CN105017041B - Dibenzosuberenone derivative and its preparation and application - Google Patents
Dibenzosuberenone derivative and its preparation and application Download PDFInfo
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Abstract
The invention belongs to organic semiconducting materials and devices field, it is related to new dibenzosuberenone derivative and its preparation and application, the general structure of such dibenzosuberenone derivative is as follows：, this method is skeleton structure, with the substituent with hole transport performance using dibenzosuberenone, replaces the hydrogen in skeleton structure to prepare dibenzosuberenone derivative by coupling reaction；Using prepared dibenzosuberenone derivative as organic semiconductor layer, the method for preparing the luminous organic electroluminescence device of blue-green.The substituent with hole transport performance can improve the heat endurance of material and the performance of electroluminescent device in the preparation method, and the luminous organic electroluminescence device of blue-green is obtained using it as luminescent layer.
Description
Technical field
The invention belongs to organic semiconducting materials and devices field, it is related to new dibenzosuberenone derivative and its system
Standby and application.
Background technology
Organic electroluminescent（OLED）Device due to its full color flat panel show and the field such as solid state light emitter huge applications
Potentiality and receive significant attention, the performance of wherein luminescent material is to influence the key factor of organic electroluminescence device application.For
The efficient organic electroluminescence device of acquisition, it usually needs luminous organic material has high thermal stability, excellent film forming,
High carrier injection or transmittability, appropriate energy level and the excellent characteristics of luminescence etc..Organic molecule with conjugated structure
Generally there is the good characteristics of luminescence and carrier transmission characteristics, and its performance can be changed by adjusting molecular structure, therefore,
Adjusting molecular structure turns into the effective way for obtaining and having superperformance new material.However, up to the present, exploitation has excellent
The luminescent material of carrier transport ability is still one of problem of luminous organic material and device research field.
Aromatic amine is the strong electron donor of a class, can be used to construct organic electroluminescence device as hole mobile material
（S.B. Jiao, Y. Liao, X.J. Xu, et al. Advanced Functional Materials, 2008, 18:
2335; K.F. Shao, Y.F. Li, L.M. Yang, et al. Chemistry Letters, 2005, 34:
1604.）.Research shows that functionalization aromatic amine has many applications, for example, trans- 4,4- is double（Diaryl-amine base）Stilbene spreads out
Biology is excellent luminescent material（M. Rumi, J.E. Ehrlich, A.A. Heikal, et al. Journal of
the American Chemistry Society, 2000, 122: 9500; J.S. Yang, K.L. Liau, C.M.
Wang, et al. Journal of the American Chemistry Society, 2004, 126: 12325.）, but
It is due to that its design feature easilys lead to the generation of cis-trans configurations isomerization, so as to limit the application of this kind of material.To keep away
Exempt from the generation of above-mentioned configuration conversion, it is necessary to be changed to the molecular structure of material, make it have a certain degree of rigidity.
The content of the invention
Technical problem underlying to be solved by this invention is to provide the cis-trans isomerism for how limiting stilbene structure
The method of change, prepares new luminous organic material and device and improves its performance.The main object of the present invention is to contain carbonyl with one
The heptatomic ring of base limits the isomerization of stilbene structure, by introducing the base with hole transport performance on phenyl ring
Group, prepares the new dibenzosuberenone derivative with good luminous characteristic.
The technical scheme is that：Dibenzosuberenone derivative, the knot of such dibenzosuberenone derivative
Structure formula is as follows：
,
Wherein, R in formula1Structural formula be：、、、、Or, R2For alkyl, alkoxy, ammonia
Base, cyano group or nitro, R3For alkyl, alkoxy, amino, cyano group or nitro, n is positive integer.
