son forms ring structure together.
In the present invention, described ring structure is preferably selected from substituted or unsubstituted furan nucleuss, substituted or unsubstituted thiophene Ring, substituted or unsubstituted pyrrole ring, substituted or unsubstituted pyranoid ring, substituted or unsubstituted pyrazine ring, replacement or do not take The phenyl ring in generation, substituted or unsubstituted cyclohexyl biphenyl, substituted or unsubstituted benzofuran ring, substituted or unsubstituted benzothiophene Ring, substituted or unsubstituted .alpha.-5:6-benzopyran ring, substituted or unsubstituted indole ring, substituted or unsubstituted fluorenes ring, replacement or not Naphthalene nucleus, substituted or unsubstituted indenes ring, substituted or unsubstituted acridine ring and the substituted or unsubstituted anthracene nucleus replacing.
In the present invention, described C1-C10Alkyl includes C1、C2、C3、C4、C5、C6、C7、C8、C9Or C10Alkyl group.Preferably Example include but is not limited to methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group, n-pentyl, sec-amyl or N-hexyl.
Preferably, R1、R2Or R3Selected from following group：Phenyl, xenyl,
Wherein asterisk represents the junction point with other parts.
In second aspect, present invention also offers above-mentioned organic compound is in electronic device particularly organic electroluminescent Application in device.
According to the preferred embodiment of the present invention, described organic compound is used as fluorescent illuminant, phosphorescent emitter or prolongs Fluorescent illuminant late.
According to the preferred embodiment of the present invention, described organic compound is used for the substrate material of fluorescence or phosphorescent emitter Material.
According to the preferred embodiment of the present invention, for electron transfer layer, hole blocking layer, electronic barrier layer, exciton resistance In barrier and/or hole transmission layer.
The present invention has following beneficial technique effect：Extraordinary power efficiency is had using the OLED of described compound Very long life-span, and low running voltage.
Specific embodiment
The present invention is described in detail with reference to embodiments, but the present invention is not limited by following embodiments.
The synthesis of synthetic example 1. compound 102
The synthesis of 102-1：By 50g (0.272mol) 4- ADP and furan, 87g (0.408mol) o-bromobenzoic acid first Ester and 32g (0.326mol) sodium tert-butoxide are dissolved in 500ml toluene successively, under nitrogen protection, add 5.46ml (0.0027mol) tri-butyl phosphine and 2.46g (0.0027mol) Pd2(dba)3, stir and be warming up to 90 DEG C, react about 2 hours.Will Gained reactant liquor crosses diatom soil hopper, and filtrate makes solvent evaporate by Rotary Evaporators, obtains 55g102-1 (yield：65%).
The synthesis of 102-2：55g102-1 (0.176mol) is dissolved in the anhydrous THF of 500ml, is cooled to -78 DEG C, add 8.38g (0.352mol) lithium methide, stirs 2h, is warmed to room temperature, and after stirring 1h, pours in trash ice, reactant liquor crosses silica gel funnel, filter Liquid is extracted with water, and organic faciess make solvent evaporate by revolving, and column chromatography obtains 29g102-2 (yield：55%).
The synthesis of 102-3：29g102-2 (0.096mol) is added in 550ml sulphuric acid, heated and stirred extremely flows back, during reaction Between 2h, reactant liquor is poured in trash ice, reactant liquor crosses diatom soil hopper, filtrate water extracts, organic faciess make solvent by revolving Evaporation, column chromatography obtains 11.9g102-3 (yield 56%).
The synthesis of 102-4：By 8.86g (0.026mol) 4,5- dibromo dibenzothiophenes, 16.0g (0.053mol) 102-3 It is dissolved in successively in 90ml toluene with 6.0g (0.063mol) sodium tert-butoxide, under nitrogen protection, add 1.07ml (0.00053mol) tri-butyl phosphine and 0.48g (0.00053mol) Pd2(dba)3, stir and be warming up to 90 DEG C, react about 2 hours. Gained reactant liquor is crossed diatom soil hopper, organic faciess are made solvent evaporate by Rotary Evaporators, obtain 14.1g102-4 and (produce Rate：70%).
The synthesis of compound 102：140mlMCPBA is slowly added to 140mlAcOH and 14.1g102-4 (0.018mol) mix In compound, it is stirred at room temperature 24 hours.After reaction terminates, it is poured into water, extraction is filtered, organic faciess are dried, and solid is added ethanol Recrystallization, obtains 7.27g (yield after being dried：50%).Value of calculation C54H38N2O4S:LC-MS:810.96+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (12H, s), 6.53～6.55 (2H, d), 6.67～6.75 (6H, m), 7.02～ 7.07 (4H, m), 7.13～7.19 (4H, m), 7.31～7.40 (4H, m), 7.62～7.72 (4H, m), 7.87～7.89 (2H, d)
The synthesis of synthetic example 2. compound 104
The synthetic method of 104-1 is with the synthesis of 102-1, yield：60%；The synthetic method of 104-2 with the synthesis of 102-2, Yield：50%；The synthetic method of 104-3 is with the synthesis of 102-3, yield 63%；The synthetic method of 104-4 with the synthesis of 102-4, Yield：73%；The synthetic method of compound 104 is with the synthesis of compound 102, yield：55%.Value of calculation C54H40N2O4S:LC- MS:812.97+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (12H, s), 6.30～6.33 (2H, d), 6.51～ 6.55 (2H, m), 6.71～6.74 (2H, m), 6.79～6.81 (4H, m), 7.01～7.06 (4H, m), 7.21～7.25 (2H, M), 7.30～7.40 (4H, m), 7.56～7.60 (4H, m), 7.64～7.70 (2H, m), 7.87～7.90 (2H, m).
The synthesis of synthetic example 3. compound 109
The same 102-1 of synthesis of 109-1, yield：60%；The same 102-1 of synthesis of compound 109, yield：65%.Value of calculation C41H30N2O:LC-MS:594.70+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 6.30～6.33 (1H, D), 6.51～6.55 (1H, m), 6.61～6.65 (2H, d), 6.71～6.74 (1H, m), 7.01～7.06 (2H, m), 7.21～ 7.25 (1H, m), 7.30～7.42 (6H, m), 7.50～7.55 (4H, m), 7.64～7.66 (1H, d), 7.87～7.90 (1H, M), 8.25～8.30 (4H, m).
The synthesis of synthetic example 4. compound 108
The synthetic method of compound 108 is with compound 109, yield：63%.Value of calculation C42H30N4O:LC-MS:606.71+ 1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 6.30～6.33 (1H, d), 6.51～6.55 (1H, d), 6.67～6.75 (3H, m), 7.01～7.06 (2H, m), 7.21～7.25 (1H, m), 7.30～7.42 (4H, m), 7.50～ 7.55 (4H, m), 7.64～7.66 (1H, m), 7.87～7.90 (3H, m), 8.25～8.30 (4H, m).
The synthesis of synthetic example 5. compound 57
The synthetic method of 57-1 is with the synthesis of 102-1, yield：65%；The synthetic method of 57-2, with the synthesis of 102-2, is received Rate：57%；The synthetic method of 57-3 is with the synthesis of 102-3, yield 60%；The synthetic method of compound 57 with the synthesis of 102-4, Yield：75%.Value of calculation C46H32N4S:LC-MS:672.84+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, S), 6.52～6.60 (2H, m), 6.71～6.79 (2H, m), 6.89 (1H, s), 7.01～7.06 (2H, m), 7.40～7.55 (8H, m), 7.62～7.67 (3H, m), 7.77～7.80 (2H, m), 8.14～8.17 (1H, m), 8.25～8.30 (4H, m), 8.52～8.55 (1H, m)
The synthesis of synthetic example 6. compound 60
The synthetic method of compound 60 is with compound 109, yield：67%.Value of calculation C47H33NS:LC-MS:643.84+1.
1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 2.61～2.65 (1H, d), 3.65～3.67 (1H, d), 5.79～5.82 (1H, m), 6.07～6.10 (1H, m), 6.53～6.57 (2H, m), 6.71～6.70 (4H, m), 7.01～7.06 (3H, m), 7.40～7.55 (3H, m), 7.65～7.71 (3H, m), 7.77～7.84 (4H, m), 8.14～ 8.17 (1H, m), 8.52～8.55 (1H, m).
The synthesis of synthetic example 7. compound 36
The synthetic method of 36-1 is with the synthesis of 102-1, yield：50%；The synthetic method of 36-2, with the synthesis of 102-2, is received Rate：52%；The synthetic method of 36-3 is with the synthesis of 102-3, yield 63%；The synthetic method of 36-4, with the synthesis of 102-4, is produced Rate：65%；The same 102-1 of synthesis of 36-5, yield：75%；The synthetic method of 36-6 is with the synthesis of 102-2, yield：50%；36- 7 synthetic method is with the synthesis of 102-3, yield 60%；The synthetic method of compound 36 is with the synthesis of 102-4, yield：75%； Value of calculation C54H43N3:LC-MS:733.94+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (12H, s), 5.82～ 5.84 (1H, d), 5.91～5.93 (1H, d), 6.61～6.57 (4H, m), 6.71～6.74 (2H, m), 6.87～6.90 (2H, M), 7.01～7.06 (4H, m), 7.27～7.30 (1H, m), 7.40～7.65 (15H, m), 8.11～8.13 (1H, d).