It is a further object of the present invention to provide the synthesis technique of above-mentioned dibenzosuberenone derivative,
Specifically include following steps：
Step 1：Synthesize 3,7- dibromos dibenzo [a, d] cycloheptene -5- ketone (compound 2)（）
Cyanuric acid and lithium hydroxide are first pressed 1:4 mol ratio is soluble in water, then is slowly added dropwise appropriate bromine thereto,
It is stirred overnight.Appropriate sodium hydroxide solution is added in solution after terminating to reaction to neutralize unreacted bromine, through depressurizing suction filtration
White solid product (cyanuric acid of dibromo substitution, DBI) is obtained afterwards.By 10,11- dihydro-dibenzos [a, d] cycloheptene -5- ketone
The concentrated sulfuric acid is dissolved in respectively by equimolar ratio with DBI, then the solution of 10,11- dihydro-dibenzos [a, d] cycloheptene -5- ketone is slow
DBI solution is instilled, is stirred overnight.Solution after terminating to reaction is neutralized, extraction, drying, revolving, column chromatography etc. are handled
To solid product 3,7- dibromos dibenzo [a, d] cycloheptene -5- ketone (compound 2)；
Step 2：The compound that step 1 is synthesized（2）With triphenylamine derivative according to mol ratio be 1:1-1:4 amounts add four
In hydrogen furans, stir, add 2M K2CO3PH value is adjusted to 7-10, under a nitrogen atmosphere, 1wt%- is added into system
5wt% Pd (PPh3)4, stirring reaction is heated to reflux at 60-80 DEG C 12-48 hours.Reaction terminate after, organic phase through separation,
Purification, obtains yellow solid product.
Further, the synthesis technique of above-mentioned dibenzosuberenone derivative, specifically includes following steps：
Step 1：Synthesize 3,7- dibromos dibenzo [a, d] cycloheptene -5- ketone (compound 2)（）
Cyanuric acid and lithium hydroxide are first pressed 1:4 mol ratio is soluble in water, then is slowly added dropwise appropriate bromine thereto,
It is stirred overnight.Appropriate sodium hydroxide solution is added in solution after terminating to reaction to neutralize unreacted bromine, through depressurizing suction filtration
White solid product (cyanuric acid of dibromo substitution, DBI) is obtained afterwards.By 10,11- dihydro-dibenzos [a, d] cycloheptene -5- ketone
The concentrated sulfuric acid is dissolved in respectively by equimolar ratio with DBI, then the solution of 10,11- dihydro-dibenzos [a, d] cycloheptene -5- ketone is slow
DBI solution is instilled, is stirred overnight.Solution after terminating to reaction is neutralized, extraction, drying, revolving, column chromatography etc. are handled
To solid product 3,7- dibromos dibenzo [a, d] cycloheptene -5- ketone (compound 2).
Step 2：The compound that step 1 is synthesized（2）It is 1 according to mol ratio with diphenylamines or carbazole:1-1:4 amounts add first
In benzene, stir, it is 1 to add with compound (2) mol ratio:1-1:The tertiary butyl oxygen sodium of 4 amounts, is filled with nitrogen, in stirring
Lower addition mol ratio is 1:1-1:The Pd of 2 amounts2(dba)3With P (t-Bu)3, it is heated to reflux 8- in 90-110 DEG C in a nitrogen atmosphere
16 hours.After reaction terminates, organic phase obtains yellow solid product through separation, purification.
The application for the dibenzosuberenone derivative that above-mentioned preparation method is obtained, the dibenzosuberenone derivative
Luminous organic material applied to organic electroluminescence device.
Further, the organic electroluminescence device be sandwich construction, its typical structure be anode/hole transmission layer/
Dibenzosuberenone derivative layer/electron transfer layer/negative electrode.
The preparation of the organic electroluminescence device：Scrubbed dose successively of ito glass, deionized water, acetone, ethanol are washed
Wash, then dry.In the vacuum chamber, 4 × 10-4-4×10-5Under Pa vacuums, above-mentioned Huang is deposited according to required device architecture
Color solid product and electrode etc..