The synthesis of synthetic example 8. compound 39
The synthesis of 39-1：Biphenyl -4- base (2- bromophenyl) methyl ketone (50g, 0.149mol) is added in 500mlTHF Afterwards reaction is cooled to after 0 degree about not higher than 0 degree of Deca phenyl-magnesium-bromide (3M/L, 50ml) keeping temperature, after will react oneself After being so warming up to room temperature reaction 3 hours, reaction is cooled to addition acetic acid after Deca saturated aqueous ammonium chloride after 10 degree about The crude product obtaining is crossed column purification after after extracting 3 times being evaporated organic faciess and is obtained 39-1,43g, purity 98.5%, yield by ethyl ester 70%.
The synthesis of 39-2：39-1, o-phenol (6g, 0.052mol) are added in THF and for reaction to be cooled to 0 degree of left side The right side, is dividedly in some parts NaH (3g, 0.104mol), and reaction is dividedly in some parts compound 2 after 1 hour and is dividedly in some parts, and keeping temperature is not higher than After 0 degree is reacted 3 hours, it is divided into the crude product chromatography obtaining after organic faciess are spin-dried for after Deca water in reacting and obtains 39-2, 16g, yield 40%.
The synthesis of compound 39：After compound 39 (16g, 0.021mol) is added in 200ml concentrated sulphuric acid, reaction is risen Temperature reacts 16+ hours to 100 degree, after reaction be cooled to after room temperature pour in ice, after be filtrated to get solid re crystallization from toluene Obtain compound 5,11g, yield 75%.Value of calculation C56H38O2:LC-MS:742.90+1.1H-NMR (400MHz, CDCl3) (ppm) δ=6.10～6.12 (2H, d), 6.78～6.80 (4H, m), 7.18～7.24 (8H, m), 7.25～7.27 (2H, m), 7.27～7.30 (2H, m), 7.31～7.35 (8H, m), 7.50～7.54 (8H, m).
The synthesis of synthetic example 9. compound 62
The same 102-1 of synthesis of 62-1, yield：67%；
The synthesis of 62-2：52g (0.136mol) 62-1,8.7g (0.136mol) butyl lithium is added in 250ml ether, Under nitrogen protection, it is cooled to -78 DEG C, continues 1.5 hours, 24.5g (0.136mol) Fluorenone is added in 120ml ether, Deca To reactant liquor, sustained response 2h, reactant liquor crosses diatom soil hopper, and filtrate water extracts, and organic faciess make solvent steam by revolving Send out, column chromatography obtains 28.4g compound 9-2 (yield:50%)
The synthesis of 62-3：28.4g (0.068mol) 62-2 is dissolved in 300ml sulphuric acid, heated and stirred is to backflow, response time 2h, reactant liquor is poured in trash ice, and reactant liquor crosses diatom soil hopper, and filtrate water extracts, and organic faciess make solvent steam by revolving Send out, column chromatography obtains 17.5g62-3 (yield:62%).
The synthesis of 62-4：17.5g (0.0421mol) 62-3 is dissolved in 90mlTHF, 14.5g (0.082mol) NBS is dissolved in In 80mlTHF solvent, then NBS solution is entered in substrate solution with the speed Deca of 3 to 5 per second, stirring.Under room temperature, Deca After complete, reaction also stops therewith.Deca 60ml water in reactant liquor, crystallize, sucking filtration, obtain 9-4 (yield in the middle of 26.5g: 80%).
The synthesis of 62-5：By 16.5g (0.033mol) 62-4,4.7g (0.039mol) phenylboric acid and 6.66g (0.049mol) potassium carbonate sequentially adds in the mixed solution of 165ml toluene, 80ml ethanol and 40ml water, under nitrogen protection, plus Enter 0.37g (0.00033mol) four (triphenyl phosphorus palladium), heated and stirred, to flowing back, is reacted 3 hours.Reactant liquor is crossed kieselguhr leakage Bucket, filtrate water extracts, and organic faciess make solvent evaporate by revolving, obtain 11.9g62-, 5 (yields:75%).
The same 102-4 of synthesis of compound 62, yield：63%.Value of calculation C52H35NO:LC-MS:689.84+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 6.94 (1H, S), 7.04～7.07 (2H, m), 7.16～7.40 (12H, M), 7.77 (1H, s), 7.85～7.88 (4H, m), 7.95 (1H, s), 7.98～8.00 (1H, m), 8.18～8.19 (1H, m).
The synthesis of synthetic example 10. compound 63
The synthesis of 63-1：40g (0.112mol) 2- (4- bromophenyl) -5- phenyl nitro benzene is dissolved in 400ml neighbour's dichloro In benzene, add 146g (0.56mol) triphenyl phosphorus, heat temperature raising stirs to 200 degree.After the completion of reaction, adjacent dichloro is distilled off Benzene, solid is extracted using dichloromethane, and organic layer is dried using MgSO4, then divides produced organic layer by silicagel column From, recrystallization, obtain 25.2g63-1 (yield 70%).
The same 102-1 of synthetic method of 63-2, yield：63%；The same 9-2 of synthetic method of 63-3, yield:50%；63-4's The same 9-3 of synthetic method, yield：52%；The synthetic method of compound 63 is with compound 62, yield：53%.Value of calculation C52H35NO: LC-MS:689.84+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 6.94 (1H, S), 7.04～7.07 (2H, m), 7.16～7.40 (15H, m), 7.50～7.57 (4H, m), 7.85～7.88 (4H, m), 8.07～8.09 (1H, m), 8.68 (1H, s).
The synthesis of synthetic example 11. compound 98
The same 62-5 of synthesis of 98-1, yield:68%；The same 62-2 of synthetic method of 98-2, yield:54%；The synthesis of 98-3 The same 62-3 of method, yield:50%；
The same 102-1 of synthetic method of compound 98, yield：57%.Value of calculation C52H35N:LC-MS:673.84+1.
1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 7.04～7.21 (9H, m), 7.23～7.35 (6H, m), 7.40～7.52 (5H, m), 7.60～7.62 (1H, d), 7.74～7.76 (2H, d), 7.87～7.89 (2H, d), 8.05 (1H, s), 8.28～8.31 (1H, m), 8.49～8.52 (1H, m).
The synthesis of synthetic example 12. compound 65
65-3 synthesis is with 102-1 synthesis, yield 80%；65-4 synthesizes same 62-2, yield 85%；65-5 synthesizes same 62-3, Yield 75%；Compound 65 synthesizes same compound 82, yield 60%.Molecular formula:C52H32N4S；LC-MS:744+1.
1H-NMR(400MHzCDCl3)(ppm)δ:8.45(1H,dd),8.28(4H,m),7.87-7.89(5H,m), 7.41-7.52(15H,m),7.01-7.05(4H,m),6.69(3H,m),6.51(1H,dd).
The synthesis of synthetic example 13. compound 69
69-3 synthesizes same 102-1, yield 85%；69-4 synthesizes same 62-2, yield 75%；69-5 synthesizes same 62-3, yield 90%；Compound 69 synthesizes same compound 82, yield 60%.Molecular formula：C53H33N3S LC-MS:743+1
1H-NMR(400MHzCDCl3)(ppm)δ:8.45(1H,d)7.98(1H,d)7.52-7.79(4H,m)7.38- 7.51(21H,m)7.28(3H,m)7.01-7.03(3H,m)6.69(1H,t)6.51(1H,d).
The synthesis of synthetic example 14. compound 71
The synthesis of compound 71 is with compound 82, yield 60%.Molecular formula：C53H31N3S LC-MS:741+1.
NMR:8.93(2H,dd),8.45(1H,d),8.12(2H,dd),7.88-7.98(9H,m),7.38-7.51(12H, m)7.01-7.05(3H,m)6.69(1H,t),6.51(1H,m).
The synthesis of synthetic example 15. compound 144
Compound 144 synthesizes same compound 82, yield 60%.Molecular formula：C45H35NOSi LC-MS:633+1.
NMR:7.89(1H,m),7.66(1H,m)7.32-7.55(17H,m)7.17-7.36(3H,m),7.02-7.05 (2H,m)6.73-6.75(4H,m),6.55(1H,dd),1.72(6H,s).
The synthesis of synthetic example 16. compound 17
Compound 17 synthesizes same compound 82, yield 60%.
Molecular formula：C66H56N2O2 LC-MS:908+1.
NMR:7.89(2H,m),7.68-7.71(6H,m),7.32-7.38(4H,m),7.17(2H,m),7.02-7.05 (6H,m)6.73-6.75(4H,m),1.72(12H,s)1.48(18H,s).
The synthesis of synthetic example 17. compound 19
19-3 synthesizes same 102-1, yield 84.5%；The synthesis of 19-4 is with the synthesis of 102-2, yield：85%；The conjunction of 19-5 The same 102-3 of one-tenth method, yield 90%；The synthesis of compound 19 is with compound 82, yield：60%.
Molecular formula：C70H48N2O2 LC-MS:948+1.
NMR:7.89(2H,m),7.71-7.75(8H,m),7.51(4H,m)7.32-7.41(8H,m)7.17(2H,dd), 7.01-7.08(8H)6.75-6.79(4H,m)1.72(12H,s).
The synthesis of synthetic example 18. compound 148
148-3 synthesizes same 102-1, yield 65%；The synthesis of 148-4 is with the synthesis of 102-2, yield：85%；148-5's The same 102-3 of synthetic method, yield 80%；The synthesis of compound 148 is with compound 82, yield：60%.