Further, in methods described：Anode and cathode material are respectively ITO and Li/Al, and hole transmission layer is organic
Layer NPB, electron transfer layer is 8-hydroxyquinoline aluminium（Alq3）.
Advantages of the present invention：The method of the present invention is from dibenzosuberenone structure, with seven yuan containing carbonyl
Ring limits stilbene structure, prevents it from occurring the isomerization of cis-trans configurations, while being introduced on phenyl ring has
The aromatic amine groups of hole transport performance, so as to reach the purpose of optimization performance.Synthesized new dibenzosuberenone spreads out
Biology has higher heat endurance, good film forming and the characteristics of luminescence, is obtained using it as luminescent layer blue-green luminous
Organic electroluminescence device；
1. using dibenzosuberenone as skeleton structure, with the substituent with hole transport performance, prepare dibenzo ring
Heptene ketone derivatives.
2. prepared blue-green luminous as organic semiconductor layer using prepared dibenzosuberenone derivative
Organic electroluminescence device.
3. the substituent with hole transport performance can improve the heat endurance of material and the performance of electroluminescent device.
Brief description of the drawings
Fig. 1 is the luminescence generated by light and electroluminescent spectrum curve synoptic diagram of dibenzosuberenone derivative.(a) it is photic
Luminescent spectrum,（b）Electroluminescent spectrum.
Fig. 2 is the luminous efficiency curve of the OLED of the dibenzosuberenone derivative of the present invention.
Embodiment
Technical scheme is described further with reference to specific embodiment.
Dibenzosuberenone derivative of the present invention, the following institute of general structure of such dibenzosuberenone derivative
Show：
,
Wherein, R in formula1Structural formula be：、、、、Or, R2For alkyl, alkoxy, ammonia
Base, cyano group or nitro, R3For alkyl, alkoxy, amino, cyano group or nitro, n is positive integer.
The technique for preparing above-mentioned dibenzosuberenone derivative, specifically includes following steps：
Step 1：Using dibenzosuberenone as skeleton structure, compound is synthesized by bromo-reaction（2）；
Step 2：The compound that step 1 is synthesized（2）With triphenylamine derivative according to mol ratio be 1:1-1:4 amounts add four
In hydrogen furans, stir, add 2M K2CO3PH value is adjusted to 7-10, under a nitrogen atmosphere, 1wt%- is added into system
5wt% Pd (PPh3)4, stirring reaction is heated to reflux at 60-80 DEG C 12-48 hours.Reaction terminate after, organic phase through separation,
Purification, obtains yellow solid product.
The technique for preparing above-mentioned dibenzosuberenone derivative, specifically includes following steps：
Step 1：Using dibenzosuberenone as skeleton structure, compound is synthesized by bromo-reaction（2）,
Step 2：The compound of synthesis（2）It is 1 according to mol ratio with diphenylamines or carbazole:1-1:4 amounts are added in toluene,
Stir, it is 1 to add with compound (2) mol ratio:1-1:The tertiary butyl oxygen sodium of 4 amounts, is filled with nitrogen, adds under agitation
Mol ratio is 1:1-1:The Pd of 2 amounts2(dba)3With P (t-Bu)3, it is heated to reflux in a nitrogen atmosphere in 90-110 DEG C 8-16 hours.
After reaction terminates, organic phase obtains yellow solid product through separation, purification.
Embodiment 1
The synthesis of 3,7- bis--(4- hexichol amidos benzene)-dibenzocycloheptene -5- ketone (DBHO-TPA)：3,7- dibromos two
Benzo [a, d] cycloheptene -5- ketone (2) (49.14mg, 0.135mmol) and 4- borates triphenylamine (3) (100mg, 0.27mmol)
It is dissolved in tetrahydrofuran, adds 2M K2CO3It is 8 to adjust pH value.Then whole system is taken out into air, is filled with nitrogen, in nitrogen
Under the conditions of gas, Pd (PPh are added into system3)4(7.8mg), then that the mixed system is heated to reflux into stirring at 70 DEG C is 48 small
When.After reaction terminates, removal of solvent under reduced pressure adds dichloromethane dissolving, and inorganic salts, organic phase are removed with the extraction of NaCl salting liquids
Dry, filter through anhydrous magnesium sulfate, filtrate removes solvent with rotary evaporation, crude product passes through silica gel column chromatography (petroleum ether-acetic acid
Ethyl ester), yellow solid product (DBHO-TPA) 57mg is obtained, yield is 61%.DBHO-TPA synthetic route is shown in Table 1.