Molecular formula：C70H44N2O4 LC-MS:976+1 NMR:7.89 (4H, m), 7.66-7.75 (10H, m)
7.32-7.38(8H,m),7.17(4H,m),7.02(2H,m),6.75(4H,m),1.72(12H,s).
The synthesis of synthetic example 19. compound 15
The same 102-4 of synthesis of compound 15, yield 56%.
Value of calculation：C,83.26；H,4.92；N,3.60；O,4.11；S,4.12；Measured value：C,83.25；H,4.90；N, 3.62；O,4.10；S,4.13.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72～1.73 (12H, s), 6.31～6.33 (2H, d), 6.54～6.56 (2H, m), 6.73～6.74 (2H, m), 6.86～6.87 (2H, m), 7.02～7.05 (4H, m), 7.23～7.24 (2H, d), 7.31～7.40 (6H, m), 7.66～7.67 (2H, m), 7.72～7.73 (2H, d), 7.89～ 7.90 (2H, m).
The synthesis of synthetic example 20. compound 112
112-1 synthesizes same 102-1, yield 66%；112-2 synthesizes same 62-2, yield 51%；112-3 synthesizes same 62-3, receives Rate 85%；Compound 112 synthesizes same 102-4, yield 55%.
Value of calculation：C,88.74；H,4.73；N,1.99；O,4.55；Measured value：C,88.73；H,4.75；N,1.98；O, 4.54.
1H-NMR (400MHz, CDCl3) (ppm) δ=1.72～1.73 (6H, s), 6.58～6.59 (1H, m), 6.75～ 6.76 (1H, d), 6.91～6.92 (2H, s), 7.28～7.32 (5H, m), 7.37～7.39 (5H, m), 7.53～7.56 (5H, M), 7.62～7.66 (3H, m), 7.87～7.89 (5H, m).
The synthesis of synthetic example 21. compound 111
The same 102-4 of compound 111 synthetic method, yield 52%.
Value of calculation：C,88.67；H,4.40；N,2.11；O,4.82；Measured value：C,88.68；H,4.41；N,2.09；O, 4.82
1H-NMR (400MHz, CDCl3) (ppm) δ=6.69～6.70 (2H, d), 6.92～6.93 (2H, s), 7.28～ 7.32 (4H, m), 7.38～7.41 (5H, m), 7.51～7.55 (10H, m), 7.66～7.67 (2H, m), 7.87～7.89 (4H, D) the same 102-4 of 24. compound 115 synthetic method, yield 50%.Value of calculation：C,87.74；H,4.28；N,3.72；O,4.25；Real Measured value：C,87.73；H,4.27；N,3.73；O,4.27.1H-NMR (400MHz, CDCl3) (ppm) δ=6.63～6.64 (2H, D), 6.91～6.93 (2H, s), 7.25～7.29 (4H, m), 7.32～7.33 (3H, m), 7.37～7.39 (6H, m), 7.50～ 7.55 (5H, m), 7.63～7.66 (3H, d), 7.87～7.89 (4H, m), 7.94～7.95 (1H, m), 8.11～8.12 (1H, M), 8.55～8.56 (1H, m).
The synthesis of synthetic example 22. compound 115
The same 1-4 of compound 115 synthetic method, yield 50%.Value of calculation：C,87.74；H,4.28；N,3.72；O,4.25； Measured value：C,87.73；H,4.27；N,3.73；O,4.27.1H-NMR (400MHz, CDCl3) (ppm) δ=6.63～6.64 (2H, d), 6.91～6.93 (2H, s), 7.25～7.29 (4H, m), 7.32～7.33 (3H, m), 7.37～7.39 (6H, m), 7.50～7.55 (5H, m), 7.63～7.66 (3H, d), 7.87～7.89 (4H, m), 7.94～7.95 (1H, m), 8.11～ 8.12 (1H, m), 8.55～8.56 (1H, m).
The synthesis of synthetic example 23. compound 116
116-1 synthesizes same 102-1, yield 71%；116-2 synthesizes same 62-2, yield 51%；116-3 synthesizes same 62-3, receives Rate 85%；Compound 116 synthesizes same 102-4, yield 53%.Value of calculation：C,88.80；H,4.56；N,4.23；O,2.41；Actual measurement Value：C,88.81；H,4.56；N,4.22；O,2.41.1H-NMR (400MHz, CDCl3) (ppm) δ=6.93～6.94 (2H, s), 7.25～7.29 (4H, m), 7.33～7.38 (4H, m), 7.45～7.50 (6H, m), 7.55～7.58 (6H, m), 7.87～ 7.88 (2H, m), 7.94～7.95 (4H, m), 8.55～8.56 (2H, m).
The synthesis of synthetic example 24. compound 117
The same 102-4 of compound 117 synthetic method, yield 52%.
Value of calculation：C,83.26；H,4.92；N,3.60；O,4.11；S,4.12；Measured value：C,83.25；H,4.90；N, 3.62；O,4.10；S,4.13.1H-NMR (400MHz, CDCl3) (ppm) δ=6.93～6.94 (2H, s), 7.25～7.29 (4H, m), 7.33～7.38 (4H, m), 7.40～7.51 (2H, m) .7.51～7.53 (8H, m), 7.55～7.56 (2H, m), 7.68～7.69 (4H, d), 7.79～7.80 (4H, d), 7.87～7.88 (2H, m), 7.94～7.95 (4H, m), 8.55～ 8.56 (2H, m).
The synthesis of synthetic example 25. compound 119
The synthesis of intermediate 119-1：50g (0.126mol) 9- (3- xenyl) 3- bromine carbazole is added to filling 310ml Put into ice salt bath in the flask of acetic acid, 20ml nitric acid added to 200ml acetic acid, by the nitric acid liquid having configured be slowly added dropwise to In the acid solution of 9- (3- xenyl) 3- bromine carbazole, reaction temperature is kept to be less than 40 degree, after completion of dropping, sustained response 1 is little When, reactant liquor is poured in a large amount of frozen water, pH value is adjusted to after alkalescence plus ethyl acetate extraction, organic faciess are made by revolving molten Agent is evaporated, and obtains 25.1g (0.0567mol) intermediate 119-1 (yield：45%)
The synthesis of intermediate 119-2：By the intermediate 119-1 of 25.1g (0.0567mol), 15.6g (0.284mol) 5 works as Amount iron powder, adds to ethanol 50ml, water 140ml, in the mixed solution of concentrated hydrochloric acid 2.5ml, is warmed up to backflow, reacts hour.Instead Should finish, add ethyl acetate extraction, organic faciess make solvent evaporate by revolving, and column chromatography obtains in the middle of 15g (0.0363mol) Body 119-2 (yield:64%)
The synthesis of intermediate 119-3：15g (0.0363mol) intermediate 119-2 is poured into the 75m of 15ml diluting concentrated sulfuric acid L in sulphuric acid, the aqueous solution that Deca 4g sodium nitrite is prepared with 8ml water, then Deca 15g (0.0907mol) potassium iodide, keeping temperature Less than 10 degrees Celsius, react 1h after completion of dropping, reaction system is warming up to backflow, after sustained response 2h, pH value is adjusted to weak Ethyl acetate extraction is added, organic faciess make solvent evaporate by revolving, and column chromatography obtains in the middle of 12.2g (0.0232mol) after alkalescence Body 119-3 (yield:64%)
The synthesis of intermediate 119-4 is with compound 82, yield 49%；119-5 synthesizes same 62-2, yield 58%；119 synthesis Same 62-3, yield 87%.Value of calculation：C,88.16；H,4.61；N,3.37；S,3.86；Measured value：C,88.15；H,4.60；N, 3.36；S,3.89.1H-NMR (400MHz, CDCl3) (ppm) δ=7.22～7.25 (4H, m), 7.28～7.33 (4H, m), 7.38～7.41 (4H, m), 7.46～7.47 (1H, m), 7.51～7.55 (12H, m), 7.68～7.69 (2H, d), 7.79～ 7.80 (4H, m), 7.87～7.88 (2H, m), 7.94～7.95 (2H, m), 8.09～8.10 (1H, m), 8.55～8.56 (2H, m).
The synthesis of synthetic example 26. compound 45
45-1 synthesizes same 62-5, yield 81%；The same 63-1 of synthesis of 45-2, yield 74%.
The synthesis of intermediate 45-3：57.2g (0.1933mol) intermediate 45-2 adds to the anhydrous THF of 350ml, cooling To -78 DEG C, add 140ml (0.28mol) butyl lithium (2M), after stirring 2h, be warmed to room temperature, Deca 9.12g (0.285mol) sulfur After the THF solution stirring 6h of sulphur, it is down to 0 DEG C about the ammonium chloride solution 420ml to Deca saturation in reactant liquor, after stirring 1h, Plus ethyl acetate extracts, decompression is spin-dried for organic faciess and obtains 32.8g (0.1314mol) 39-3 (yield 68%).
45-4 synthesizes with compound 82, yield 55%；45-5 synthesizes same 102-2, yield 57%；45-6 synthesizes same 102-3, Yield 87%；The 45 same 102-4 of synthesis, yield 51%.Value of calculation：C,82.22；H,4.78；N,7.38；S,5.63；Measured value：C, 82.22；H,4.77；N,7.39；S,5.62.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72～1.73 (6H, s), 6.93 ～6.94 (1H, d), 7.10～7.11 (2H, m), 7.25～7.26 (1H, d), 7.34～7.41 (2H, m), 7.51～7.52 (2H, t), 7.67～7.69 (3H, m), 7.79～7.80 (3H, m), 7.94～7.96 (2H, m), 8.05～8.06 (2H, m), 8.16～8.17 (2H, m), 8.54～8.55 (1H, m).
The synthesis of synthetic example 27. compound 46
46-1 synthesizes same 62-5, yield 76%；46-2 synthesizes same 45-2, yield 76%；46-3 synthesizes same 102-1, yield 73%；46-4 synthesizes same 102-2, yield 57%；46-5 synthesizes same 102-3, yield 82%；46-6 synthesizes same 102-4, yield 48%.Value of calculation：C,82.22；H,4.78；N,7.38；S,5.63；Measured value：C,82.22；H,4.77；N,7.39；S,5.62.
1H-NMR (400MHz, CDCl3) (ppm) δ=1.72～1.73 (6H, s), 6.91～6.92 (1H, d), 7.09～ 7.10 (1H, m), 7.23～7.26 (3H, m), 7.40～7.41 (1H, m), 7.51～7.52 (2H, t), 7.58～7.59 (1H, M), 7.63～7.65 (2H, m), 7.79～7.80 (3H, m), 7.94～7.96 (2H, m), 8.05～8.06 (2H, m), 8.16～ 8.17 (2H, m), 8.54～8.55 (1H, m).
The synthesis of synthetic example 28. compound 48
48-1 synthesizes same 102-1, yield 74%；48-2 synthesizes same 102-2, yield 57%；48-3 synthesizes same 102-3, receives Rate 86%；Compound 48 synthesizes same 102-4, yield 56%.Value of calculation：C,85.96；H,5.13；N,8.91；Measured value：C, 85.94；H,5.14；N,8.92.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72～1.73 (6H, s), 6.52～6.55 (2H, m), 6.73～6.74 (1H, m), 7.02～7.05 (2H, m), 7.41～7.45 (2H, m), 7.50～7.51 (4H, m), 7.58～7.63 (4H, d), 7.65～7.67 (3H, m), 7.79～7.84 (4H, m), 8.16～8.17 (2H, m), 8.54～ 8.55 (2H, m).
The synthesis of synthetic example 29. compound 27
27-1 synthesizes same 62-5, yield 45%；27-2 synthesizes same 45-3, yield 69%；27-3 synthesizes with compound 102- 1, yield 60%；27-4 synthesizes same 102-2, yield 57%；The 27 same 102-3 of synthesis, yield 79%.Value of calculation：C,85.41；H, 5.10；N,4.43；S,5.07；Measured value：C,85.40；H,5.11；N,4.42；S,5.07.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72～1.73 (6H, s), 7.10～7.11 (2H, m), 7.29～7.34 (2H, m), 7.41～7.45 (3H, m), 7.50～7.51 (5H, m), 7.58～7.63 (5H, m), 7.69～7.70 (2H, d), 7.77～7.78 (2H, d), 7.87～ 7.88 (1H, m), 8.00～8.01 (1H, d), 8.12～8.13 (2H, m).
The synthesis of synthetic example 30. compound 131
The same 119-3 of synthesis of intermediate 131-1, yield:65%；131-2 synthesizes same 62-5, yield 53%；131-3 synthesizes Same 62-2, yield 55%；The 131 same 62-3 of synthesis, yield 83%.Value of calculation：C,91.70；H,4.79；N,3.51；Measured value：C, 91.73；H,4.77；N,3.50.1H-NMR (400MHz, CDCl3) (ppm) δ=7.16～7.19 (4H, m), 7.25～7.29 (3H, m), 7.33～7.35 (3H, m), 7.41～7.46 (3H, m), 7.50～7.52 (11H, m), 7.63～7.68 (5H, m), 7.75～7.79 (4H, m), 7.94～7.95 (1H, d), 8.09～8.12 (2H, m), 8.32～8.33 (1H, s), 8.55～ 8.56 (1H, d).
The synthesis of synthetic example 31. compound 134
134-1 synthesizes same 62-5, yield:73%；134-2 synthesizes same 63-1, yield:57%；134-3 synthesizes same compound 82, yield:77%；134-4 synthesizes with compound 82, yield 76%；134-5 synthesizes same 62-2, yield:53%；Compound 134 Synthesize same 62-3, yield:66%；Value of calculation C61H38N2：C,91.70；H,4.79；N,3.51；Measured value：C,91.72；H, 4.79；N,3.49；
1H-NMR(400MHZ,CDCl3) (ppm) δ=7.00～7.02 (2H, d), 7.07～7.08 (2H, m), 7.16～ 7.19 (6H, m), 7.20～7.22 (3H, m), 7.26～7.27 (2H, d), 7.30～7.32 (7H, m), 7.34～7.35 (2H, D), 7.40～7.41 (2H, d), 7.48～7.50 (8H, m), 7.55～7.56 (2H, d), 7.72～7.73 (2H, d).
The synthesis of synthetic example 32. compound 132
132-1 synthesizes same 131-1, yield 67%；132-2 synthesizes same 62-5, yield 77%；132-3 synthesizes same 62-2, receives Rate 55%；The 132 same 62-3 of synthesis, yield 63%；Value of calculation C61H38N2S：C,88.16；H,4.61；N,3.37；S,3.86；Actual measurement Value：C,88.13；H,4.62；N,3.37；S,3.88.1H-NMR(400MHZ,CDCl3) (ppm) δ=6.86～6.88 (6H, m), 7.00～7.02 (2H, m), 7.06～7.08 (4H, m), 7.20～7.22 (4H, m), 7.24～7.26 (2H, d), 7.30～ 7.32 (6H, m), 7.40～7.41 (2H, d), 7.48～7.50 (8H, m), 7.55～7.56 (2H, d), 7.65～7.67 (2H, d).
The synthesis of synthetic example 33. compound 76
76-1 synthesizes same 102-1, yield 72%；76-2 synthesizes same 62-2, yield 54%；76-3 synthesizes same 62-3, yield 64%；Compound 76 synthesizes same 102-1, yield 71%；Value of calculation C53H34N4：C,87.58；H,4.71；N,7.71；Measured value： C,87.59；H,4.72；N,7.69；1H-NMR(400MHZ,CDCl3) (ppm) δ=6.33～6.34 (1H, d), 6.48～6.50 (2H, m), 6.55～6.56 (1H, d), 6.79～6.80 (1H, d), 6.90～6.91 (1H, d) 7.00～7.02 (1H, m), 7.08～7.10 (2H, m), 7.21～7.23 (2H, m), 7.26～7.28 (2H, m), 7.29～7.30 (5H, m), 7.31～ 7.32 (4H, m), 7.38～7.40 (3H, m), 7.46～7.48 (4H, m), 7.55～7.56 (3H, m), 7.82～7.84 (2H, m).
The synthesis of synthetic example 34. compound 36
26-1 synthesizes same 102-1, yield 71%；26-2 synthesizes same 102-2, yield 57%；26-3 synthesizes same 102-3, receives Rate 63%；Compound 26 synthesizes same 102-1, yield 69%；Value of calculation C48H35N5：C,84.55；H,5.17；N,10.27；Actual measurement Value：C,84.56；H,5.17；N,10.26；1H-NMR(400MHZ,CDCl3) (ppm) δ=1.66～1.68 (6H, s), 6.38～ 6.42 (2H, m), 6.52～6.54 (2H, m), 6.67～6.68 (1H, s), 6.83～6.84 (2H, m), 6.87～6.88 (1H, D), 7.00～7.02 (1H, m), 7.06～7.08 (2H, m), 7.16～7.17 (1H, s), 7.22～7.24 (2H, m), 7.29～ 7.30 (5H, m), 7.31～7.32 (4H, m), 7.40～7.41 (1H, d), 7.46～7.48 (4H, d), 7.55～7.56 (1H, d).
The synthesis of synthetic example 35. compound 95
95-1 synthesizes same 62-5, yield 73%；By 13.2g (0.035mol) intermediate 95-1,2.12g (0.053mol) hydrogen Sodium oxide adds to heated and stirred in 200ml methanol to backflow, sustained response 2 hours.Reactant liquor is crossed diatom soil hopper, filtrate Extracted with ethyl acetate with water, organic faciess make solvent evaporate by revolving, and column chromatography obtains 10.2g intermediate 95-2 (yield: 80%)；95-3 synthesizes same 84-4, yield 79%；95-4 synthesizes same 62-2, yield 55%；95-5 synthesizes same 62-3, yield 65%；Compound 95 synthesizes same 102-1, yield 70%；Value of calculation C52H33N5：C,85.81；H,4.57；N,9.62；Measured value： C,85.80；H,4.56；N,9.64；1H-NMR(400MHZ,CDCl3) (ppm) δ=6.34～6.36 (2H, m), 6.50～6.51 (2H, m), 6.81～6.82 (4H, m), 7.00～7.02 (1H, m), 7.06～7.08 (1H, m), 7.22～7.24 (3H, m), 7.29～7.30 (5H, m), 7.31～7.32 (4H, m), 7.38～7.40 (2H, d), 7.41～7.44 (2H, m), 7.48～ 7.50 (4H, d), 7.55～7.56 (1H, d), 7.60～7.61 (1H, d), 8.05～8.06 (1H, d).