Structural formula is as follows：
。
Embodiment 2
The synthesis of bis--diphenyl of 3,7- amido-dibenzocycloheptene -5- ketone (DBHO-DPA)：By compound 3,7- dibromos
Dibenzo [a, d] cycloheptene -5- ketone (2) (245mg, 0.68mmol) and diphenylamines (230mg, 1.36mmol) are dissolved in toluene,
Add tertiary butyl oxygen sodium (146.4mg, 1.52mmol) thereto again, be filled with nitrogen, after stirring at normal temperature half an hour, add Pd2
(dba)3(19.55mg, 0.03mmol) and P (t-Bu)3(0.03mmol), is heated to reflux 16 small in 100 DEG C in a nitrogen atmosphere
When.After reaction terminates, removal of solvent under reduced pressure adds ethyl acetate dissolving, the extraction of NaCl salting liquids, organic phase anhydrous magnesium sulfate
Dry.Yellow solid product (DBHO-DPA) 122mg is obtained by silica gel column chromatography (petroleum ether-ethyl acetate), yield is
33%.DBHO-DPA synthetic route is shown in Table 1.
Structural formula is as follows：
。
Embodiment 3
The synthesis of 3,7- bis--carbazole -9- benzo ring heptene -5- ketone (DBHO-C)：By compound 3,7- dibromos dibenzo [a,
D] cycloheptene -5- ketone (2) (245mg, 0.68mmol) and carbazole (227mg, 1.36mmol) are dissolved in toluene, then inwardly add special
Butyl oxygen sodium (146.4mg, 1.52mmol), is filled with nitrogen, after stirring at normal temperature half an hour, adds Pd2(dba)3 (19.55mg,
0.03mmol) and P (t-Bu)3(0.03mmol), is heated to reflux 16 hours in 100 DEG C in a nitrogen atmosphere.After reaction terminates, subtract
Pressure removes solvent, adds ethyl acetate dissolving, and NaCl salting liquids extraction, organic phase is dried with anhydrous magnesium sulfate.Pass through silicagel column
Chromatography (petroleum ether-ethyl acetate) obtains yellow solid product (DBHO-C) 200mg, and yield is 87.5%.DBHO-C synthesis road
Line is shown in Table 1
Structural formula is as follows：
。
Embodiment 4
The synthesis of 3,7- bis--(4- (4 '-methyl -4 ' '-methoxy diphenylamine base benzene))-dibenzocycloheptene -5- ketone：3,
7- dibromos dibenzo [a, d] cycloheptene -5- ketone (2) (0.135mmol) and 4- (4 '-methyl -4 ' '-methoxy diphenylamine base benzene),
Its structure referring to corresponding reaction in the partially synthetic route of processing step of specification starting compound) (0.27mmol) be dissolved in
In tetrahydrofuran, 2M K is added2CO3It is 7 to adjust pH value.Then whole system is taken out into air, is filled with nitrogen, in condition of nitrogen gas
Under, 5wt% Pd (PPh are added into system3)4, then by the mixed system be heated to reflux at 70 DEG C stirring 12 hours.Reaction knot
Shu Hou, removal of solvent under reduced pressure adds dichloromethane dissolving, removes inorganic salts with the extraction of NaCl salting liquids, organic phase is through anhydrous sulphur
Sour magnesium is dried, and filtering, filtrate removes solvent with rotary evaporation, and crude product is obtained by silica gel column chromatography (petroleum ether-ethyl acetate)
To the target product of solid-state, yield is about 60%.Its synthetic route referring to specification processing step part DBHO-TPA synthesis.