The synthesis of synthetic example 36. compound 97
97-1 synthesizes same 62-5, yield 76%；97-2 synthesizes same 95-2, yield 80%；97-3 synthesizes same 84-4, yield 79%；97-4 synthesizes same 62-2, yield 61%；97-5 synthesizes same 62-3, yield 67%；Compound 97 synthesizes same 102-1, yield 74%；Value of calculation C45H27N3S：C,84.22；H,4.24；N,6.55；S,5.00；Measured value：C,84.21；H,4.25；N,6.53； S,5.02；1H-NMR(400MHZ,CDCl3) (ppm) δ=6.34～6.36 (2H, d), 6.50～6.51 (2H, m), 6.81～ 6.82 (4H, m), 7.22～7.24 (1H, m), 7.31～7.33 (4H, m), 7.42～7.44 (1H, m), 7.48～7.50 (2H, D), 7.58～7.59 (2H, d), 7.61～7.64 (2H, d), 7.78～7.79 (1H, d), 7.83～7.84 (2H, m), 7.85～ 7.86 (1H, d), 7.96～7.97 (1H, s), 8.01～8.02 (1H, and d) 8.05～8.06 (1H, d).
The synthesis of synthetic example 37. compound 101
Compound 101 synthesizes same 102-1, yield 74%.Value of calculation C47H29N3S：C,84.53；H,4.38；N,6.29；S, 4.80；Measured value：C,84.52；H,4.39；N,6.27；S,4.82；1H-NMR(400MHZ,CDCl3) (ppm) δ=6.34～ 6.36 (2H, d), 6.50～6.51 (2H, m), 6.81～6.82 (4H, m), 6.90～6.92 (1H, s), 7.22～7.24 (3H, M), 7.31～7.33 (6H, m), 7.42～7.44 (1H, m), 7.48～7.50 (4H, m), 7.61～7.64 (2H, d), 7.78～ 7.79 (1H, d), 7.85～7.86 (1H, d), 7.96～7.97 (1H, s), 8.05～8.06 (1H, d).
The synthesis of synthetic example 38. compound 2
2-1 synthesizes same 102-1, yield 71%；2-2 synthesizes same 102-2, yield 58%；2-3 synthesizes same 102-3, yield 68%；2-4 synthesizes same 62-5, yield 80%；The compound same 102-1 of 2-in-1 one-tenth, yield 72%；Value of calculation C54H42N2：C,90.21； H,5.89；N,3.90；Measured value：C,90.21；H,5.88；N,3.91；1H-NMR(400MHZ,CDCl3) (ppm) δ=1.67～ 1.68 (12H, s), 6.44～6.45 (1H, d), 6.50～6.52 (2H, d), 6.67～6.68 (1H, s), 7.00～7.02 (1H, D), 7.05～7.06 (1H, d), 7.08～7.10 (2H, m), 7.22～7.23 (3H, m), 7.28～7.29 (1H, m), 7.30～ 7.31 (6H, m), 7.32～7.33 (2H, m), 7.38～7.40 (2H, m), 7.45～7.46 (2H, m), 7.48～7.49 (2H, M), 7.55～7.56 (2H, d), 7.77～7.78 (1H, s), 7.84～7.85 (1H, d).
The synthesis of synthetic example 39. compound 33
33-1 synthesizes same 62-5, yield 79%；33-2 synthesizes same 102-1, yield 70%；33-3 synthesizes same 102-1, yield 74%；33-4 synthesizes same 102-2, yield 59%；33-5 synthesizes same 102-3, yield 66%；33-6 synthesizes same 102-1, yield 71%；33-7 synthesizes same 102-2, yield 59%；33-8 synthesizes same 102-3, yield 66%；Compound 33 synthesizes same 102-1, receives Rate 73%；Value of calculation C54H43N3：C,88.37；H,5.91；N,5.73；Measured value：C,88.35；H,5.91；N,5.75.
1H-NMR(400MHZ,CDCl3) (ppm) δ=1.67～1.68 (12H, s), 5.66～5.67 (1H, d), 6.38～ 6.39 (2H, d), 6.45～6.46 (3H, d), 6.52～6.53 (2H, d), 6.54～6.56 (2H, m), 6.62～6.63 (1H, M), 6.83～6.84 (2H, m), 6.88～6.89 (2H, d), 7.00～7.01 (3H, m), 7.08～7.09 (1H, m), 7.23～ 7.24 (2H, d), 7.30～7.31 (6H, m), 7.40～7.41 (1H, d), 7.45～7.46 (1H, d), 7.55～7.56 (1H, D), 7.77～7.78 (1H, d).
The synthesis of synthetic example 40. compound 3
3-1 synthesizes same 62-5, yield 70%；Compound 3 synthesizes same 102-1, yield 79%；Value of calculation C54H42N2：C, 90.21；H,5.89；N,3.90；Measured value：C,90.22；H,5.89；N,3.89；1H-NMR(400MHZ,CDCl3) (ppm) δ= 1.67～1.68 (12H, s), 6.44～6.45 (1H, d), 6.52～6.53 (1H, d), 6.67～6.68 (2H, m), 6.97～ 7.00 (2H, m), 7.04～7.05 (1H, d), 7.08～7.10 (2H, m), 7.22～7.23 (2H, m), 7.26～7.28 (1H, M), 7.30～7.31 (6H, m), 7.32～7.33 (2H, m), 7.38～7.40 (2H, m), 7.45～7.46 (2H, m), 7.47～ 7.48 (2H, m), 7.55～7.56 (2H, m), 7.77～7.78 (1H, and d) 7.83～7.84 (1H, d).
The synthesis of synthetic example 41. compound 121
121-1 synthesizes same 119-1, yield 45%；121-2 synthesizes same 119-2, yield 65%；121-3 synthesizes same 119-3, Yield 69%；121-4 synthesizes same 102-1, yield 75%；121-5 synthesizes same 62-2, yield 58%；121-6 synthesizes same 62-3, Yield 66%；121-7 synthesizes same 62-4, yield:58%；121-8 synthesizes same 62-5, yield 78%；Compound 121 synthesizes same 102-1, yield 75%.
The synthesis of synthetic example 42. compound 22
Compound 22 synthesizes same 102-4, yield 56%.Value of calculation C67H46N2O2:C,88.32；H,5.09；N,3.07； Actual value C, 88.45；H,5.21；N, 3.141H-NMR (400MHz, CDCl3) (ppm) δ=1.75～1.78 (12H, s), 6.65 ～6.72 (4H, t), 6.79～6.85 (6H, m), 7.08～7.14 (4H, m), 7.21～7.25 (6H, m), 7.36～7.44 (6H, m), 7.72～7.78 (4H, m), 7.82～7.85 (2H, and d) 7.92～7.95 (2H, d).
The synthesis of synthetic example 43. compound 122
122-1 synthesizes：By 100g (0.5458mol) 1- ADP and furan is dissolved in 500mlN, dinethylformamide, 92.3g (0.5185mol) NBS of Deca 500ml dissolving at 0 DEG C, controls temperature at 0 DEG C about, stirs 2h after completion of dropping, Detection reaction finishes, Deca 1000ml water, after stirring 1h, filters, obtains 83.7g122-1 (yield by column chromatography after drying 58.5%).
The synthesis of 122-2：83.7g (0.3193mol) 122-1 is dissolved in 837ml acetic acid, is warming up to 50 DEG C, add 35.3gKI, adds 2.8gKIO3, and question response liquid becomes red, then is changed into addition 20gKIO3 during white by redness, after 3h Detection reaction finishes, and after being down to room temperature, is filtrated to get solid, obtains 52.03g122-2 (yield 42%) with ethyl alcohol recrystallization.
The synthesis of 122-3：Deca 200ml sulphuric acid in 5ooml water, temperature is maintained at 0 DEG C, adds 52.03g (0.1341mol) 122-2, then Deca 500ml water-soluble 22.67g (0.3285mol) sodium nitrite, stir after completion of dropping 12h, reactant liquor is poured in frozen water, adjusts PH to 9 about with the sodium hydrate aqueous solution of saturation, is filtrated to get solid, utilizes Ethyl alcohol recrystallization obtains 37.04g122-3 (yield 71%).
The synthesis of 122-4：37.04g (0.0952mol) 122-3 is dissolved in 370ml oxolane, adds 6g (0.0476mol) dimethyl sulfate, is warming up to backflow, and reaction detection reaction after 6h finishes, and reactant liquor is poured into water, plus acetic acid Ethyl ester extracts, and obtains 21.49g122-4 (yield 56%) by column chromatography after taking organic faciess choosing dry.
The synthesis of 122-5：21.49g (0.0533mol) 122-4 is dissolved in 215ml oxolane, at subzero 78 DEG C Deca 23.46ml butyl lithium, after stirring 5h, reactant liquor is poured on dry ice, after CO2 not re-absorption, adds the stirring of 100ml water Filter, drying obtains 9.07g122-5 (yield 53%).
The synthesis of 122-6：9.07g (0.02825mol) 122-5 is added in 20ml methanol, further drips one after another drop of adding 10ml sulphuric acid, is heated to back flow reaction 16h, detection reaction finishes, and after decompression screws out solvent, obtains by column chromatography (6.06g122-6 yield 64%).
The synthesis of 122-7：6.06g (0.01808mol) 122-6 is added in 240ml hydrogen bromide (48%), stirring rises Temperature to back flow reaction, stopped reaction after 2h, by reactant liquor decompression be spin-dried for after 2.09g122-7 (yield is obtained by Diethyl ether recrystallization 36%).
The synthesis of 122-8：The 122-7 of 2.09g (0.0065mol) is dissolved in 20ml dichloromethane solvent, is slowly added dropwise Trifluoromethanesulfanhydride anhydride, drips distillation back flow reaction, stopped reaction after 2h.After vacuum distillation goes out 15ml dichloromethane, it is down to room Filter after temperature, dry and obtain 2.3g122-8 (yield 78%).
The synthesis of 122-9：2.3g (0.00507mol) 122-8 is dissolved in 23ml1.4- dioxane, under logical nitrogen Stirring 15min, sequentially adds 1.48g (0.00507mol) 1- bromine dibenzofurans -4- boric acid, 1.4g (0.01014mol) K2CO3,2ml water, 0.06g (0.00005mol) tetrakis triphenylphosphine palladium, are warming up to back flow reaction 6h, stopped reaction, will react Liquid decompression is spin-dried for, and residue is obtained 1.925g122-9 (yield 69%) by column chromatography.
The synthesis of 122-10：1.925g (0.0035mol) 122-9 is dissolved in 20ml methanol, is slowly added dropwise at 0 DEG C 3.5ml aqueous lithium hydroxide (1M), is warming up to back flow reaction 6h, stopped reaction, reactant liquor decompression is spin-dried for, molten with ethyl acetate Solution adds water washing twice, with salt pickling 3 times, takes organic faciess decompression to be spin-dried for obtaining 1.48g122-10 (yield 85%).
122-11 synthesizes same 84-4, yield 41%；122-12 synthesizes same 62-2, yield 51%；122-13 synthesizes same 62-3, Yield 46%；The 122 same 102-4 of synthesis, yield 56%.
Value of calculation C83H75N3O2:C,86.95；H,6.59；N,3.67；Actual value C, 86.72, H, 6.68；N,3.57
1H-NMR (400MHz, CDCl3) (ppm) δ=1.38～1.41 (36H, s), 6.18～6.21 (1H, s), 6.28～ 6.31 (1H, s), 6.56～6.68 (10H, m), 6.71～6.77 (4H, m), 7.05～7.08 (12H, m), 7.24～7.27 (2H, t), 7.38～7.44 (4H, m), 7.69～7.72 (2H, d), 7.92～7.95 (2H, d).
The synthesis of synthetic example 44. compound 123
123-1 synthesizes same 122-9, yield 66%；123-2 synthesizes same 122-10, yield 85%；123-3 synthesizes same 84-4, Yield 40%；123-4 synthesizes same 62-2, yield 49%；123-5 synthesizes same 62-3, yield 52%；The 123 same 102-4 of synthesis, receive Rate 58%.Value of calculation C83H75N3O2:C,86.95；H,6.59；N,3.67；Actual value C, 86.76；H,6.48；N,3.75
1H-NMR (400MHz, CDCl3) (ppm)=1.39～1.42 (36H, s), 6.29～6.32 (1H, s) .58～ 6.61 (10H, m), 6.65～6.68 (4H, m), 7.04～7.07 (12H, m), 7.24～7.27 (2H, t), 7.36～7.42 (4H, m), 7.69～7.72 (2H, d), 7.92～7.95 (2H, d).
The synthesis of synthetic example 45. compound 129
Compound 129 synthesizes the synthesis of same compound 122.
Value of calculation C83H75N3S2：:C,84.58；H,6.41；N,3.57；Actual value C, 84.67；H,6.37；N,3.47
1H-NMR (400MHz, CDCl3) (ppm) δ=1.36～1.39 (36H, s), 6.41～6.44 (2H, d), 6.61～ 6.64 (10H, m), 6.68～6.74 (4H, m), 7.04～7.07 (12H, m), 7.21～7.24 (2H, m), 7.54～7.57 (4H, m), 8.01～8.04 (2H, d), 8.48～8.51 (2H, d).
The synthesis of synthetic example 46. compound 127
127-1 synthesizes same 62-2, yield 53%；127-2 synthesizes same 62-3, yield 47%；The 127 same 102-4 of synthesis, yield 58%.Value of calculation C77H70N2O3:C,86.32；H,6.59；N,2.61；Actual value C, 86.17；H,6.51；N,2.71
1H-NMR (400MHz, CDCl3) (ppm) δ=1.37～1.40 (36H, s), 6.28～6.31 (2H, s), 6.58～ 6.61 (8H, d), 7.04～7.07 (10H, m), 7.24～7.27 (6H, m), 7.36～7.42 (4H, m), 7.69～7.72 (2H, D), 7.92～7.95 (2H, d).
The synthesis of synthetic example 47. compound 124
124-1 synthesizes same 62-2, yield 50%；124-2 synthesizes same 62-3, yield 47%；The 124 same 102-1 of synthesis, yield 56%.Value of calculation C77H70N2O2S:C,85.04；H,6.49；N,2.58；O,2.94；S,2.95；Actual value C, 85.14；H, 6.37；N, 2.781H-NMR (400MHz, CDCl3) (ppm) δ=1.36～1.39 (36H, s), 6.15～6.18 (1H, s), 6.25～6.28 (1H, s), 6.58～6.61 (8H, d), 7.04～7.10 (12H, m), 7.32～7.47 (6H, m), 7.68～ 7.71 (4H, d), 7.92～7.95 (2H, d).
The synthesis of synthetic example 48. compound 25
25-1 synthesizes same 102-1, yield 68%；25-2 synthesizes same 102-2, yield 53%；25-3 synthesizes same 102-3, receives Rate 78%；The 25 same 102-4 of synthesis, yield 62%.Value of calculation C45H31NS:C,87.48；H,5.06；N,2.27；Actual value C, 87.37；H, 5.12；N, 2.18.1H-NMR (400MHz, CDCl3) (ppm) δ=1.75～1.78 (6H, s), 6.55～6.58 (2H, m), 6.75～6.78 (1H, m), 6.91～6.94 (2H, d), 7.05～7.08 (3H, m), 7.35～7.38 (1H, d), 7.45～7.54 (3H, m), 7.86～7.92 (4H, m), 8.07～8.10 (2H, m), 8.15～8.18 (3H, m), 8.46～ 8.49 (1H, d), 8.96～8.99 (2H, d), 9.16～9.19 (1H, s).
The synthesis of synthetic example 49. compound 5
5-1 synthesizes same 102-1, yield 65%；5-2 synthesizes same 102-2, yield 49%；5-3 synthesizes same 102-3, yield 72%；The 5 same 102-4 of synthesis, yield 61%.Value of calculation C45H36N4:C,85.41；H,5.73；N,8.85；Actual value C, 85.48；H,5.68；N,8.84.1H-NMR (400MHz, CDCl3) (ppm) δ=1.74～1.77 (12H, s), 6.57～6.62 (2H, m), 6.65～6.68 (1H, s), 6.72～6.75 (1H, d), 6.85～6.88 (1H, s), 7.06～7.09 (2H, m), 7.30～7.33 (1H, m), 7.46～7.58 (10H, m), 7.62～7.65 (1H, d), 7.90～7.93 (1H, d), 8.32～ 8.35(4H,d).
The synthesis of synthetic example 50. compound 6
The same 102-4 of synthesis of compound 6, yield 65%.Value of calculation C38H31N3:C,86.17；H,5.90；N,7.93；Real Actual value C, 85.98；H, 6.12；N, 7.9.1H-NMR (400MHz, CDCl3) (ppm) δ=1.75～1.78 (12H, s), 6.58～ 6.61 (1H, d), 6.72～6.75 (2H, m), 7.04～7.07 (2H, m), 7.30～7.33 (1H, m), 7.45～7.57 (7H, M), 7.82～7.91 (5H, m), 8.18～8.21 (1H, d).
The synthesis of synthetic example 51. compound 4
The same 102-4 of synthesis of compound 4, yield 57%.Value of calculation C46H37N3:C,87.45；H,5.90；N,6.65；Real Actual value C, 87.31；H,6.04；N,6.65.1H-NMR (400MHz, CDCl3) (ppm) δ=1.74～1.77 (12H, s), 6.58 ～6.61 (1H, d), 6.71～6.77 (2H, m), 7.05～7.08 (2H, m), 7.30～7.33 (1H, m), 7.42～7.57 (14H, m), 7.82～7.85 (4H, m), 7.89～7.92 (2H, d).
The synthesis of synthetic example 52. compound 156
156-2 synthesizes same 98-2, yield 80%；156-2 is added in phosphorous acid three formicester reaction is warming up to backflow Reaction was lowered the temperature after 20 hours by reaction, and having solid to separate out will be filtrated to get 156-3, yield 70% after adding ethanol in reacting；156 Synthesize same 102-1, yield 60%.M.W=666+1 W.F=C48H30N2S
NMR:8.55(1H,d),8.09-8.12(3H,m),7.49(1H,d),7.78(2H,m),7.63(1H,m)7.25- 7.51(20H,m)
The synthesis of synthetic example 53. compound 157
The synthesis of 157-1 is with compound 102-1, yield 51%；20g (0.0449mol) intermediate 157-1 is dissolved in In 200mlN, N- dimethyl acetylamide, nitrogen protection is lower to add 34g (0.2245mol) DBU, 0.4g (DBA) 3Pd2,1ml tri- uncle Butyl phosphine, is warming up to back flow reaction, and after 5h, detection raw material reaction finishes, and stopped reaction is poured reactant liquor in frozen water into, filtered The solid arriving, obtains 7g intermediate 157-2, yield 42% with re crystallization from toluene；The synthesis of compound 157, with compound 102, is received Rate 58%.Value of calculation C51H36N2：C,90.50；H,5.36；N,4.14；Actual value：C,90.89；H,5.25；N,4.86.