Embodiment 5
The synthesis of 3,7- bis--(4- -4 '-nitrodiphenylamines of amino base)-dibenzocycloheptene -5- ketone：By compound 3,
4--the 4 '-nitrodiphenylamines of amino of 7- dibromos dibenzo [a, d] cycloheptene -5- ketone (2) (0.68mmol) and 1.36mmol
Base, its structure referring to corresponding reaction in the partially synthetic route of processing step of specification starting compound）It is dissolved in toluene,
Add tertiary butyl oxygen sodium (1.52mmol) thereto again, be filled with nitrogen, after stirring at normal temperature half an hour, add Pd2(dba)3
(0.03mmol) and P (t-Bu)3(0.06mmol), is heated to reflux 8 hours in 90 DEG C in a nitrogen atmosphere.After reaction terminates, subtract
Pressure removes solvent, adds ethyl acetate dissolving, and NaCl salting liquids extraction, organic phase is dried with anhydrous magnesium sulfate.Pass through silicagel column
Chromatography (petroleum ether-ethyl acetate) obtains the target product of solid-state, and yield is about 35%.Its synthetic route is referring to explanation writing technology
Step part DBHO-DPA synthesis.
Embodiment 6
The preparation of OLED：Ito glass is sequentially passed through into detergent, deionized water, acetone, ethanol washing, then dried
It is dry.In the vacuum chamber, 4 × 10-4Under Pa vacuums, according to anode/hole transmission layer ,/dibenzosuberenone derivative/is repaiied
The device architecture of layer/negative electrode is adornd, the thick dibenzosuberenone of the thick NPB layers of 25nm, 50nm is deposited successively in ITO substrate surfaces
Derivative layer（DBHO-TPA, DBHO-DPA or DBHO-C）, the thick Alq of 20nm3Layer, 1nm thick LiF layers and the thick Al of 100nm.
Prepared new dibenzosuberenone derivative DBHO-TPA and DBHO-DPA mono-crystalline structures belong to monoclinic system, and it is empty
Between group be P2 (1)/c, DBHO-TPA, DBHO-DPA and DBHO-C heat decomposition temperature be respectively 413.9 DEG C, 338.9 DEG C and
419.7℃.Under ultraviolet light, the emission peak of DBHO-TPA, DBHO-DPA and DBHO-C film is respectively 542nm, 504nm
And 502nm, see accompanying drawing 1.It is 1460cd/m by the brightness of the DBHO-TPA devices prepared in prepared device2, maximum electricity
Stream efficiency is 0.91cd/A；It is 436cd/m by the brightness of the DBHO-DPA devices prepared2, maximum current efficiency is 0.29cd/A；
It is 688cd/m by the brightness of the DBHO-C devices prepared2, maximum current efficiency is 0.56cd/A；See accompanying drawing 2.
Synthetic route is as shown in table 1；
。
Claims (4)
1. dibenzosuberenone derivative, it is characterised in that the general structure of such dibenzosuberenone derivative is as follows
It is shown：
Wherein, R in formula1Structural formula be：
2. a kind of technique for preparing dibenzosuberenone derivative, it is characterised in that the dibenzosuberenone derivative
General structure it is as follows：
Wherein, R in formula1Structural formula be：
Specifically include following steps：
Step 1：Using dibenzosuberenone as skeleton structure, compound (2) is synthesized by bromo-reaction, its structural formula is
Step 2：The compound (2) that step 1 is synthesized is 1 according to mol ratio with triphenylamine derivative:1-1:4 amounts add tetrahydrochysene furan
In muttering, stir, add 2M K2CO3PH value is adjusted to 7-10, under a nitrogen atmosphere, 1wt%- is added into system
5wt% Pd (PPh3)4, stirring reaction is heated to reflux at 60-80 DEG C 12-48 hours, reaction terminate after, organic phase through separation,
Purification, obtains yellow solid product.