1H-NMR (400MHz, CDCl3) (ppm) δ=1.74 (6H, s), 7.31～7.34 (2H, m), 7.43～7.58 (18H, m), 7.66～7.69 (2H, d), 7.71～7.74 (2H, s), 8.12～8.15 (4H, m), 8.45～8.48 (2H, s).
The synthesis of synthetic example 54. compound 169
The same 119-1 of synthesis of 169-1, yield 43%, the same 119-2 of synthesis of 169-2, yield 62%, the synthesis of 169-3 is same 131-1, yield 52%, the same 102-1 of synthesis of 169-4, yield 67%, the same 157-2 of synthesis of 169-5, yield 40%, 169 Synthesize same 62-5, yield 79%.Value of calculation C50H31N5：C,85.57；H,4.45；N,9.98；Measured value：C,85.56；H, 4.43；N,10.01；1H-NMR (400MHZ, CDCl3) (ppm) δ=7.00～7.01 (2H, m), 7.08～7.10 (2H, m), 7.21～7.22 (1H, m), 7.27～7.30 (14H, m), 7.32～7.33 (2H, m), 7.38～7.40 (2H, d), 7.46～ 7.48 (2H, d), 7.55～7.56 (2H, d), 7.59～7.60 (1H, d), 7.79～7.80 (2H, m), 8.00～8.01 (1H, d)
The synthesis of synthetic example 55. compound 171
The same 102-1 of synthesis of compound 171, yield：62%.Value of calculation C57H36N6:LC-MS:804.94+1.
1H-NMR (400MHz, CDCl3) (ppm) δ=7.24～7.25 (2H, m), 7.33～7.34 (2H, m), 7.40～ 7.42 (4H, m), 7.45～7.46 (2H, m), 7.50～7.52 (8H, m), 7.55～7.58 (6H, m), 7.67～7.68 (2H, D), 7.79～7.80 (2H, d), 7.94～7.95 (2H, m), 8.28～8.29 (4H, m), 8.55～8.56 (2H, m).
The synthesis of synthetic example 56. compound 175
The same 62-5 of synthesis of 175-1, yield：67%；The same 62-2 of synthetic method of 175-2, yield：53%；The conjunction of 175-3 The same 62-3 of one-tenth method, yield：51%；The same 102-1 of synthetic method of compound 175, yield：60%.Molecular formula C54H38N2O4S: LC-MS:673.84+1.1H-NMR (400MHz, CDCl3) (ppm) δ=1.72 (6H, s), 6.03～6.05 (1H, d), 7.06～ 7.25 (10H, m), 7.33～7.37 (4H, m), 7.40～7.63 (6H, m), 7.74～7.80 (3H, m), 7.86～7.89 (3H, D), 8.05～8.09 (2H, m)
Embodiment 1-1 TADF
First with distilled water and then with solvent such as isopropanol, acetone and methanol supersound washing, there are about 1500 angstroms of thickness After the glass substrate of tin indium oxide (ITO) electrode (first electrode, anode), scrubbed glass substrate is dried, moves on to Gas ions cleaning systems, are then cleaned about 5 minutes using oxygen plasma.Then described glass substrate is loaded into vacuum moulding machine In equipment.
The sky of about 400 angstroms of thickness will be had on compound N PB vacuum moulding machine to the ITO electrode of described glass substrate with formation Cave implanted layer, by compound mCP vacuum moulding machine on hole injection layer to form about 120 angstroms of thick hole transmission layers.
DPEPO (main body) and compound 4 (dopant, 6 percetages by weight (weight %)) codeposition are passed in described hole To form the EML with about 300 angstroms of thickness on defeated region.
Subsequently, Bphen vacuum moulding machine had on EML the ETL of about 250 angstroms of thickness with formation.Then, LiF is deposited To form the EIL with about 5 angstroms of thickness on described ETL, and Al is deposited on the thickness of up to about 1000 angstroms of described EIL with shape Become second electrode (negative electrode), thus complete the manufacture of organic luminescent device.
Embodiment 1-2 is to embodiment 1-12
To manufacture organic luminescent device with identical mode in embodiment 1-1, except using the compound generation in table 1 below Alternative compound 4 as dopant to form EML outside.
Comparative example 1
Manufacture organic luminescent device in the same manner as in example 1, except replacing compound 4 to make using IDE-102 For dopant to form EML outside.
Table 1
Excellent efficiency is shown by the OLED that the data in table 1 can be seen that the present invention, relatively low driving voltage, Higher external quantum efficiency (EQE).
Embodiment 2-1 HTL
First with distilled water and then with solvent such as isopropanol, acetone and methanol supersound washing, there are about 1500 angstroms of thickness After the glass substrate of tin indium oxide (ITO) electrode (first electrode, anode), scrubbed glass substrate is dried, moves on to Gas ions cleaning systems, are then cleaned about 5 minutes using oxygen plasma.Then described glass substrate is loaded into vacuum moulding machine In equipment.
To be formed, will there are about 1000 angstroms of thickness in compound 2-TNATA vacuum moulding machine to the ITO electrode of described glass substrate The HIL of degree, compound 2 vacuum moulding machine is formed on hole injection layer the HTL with about 200 angstroms of thickness.
By compound ADN and DPAVBi (dopant) with 98:2 mass ratio codeposition on described hole transporting zone with Form the EML with about 300 angstroms of thickness.
Subsequently, by Alq3Vacuum moulding machine is on described EML to form the ETL with about 250 angstroms of thickness.Then, LiF is sunk Amass and to be formed, there is the EIL of about 5 angstroms of thickness on ETL, and Al is deposited on the thickness of described EIL up to about 1000 to form the Two electrodes (negative electrode), thus complete the manufacture of organic luminescent device.
Embodiment 2-2 is to embodiment 2-9
To manufacture organic luminescent device with identical mode in embodiment 2-1, except using the compound replacementization in table 2 Outside compound 2 is as hole transmission layer.
Comparative example 2
To manufacture organic luminescent device with identical mode in embodiment 2-1, except replacing compound 2 with shape using NPB Become outside hole transmission layer.
Table 2
The driving electricity of OLED can be reduced by the hole mobile material that the data in table 2 can be seen that the present invention Pressure, improves life-span, efficiency and the brightness of OLED.
Embodiment 3-1 HONGGUANG main body
First with distilled water and then with solvent such as isopropanol, acetone and methanol supersound washing, there are about 1500 angstroms of thickness After the glass substrate of tin indium oxide (ITO) electrode (first electrode, anode), scrubbed glass substrate is dried, moves on to Gas ions cleaning systems, are then cleaned about 5 minutes using oxygen plasma.Then described glass substrate is loaded into vacuum moulding machine In equipment.
To be formed, will there are about 600 angstroms of thickness in compound 2-TNATA vacuum moulding machine to the ITO electrode of described glass substrate HIL, compound N PB vacuum moulding machine is formed on hole injection layer the HTL with about 300 angstroms of thickness.
Will be coprecipitated to compound 45 (red phosphorescent main body) and PtOEP (red dopant, 10 percetages by weight (weight %)) Amass on described hole transporting zone to form the EML with about 300 angstroms of thickness.BCP vacuum moulding machine is formed on luminescent layer 50 angstroms of thick hole blocking layers.
Subsequently, by Alq3Vacuum moulding machine is on described hole blocking layer to form the ETL with about 250 angstroms of thickness.Then, LiF is deposited on to form the EIL with about 5 angstroms of thickness on ETL, and Al is deposited on the thickness of up to about 1000 angstroms of described EIL Degree, to form second electrode (negative electrode), thus completes the manufacture of organic luminescent device.
Embodiment 3-2 is to embodiment 3-13
To manufacture organic luminescent device with identical mode in embodiment 3-1, except being replaced using the compound in table 3-1 Outside compound 45 is as emitting red light layer main body.
Comparative example 3-1
To manufacture organic luminescent device with identical mode in embodiment 3-1, except replacing compound 45 with shape using CBP Become outside emitting red light layer main body.
Table 3-1
Can be seen that compared with current material CBP by the data in table 3-1, the HONGGUANG main body of the present invention can reduce The driving voltage of OLED, improves efficiency and the brightness of OLED.
Embodiment 3-14 green glow main body
To manufacture organic luminescent device with identical mode in embodiment 3-1, except using compound 5 (green phosphorescent master Body) and Ir (ppy) 3 (green glow dopant, 10 percetages by weight (weight %)) formed luminescent layer outside.
Embodiment 3-15 is to embodiment 3-32
To manufacture organic luminescent device with identical mode in embodiment 3-13, except using the compound generation in table 3-2 Outside alternative compound 5 is as green emitting layer main body.
Comparative example 3-2
To manufacture organic luminescent device with identical mode in embodiment 3-13, except replacing compound 5 with shape using CBP Become outside green emitting layer main body.
Table 3-2
Can be seen that compared with current material CBP by the data in table 3-2, the green glow main body of the present invention can reduce The driving voltage of OLED, improves efficiency and the brightness of OLED.