3. a kind of technique for preparing dibenzosuberenone derivative, it is characterised in that the dibenzosuberenone derivative
General structure it is as follows：
Wherein, R in formula1Structural formula be：
Specifically include following steps：
Step 1：Using dibenzosuberenone as skeleton structure, compound (2) is synthesized by bromo-reaction, its structural formula is
Step 2：The compound (2) that step 1 is synthesized and diphenylamines or carbazole, are 1 according to mol ratio:1-1:4 amounts add toluene
In, stir, it is 1 to add with compound (2) mol ratio:1-1:The tertiary butyl oxygen sodium of 4 amounts, is filled with nitrogen, under agitation
It is 1 to add mol ratio:1-1:The Pd of 2 amounts2(dba)3With P (t-Bu)3, it is heated to reflux 8-16 in 90-110 DEG C in a nitrogen atmosphere
Hour, after reaction terminates, organic phase obtains yellow solid product through separation, purification.
4. the dibenzosuberenone derivative prepared according to the method in claim 2 or 3 is in organic electroluminescence
Applied in the luminous organic material of luminescent device.
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| DE112016000388A5 (en) * | 2015-01-20 | 2017-09-28 | Cynora Gmbh | ORGANIC MOLECULES FOR USE IN OPTOELECTRONIC COMPONENTS |
| CN106397130A (en) * | 2016-04-11 | 2017-02-15 | 上海博康精细化工有限公司 | Preparation method for 5-hydroxyl-5-phenylacetylene dibenzosuberenone |
| CN109354588B (en) * | 2016-08-19 | 2021-04-27 | 中节能万润股份有限公司 | Organic electroluminescent compound with nitrogen-containing five-membered heterocyclic ring as core and application thereof |
| CN106397415A (en) * | 2016-08-31 | 2017-02-15 | 江苏三月光电科技有限公司 | Pyridine-based five-membered-ring substituted compound and application thereof |
| CN106496198A (en) * | 2016-08-31 | 2017-03-15 | 江苏三月光电科技有限公司 | A kind of organic compound and its application with pyridine as core |
| CN106543071B (en) * | 2016-11-08 | 2020-05-05 | 中节能万润股份有限公司 | Compound with dibenzoheptenone as core and application of compound in OLED |
| CN106977446A (en) * | 2017-03-29 | 2017-07-25 | 江苏三月光电科技有限公司 | It is a kind of using three benzo cycloheptene ketone as the compound of core and its application in OLED |
| JP2018174266A (en) * | 2017-03-31 | 2018-11-08 | 株式会社ダイセル | Organic semiconductor and manufacturing method of the same |
| CN116332828A (en) * | 2021-12-10 | 2023-06-27 | 四川大学 | Dibenzocycloheptanone derivatives and application thereof in OLED (organic light emitting diode) device |
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| US20120115862A1 (en) * | 2008-10-09 | 2012-05-10 | Stefan Laufer | Dibenzocycloheptatone derivatives and pharmaceutical agents containing said compounds |
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| CN103833507B (en) * | 2013-12-25 | 2016-08-17 | 石家庄诚志永华显示材料有限公司 | A series of electroluminescent organic materials and preparation method and application |
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| CN1372536A (en) * | 1999-08-30 | 2002-10-02 | 哈尔曼及赖默股份有限公司 | Production of dibenzosuberenone derivatives by catalytic dehydrogenation |
| US20120115862A1 (en) * | 2008-10-09 | 2012-05-10 | Stefan Laufer | Dibenzocycloheptatone derivatives and pharmaceutical agents containing said compounds |
| CN103012098A (en) * | 2012-12-18 | 2013-04-03 | 华东师范大学 | Fluorene derivative and preparation method thereof |
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