Embodiment 3-33 blue light main body
To manufacture organic luminescent device with identical mode in embodiment 3-1, except using compound 15 (blue phosphorescent master Body) and DPAVBi (blue light dopant, 10 percetages by weight (weight %)) formed luminescent layer outside.
Embodiment 3-34
To manufacture organic luminescent device with identical mode in embodiment 3-29, except compound is replaced using compound 39 Outside 15 to form blue-light-emitting layer main body.
Comparative example 3-3
To manufacture organic luminescent device with identical mode in embodiment 3-29, except using ADN replace compound 15 with Formed outside blue-light-emitting layer main body.
Table 3-3
Can be seen that compared with current material ADN by the data in table 3-3, the blue light main body of the present invention can reduce The driving voltage of OLED, improves efficiency and the brightness of OLED.
Embodiment 4-1 dopant material
First with distilled water and then with solvent such as isopropanol, acetone and methanol supersound washing, there are about 1500 angstroms of thickness After the glass substrate of tin indium oxide (ITO) electrode (first electrode, anode), scrubbed glass substrate is dried, moves on to Gas ions cleaning systems, are then cleaned about 5 minutes using oxygen plasma.Then described glass substrate is loaded into vacuum moulding machine In equipment.
To be formed, will there are about 600 angstroms of thickness in compound 2-TNATA vacuum moulding machine to the ITO electrode of described glass substrate HIL, compound N PB vacuum moulding machine is formed on hole injection layer the HTL with about 300 angstroms of thickness.
Compound ADN and compound 17 (dopant, 10 percetages by weight (weight %)) codeposition are passed in described hole To form the EML with about 300 angstroms of thickness on defeated region.
Subsequently, by Alq3Vacuum moulding machine is on described EML to form the ETL with about 250 angstroms of thickness.Then, LiF is sunk Amass and to be formed, there is the EIL of about 5 angstroms of thickness on ETL, and Al is deposited on the thickness of described EIL up to about 2000 to form the Two electrodes (negative electrode), thus complete the manufacture of organic luminescent device.
Embodiment 4-2 is to embodiment 4-10
To manufacture organic luminescent device with identical mode in embodiment 4-1, except using the compound replacementization in table 4 Outside compound 17 is as luminescent layer dopant.
Comparative example 4-1 to 4-2
To manufacture organic luminescent device with identical mode in embodiment 4-1, except using compound A or compound DPAVBi replace compound 17 to form luminescent layer outside.
Table 4
Can be seen that compared with current material by the data in table 4, the dopant material of the present invention can reduce OLED device The driving voltage of part, improves efficiency and the brightness of OLED.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all spirit in the present invention and Within principle, any modification, equivalent substitution and improvement made etc., should be included within the scope of the present invention.

Claims (11)

1. a kind of organic compound, its structure is as shown in Formulas I or II：
Wherein, X1、X2、X3And X4Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group；R1、R2、R3、R4、R5、R6、R7、R8、 R9And R10Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9 And R10Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together.
2. organic compound according to claim 1 it is characterised in that the structure such as formula III of described organic compound, Shown in IV, V, VI or VII：
Wherein, X1、X2、X3、X4、X5、X6And X7Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group, R1、R2、R3、R4、R5、 R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6- C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、 R18、R19、R20、R21And R22Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together.
3. organic compound according to claim 1 and 2 it is characterised in that structure such as formula G1 of described organic compound, Shown in G2 or G3：
Wherein, X1、X2、X3、X4、X5、X6And X7Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group；R1、R2、R3、R4、R5、 R6、R7、R8、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Virtue Perfume base or C6-C40Heteroaryl perfume base；Or R1-R22Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together.
4. the organic compound according to any one of claim 1-3 is it is characterised in that the structure of described organic compound As shown in formula G4, G5, G6, G7, G8, G9, G10, G11 or G12,
Wherein, R3Stand alone as singly-bound, oxygen, sulfur, nitrogen-containing group or carbon-containing group；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、 R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Miscellaneous Aromatic radical；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22 Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together.
5. organic compound according to claim 1 and 2 it is characterised in that structure such as formula G13 of described compound, Shown in G14, G15, G16, G17, G18, G19, G20, G21 or G22：
Wherein, in formula G13, G14, G15, G16, G17 and G18, X1、X2、X3And X4Stand alone as singly-bound, N-R3Or O, R3For hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、 R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base； Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22In any phase Two adjacent carbon atoms being bonded with them form ring structure together；
In formula G19, G20, G21 and G22, X3And X4Each stand alone as singly-bound, O, S, N-R3Or CR1R2；R1、R2、R3、R4、R5、 R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6- C40Aromatic radical or C6-C40Heteroaryl perfume base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、 R18、R19、R20、R21And R22Two carbon atoms being bonded with them of middle arbitrary neighborhood form ring structure together；R1、R2、R3、R4With R5It is independently selected from hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base, R4And R5Exclude following group：
6. organic compound according to claim 1 and 2 is it is characterised in that structure such as formula G23, G24 of described compound Or shown in G25：
X3And X4It is independently each singly-bound, O, S, N-R3Or CR1R2；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、 R13、R14、R15、R16、R17、R18、R19、R20、R21And R22Stand alone as hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl is fragrant Base；Or R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21And R22In appoint Two adjacent carbon atoms being bonded with them of anticipating form ring structure together；R1、R2、R3、R4And R5Independently selected from following group：
7. the organic compound according to any one of claim 1-6 is it is characterised in that X1、X2、X3、X4、X5、X6And X7Solely Stand as CR1R2Or NR3, wherein R1、R2And R3It is independently selected from hydrogen, C1-C10Alkyl, C6-C40Aromatic radical or C6-C40Heteroaryl perfume base；Or Person R1And R2Form ring structure with the carbon atom that they are bonded together.
8. the organic compound according to any one of claim 1-7 it is characterised in that described ring structure be selected from replace or Unsubstituted furan nucleuss, substituted or unsubstituted thiphene ring, substituted or unsubstituted pyrrole ring, substituted or unsubstituted pyrans Ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted phenyl ring, substituted or unsubstituted cyclohexyl biphenyl, replacement or unsubstituted Benzofuran ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted .alpha.-5:6-benzopyran ring, substituted or unsubstituted Indole ring, substituted or unsubstituted fluorenes ring, substituted or unsubstituted naphthalene nucleus, substituted or unsubstituted indenes ring, replacement or unsubstituted Acridine ring and substituted or unsubstituted anthracene nucleus.
9. the organic compound according to any one of claim 4-8 is it is characterised in that R1、R2、R3、R4And R5Independent choosing From following group：Phenyl, xenyl,
Wherein asterisk represents the junction point with other parts.
10. organic compound according to claim 1 is it is characterised in that described organic compound is selected from following compound In any one：
11. organic compound according to any one of claim 1-10 are in electronic device particularly organic electroluminescence Application in part it is preferable that described organic compound is used as fluorescent illuminant, delayed fluorescence luminous body or phosphorescent emitter, and/ Or the host material for fluorescence or phosphorescent emitter, and/or it is used for electron transfer layer, hole blocking layer, electronic barrier layer, swashs In sub- barrier layer and/or hole transmission layer.
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101490207A (en) * 2006-07-11 2009-07-22 默克专利有限公司 Novel materials for organic electroluminescent devices
CN103842339A (en) * 2011-09-21 2014-06-04 默克专利有限公司 Carbazole derivatives for organic electroluminescence devices
CN103889952A (en) * 2011-10-20 2014-06-25 默克专利有限公司 Materials for organic electroluminescent devices
CN104271700A (en) * 2012-04-03 2015-01-07 罗门哈斯电子材料韩国有限公司 New organic electroluminescent compound and organic electroluminescent device comprising the same
CN104603122A (en) * 2012-09-03 2015-05-06 保土谷化学工业株式会社 Compound having indeno acridan ring structure, and organic electroluminescence element
CN104829626A (en) * 2014-02-12 2015-08-12 三星电子株式会社 Condensed cyclic compound and organic light-emitting device including the same
CN105636944A (en) * 2013-10-14 2016-06-01 默克专利有限公司 Materials for electronic devices

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101490207A (en) * 2006-07-11 2009-07-22 默克专利有限公司 Novel materials for organic electroluminescent devices
CN103842339A (en) * 2011-09-21 2014-06-04 默克专利有限公司 Carbazole derivatives for organic electroluminescence devices
CN103889952A (en) * 2011-10-20 2014-06-25 默克专利有限公司 Materials for organic electroluminescent devices
CN104271700A (en) * 2012-04-03 2015-01-07 罗门哈斯电子材料韩国有限公司 New organic electroluminescent compound and organic electroluminescent device comprising the same
CN104603122A (en) * 2012-09-03 2015-05-06 保土谷化学工业株式会社 Compound having indeno acridan ring structure, and organic electroluminescence element
CN105636944A (en) * 2013-10-14 2016-06-01 默克专利有限公司 Materials for electronic devices
CN104829626A (en) * 2014-02-12 2015-08-12 三星电子株式会社 Condensed cyclic compound and organic light-emitting device including the same

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Publication number Priority date Publication date Assignee Title
EP3459956A4 (en) * 2016-07-01 2019-06-19 LG Chem, Ltd. COMPOUND AND ORGANIC ELECTRONIC ELEMENT COMPRISING SAME
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Application publication date: 20170215